147. The Ultimate Guide to Gaycations (with Jason Heidemann)

Snarky Opener (0:00)

Jason Heidemann

A lot of the men you meet, they come from small towns, and they're there because, for them, it's an opportunity to connect with other gay men.

So, I think that travel for gay men in particular is about a way to continue to build and foster community.

Episode Introduction (0:37)

Rob Loveless

Hello, my LGBTQuties, and welcome back to another episode of A Jaded Gay. I'm Rob Loveless and, today, I am a jaded gay because I'm having some issues with SoundCloud.

So usually, I post like little like episode snippets on YouTube, and then I'll convert those clips to MP3s and upload them to SoundCloud.

But for the past few months, they've been starting to phase in this new upload tool, and whenever I use that upload tool, it wouldn't work. Like it would let me upload it.

I'd enter in all the metadata, and then when I'd hit publish, there'd be an issue, and it wouldn't post. But they always had options to revert back to the original upload tool. So, I've just done that.

Well, like three weeks ago, it's fully now this new upload tool. It doesn't work for me, and there's no option to go back to revert to the original one.

So, I've reached out to SoundCloud's customer service via email because they don't have a phone number, and it's been three weeks, and I haven't gotten any response or any help.

I followed up a few times, and I keep getting a generic notice saying, oh, we have a high volume of customer service tickets we're trying to fix. So, like, this is really, like, ticking me off.

Like, I mean, I pay about $100 a year to maintain that profile so that way can upload these tracks, and it's SoundCloud, if you don't get your act together, I'm canceling my subscription.

So, everybody listening, there may not be a sound cloud profile for A Jaded Gay shortly after this. Ugh, but I digress.

Gaycations (1:57)

Rob Loveless

Anyway, while there may be clouds on the horizon with my relationship with SoundCloud, hopefully, there are clear skies ahead because we are quickly approaching summer.

And with that, I'm sure many of us want to get away on some vacations. Or if we're going to a gay travel destination, maybe a gaycation.

So, I am very excited to have a special guest joining us today to talk all things about gay travels. But before we get into it, you know the drill, let's pull our tarot card.

Tarot (2:26)

Rob Loveless

So, the card for this episode is the Five of Cups. As you remember, Cups is tied to the element of water. It's feminine energy.

So, it's all about reflecting and meditating, and Cups is representative of our emotions. So, you can think of our emotions flowing freely like water.

And in numerology, five is associated with change, instability, and loss, and it can sometimes be referred to as the conflict number.

So, when we draw the Five of Cups, it's signaling that we might be experiencing grief or sadness, and as a result, there might be some feelings of regret and disappointment.

Typically, this card appears when a situation hasn't gone our way and we may be stuck in a rut focusing on this loss. However, we can't allow ourselves to wallow, because that blocks us from moving forward. 

So instead, let's reflect on what actions led us to this current state, and then assess on what we can do to move beyond our grief and hurt.

And a key theme to overcoming this card is forgiveness, whether that's forgiving ourselves or forgiving those who have hurt us.

Guest Introduction (3:25)

Rob Loveless

And with that in mind, I am very excited to welcome our next guest. He is a Los Angeles-based LGBTQ+ travel writer and podcast host.

Please welcome Jason Heidemann. Hi, Jason. How are you today?

Rob Loveless

I'm great. How are you, Rob?

Rob Loveless

Doing well, thanks. It's great to connect after almost like we were saying three years ago. You came through in Pittsburgh.

We met through Misterb&b, you were doing one of the gayest road trips in America, as you called it. So, we got to connect then and years later, here we are to talk all things about gaycations. 

Jason Heidemann

Yeah, I've stayed at your house before. You welcomed me into your home. It was fantastic.

Rob Loveless

Yeah, definitely. It was a great visit. So, I'm glad we're able to connect here again, especially as spring is upon us. We'll be getting into the summer months soon.

So, I'm sure a lot of people, myself included, want to kick off their work clothes, get to a beach somewhere, find some gay travel destination.

So, we're going to talk all things about that, but before we get into it, can you introduce yourself to the listeners?

Tell them a little bit about what you do, your background, how you identify, pronouns, all that fun stuff?

Jason Heidemann

Yeah, sure. My name is Jason. My pronouns are he/him, and I'm a travel writer and cultural reporter. And as a I mean, I'm really as a writer, I've done it all.

I've had a lot of different kind of writing gigs in my life, but I really broke into writing through travel writing for an LGBTQ travel magazine.

So when I was in my twenties, I was living in San Diego, and I was at a LGBTQ travel show in San Francisco and ran into a friend of mine named Philip, who, at the time had been hired to be the managing editor of a brand new, first of its kind, LGBTQ, but gay male-focused, travel magazine called Passport, which is still around, and I still write for them today, which is crazy to think about.

But what happened was I had, he had known me because I had lived in San Francisco and I had done some TV work. I was actually on a television show on CBS as a correspondent, right?

So, it was like a news magazine show, and they would cut away to me talking about nightlife in the Bay Area, which I was hired because, at the time, I was like 23 years old, right?

So, he said, you know, I've seen your TV work. Do you ever do any writing? And I had not at the time, but I said, Sure. I sort of lied a little bit; it was like kind of a Pinocchio moment.

But I went back to San Diego, and I forgot all about this conversation. And then he ended up kind of needling me over and over again, and said, Send me clips. Send me clips. But I didn't have any clips.

So, what I ended up doing was I wrote a bunch of restaurant reviews for him based on the restaurants I had visited on that trip to San Francisco. And he liked him so much, he published them in the other magazine that this company owned at the time called QSF, so Queer San Francisco.

But it was a, it wasn't a free magazine that you get it like gay bars. It was an actual magazine you'd buy in bookstores or subscribe to.

So, through that, I actually, you know, got my first writing gigs, but I really wanted to write for this travel magazine, which was about to be launched. It hadn't come out yet.

So, I wrote a story for them on spec about San Diego. It was because I was living in San Diego at the time, so it was like 48 perfect hours in San Diego.

And I said, hey, I know the magazine's coming out soon, the debut issue. I've written a story on San Diego. Would you like to see it?

And at this point, I'd written a bunch of pieces for them, for QSF, this other magazine, and they said, we think you're great, but we don't think you're ready for a feature in the travel magazine.

I was like, okay, darn but all right. And then, about a month before that magazine launched, they had a story on Atlanta fall through, and they reached out to me and said, hey, can we see that story that you wrote on San Diego?

We just want to take a look at it. They loved it so much they published it in the debut issue of the magazine. And not only that, but that story became a template that they would give new writers.

And they said, just do what this guy does, follow his like format. So obviously, like, they really liked my work and and it sort of took off from there. After I wrote that San Diego story, they sent me to Australia.

I mean, like almost immediately afterwards, then to Sweden. I went to northern Sweden in like, January, I did, like, gay ski week, and then on and on, and really took off from there.

I ended up relocating back to Chicago, where I'm from, and then I ended up as a cultural reporter. I was an editor for Time Out for eight years. I'm sure you've heard of Time Out New York, Time Out London. 

They had a print version in Chicago for about eight and a half years. And for the entire time, I was the LGBTQ editor, and ended up doing some travel stories there as well.

And while I was there, I did more television work because I have a loud, booming, you know, camera-friendly face and personality.

I ended up becoming a part-time professor at Columbia College Chicago, which is the largest privately funded arts college in the country, where I taught social media marketing for seven years.

And then after Time Out stopped printing, and most of us either lost our jobs or left I ended up having my own column in the Chicago Tribune, though this was a column devoted to stand-up comedy, which is another passion of mine, and that is that that is a improv sketch comedy.

So, since that time, Rob, I've, you know, I've written eight guide books. I ended up working.

I got a corporate job for, I just left it about a year ago, but for about eight years, I was working for Expedia, writing, managing, and co-editing all their travel blogs, which was really fun.

And then after I left that job in June of last year, I've gone back to travel writing full-time. I'm still writing for Passport.

I'm working on a ton of stories for them right now, including a piece on Misterb&b, and since leading Expedia, I've written for National Geographic, AAA, US News & World Report.

And so, I'm off and running. So that's that's my background in a nutshell.

Rob Loveless

That's awesome. I mean, I definitely think that's a really impressive career. It sounds like you've gone to some great places, especially some gay destinations, which we will be covering a little bit more of.

Jason Heidemann

Yes, please.

Rob Loveless

Yeah. But before we get into that, I do like to ask all my guests today, are you a jaded or non-jaded gay, and why?

Jason Heidemann

Uh, you know what? I'm a, I'm a non-jaded gay. I sort of feel like I, you know, I know you. I've met you. I feel like you're a non-jaded gay too, but it's situational. I get it right? We all have our jaded moments.

But I went to bed last night for whatever reason, thinking, I'm not in a relationship right now. And I went to bed last night thinking, you know what?

The hardest part about not being in a relationship is keeping all this joy to myself. I think that's a pretty non-jaded way of looking at the world, don't you think?

Rob Loveless

I think so. Definitely.

Jason Heidemann

Yeah, so I'm non-jaded. Also, I'm talking to you, and this is fun. I love talking. I love public speaking. So, you know, I'm certainly not jaded at the moment. I'm happy as a little clam.

Rob Loveless

Awesome. Glad to hear that. And just from meeting you back in 2022 and even today on this recording, I can definitely feel the non-jaded energy coming through.

So, we love having a non-jaded gay in the house.

Jason Heidemann

Happy to be one.

Rob Loveless

Well, you gave us a great overview of your career as a travel writer. So, with that in mind, would you say, have you always had a sense of wanderlust?

Jason Heidemann

Yeah, I have. I mean, look, travel is something that a lot of people love and cherish, right? It's not a it's not a niche passion; it's something that a lot of people have an interest in.

And so, and I'm one of those people. I sort of attribute it to growing up in the Midwest. Now, of course, wanderlust is not exclusive to the Midwest, but what I mean by that is that, you know, I grew up in a great city where travel was readily available because Chicago is near O'Hare Airport.

And from O'Hare, you can be anywhere in the country, in the continental US, in three hours or less, right? I mean, I think the furthest destination would be Seattle, maybe LA, Miami, whatever's on the coast.

But it's what Chicago's called, calls itself the hub of the world. I mean, it's the world's busiest airport. So, it was easy to travel if you had some means, which, as an adult professional, I did.

But also, I attribute it to being a Midwesterner, because as great as I think the Midwest is, and as proud as I am to be from the greatest city in the Midwest, Chicago, it is the plains, right? It is quite flat.

So, you grow up being really curious about a lot of what a mount, excuse me, what a mountain looks like, what the ocean looks like.

You know, there is just, it's just, there's geographical features that you don't get when you grow up in the Midwest. And you think, I want to see these places. I want to see these things for myself.

I want to put my toes in the sand, in the Atlantic Ocean, you know? I want to see, you know, Half Dome in El Capitan at Yosemite National Park. And so, I think that fueled some of my wanderlust.

You know, I want to put my coins in a slot machine in Vegas. Like, you know, it's just I was, I was raised with a desire to see places that were not like my own.

So, yeah, I grew up with a sense of wanderlust.

Gay Men & Travel (12:02)

Rob Loveless

And it seems like traveling is a big thing for gay men. I mean, if you go on Instagram, you'll see the instagays in different destinations, or, you know, couples saying, look who's visiting.

Or if you go on apps, you'll see the travel feature where people might be visiting from somewhere, or showing their upcoming travel plans.

So, with all that in mind, why do you think travel is such an important part of gay men's lives?

Jason Heidemann

Yeah, well, so as I said before, of course, it's an important part of of of the lives of most people who have the means to do it, right? But if we're going to talk about gay men in particular, I think it comes down to a few things.

First of all, economically, it's more available to a lot of us, right? And by that, I mean, obviously, I have friends who, you know, work hard to pay their bills and can't afford to travel the way I can, because I'm paid to do it and and have the means to do it.

But men are more economically advantaged than women. Gay men are less likely to have children than their hetero counterparts, or even their lesbian counterparts.

So that frees up income, and if you're in a relationship, especially, you put two men together, right? That's double income, no kids, you know. And plus, the advantage of gender, right?

I feel like travel has been more economically available to us than maybe some other groups, okay, but there's also a couple other things, right? So, there's travel is an opportunity to connect with community, and I think that's really important.

You know, Rob, I go, because I live in Los Angeles, I go to Palm Springs all the time. And what, I stay at one of the gay resorts there, right? So, if Palm Springs is home to about 12, you know, men-only, clothing-optional resorts.

I stay at a very, very nice one that I wrote about a couple years ago called Twin Palms. And I'm actually going to be there again in April, right? It's sort of my home away from Los Angeles.

And when I go there and I meet other guests, some of those guests are from, traditionally, cities that have a lot of LGBTQ people, like Chicago, Los Angeles, San Francisco, Boston, you know, Philadelphia, and so forth. But a lot of the men you meet come from the suburbs. They come from small towns.

They come from rural areas, right? They're just almost like Joe Average, you know. And they're there because, for them, it's an opportunity to connect with other gay men, because back at home, they don't go out to the bars, or there are no bars, or they're in a community that doesn't have a an LGBTQ sports league and so forth.

So, I think that, you know, travel for gay men, in particular, is about a way to continue to build and foster community. I mean, I always say as a storyteller, right? Because I write travel stories for a living, my job is, only half of my job is describing a destination, right?

I'm not, like the other half of my job is talking about the people that you meet along the way, and that's both the locals and fellow travelers. Right? Those are the people that really make New York, New York, or Paris, Paris. Or, you know, Africa, Africa.

It's the people that live there. It's not just the climate and the geography. So, I think a lot of gay men travel because they want to connect with other gay men. And then, of course, brings up the other thing, which is, a lot of times they travel because they want to connect physically with other gay men, right? 

Like, look, sex, and romance are not exclusive to gay travelers. But again, because we're maybe less likely to be in monogamous, committed relationships, we might be more likely to be single, or we might be more likely to be in an open relationship, there is that opportunity to go to a new place, which always opens you up in new ways, right?

You always feel more alive when you travel. A sense of adventure. Maybe you'll do something you wouldn't normally do at home. You're more curious, you're more open.

And so, of course, if you have sex and even romance on the brain, you know you're more likely to go after, to go after and get those things.

So, I think that's I mean, again, I can assure you that when I stay at one of these gay resorts in Palm Springs, people often have hookups on their brain.

So yeah, I think those things that are particular to our community for sure.

Gay Destinations (16:15)

Rob Loveless

And with that in mind, you know, you talk to us a little bit about how you've gone to Palm Springs, places like gay ski week in Sweden.

So, what have been some of your favorite gay travel locations? And how do you choose these destinations?

Jason Heidemann

Yeah, all right, so that's that's sort of two questions. We'll tackle the former one first, right? So, what have been some of my favorite destinations? You know, I get asked this question all the time.

It's a difficult question to answer, because I've been many, many places, and I love a lot of places for different reasons, but I'm going to, kind of, I thought about this question in advance, and I'm going to kind of break it down for you.

So, I think for a lot of people, myself included, oftentimes, the first time we visit somewhere, it leaves a huge impression on us. I've had that many times, but I'm going to throw you two places.

One is Tokyo, and the other is Africa. So, I've been on safari in Africa twice now, both times with my family. The first time was about 15 years ago, the last time was just a couple years ago.

But when you go to a place like Africa, which is so different than what the Western world looks like, right? Very different from the United States, it leaves a huge impression. Africa is a huge continent.

It's very diverse. I was on safari, which a lot of, which is what, you know, draws a lot of travelers to Africa. And, you know, we're raised to think of animals as being something you see on television or in a zoo, and when they are walking amongst you, it is a whole other experience.

I mean, it is really something that leaves a profound impression on you. I'm also gonna say Tokyo because Tokyo couldn't be more different than, you know, Mount Kilimanjaro or the Serengeti, right?

But when I went to Tokyo, it was a bucket list trip. I found cheap flights from Los Angeles to Tokyo for $400 and I booked a weekend trip to Tokyo. So, I think I was there for only three or four nights.

I mean, it was crazy. I literally got on a plane and sailed over the Pacific just to go to Tokyo for a weekend. But it was like New York City but on the other side of the world. So, it had all the drama of New York City, all the energy, all the art and culture, but it's this, but it's, it's the people are so different.

They're so polite. There's no, everybody squeezes onto the subway. There's no pushing or shoving. There's no road rage. Nobody honks at each other in traffic. Everybody bows at each other.

I mean, it was really like, I just loved it. So, places like that, where you set it, you set your eyes upon it for the first time, and it leaves a big impression.

Now, I've visited just about every gay Mecca there is, and I've always longed, you know, I hear gays who are much older than, you know, yourself and myself also because I'm older than you.

But I hear gays talk about like, oh, if only you visited Providence, you know, Provincetown 30, 40, years ago, when it was a little bohemian village. If only you got to see Fire Island, way back when, Key West, Palm Springs.

I always hear those stories. And a destination that's like that right now is Zipolite. Have you heard of this town, Rob?

Rob Loveless

I haven't. No.

Jason Heidemann

Zipolite is in the state of Oaxaca in Mexico. It's on the ocean, but nestled in the jungle, or rather surrounded by jungle, and it's a little village of 900 people, so kind of like what you'd imagine Provincetown would have been like 30, 40, years ago.

But it's famous because it's home to the only legal nude beach in the entire country of Mexico, and the entire town is on this beach, and the entire beach is clothing optional. So, the entire town basically has this, like, hippie, queer nudist, like, you know, vibe to it, and it's become this under-the-radar gay Mecca. 

It's a little difficult to get to. I mean, even from Los Angeles, you have to fly to Mexico City. Then from Mexico City, you have to fly to either Porto Escondido, which is a surfer town, or Huatulco, which is in the jungle. And then from either those places, you have to take an hour cab ride through the jungle.

So, it's really difficult to get to, but once you get there, it is this, like, serene, out of this world, little again, kind of like hippie, queer nudist paradise. It's just fantastic. And it's, it's really having a moment right now. So much so that people hate when I talk about it, because they're like, don't ruin it, you know.

And I've written about it before, but it's a great place. If you want to know what it's like to be in the game Mecca in its infancy, go to Zipolite. And then lastly, I think it's fun.

And this is sort of along the lines of talking about Zipolite, but it's also fun as a travel writer to visit a destination just before it's discovered. And Zipolite falls into that, but that's I'm bucketing that under queer meccas. I want to give you a mainstream place.

So, a handful of years ago, on assignment, I traveled through the Balkans. I did Greece, Albania, Montenegro, and Croatia. Everybody goes to Croatia now, even Montenegro's starting to pop. But Albania, which, during its communist rule, broke away from the Soviet Union.

So, it was isolated, not only from Soviet, you know the you know the Eastern Bloc, but also from Western Europe. So, people called it the North Korea of Europe. It was so isolated, and now it's opened itself up. 

And I wouldn't necessarily recommend you go there yet, because you would only go there if you want to be, if you want to visit a place that's about to be discovered, right? So, you can tell it's still like, it's the capital city Tiranë is very exciting place, super, super fun, but it's not quite sexy yet.

You know, it doesn't quite have all the bars and clubs you'd want. It's still a little conservative, certainly not particularly LGBTQ-friendly. But the coast is very, very beautiful, especially the southern coast, which, you know, borders Greece, right?

That's where actually all the expats and backpackers in US and Australia and European travels are going right now.

But if you're like, you know, if you're someone who seeks out visiting a destination before the rest of the crowds have shown up, you know, a place like Albania was for me four years ago when I was there, that kind of place. So, the second part of your question was, you know, how do I choose my destinations?

And I love that you ask this question, because the truth is, I just get a feeling. So, I read a lot of books. I don't actually read a lot of travel books, per se, because I don't want other travel writers to lead my writing in one direction or the other, right?

I don't want to be influenced by their voice. But when you think about it, Rob, every book or novel you read is set in a destination. It's set somewhere, and that can become, you know, it becomes its own travel book, right? So, I read a lot of nonfiction.

So, if I'm reading a nonfiction, you know, book set in Australia, suddenly I might get the feels for Australia. If I'm reading an article in The New Yorker that happens to take place in, you know, London, and it might get me excited for London, but that's usually what happens for me is I just start, you know, I'm always reading.

I do sometimes look at, you know, travel-inspired video. I'll read, you know, I will read articles in like Conde Nast, travel and leisure, a farm magazine, so forth. And then, you know, like last year, I went back to Chicago, where I'm from, for three or four days.

But I had read that the old Coca-Cola Bottling plant in Indianapolis had been transformed into a new hotel bowling alley. And by bowling alley, I mean duck pin bowling, which Indianapolis is famous for, right? Bowling balls that you hold in the palm of your hand.

And then it opened a food hall, and like, cute little shops and a yoga studio. And I thought, I want to see that. So, I just kind of got this, like Indianapolis feeling inside me. And then I started looking at other things going on in things going on in the city. I said, Yeah, it feels like it's time I revisit Indie.

And so, from Chicago, I just rented a car, drove down there for three hours. But that's usually what happens for me, whether it's a destination I'd never been to, or one I've been to many times before, I just start to get this feeling like, this summer, I'm gonna go to the East Coast, and it sounds like you and I are gonna be able to connect.

And it had, it's been two years since I've been in New York City, which is a shame.

I almost never go a year without visiting New York. But it's been even longer since I've been able to, like, really go around the East Coast and go to, you know, Vermont and, you know, P Town, and I'm gonna go to Atlantic City to see a show that I want to see, and go to Philadelphia and go to the Poconos.

Like, I haven't done that trip in a while, so I'm like, it, I just started getting, like, the tingles. And I was like, I'm doing it. I'm booking it. So that's kind of how it happens for me.

Safety for LGBTQ+ Travelers (24:26)

Rob Loveless

And as you were answering that, you mentioned that there are some areas that are a little conservative and not LGBTQ+ friendly.

You know, I think a lot of gay men in the past, some of their gay travels have been to more liberal areas. 

But even if you think of some of these areas, like Miami, Key West, they're in states that are majorly conservative.

So, with that in mind, what are some unique safety concerns for gay men traveling?

Jason Heidemann

Yeah, so I hope, I really hope, that LGBTQ travelers don't abandon red states, right? Florida in particular. I'm glad you brought that up, because not only has Florida turned red, it's sort of become like MAGA headquarters.

It's really a shame to think about that. Having said that, though, Florida is also home to a lot of great gay cities, right? Like Miami, like Orlando, like Key West, like Fort Lauderdale and Wilton Manors, like Tampa, St. Pete, and there's gay hotels, gay bars, gay beaches.

And I really don't, I don't want people to not go there anymore, because then we'll lose those businesses. And that doesn't make the world better for LGBT, LGBTQ people. I think it makes it worse.

So, I always say that, you know, the world becomes a better place when we go everywhere, when we flood the zone.

I mean, I travel as a road tripper, as an avid road tripper, which I am, and someone who, as you know, when I travel the country, I don't take the interstate, I take state highways and back country roads.

So, I'm going into the most rural parts of America, which is a nice segue into talking about safety concerns, right? Okay, so they exist on sort of a few fronts, and it's funny, I actually just wrote an article on LGBTQ safety for AAA that will be due out any day now.

So, you know, hopefully, you can find that, and your listeners can find that. But so first of all, we have all the same concerns a lot of mainstream travelers have right now. Women travelers have their own separate set of concerns, right?

And, you know, I understand that we're really talking primarily about gay men today, but I think all travelers want to make sure that when they go somewhere they've never been to before, that they're in a safe neighborhood.

You know that they're I think, I think it can be especially intimidating sometimes to travel when you don't know the language, right, you worry that you'll be taken advantage of.

There are, you know, there are places around the world that are tourist hubs, but where, you know, sometimes the police don't always cooperate with tourists.

You know, people have reported problems in like Mexico and Thailand, which are both amazing countries I love, by the way, but I know I've been harassed by the police twice in Mexico, which I hate to say, but you know, it's happened, and it all worked out.

But you know, sometimes those things happen, right? However, as LGBTQ people and gay men in particular, there's sort of a couple things, right? There still exists, I think, the awkwardness around the hotel room.

Now, if I'm traveling solo, I don't have to think about this, right? But if you're traveling with a husband, a boyfriend, a significant other, right, there still is that question of like, okay, when we check-in, you know, is it going to be awkward that we ask for, you know, one king bed or one queen bed or whatever, especially, I think, when you're traveling through rural areas, right?

Or maybe through more redder states. So that's one. And then the other thing is, look, we live in a time, especially in the most recent months, which is just so sad and painful to talk about and think about, but of increasing anti-LGBTQ legislation.

I mean, it was even happening during the Biden administration, you know, under, you know, on the local level, in red states. But, you know, we live in this era now of increasing anti-LGBTQ legislation nationwide.

And then, of course, we still live in a world where there's a lot of countries that you know are very hostile to LGBTQ people.

So, I think those safety concerns are are valid and legitimate and and top of mind for, you know, for gay travelers.

Now, I'm guessing the rest the next question you're going to ask is, so you know, what are some like? What do we do about that? How do we think about that? But I'll let you ask that question. Yeah?

Rob Loveless

Yeah. You're taking the words right out of my mouth. I was gonna say, especially given the AAA article you were talking about, what resources do you personally use to stay safe when traveling?

Jason Heidemann

Yeah, so there's a couple things, right? So, as I said, before I go everywhere, and I want to start by telling you the good news.

And the good news is that when you're LGBTQ or you live in a big city like a lot of gay and lesbian people do, LGBTQ people do, trans as well, you know, we tend to live in our own bubbles, right?

That's one of the problems with the world we live in now, is the folks who live in the rural places don't come to the cities anymore. The people live in the cities don't go to the and I can tell you, as someone who goes everywhere, people are much gay friendlier than you think they are right.

Like sometimes we mistake political hostility, meaning politicians who are trying to score points with their base as people hate gays. And that's simply not true. You know, I traveled the country when you and I met up a couple years ago, and did it again last summer.

And I mean, I can't tell you how many small towns that I drove through that I saw Pride flags, rainbow crosswalks, met friendly people, welcoming people.

So that's the good news, but in terms of actual resources, I use, you and I met through Misterb&b, right? Which is a great resource.

So Misterb&b is a home-sharing site, much like Couchsurfing, though you pay for it, and I think Couchsurfing is free, much like Vrbo, though Vrbo is usually entire, you know, it's not usually, it's always entire places.

I should know I work for Vrbo because they're Expedia-owned, but much more akin to Airbnb, right, where you offer up a room.

But of course, your hosts are all LGBTQ, and Misterb&b has made efforts to reach a wider LGBTQ audience, but really, it's mostly gay men who book through it. And you know, it's a great opportunity to connect with hosts in big cities like you and I do.

You were living in Pittsburgh at the time, but if you go to Misterb&b and you search using their map filter, meaning you actually get to see a map, you will see that there are Misterb&b's all over the country and in some of the most rural places.

I encourage people to use that as a resource because you can be driving through rural Nebraska and boom, there's some gay couple who's offering up their home.

And by the way, in rural places, people don't live in apartments like we do in big cities. They have homes with backyards and multiple bedrooms. I mean, it's really remarkable.

So Misterb&b is a good resource, because there's not only a ton of listings in big urban areas, but you might be surprised to find that there's a lot of people offering up their homes in red states and more rural parts of the country.

Also, a lot of companies now, like Booking.com which is a large competitor to Expedia, right? They have what's called LGBTQ certified, so they put their hotel partners through a rigorous program where they have to prove they're LGBTQ friendly and you can actually search and look for that.

You know, I think it's like a little rainbow icon or whatever, but you can search to find an LGBTQ-friendly hotel. The last thing that people should know on the sort of the booking front is that a lot of these hotels that we think a lot about, like a Holiday Inn Express or, you know, you know, a Motel 6.

A lot of them are owned by larger companies that have, you know, again, I know DEI is under attack, right? But they have LGBTQ training in place.

So, you can, you can really walk into just about any chain hotel, and that they have been trained to know that gay couples are going to be coming to them and that they are expected and required to treat them no differently than any other couple.

So, you know that should, that should help people rest a little bit easier. But you know what? There's a couple other things you can do too, right?

So, first of all, when I travel to places, whether it's rural or big cities, I rely on locals, including straight people, to tell me what's LGBTQ-friendly. So obviously, you know, queer locals are a great resource. You know, queer locals who I've stayed with through Misterb&b, right?

I stayed with you, and you can tell me, where do I go on a Tuesday night in Pittsburgh, you know, or, or, where can I, can I hold my hand with my partner or my boyfriend? Right? But also, you know, I've encountered many straight people, uh, concierges at hotels, people you meet at a restaurant.

You know, the tourism industry in particular, right, they're used to encountering gay people all the time, because we travel so much. So, they're actually even straight folks are a great resource because they're used to encountering us, so they know how to answer our questions.

But also, too, you know, because a lot of the world is still hostile to LGBTQ people, but we are curious about that world, a great thing to do is book a gaycation through an LGBTQ travel, uh, tour operator, right?

So, some that come to mind would be like Atlantis. Everybody knows Atlantis, right? Or Vacaya, which is, which is a emerging competitor to Atlantis. But also, there's Brand G, uh, Source Events, right? These are places that will book two weeks in India, a week in Egypt, 12 days in Cuba.

They will take you to places that you might think I don't know that I'm comfortable going there on my own, but they work with LGBTQ tour operators on the ground.

You know, they work with the local governments. Hey, we're a gay group. We're coming to your country to do sightseeing. And you know that there's going to be a built-in element of like safety and also safety in numbers because you're traveling with a group.

So, you know, we could talk safety all day. But those are some of the things I think about when I travel. And of course, too, you know, look, people will say to me, well, you go out on the road.

I mean, you know, that's great. You're a white gay man, you know, like, it's easier for you.

But I would say to you know, my trans friends, my lesbian friends, like, you should still go out there, but travel with a white gay man, travel with your parents, travel with a group, travel with a bunch of people, you know, like, find a way to make it happen.

Because I think the more visible we are, we're great travelers. We show up in local communities.

We're polite, we spend money, you know, we are we are the kind of traveler that most cities want and and so I want all of us to be out there and show up and show who we are because that makes the world a safer place for all of us.

Gay Road Trips (34:26)

Rob Loveless

And we both have touched upon that we connected back in the summer of 2022 through Misterb&b, and during that time, you were writing an article called P Town to Palm Springs, and then a second article called Pride Across America, where you traveled from Key West to Seattle, and you won the 2024 Excellence in Travel Writing award from the National Lesbian and Gay Journalists Association for the former, which is very exciting. Congratulations.

Jason Heidemann

Thank you.

Rob Loveless

Can you tell us a little bit more about those articles?

Jason Heidemann

Yeah, so let me start with the article that took me from Provincetown back home to California.

So, what had happened was the context of that story was, you're right, it was summer of 2022, and at the time, I was fully employed by Expedia, so I wasn't really allowed to write for competitors, because I had an editorial job with an Expedia, but they let me write for Passport, this gay travel magazine, because they didn't see this a real competition or real threat.

So, a few times a year I would, you know, sneak away from my job and write these stories on the side. So, I was invited to a friend's 40th birthday party in Provincetown.

These are friends of mine who, at the time, were living in London, but I met them in Chicago. So, they had all these Chicago friends and all these London friends, and they thought, let's have them meet up in the middle. And they picked Provincetown, and they rented a big house.

It was beautiful, but I thought, you know, there's no reason to fly six hours from Los Angeles to Boston and then another hour and a half ferry ride to P Town and just spend two or three days there.

So, I thought I should make a bigger trip out of it. And I had an idea. I thought, what if I just drove home? What if I just rented a car and drove home to Los Angeles? And then I had a second idea, and that was, what if I sold it as a story? Because if I sell it, then I get a paycheck, and then I can write off the trip.

But I didn't think Provincetown to Los Angeles had the right ring to it from a story standpoint. So, I kind of scratched my head, and I thought, you know what? How about P Town to Palm Springs, the gayest road trip of all time? So that was that trip.

It was 12 days long, and I very quickly, I went from P Town, I picked up the car in Boston, of course, and then I went Boston to New York City. Then I went to Philadelphia and the Poconos, then to Pittsburgh, where you and I met.

Then I went to Detroit, and then over to Saugatuck, which is the little gay village on Lake Michigan. And then I went to the Quad Cities, and then over to Omaha, Nebraska, then to Denver, Colorado, then down to Taos, Albuquerque, and then across, across the West, across the desert, to Phoenix, and then Palm Springs.

That story was fantastic. I did the whole thing taking only back country roads and state highways, no interstates, unless I was going in and out of a city.

Obviously, you know, it can be maddening to just drive block by block through a city, so I would take the interstates, you know, just in the morning as I was leaving and then just as I was entering a new city at the end of the day. But that said that trip was practically life-changing. I loved every minute of it.

I also love being out in the open road, and I love, you know, when you when you take the interstate, Rob, I always tell people, that's not how you see America. That's how you skip America.

The interstates are filled with Chick-fil-A's and McDonald's and, you know, ARCO gas stations and you know La Quinta Inns. But when you take state highways and back country roads, you see an entirely different America you didn't know existed.

It's a wild place out there in ways, mostly good and occasionally bad, but like, you know, Rob, I was driving through a small town in western Illinois. Now, Illinois is a solidly blue state, but it's only blue because Chicago and the suburbs are blue, and that's where 80% of the population lives.

The rest of the state is ruby red. But I was driving through the western portion of the state, heading into the Quad Cities, which are four little cities that are on the Iowa/Illinois border, on the Mississippi River. And I drove through this little small town, and it was a very cute, charming, small Midwest town.

It had the town square with the gazebo in the middle, and the little cafe and the bookstore. It was really adorable. But right outside the town square was a big church, and I don't know the denomination of the church, I forge.

And it had a big grassy lawn in front of it, and there were seven Adirondack chairs lined up, all painted a different color of the Pride flag with a sign at the end that said, everybody is welcome to sit here. And you see stuff like that everywhere you go, and it always like, you know, moves me and surprises me.

So, I enjoyed that. I submitted that story. It came out in 2023 I had so much fun. I thought, what would it be like to do this again? I want to, I want to get out there and do another journey like this.

So that's where I dreamed up, its, its follow-up, which actually will be out in the May issue of Passport magazine this year. So, it's coming up real soon, and that story is Pride Across America. So last June, I took almost the entirety of of the month.

I left my job at Expedia, like June 4, and the next day, got on a plane and flew to Key West and spent the weekend doing Key West Pride. I also wrote a separate Key West story, which just came out in the most recent issue of Passport magazine.

But I was there for Pride weekend, and then I drove, taking only state highways and back country roads from Key West to Seattle, so that's an even further distance than P Town to Palm Springs, right? I mean, that's like because Florida is such a long, spindly state.

And what I did was, in the middle of the month, I visited Denver for their 50th Pride, and then I ended in Seattle, where they were also celebrating their 50th Pride.

And Seattle, they align their Pride with, you know, the same you know, the traditional Pride weekend, the last weekend in June when New York and Chicago and San Francisco do it. So, it was great.

And on that trip, I went from Key West to Miami, to Tampa, St. Pete to Orlando, to Atlanta, and did a gay campground on my way to Atlanta. And then from Atlanta, I went to Dollywood, so Pigeon Forge, Tennessee.

And then I went to Knoxville, Nashville. I went to Eureka Springs, a little gay mountain village. I don't know if you've heard of it, but that's a great, sleepy little gay Mecca. And then I went to Springfield, Missouri, and then Kansas City, and then to Denver.

And then from Denver, I went to Salt Lake City, and then to Reno, Tahoe, and then to Bend, Oregon, Portland, and Seattle. So that one was a little bit longer than the first one. It was, I think it came out to maybe be 19 or 20 days, almost three weeks on the road, but it was brilliant.

And actually, I think that story turned out even better than P Town to Palm Springs, which is a story I won the award for.

So, it's funny, while I was on that trip, Pride Across America, unbeknownst to me, my editor had submitted that story for this, for this award from the National Lesbian Gay Journalists Association, and it ended up winning the Excellence in Travel Writing category.

And by luck, the conference was in Los Angeles, where I live, and so I was able to be there in person in September and accept the award. And it was great.

But I actually think the follow-up is even better. I'm even more proud of that one. So, I can't wait for the world to see it in in, what, just a couple months now.

Rob Loveless

That's awesome. I can't wait to read that.

Jason Heidemann

Yeah, I'll make sure I send it to you. But you're not in that one. You are in the first one, you are, you are, you are an award-winning part.

You are part of an award-winning story, Rob, because you were featured in that. And by the way, your very handsome face is also in that story, as you know.

I submitted a photo of you, and they included it which is, which is so fun and funny, right? It's great.

Rob Loveless

Awesome. Well, I am honored. And that was a great read. You had sent that over when it came out. So, I loved reading that article.

Jason Heidemann

And by the way, it should be worth noting that I submitted it as P Town of Palm Springs: The Gayest Road Trip of All Time, but they changed the title, I assume, for SEO purposes, to The Great Gay American Road Trip.

So, if anyone wants to see that article and wants to go to passportmagazine.com you just want to search under Great Gay American Road Trip, which is, you know, a fine title.

Best Gaycation Ever! (42:10)

Rob Loveless

And in addition to your writing career, last year, you also launched your podcast, Best Gaycation Ever!

So, can you tell us a little bit more about that and what inspired you to start it?

Jason Heidemann

Yeah, so it's called Best Gaycation Ever! 101 Queer Places to Visit Before You Die, right? So, it's really each episode, we devote ourselves, me and a special guest, to an iconic queer place.

And by place, I don't mean a city or a town. I mean something within that, right? So, for example, I did an episode on Stonewall National Monument. That's the place. The wider destination, of course, is New York City.

And, you know, we did a P Town episode, but that episode was about the Boatslip Hotel, right? The famous hotel that all the gays go to for afternoon tea dance. And of course, underneath the hotel is the infamous dick dock, where gays go at like, one or two in the morning to, you know, have their fun.

And then the wider destination was P Town. So, it always focuses on iconic, you know, an iconic beach, an iconic gay hotel, bar, monument, roadside attraction, museum, whatever the case may be.

And our, my guests and I talk about that for about 20 minutes, and then we pull back and look at the wider destination.

And in the case of New York, offer our favorite, you know, gay bars in New York, gay beaches, restaurants, hotels, mainstream attractions, you know, museums, all those things.

So, I've been doing it for about a year, maybe not quite a year. I do an episode a month. I'd like to get it up to an episode every three weeks, but, you know, I'm a busy man, so it doesn't always quite happen, but I'm about to drop Episode 10 next week. It's going very well, and it's a lot of fun.

So, thanks for asking that. So yeah, people can, people, it's it, you know, people always ask me, like, how do I find this? And it's like, you probably get that asked that same question. And it's so funny.

It's like, it's everywhere, you know, it's on Spotify, it's on Apple, it's, I mean, it's hosted through Buzzsprout, but you can find it there too.

But like, you just, you just type in Best Gaycation Ever!, and it kind of pops right up. So, it's not hard to find.

Jason’s Favorite Travel Story (44:00)

Rob Loveless

Through all your gaycations, do you have a favorite travel story you can share with us?

Jason Heidemann

Yeah, you know, I'm gonna give you one, and it's really about, it's a story that kind of made me a better travel writer.

And some of your I suspect the name that I'm gonna drop in this might be more known among some of your older listeners, but when I was young and starting out doing this, I went to New Orleans for the first time as an adult.

I'd been as a kid for, I think it was a Final Four basketball with my family in, you know, I mean, I was 13 or 14 years old at the time, but I went for the first time as an adult, and I was quite excited.

And I was staying at a gay-owned hotel in the Marigny. Have you been to New Orleans, Rob?

Rob Loveless

I have. I was actually just there this past fall.

Jason Heidemann

Oh, great. Okay, so of course, everybody knows the French Quarter, right? The Boucherie. But and in New Orleans, everything is either upriver or downriver. They don't really use north and south.

So, the next neighborhood downriver from the quarter is the Marigny, and the Marigny is very queer, very queer-friendly. And I stayed at this place called The Lions Inn.

The owners are no longer associated with it. I don't know if it's still open or not. It might be, but the the owner at the time was an old Southern gentleman named Floyd McLamb.

He was probably in his late 60s. I looked him up recently. He's still alive, and any and you know, and at the time, he was sort of a New Orleans legend. He was very much a man about about town in his youth and in his formative years.

And so, he was very well known locally, but I stayed at this maybe eight or nine, you know, room in it was oriented toward LGBTQ people, open to all, but sort of like, you know, gay and gay friendly.

It had a pool in the backyard, clothing optional, and very, very sort of a sort of bread and breakfast, bed and breakfast experience, where every morning you'd wake up and there'd be a big, lavish breakfast. 

And you know, I was having breakfast one morning, and there were just all these people there, and so I was asking them, oh, where are you visiting from? What room are you staying in?

And all these people said, we live here in New Orleans. We just come by each day because Floyd makes the best breakfast. And I thought, oh my gosh, how fun is this? So, I got to talking to these people, and they said, Oh, you're a writer. You know who you should visit? You should go visit Marta Burton.

She's like, the doyenne of the French Quarter. She's this, like, you know, she lives in Floyd's old apartment in the French Quarter. And of course, all the apartments in the apartments in the corner are usually above, right? They're not at street level.

The shops are on the street level, and the apartments are above them. And they said, every Sunday, she hosts a salon for writer types like yourself, you should just go knock on her door, and you know, she's hosting a salon this Sunday, and just she'll let you in.

And I thought, I'm never gonna do that. That's crazy. Another guest said, and this is where I'm gonna name drop a name that hopefully you know, but maybe you're not, you don't.

Is someone said, do you know who Robert Mapplethorpe is? Do you know who that is?

Rob Loveless

I don't. Not off the top of my head.

Jason Heidemann

Okay, he's a famous gay photographer who died of AIDS in, I think, the early 90s. But he's famous for photographing, for black and white photography, primarily three subjects.

He photographed, um, flowers, portraits of women, and then male nudes. And the male nudes are probably what he's most famous for among gay men, but he's a legendary photographer.

The poet and punk singer Patti Smith wrote a memoir about her life growing up with spending time with him in New York City, called Just Kids. It's brilliant. Came out about 10 or 12 years ago. Fantastic book, but Robert Mapplethorpe. Google him. You'll probably recognize his images.

He's quite well known, but he has been dead now for probably 30-plus years. But anyway, someone said, Oh, his mentor lives here in New Orleans. You should go meet him too. His name is George Dureau. He's a real character. And I was just like, I'm not going to do these things.

But I was out and about New Orleans, Floyd, the owner of the lions, and had given me the address of Marta Burton. It was on Royal Street. It was Sunday afternoon. I thought, I'm kind of, I kind of have time to kill. What if I just knocked on her door and see what happens?

I knock on the door, she answers it this older, attractive dress to the nines, you know, lady with blonde hair opens it, and she was like, you know, may I help you? Like, in her sort of southern accent. And I said, Yeah, my name is Jason. I'm staying with Floyd. I'm a writer.

He said I should. And she was like, she sort of gasped, and she said, Jason. And she took my hand, led me upstairs, and she was having this Sunday salon. And it was a, it was a holiday weekend, right? Spring is festival season in New Orleans.

So, there were all these, not only were there all these writers there from like the New York, sorry, the New Orleans Times-Picayune, but there was, she had hired an opera singer from the New York Metropolitan Opera to come perform.

And there was a Miss America there from a handful of years, like all these people, so all these men, male journalists in like, white suits, which is very like, you know, Deep South, all these women in sundresses and big hats, all much older than me, all who just like, spent the whole day hanging out with me and taking me under their wing.

I mean, it was really, really, really fun and crazy. And I thought, I'm on a roll here. Let's go meet this George Dureau guy. So, this was 20 years ago. I didn't even have a cell phone at the time. Though cell phones were sort of, it was at the era where they were kind of becoming readily available.

So, I actually looked up his address in the phone book. I went to his flat. Again, he lived in a big corner studio above in the French Quarter, above a shop. I knocked on his door, thinking, what am I doing? He opens the door. He looked like Paul Bunyan, okay, older guy, probably about 70 at the time.

He's recently passed away. So is Marta Burton, by the way. I noticed both of them. She died a few years ago. He died maybe six or seven years ago, but he answered the door. So, he's got long, brown and gray hair tied in a ponytail, big, thick beard. He's wearing baggy clothes, and he's like, who are you?

And he's like, Are you the delivery boy? Are you the FedEx boy? And I was like, no, I'm My name is Jason. I'm a writer. He's like, Oh, you're a writer. He's like, and I said, someone told me I should meet you. He's like, well, come on in then.

So, he invites me in, and what he is famous for, and this is where Robert Mapplethorpe would have borrowed from him is he used to go into the slums of New Orleans, and he would find little people, right, often, amputees. He would invite them back to his house.

They would live with him for a month or several months at a time, they would become his, he would call, this was his words, husbands, and he would photograph them nude. So, all over his apartment, he had all these beautiful photos of little people who were also like amputees and nude in these photos.

And so, I had stumbled onto something, and I asked him about Robert Mapplethorpe, and he had terrible things to say about Mapplethorpe. He was like he was a crook. I didn't want to spend my life with him. He and I were in New York together, but I hated him, so I came back to New Orleans like it was.

So, I got all this, like art world gossip. I got to be in the studio of a legend. I mean, George Dureau is fairly well known. You can, you can look him up. And then he also, he had photographed the first openly gay football player, but never published those photos.

So, he showed me contact sheets of, you know, nude photos of the first ever openly gay football player. And of course, this was before my time, so I don't remember who it was, but it was wild. I spent the whole afternoon there hanging out with him.

I ended up telling my editor at Passport magazine about this, and I said can I write a story about this. He was like, Sure, and that story has been picked up and cited in like, you know, like art magazines and stuff. 

It was really wild, but it really made me rethink about travel and about my job as a travel writer, which is, like, you know, being the person who knocks on doors and listens to locals and says yes and, you know, and stays open, right?

Like, I mean that, you know, the trouble I got into just by being open was, was, you know, and being available to, you know, to do things outside my comfort zone. I mean, it was, that was a wild weekend I'll never forget. And to this day, you know, Floyd is still alive.

He's probably about 90 now, but he's, I think he's retired in Mississippi where he grew up. And sadly, George and Marta have passed away, but, but I'll never forget that story.

Rob Loveless

Wow, that's definitely an amazing story. Like, talk about a total whirlwind.

Jason Heidemann

Totally for sure. Yeah.

Financial Tips for Traveling (52:09)

Rob Loveless

Yeah. You know earlier, we talked about how traveling can be costly. For gay men, specifically single gay men, it could work out a little bit more economically in their favor.

But going off of that, some consider traveling to be a luxury due to the cost.

So, what financial hacks do you have for gay men who want to start traveling more?

Jason Heidemann

Yeah, so, you know, we talked about this earlier, but I'll bring it up again, right?

Something like Misterb&b, really is a great resource, because, you know, I sort of emphasized before how nice it is to find a Misterb&b in rural areas, but let's talk about the value, meaning the financial value, of booking a Misterb&b in urban areas.

So, unfortunately, a lot of cities have cracked down on room-sharing services like Airbnb and Misterb&b, right? I mean, really, the target is Airbnb, but Misterb&b kind of becomes a fallout of that, right? They get sort of swept up in that.

But New York City has made it so difficult to have Airbnb and Misterb&b that they're virtually all gone there. And, look, I get it. I understand why. New, you know, New York is a competitive market. It's a tough city. People don't like the idea of people, you know, landlords, taking entire apartments and renting up. 

So, I get it, but it's unfortunate because I have a good friend I stayed with in New York. He's like a brother to me.

But like many New Yorkers, even though he's successful and doing well, he lives in a one-room studio with one bed, and so even though we can share that bed, I wake up early, he wakes up late, he snores, I snore. You know, it's just not always a great fit.

And what I loved about Misterb&b was that I could stay in Hell's Kitchen, which is the gayborhood where he lives. I could stay close by him for a half, maybe a third, of the cost of a hotel room.

I mean, you could find a Misterb&b in New York City for $150 a night, versus the average hotel room there, which is about $400.

And again, it's a shame that they're gone now, but other cities still have them. You know, I mean, I'm going to Chicago for a conference in June, staying in the Misterb&b, why? Because it's such a big value. 

Plus Misterb&b's are often located in the neighborhoods you want to be in, right? Like hotel zones are not always where the gay bars are, right, like in Chicago as an example, most of the hotels are located in River North and downtown in the loop, but Boystown, Andersonville are much further north than that. 

So, something like Misterb&b is a great resource economically. Another site that I mentioned briefly, that I've only explored a little bit, is Couchsurfing. I mean, if you're really penny-pinching, you can go into Couchsurfing. You can join a group like gay travelers, gay male travelers, you know, whatever it is.

And you can say, hey, I'm coming to, you know, Barcelona for a weekend. Does someone have a couch I can crash on? And someone will say, yep, you can crash on my couch and it's for free. I mean, that's really amazing.

And, you know, I'm, I'm, I've been nosing around that site a little bit, you know, I I'm at a place in life where I'm reluctant to sleep on a couch. But some people are actually offering up spare bedrooms because they just have them.

You know, everyone's living situation is different, but that's something else. You know, I also recommend people sign up for websites that offer travel discounts. You know, I used to be an avid subscriber to Travelzoo, and I haven't thought about them in a long time.

But like that was the site that announced the flash sale on um ANA airlines from Los Angeles to Tokyo. That was this. That was the site where I found these deals to that I booked my flight, round trip, nonstop for $400, $400 to go to Tokyo and back.

So, I recommend signing up to travel sites that offer deals. You know, sign up for, you know, become a rewards member for, you know, Expedia. I don't know if Airbnb offers rewards program. I'm not sure they do. I mean, Misterb&b actually does. I mean, I use it so much, I'm an iconic explorer, right?

But like, you know, and by the way, also get a credit card that works for you. Pay it off monthly and earn those miles, right? Earn those points. I have, I finally got a friend of mine who, several years ago, was like, hey, you need to throw away that stupid Southwest credit card you have.

You're such an avid traveler, and you need a better card. He got me on a better car. And right now, I think I'm sitting on more than 300,000 miles.

And think about, like, how many round trip first-class flights, even to, like, international destinations I can take with that. So, make your travel dollars stretch for you. So yeah, those are some of the hacks I use. 

But you know, look, I will, I'll fully admit too, through my work, I travel much cheaper than a lot of people do, and even trips that I pay for fully out of my own pocket, I often sell the story, which means I get a paycheck out of it, and I can write off much of the trip.

So, you know, I'm advantaged in the way a lot of travelers aren't. But even when I was young, though, I found ways to make it, you know, sleep on someone's couch, used Couchsurfing, find a friend, travel with friends. Obviously, I love solo travel, Rob. I also love traveling with people.

And you're, you know, you're cutting hotel costs in half when you travel with people, and that's a huge advantage. You're traveling it. You're cutting it even more if you travel with even a larger group, right?

If you, if you feel comfortable doing four people, doing four people to a room, which I wouldn't do at this point in life, but, you know, some people will. Also too, you know, I think a lot of gay men, they want to go to festival and party weekends, right?

They want to go to Market Days in Chicago. They want to go to Balsam in San Francisco. They want to go to, you know, a Carnival in P Town, but you're going to pay a premium for that.

You know, if you if you're willing to travel during the week, if you're willing to travel on non-festival weekends, if you're willing to travel even slightly off-season, you can save exponentially more money. 

You know, the the hotel I was telling you about in Palm Springs, Twin Palms, I got news for you that hotel is nearly fully booked every weekend. Like, maybe, maybe not in summer, when it's 110 degrees, but most of the year it is fully booked out.

So even if you think like, oh, I want to go in spring, because that's high season, people are gonna be there. You can go in October, and the hotel will be full.

Like, if you want to be around other gay men, naked gay men around the pool, like you don't have to go in March or April, which is high season for Palm Springs, or, you know, Coachella season. You can go other times a year and still find a community.

Um, I even, you know, as a writer, I prefer, I don't like going to gay festival weekends, because, to me, that's not where you meet the locals. That's not where the stores are.

That's where you pay high prices and stand in long lines. So that's not really what appeals to me, though, having said that, I do have plans to go to Southern Decadence this year, which I haven't done in a long time, and actually excited to go to again.

Rob Loveless

Nice. That'll be a lot of fun.

Jason Heidemann

I think so. Yeah, yeah. I you know, the thing about New Orleans is that it really, it really became a different city after Hurricane Katrina.

Unfortunately, a lot of people, including a lot of LGBTQ people, moved out of the city. And so, I have found that, you know, it kind of, it kind of feels a little dead on non-festival weekends, right?

I mean, I was there in October about five or six years ago, and it was just so quiet. And I thought, well, I needed to be a little busier than this.

So, I actually think I'm going to go for Southern Decadence, which you will, you will see a lot during Southern Decadence. Let me assure you. It's quite an eye-opening weekend, but it's fun.

Travel Advice for Gay Men (59:24)

Rob Loveless

Well, for any gay men out there who have that sense of wanderlust and want to go on a gaycation, what advice would you have for them?

Jason Heidemann

Yeah, you know my advice would be, learn to travel solo, because I really am a big fan and believer in traveling with a friend, traveling with a boyfriend, traveling with a group, but those can be hard to put together, and it ends up, I think, you know, it ends up changing your experience, of course, which we'll talk about in a second.

But also, too, it becomes a hindrance, because. When you have you know, when there's too many cooks in the kitchen, no one can make a decision.

But when you travel solo, you are in charge of everything. You're in charge of where you go, where you stay, how much time you spend, the people you interact with.

So, I would say, if gay men are thinking, I'd really like to travel more, and I can afford to travel more, but my friends don't want to go, forget about your friends. Just go.

If you're nervous about it, start small. You know, start by going somewhere like Palm Springs or P Town where, you know, there's gonna be a lot of you know, start by going to a big city that, you know, start small, but um, you know, be be fearless, and travel and um, and don't be afraid to go to places that are off the beaten path.

I don't want to ever advocate putting people in harm's way. I mean, all travel involves being smart. You know, I road trip constantly. I don't ever drive at night. I am off the road each day by 5 or 6 pm. First of all, when you drive at night, you miss everything.

You can't see everything because it's dark. So, there's that, but also, you know, and I don't, I don't wander alone through, you know, dangerous neighborhoods. I'm very smart and cautious about those things, but you only get one life.

So, if you have wanderlust, you need to take advantage of it. And when you travel solo, this is the other part of that, right? You wake up when you want to wake up. If you're like, I like to go to museums, go to that museum. If you want to stay out at a bar till four in the morning, stay out at that bar.

If you want to go to a bathhouse afterwards, you can do that, right? Like when you travel solo, you're fully in charge of your of your destiny, and you're, you know.

So, and also, too, you're going to get a little lonely, and that loneliness is going to force you to engage with other travelers, which to me is where, and not just travelers, but locals as well, which to me is where the magic happens.

Um, so yeah, maybe start by traveling solo.

Episode Closing (1:01:52)

Rob Loveless

And connecting it back to the tarot, the Five of Cups, it's telling us that we might be experiencing grief or sadness. So, take a vacation, it'll fix all your problems. Just kidding. It's not that simple.

You know, I think something Jason talked about that really jumped out to me was that there may be a belief that these conservative states are not accepting of LGBTQ+ people.

But like he said, some of the politics that are happening in those states are more self-serving for the politicians than actually reflecting the communities there.

And even in very conservative states, there can still be LGBTQ+ meccas, because LGBTQ+ people exist everywhere.

So maybe we need to check our assumptions at the door that are preventing us from seeing other parts of the world, because we might be writing them off, as, you know, conservative or not friendly to LGBTQ+ people, when in reality, like Jason said, driving through the roads of any state, he's seen Pride flags, he's seen equality signs, he's seen representation.

And just as much as travel can be something that's fun for us, it also allows opportunities to build community within the LGBTQ+ community.

And of course, we always want to prioritize our safety, that's the most important thing, but maybe allow this tarot card to challenge your limiting beliefs and encourage you to wander the road less traveled.

Connect with Jason (1:03:02)

Rob Loveless

Well, Jason, thank you so much for joining us today to go over all these travel hacks.

This was a really fun episode. As we're wrapping up here, I know you talked a little bit about your planned upcoming travels.

Can you tell us more about what's on your your map list, let's say?

Jason Heidemann

Yeah. So, I do have a few things coming up. So funny, funny enough, I'm based in Los Angeles, but I live on the east side, which is more of the like hipster side of LA and I also live in I live in Silver Lake, which is a gay neighborhood.

There's a few gay bars here. It's where all the daddies, the bears, and the hipster gays live. But of course, West Hollywood, which is its own city within Los Angeles, is the is the more traditional gay Mecca.

And believe it or not, I'm actually on assignment this weekend in West Hollywood. So, they're putting me up at a hotel, and they're taking me to all these bars and restaurants. So West Hollywood comes next.

In April, it's kind of a nice, lazy month where I'm going to go to Vegas with the boys for a few days, and that's going to be fun.

And by the way, a gay hotel that opened in Vegas a year ago and then shut down, but just reopened again, called the Bent Inn, it's a great little property.

You know, I think Vegas struggles with, uh, with gay bars and gay life sometimes, because most tourists want to just stay on the strip.

But this little hotel opened, and then after about 10 months, it closed because the owners got into a lawsuit with their contractor. But it sounds like that dispute has been resolved.

They have new investors, and it opens, reopens April 4. So, I'm excited to go spend money there. It's a fun little gay hotel. And then I am going to Palm Springs in April, just to lay out naked by the pool and read a book for a few days.

But bigger trips coming up. I am going to Puerto Vallarta on assignment in the first weekend of May. That's going to be really fun.

I'm checking out a new gay hotel called Tryst, and it's opening in Puerto Vallarta, and the same owner is going to open one in Fire Island and San Juan, Puerto Rico. So, listeners should pay attention to that.

And then at the end of May, I'm actually going to Norway for a week. I'm not going on assignment. I booked this because I had miles that were about to expire on Air France.

And I was like, oh, crap, these miles expire in like two days. I guess I'm going to Europe. So, I got this email last July, and I was like, I'm not ready to travel that far right now, so I booked it far off, but now it's coming up.

So, I'm going to be in the western fjords for five days, then meeting a friend of mine who lives in Berlin, in Oslo for the weekend, and then I'm flying back through Paris with two days in Paris on the way back.

So, I'm super excited about that. And then in in June, I'll be in Chicago for a travel writing conference.

And then in July, I'm going to meet up with my friend, Rob Loveless, as part of an East Coast mostly train journey, but there'll be some, there'll be some car rental where I'm going to be in, I'll be in Vermont and P Town and Providence and New York City and Fire Island and Atlantic City and Asbury Park and Philadelphia.

And I'm going to go to the gay campgrounds outside Philadelphia, The Woods, and camp out, which I've been to The Woods before.

And so that's going to be an exciting trip for sure, and I will probably end up I've already pitched some stories out of that. I'll probably, that will probably end up being an assignment-based trip, but I think Norway is going to be just for me, but we'll see.

Rob Loveless

Nice, that sounds awesome. And as you're going through these travels, where can listeners connect with you and learn more?

Jason Heidemann

Yeah, sure. So of course, I encourage people to listen to Best Gaycation Ever! We're about to drop episode number 10, and we've done a ton of great destinations.

I did do Zipolite already, which we talked about. I've done Los Angeles and Chicago and Provincetown in New York City. So, a lot of big ones with many, many more to come. But on social, they can find me.

So, on Instagram, my account was banned. I was permanently deleted from the app last October for, you know, posting fun, semi-spicy pics, I guess. So, I have a new account.

So, by all means, follow me, but the name that I use when I travel sometimes, and the name that I host my podcast under is homotel, and that name is a portmanteau, right?

It's two words put together, so it's homosexual and motel. And of course, motel is a portmanteau of motor hotel, right? So, it's a portmanteau of a portmanteau.

So, I use the name homotel, so you can follow me on Bluesky @homotel. I've officially, I'm off Twitter, no thanks, not interested. I'm homotel, H-O-M-O-T-E-L on Bluesky.

And then on Instagram, I used to be homotel, but that was banned, so now I'm back on as @iamhomotel. So, I-A-M-H-O-M-O-T-E-L and those are really the best places to find me.

Of course, my work is widely available, but if you're interested in my LGBTQ content, I've written a ton of stories for Passport magazine, and I always post them on my, on my Instagram and Bluesky handles as as the digital version, the online versions become available, right?

So, they come out in print, but then, once they become available online, then I post them, I let people know where they can find them, and I provide a link. So that's another place to find me.

Rob Loveless

Definitely connect with Jason after listening to this. His articles are so fun. It's so interesting to see all the places he's gone to and check out his podcast as well. All that information is in the show notes.

Connect with A Jaded Gay (1:08:01)

Rob Loveless

And for A Jaded Gay, you know the drill. Please remember to rate, review, and subscribe. Five stars only. I greatly appreciate it.

If you have any questions or feedback, you can reach out to me rob@ajadedgay.com.

For more information on this topic, links to resources, blog posts, merchandise, links to socials, all that fun stuff, you can visit the website ajadedgay.com.

You can connect with a podcast on Instagram, TikTok, maybe SoundCloud, and YouTube @ajadedgaypod. You can follow me personally, Rob Loveless, on Instagram @rob_loveless.

Also, if you're feeling generous, consider supporting the podcast on Patreon for as little as $1 a month. 

That gets you instant access to episodes ad-free, a day early, plus exclusive monthly bonus content, or you can just access those monthly bonus episodes for $3 each.

And if you're scared of commitment, don't worry. I get it. You can make a one-time donation on Buy Me a Coffee for any dollar amount, and both the Patreon and Buy Me a Coffee are @ajadedgaypod.

And also, don't forget, if you sign up for the Patreon at any dollar amount during the month of April, you will get a free A Jaded Gay gift. So don't miss out on that.

And remember: every day is all we have, so you got to make your own happiness.

Mmm-bye.