A Jaded Gay
A Jaded Gay
149. Boats, Bears, and Building Community (with Chumley Singer)
LGBTQ+ individuals often navigate the diverse landscape of the queer community to forge connections that resonate with their identities, seeking spaces where they feel seen, understood, and supported. The bear community, with its celebration of body positivity and inclusivity, provides a unique subculture within the larger LGBTQ+ spectrum, fostering a strong sense of belonging and community engagement.
In this episode, Mark Singer, founder of Chumley’s BearCruises, joins us to discuss his experiences within the bear community, detailing how it inspired him to create Chumley's BearCruises and how these cruises foster a strong sense of belonging and connection among bears.
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Snarky Opener (0:00)
Chumley Singer
I just thought, if I'm going to be on a cruise and have someone question the amount of mashed potatoes I put on my plate, it's going to be an issue.
Episode Introduction (0:30)
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 the SoundCloud saga continues.
Like I talked about before, it wasn't letting me upload and I was having trouble with customer service trying to get a response, trying to troubleshoot the issue.
Well, it's been like two months at this point, now that they still have not got back to me.
So, I literally just had to cancel my subscription with them, because I'm not paying over $100 a year to not be able to upload tracks.
So, for anyone who had been using my SoundCloud account, you know the tracks that I have up there, they're still going to live there, but I haven't been able to upload any new tracks since, like, February, so there just won't be any new uploads there.
I'm not deleting the channel itself, but yeah, there won't be any updates. So sorry about it.
Bear Cruises (1:19)
Rob Loveless
Anyway, from saying goodbye to setting sails, today, I am very excited to have a special guest joining us to talk all about bear cruises.
As we've talked about in past episodes, obviously, there are some LGBTQ+ destinations.
I'm sure you've seen Instagram posts and advertisements for gay cruises, but I think it's important to remember that, like we have talked about in some episodes, body image is a real struggle for a lot of gay men.
And obviously, with summer on the horizon, you know, laying by the beach and the pool, some of us might feel a little self-conscious.
And unfortunately, traditionally, those who did not adhere to that quote-unquote gay archetype of being muscular and masculine, body image can kind of be a daunting thing.
And that's why I think it's so important that we all work on spreading a little bit of body positivity and creating more inclusive environments. And that is exactly what today's guest does.
So, we are going to dive into that soon. But first, you know the drill, let's pull our tarot card.
Tarot (2:18)
Rob Loveless
So, we drew a Major Arcana card today, and that is The Empress in reverse. As a reminder, Major Arcana cards indicate something big and meaningful and can signal a new chapter.
And The Empress is number three in the Major Arcana, which is representative of creativity, collaboration, and community. It's feminine energy, which is very nurturing and encouraging us to meditate and reflect.
And typically, this card represents receiving love, but when we draw it in reverse, it's indicating that we may feel blocked or cut off from loving ourselves or allowing others to love and care for us.
Specifically, we may be giving too much of our personal power away to others, and that could include by trying to achieve their validation, and in turn, we're neglecting our own needs.
Maybe we're focusing too much on our masculine energy and trying to take too much action to get things done, and instead, we need to channel our feminine energy, which encourages us to reflect on what we need to show ourselves some kindness.
So, all in all, we need to make self-love and self-care a priority for ourselves.
Guest Introduction (3:17)
Rob Loveless
So, with that in mind, I'm very excited to welcome our next guest. He is the founder of Chumley's Bear Cruises. Please welcome Chumley Singer.
Hi Chumley. How are you today?
Chumley Singer
Good. How are you, Rob?
Rob Loveless
Doing well, thanks. It's great to finally connect. We are, we were just talking before we started recording that we're kind of neighbors.
We're not too far from each other, but we're doing a virtual Zoom recording today anyway.
Chumley Singer
Yeah, it's kind of like COVID days.
Rob Loveless
I know, right? A little bit of a throwback there. Well, I'm very excited to have you on today to talk to us all about your famous Chumley Bear Cruises.
But before we get into that, to kick it off, can you tell us a little bit about yourself, how you identify, your pronouns, background, all that fun stuff?
Chumley Singer
Pretty boring. Cisgender, he/him, all that stuff. I am 63 sniffing at 64, lived in Philly most of my life.
Went to school in the early 80s to be a graphic designer, and in an ironic twist, due to working on some of the early HIV and AIDS fundraisers here in Philly and New York, I kind of ass backwards, became an event producer, unintentionally, and have done that for the last 35 years or so.
Rob Loveless
And I like to ask all my guests today, are you a jaded or non-jaded gay, and why?
Chumley Singer
Specifically, today, or in general today? I would say jaded for the most part. I think I came out of the womb that way. As for why, turn on the news. Any time, any day.
Rob Loveless
Fair enough. And hopefully, you know, these bear cruises sound like a nice getaway and a little bit of a sense of escapism from all the doom and gloom around politics.
Chumley Singer
Yeah, my husband has forbidden me from talking politics on the cruises, because it is everyone's opportunity to be away from all that.
Although enough of my guests follow me on Facebook that it's hard to avoid conversations and side conversation, but when I have a microphone, I am not allowed to speak about politics.
Rob Loveless
Well, I don't know if we'll really be getting into politics in this episode, but hopefully, it is a nice sense of escapism, like you said, no talking about that on these cruises.
What is a Bear? (5:33)
Rob Loveless
Today, we're talking all about the bear community, why events like cruises matter for the bear community, and specifically Chumley's Bear Cruises.
Before we get into that, though, I do want to ask, what is your personal definition of a bear?
Chumley Singer
Boy, that's a really odd question, because I'm old enough to remember when it wasn't a commonly used phrase. I've always said that if you ask 10 gay people any question, you'll get 15 answers.
And the question as to what comprises a bear is certainly in that realm. I think it really depends on the eye of the viewer in terms of what the physical attributes are.
But I like to describe a bear from from my point of view as, there was a time growing up when some of us in the gay community, came out, and then sort of had to come out again as being either not looking like Will or Jack, or liking people that didn't look like Will or Jack.
There was a point where, you know, we went to the leather bars or the biker bars, because that was like, sort of the guys that we looked like or we were looking for, as opposed to, you know, the big clubs where everyone sort of had that similar clone look.
I think what came out of that, for better or worse, is that regardless of physical attributes or what you're attracted to the bear community, kind of was a response to that sort of shaming within our own community that you didn't look or act or dress a certain way.
And I think the most successful attribute of the bear community is its general acceptance of everyone. We've promoted the cruises since day one as for the bear and bear-friendly community.
It's not really based on what you look like as much as everybody you know, you think of a beard, you think of a beefy guy, but you know, there's a whole menagerie of, you know, otters and cubs and polar bears and panda bears and pretty much any zoo animal you can think of.
But I like to think of it more as an attitude of just being friendly and accepted. Really started at a period where I think a lot of us didn't feel like we were welcomed and accepted.
And so, within our group, like I said, everybody is welcome. We welcome straight friends and family members and allies and lesbians.
And few things upset me as much as if someone is not accepting of someone for any sort of reason, because that's what makes us different. That's why we started.
Rob Loveless
And I love that answer too, because we've done some episodes in the past on body image in the gay community. And unfortunately, gay men can be each other's own worst enemy sometimes.
And with summer around the corner, and you know, when we're talking about cruises, obviously sometimes there can be a panic around, what does my body look like?
So, it's really great that you are creating a place that is inclusive, body body-positive, where people can just enjoy community and not worry about superficial aspects.
Chumley’s Bear Cruises (8:52)
Rob Loveless
So, with that in mind, let's get right into it. Can you tell us more about Chumley's Bear Cruises?
Chumley Singer
Sure. Well, as a matter of fact, many, many I was doing gay bingo with my friend Michael, who performs as Carlota Ttendant, many years ago here in Philadelphia, we did a few years where we sort of hosted a small group of gay bingo fans through one of our sponsors.
We would take 30 people or so on a cruise. And I realized the attraction of having a group of that size, where you could reserve a room, lounge, a space, your own dining area, your own excursions in port. And I fell in love with that as an event producer.
And then towards the late 90s, a couple of my very dear friends who are not people of size, let's say, who do fit the mold of the traditional gay they invited me to go on an all-gay charter, and I looked at the collateral.
Um, back then there was, it was still printed collateral, and I didn't see anyone that looked like me. And they assured me that, no, everybody goes, all kinds of people go, it's lots of fun.
And I said, Yeah, but I don't see anyone that looks like me in their brochure. And that is concerning, but also the idea of seven days at sea with those with the you know, all the late-night parties and the you know the DJs and the light rigs and the you know the drug usage and the music and you know, it's great.
It's just not for me. It wasn't my idea of a good time, not seven days. I don't swim that well, and it's a long way to shore. So, I was at my campground at the time, and it was, you know, the the theme of the weekend, because, you know, it's a gay campground.
God forbid you have a weekend that doesn't have a theme, was bear weekend. And I thought, you know, I bet there's other guys like me who would rather be in a group on a regular sailing, as opposed to an all-gay charter, which is a great product, you know, of you know, the the entertainment is top-notch, and the DJs are top-notch, and if that's your thing, but it wasn't my idea of a good time.
And I just thought, if I'm going to be on a cruise and have someone question the amount of mashed potatoes I put on my plate, it's going to be an issue. So, this is how long ago we I started by sitting in AOL chat rooms.
If anyone remembers what AOL chat rooms were, and any city that had a bears group, I just said, hey, I'm putting together a group to go on this cruise. And in 2003, the fall 2003, we did our first Chumley's Bear Cruise, and it I think we had 150 people in that group. It just worked really well.
The good sense of community, like-minded people, it gives us the advantage of spending time. We have onboard events that are private. We have excursions in port that are private, but you have all the things that the ship normally does.
And whereas an all-gay charter obviously has to spend a lot of money, so they charge a lot of money. So that cabin that you're in might be three times what the person in that cabin the week before paid. And yes, you are getting those perks, if that's what you're interested in.
But for us, we're able to offer a group discounts, so we can give you a better price than you can almost ever get on your own. And we have all these events, so you have all the things that the ship normally provides, entertainment-wise, etc., but you can come to ours, but you can also get away from it if you don't want it.
So, I'm always fascinated that probably 80% of our guys comes to every event we do all week, which amazes me, especially since half of our guests usually repeat customers, and half are Chumley's Bear Cruise virgins.
And I say some of these guys are have sailed with us 20 times, and I'm like, you know, my same old corny jokes, why do you keep coming to our dance parties and whatever?
Because they want to be together. They want that's why they're there. But again, you can get away from it. We have, we have guys that do their annual family vacation, because, you know, the vast majority of the ship are just regular people, regular guests.
So, your friends and family can do their own thing, but you can be with us when we're having our functions, and invariably, the friends and family end up spending all their time coming to our stuff because we're where the party is.
Rob Loveless
That sounds like a great time, but obviously, there's a lot I'm sure that takes place behind the scenes of getting it all together. So, what's the process like from planning a cruise to executing it?
Chumley Singer
Yeah, well, like I said, I've been doing event production for so long that it's like anything else. The first time you do an event, it's a nightmare. There's a lot to consider, and a lot that can go wrong, and all those things that you didn't expect to happen.
But, you know, you do something enough, you sort of start to have a familiarity with it. And you know what to expect. When I was a kid, I worked in retail display. So, you know, by the you were working on holidays and vacation, all the scenes, Christmas and whatever, six, eight months ahead of time.
So, by the time they got there, you were just like, oh so over it. Similarly, we have to book well ahead of a year out, because, for instance, we just came from our spring sailing mid-March of 2025, is it? Yeah. And we present to the guests in that group on the ship our next year's sailing.
So, they sort of get a sneak peek and a preview, and they get first dibs on cabin selection, etc. And then after a couple of weeks, when we come back, then we open that up to everyone else in our groups, all the people that follow us, our website, so before we even get on the ship, we've already planned next year's sailing, and have to get all that worked out.
But then there's the host hotels and the ground transportation and the shuttles and the pre-events and the check-in registration party before we sail, and all the events that we have to work out with the cruise line. So, once we're on board and the venues and the timing and our section for dining and, you know, all the credentialing and all those things that any event producer deals with pretty much any time.
I like that. I enjoy those things. They, you know, make me a little crazy the closer we get to the sailing time. And like with any event, by the time it actually gets there, you're like, oh my god, can we stop talking about this and just do it already?
But then I get to the the departure city, and all those guests that are return guests, and all the new people that we're meeting, and it's like an, it's like plugging in the USB that you just get recharged.
Our guys are the best. They just, everything that I can do as an event producer is limited, and people may come for the ship, they may come for the pricing, they might come for the itinerary, but they come back because of the guys in our group, 100%.
They just take care of each other. They look out for each other. They're warm and friendly, and they're polite, and not just with each other, but with the other passengers on the ship. So, for 22, 23 years, we've been doing these sailings.
And I often say people don't realize our group, and we've been our largest group was 550 on a ship of 1800 which is insane. But you know these people that we meet on the ship that, at first may not understand, because a lot of these people don't know what we are.
You know, we don't look like what they think, because in their little podunk town, you know, a lot of the I think homophobia comes from not knowing, you know, people. Not being out, like Quentin Crisps said, if we were all, if we were all purple on a Thursday, there'd be no homophobia on a Friday because everyone would realize we all have someone in our lives that we love, that's that's gay.
And the experience of the rest of the passengers on the ship as they not just discover who we are and what we are as a group, but you're sailing with them for seven days or more. You're in lines together, you're dining together, you're in ports of call together, so they get a chance to actually meet us and know us.
And so, I often refer to it as like a pebble thrown into a lake, because they go home to podunk and they say, oh, we met these bears. You know what bears are?
And I think, you know, I think our nephew might be a bear or a cub, or I think someone two weeks ago said to me, I think my hairdresser might be a bear. And I was like, Oh, my God, a gay hairdresser?
That is just outrageous. I never heard of such a thing. But, you know, it's like that. You throw a pebble into a lake and those ripples, okay, keep going out and out from that spot. So, these people go home and they have an experience, because, to them, gay was the, you know, the drag queen, the leather guy, the lesbian bikers.
That's all they ever see on TV, you know, when there's a Pride parade or something. So, you know, they spend a week with us and they realize, oh, there's homos that are just as boring as we are, you know, and they actually have the time to get to know. And that's the thing about our group.
You know, when we started it, it was there were bear weekends in different cities around the country. And again, that's great if that's something you enjoy doing, but I just really like the idea of having time to actually get to know each other.
So instead of getting into a city, going to a dance party, having brunch, maybe a trip to the baths, and you know, there's a lot of sexual heat and energy and going on, which is all fine and well and good.
But being together for a week, 10 days, having dinner, having time to sit, pre-dinner, cocktails, you really make friends for life. That's the thing that I like to think our product is. It's really hard to leave one of our cruises without making new friends.
And, you know, that is the kind of thing I always wanted, and that's the kind of thing I enjoy now, because people think, oh, you know, you throw these big events all the time, but if I was just in a small group or at a cocktail party with, you know, that kind of conversation, I'm not the most gregarious.
If I'm on stage and have a mic, I'm fine, but I don't really do the small talk thing. And this group really, if someone's sitting off on their own, someone grabs them and brings them into the group.
That's the thing I think, that I'm most proud of, is the friendships that were generated over the decades.
Rob Loveless
That's great that it's providing an outlet for genuine community building, and then also, like you said, creating some visibility for people who might not see LGBTQ+ people beyond stereotypes or gross exaggerations of what political agendas are trying to push.
Chumley Singer
Absolutely.
Body Positivity Onboard (21:08)
Rob Loveless
Can you tell us about the first Chumley Bear Cruise?
Chumley Singer
That was a while ago. Yeah, so the first one was in in 2003 and we had about 150 people in the first one. That was a ship of 800 passengers, which was a significant size ship back then.
Now, yeah, now ships are 5000+, and they they're like small towns, not even such small town. But yeah, the first one was different, because anything that I had led, like the Chumley and Carlotta cruises, everyone knew who I was, and this was a group of people that we assembled that didn't necessarily knew who I was.
Some people were from the Philly region, but not everybody. And again, I think that was the most remarkable thing, was the way the group congealed with each other, how polite and pleasant and friendly everybody was.
But again, the the wish I could take credit for it, but the significance of how the rest of the guests, because there was concern, are people going to be nasty, homophobic? Are we going to have issues? And I said prior, you know, we had one. We all, we still have one.
The first night at sea, we have our only mandatory event where I know people all the things I've told everybody 100 times, at least, they're getting to hear it one time, and I know they're hearing it from my mouth. And we talk about behavior and how, you know, basically, we're not in an all-gay.
Look, it's a cruise line, so there's a lot of drinking. We, by default, include a beverage package most of the time, and drinking is clearly encouraged on a cruise vacation. And sometimes, by sheer numbers, we tend to take over a pool or an area or a lounge.
And I think sometimes it's easy to forget that you're not the only people on the ship. And generally, I say, you know, if you don't want to see other guests doing it, then you probably shouldn't be doing it. Don't care what you do in your cabin.
Tip your cabin boy, well, that's between you and them. But you know, in public, you're in a public space, and our guests will self-police if somebody's not. I mean, it's so rare. We've had less than a dozen incidents where I've had to sort of say something to any of our guests in 30 sailings over 22 years, which is kind of amazing to me.
We've had more instances of just, I mean, endless instances of positive feedback from the guests. This is an old story, but our first sailing since you asked, my mom used to come with us and help do registration and check-in and things. And she was telling me about some of the people were some of the older people were asking her what the group was.
And one night, it's a formal night, so prior to getting going into dinner, they would line up if you wanted to get pictures. I told our guys, if anybody wants me in the picture, I'll just hang out right before the photographer. Yell, if you want me to jump in, if not, yeah, that's fine.
So, this older couple was at the front of the line, and being an older couple, I think they didn't realize how loud they were being, he was clearly going to say something to me, and she was mortified, and trying to get him not to say something.
So, as they inch closer, I sort of prepared myself for a little battle. And the guy came up to me. He said, hey fella, are you with this group? Are you with this bear group? And I said, Yeah, in fact, it's my group. Is there something I can do for you?
And he got right, right in my face, and he goes, what do you guys, like a gay football team or something? So, I thought, oh yeah, they just have no idea. Especially back then, I think more so now.
I mean, there's so many bear cruises now, like this new one every day, most of them by my ex-guests, and I can't even keep up with but the effect that the group has on people who didn't really have a familiarity with gays in general, but particularly with the sort of bear subculture.
And, you know, we've had so many comments and things. I'll tell, I'll tell you one more that that struck in my mind. There was a couple, we would have private functions where we'd sort of take over a pool area or something. And there was a couple, straight couple, maybe 40s at the, in their 40s at the time.
And they were often, always wherever we were. They were, you know, the very typical looking straight couple. The guy was bald, kind of beefy, like, not a little bit hair on his chest, but he had a belly. He was, he was definitely a handsome guy.
And our guys were, like, that guy is so hot, and they're here. They're always with us. They're always. So, I was like, look, obviously, if they're comfortable hanging out with us, they're welcome to hang out with us. You know, it's fine. They're not a problem.
So, at one point I just the woman and I started chatting, the wife, and she was saying, Oh, your group's so friendly. They're so nice, and yeah. And so, everything's fine. And then toward the end of the week, I get a phone call, and in my cabin, and it's this, this woman, she says, she seemed very panicked.
And she goes and, Can I bother you just for a minute? I need to talk to you. And she seemed distraught. I said, Oh my God. What happened? What happened? Thinking the worst. Knocks on my door. She's got two cocktails, one for me.
And she said, I don't know if you realize, but my husband and I have been hanging out with your group most of the week, we didn't realize your group would be on the ship and blah, blah, blah. And I said, no, I realize, you're welcome.
And she said, you know, I just wanted to tell you that my husband was the classic high school quarterback football star, and I was a cheerleader, and we were kind of like your typical story. We have, I think she said two or three kids. But she said, you know, my husband has a little bit of a belly, and he's put on weight over the years.
And I'm like, yeah, we've, we've noticed your husband's belly. Believe me, I'm not the only one who's noticed. And she said, well, the first day we were at the back pool, and you know, your guys were walking around with their bellies hanging out, and some of them in little speedos and stuff, and he took his shirt off and got in the pool.
And I was like, yeah? And she said I want you to understand that he hasn't been in public with his shirt off in like 30 years. He's so afraid of what people would think about his body, because as a young person, he was, you know, in this perfect shape.
And I said, well, obviously that we're all about that like, you know, we we encourage that. And she said, no, he gets it. Like, he totally got it. It was life-changing. And she went on to, she went on to say about how, what a physically good week they had as well.
But she said, you know, I don't know that you realize how that can affect somebody. So again, there's things that you would never imagine.
Who would think that something like that would affect somebody like that, but just seeing people be okay with themselves, and not just okay, but of course, be attracted to all kinds of body types and size. And this guy, you know, to me, was not a heavy guy.
This was someone who had a great body with a little bit of a paunch, but hadn't been even in the ocean swimming without a shirt on, she said in over 30 years, which blew my mind. And she was crying.
She was she was just like, I just wanted to tell you that. And thank you. And again, it's just those little ripples from that in the pond. You know, you have no idea, like little crazy things that you would never think of.
Rob Loveless
That's awesome that it seems like it's not just promoting body inclusivity for the LGBTQ+ community, but those observers, those people who are seeing this representation of LGBTQ+ people.
Chumley Singer
Yeah, and you know, you know, even in all you know, in the last few decades, the advances that we've made in terms of the entertainment industry or visibility in general. You know, you still don't see a ton of people of size, you know, there's still a big gap there. And I know lots of members of our community, you know, disabled and all kinds of different sectors, feel the same way that for so long, you know, you had to have this kind of look if you were going to play LGBTQ. And you know, a lot of us, I think, just feel like, well, we don't really have time for that nonsense, because we're too busy just leading our lives and being ourselves. You know, my husband is a, you know, I guess, what you would call a classic chaser. He's not a big guy. He's half my age and half my size. And, you know, and I love the fact that, you know, he, he, he works with me to this day on my body image, because it's still rough for me. You know, there's still issues I have growing up. And, you know, as we alluded to earlier, I think there's a lot of people, and this is maybe a little bit off subject and a whole nother conversation, but you know, when he first started coming with us, you know, I was like, trying to explain to him, because he wasn't born until the 90s, that a lot of people my age, in their 50s and 60s, particularly in the bear community. First, you know, we all came out as kids for the most part, which is stressful enough in many ways. Then we sort of had that second coming out because we were like not necessarily all accepted within the general gay community because of how we looked or dressed or whatever. Then, you know, we lived through the HIV crisis. So, you know, we all sort of whatever ways we dealt with that to get through. I think many of us now have PTSD because that we don't talk about. For some reason, nobody talks about it. And then those of us that are still around have survivors’ guilt because the friends that I lost did nothing different than I did, but they caught a virus and I didn't. So, you know, we're all kind of walking around like with all this baggage and zombied in a bit of a way, and my husband being younger and thinner and, you know, in quote-unquote good shape, I said, you have to realize that people are not going to warm to you right away, because people that look like you rejected and hurt them so often, and you have to be yourself and let them talk to you, and once they get to know you, you'll be fine, and that's what happened. But that first cruise was rough for him because he thought nobody liked him. I said, no, I think you need to give them a chance to get to know you a little bit because it's hard within the bear community. There was so much rejection and so much anxiety and stress, and we are all, those of us in our 50s and 60s, I think doing ourselves a disservice by not sort of working on what we dealt with, you know, decades ago. We all muddled and found a way to get through it, but it seems like nobody talks about it, which is probably not the healthy path.
The Evolution of Chumley’s Bear Cruises (33:28)
Rob Loveless
Well, talking through that, you've talked about how the sizes of the cruises have grown. There's been some technological advancements, and you have a lot of return guests coming to this.
So, beyond that, how has Chumley's Bear Cruise grown today?
Chumley Singer
Well, we generally are almost always about half of the group are first-time guests and half are return guests. We generally are about a third single people, a third friends, and a third couples or husbands. We do a survey and try to fill in those numbers.
When we started, husbands wasn't a factor, but now I'm happy to say many are. And you know, because it's a cruise, most guests will book double occupancy, two to a cabin. So, if you book a solo cabin, you're kind of paying almost twice as much.
So, a lot of times, we don't know if you're just friends or you're dating, or you're a couple or and you know that could change five times during the course of a week, so it's hard to keep up sometimes. But yeah, it's, it's pretty much about a third, a third, a third.
And we do, you know, like a singles event once or twice early in the week, so the single guys get to meet each other and see who else is traveling solo. But the cruise ships themselves have gotten much bigger in general.
Sometimes, that's for better. Sometimes, not so much. Ironically, the really big ships now, like the Oasis Class ships that carry 5,000, 6,000 people, I think, because they don't want you to feel like you're on a giant ship, there aren't a lot of really large venues.
There's lots of small venues, lots of small lounges and clubs, and our group really wants to spend time together, so it's kind of hard. The bigger ships are hard for us to book because there's no place we can all be together for a party or by the pool.
So, we we've sort of stuck with primarily one or two lines. We are in the process of trying to change that, mix that up a little bit. But yeah, the the the the ships themselves have changed.
Cruising has changed. You know, we now, by default, as I mentioned, kind of try to include a beverage package, because the beverage package now includes so many things, gratuities and premium desserts and gym classes, and it's not just about the drinks.
So, we're trying to keep up, it changes all the time. Sometimes you wish they would just keep things the same one year so you could figure out what's going on. But yeah, we're trying to mix it up moving forward a little bit.
We started this, I used to work for our NFL franchise here, the Eagles, and didn't really have much of a life in the spring because of spring training, but we started a spring cruise in addition to our fall cruise. And the idea for the spring cruise was they would be something different.
Fall cruise was usually Caribbean, Mexican Riviera, usually a big group. Warm weather, sand, bathing suits, pools. And spring could be New England, Alaska, you know, other things.
And we're trying to get back to that, and get back to the original idea of doing some European tours, you know, keeping in mind that there are certain things, things that I might want to do, or you might want to do on a smaller like on a sailing yacht or something that sometimes don't work for bigger guys because of the size of the cabin or the shower that can get a little old after seven days.
So, we're always exploring options and trying to keep it fresh. Figure out what our onboard activities might be a little stale, and change them up. And you know, we used to do things like a dating game and a newlywed game. Someone took time off of that to mix it up a little bit.
Sometimes we do what we call Chumley Live, which is a little chat show. And we try to feature some of the staff from the ship in an interview format, and some of our guests because, you know, there's always someone who has an amazing career, some amazing karaoke talent, and we just try to have some fun with that.
What to Expect on Chumley’s Bear Cruises (38:05)
Rob Loveless
Well, that sounds like a great time. So, with all that in mind, what can someone attending one of your cruises expect?
Chumley Singer
Well, we try to be first and foremost, really good about communication. We know that some people are seasoned cruisers and some people are first-timers. We try to give this much information on our website, right up from the get-go to sort of give you the details of what's involved.
But once you go under deposit for sailing, we invite you into a private online group. So, we have a public group, of course, but the private group is just for people on that specific sailing. So, like I said, about half are first time and half are return guests.
So right off the bat, you get to chat with other people. So oftentimes, as far as questions about what to do, what to bring, what to pack, people will often answer that before I even get to see it.
I will send posts about all the things you need to, all the perfunctory details, you know, the ground transportation, the host hotel, what to pack, what to plan, all those kind of things. But then you know, also, people just enjoy making new friends.
And often, you know, will the week before we sail, they'll meet at the host hotel, and they're good friends, even though they're just meeting face to face for the first time. So, it's not like they're just walking into like a completely unknown situation.
And then again, so many of our people are return guests that they've become like a welcoming committee. Once I invite someone into a new group, there's just a thread of welcome. Hi. How are you? I'm from that city, blah, blah, blah, blah. So, I love that. I love that first and foremost.
And then we work with the cruise line, as I mentioned, we will create an onboard itinerary of activities that we do, some dance parties, will do some days at sea, kind of thing. Board games is always very popular.
We still call it board games, although it has evolved into all kinds of high-tech games and things I don't even understand half the time. But guys will post on the group what they're bringing. It might be a card game; it might be a video game.
And then we'll just reserve a space on days at sea, and people get together, and they love doing that. Sometimes we do silly like crafty things. A recent cruise, we had a guest who's an amazing watercolorist, and he did two days where he taught watercolor sessions, which was wonderful.
Sometimes it's silly things. We do a lot of pre-dinner cocktails. Obviously, we plan, at least in every port of call, one private excursion for the group, for those that want to be with the group.
Nothing too strenuous that's not bear-friendly but depending on where we are, we try to do something that at least gives you an opportunity to see the sites or spend a day at the beach or a catamaran, snorkeling, you know, all those kind of things.
There's also a host hotel. We do a registration check-in the night before, the afternoon before we sail, and that's where you get your goodie bag and your gifts, and your credentials.
And again, it's another opportunity for people to meet and greet and go to dinner together, and hang out. It's really everything that we do at the core is getting people to hang out and have time to talk and chat and get to know each other.
That's really incentive number one.
The Future of Chumley’s Bear Cruises (41:58)
Rob Loveless
And what plans do you have for the future of Chumley's Bear Cruises?
Chumley Singer
As I mentioned, we're trying to get back into the original concept of doing some smaller groups and more unique things, a little bit off-the-beaten-path kind of things.
So, we are working on some European options, which we haven't done yet. We are excited that we're about to announce our May of 2026 Alaska sailing. I think it's our fourth or fifth visit to Alaska, round trip from channel.
But it's on the new Star Princess, Sister of the Sun Princess, new sphere class ships that we sailed the sun last fall. But it's all about glass and vistas, and so we're really excited to be doing that in Alaska, where you can actually see the sites almost 24 hours a day.
But yeah, some smaller. We're looking at some possible river barge cruises around the world and maybe adding some things in addition to the two that we're doing.
Rob Loveless
That sounds awesome.
Community Through Cruises (43:07)
Rob Loveless
I know throughout a lot of this, we talked about how these bear cruises have really created an inclusive and welcoming space for one, those who identify as bears, but two, just members of the LGBTQ+ identity, even some people outside of the community just seeing body positivity.
So how do you think these types of cruises support finding a sense of community within the LGBTQ+ community?
Chumley Singer
I really do think that the the key is by nature, and most of our cruises, we have been seven-day cruises, although we just came off of a 12-day, but the amount of time spent together.
So, you know, I grew up at a time where you almost had to go to a loud, crowded gay bar to meet gay people. I was never much of a drinker. I was really more of a pothead.
So, nothing, I think drunk people find other drunk people really amusing, but when you're stoned, they're kind of really annoying, especially in a loud space.
So being in an environment where you have a week to 10 days where you actually have time to sit and chat, have a cocktail, watch some beautiful vistas going by, sit on a beach, go on an excursion in port, but you're it's really to me, 99% of it is the time to get to know people.
And it's hard to do that when you're in a loud, crowded environment. There's plenty of good products out there for people who want that, and there wasn't, at the time, something like this.
And so, I just my whole life of being an event producer was based on doing the kind of events that I would want to go to.
So, you know, I would turn down the black-tie silent auction fundraisers because I was like, oh my god, I can't do another one of those. It just wasn't my thing.
So, you know, we wanted to do something quirky, gay bingo. When I read about Seattle doing gay bingo, that's where I presented it to the then director of it was called From All Walks of Life back then, now the AIDS Fund, because it seemed like the kind of thing that I would want to go to, and so that became very successful.
And, you know, I think that's the same idea with the cruises. I just wanted to do something that would give people an opportunity to hang out and make me friends.
And they may be friends for the week or they may be friends for life, and we've had a few marriages come out of it even.
Rob Loveless
Very cool.
Advice for Cruising (45:51)
Rob Loveless
And then, as we're getting towards the end of this episode, what advice do you have for someone interested in going on a gay cruise, specifically a bear cruise, but might be nervous?
Chumley Singer
Well, I think, as with any cruise or any vacation, think about what you like and what you don't like. You know, the cruise industry, like many, has become consolidated. So, like the airlines, you have a few players that own all of the cruise lines.
And because of that, the cruise lines have become somewhat specialized. They kind of all have their own demographic. So, you know, if you're, if you're a parent and you have tween-age kids, you might want to look at like a Royal Caribbean.
You know, if you have smaller kids, you might want to look at a Disney product, but everybody's kind of specialized. Holland America tends to be a little bit of an older crowd. Lovely ships and beautiful product, but try to get something to eat past nine, not easy.
And so first look at what the different offerings are and what works for you instead of what you think you're supposed to like, because they really are do all sort of cater. And then the time is year. So, a lot of times people are like, well, I want to be on a cruise ship with a lot of kids.
Well, regardless of the cruise line, if you go when schools in session, probably not gonna be a lot of kids. A lot of the bear community that are teachers hate me because they're like, you never sail when I can go. And I'm like, yeah, and there's a reason for that because then there's just gonna be kids on.
Not that we don't love kids, but we don't want a whole, you know, a whole ship full of them. So first look at, I think, first look at what, what works for you. What do you like? Are you really someone who just wants to chill, relax, have a drink, watch the ocean slip by? Are you, are you someone who wants to spend a lot of time in the gym, take a lot of classes, you know, go to lectures or films?
There's so many things you can do in addition to the things we offer, there's, you know, a whole list, literally, a newspaper full of activities each day that the cruise line gives out.
Some of the times the most frustrating things our comments say on our surveys are, it was so frustrating trying to pick out what to do because so many things were happening.
And I always say, don't overdo it. You don't have to book an excursion in every port, you know, if you're not someone who needs to be entertained constantly.
I still say this to this day, some of the best days in port I've ever had were getting a cab and saying to the cab driver, take me to the beach you take your kids to which is always somewhere completely out of the way.
There's no facilities, there's nothing to buy, but it's the most beautiful beach you'll ever go to. In fact, once it's so fun, years ago, I had this crazy woman pick me up with half blonde, half black hair, and I asked her to take me where she takes her kids, and she said she needed to make a stop.
And we stopped at this house, and her kids got, her kids got in the cab, and we had a beach day altogether. And it was one of the best days ever. And then she picked up, she made all this food brought. We had a picnic on the beach, it was one of the best things ever.
But really, I think, don't let yourself get overwhelmed. I know with our group, we spend a lot of time, because I've had 35 years of event production, we try to take all the stress out of it. So, we will hold your hand, tell you what you need to do, when you need to do it, what your options are.
If you you know, want to be at the host hotel, if you don't. We do encourage people in this days of air travel to try to come in at least the night before because I can't think of anything more stressful than trying to make a ship that's sailing at three o'clock when you don't know what's happening with your flights and connecting flights and all that.
But I just think it boils down to, what are you looking for? What's your idea of the good time? And then we can help direct you. I think anyone in the travel business would do that to what's going to be the best outcome for you.
And then, you know, with our group specifically, we really want to know, you know, are you someone who is not that gregarious? And do you want us to seat you with other people? Because we will, but if you want to be left alone, we'll certainly do that too.
You know, we keep a reserved area of the dining room every night. And there's so many options these days for alternative dining from, you know, from an additional price specialty restaurant to having room service in your underwear in your cabin balcony, whatever.
Hot dogs by the pool and but for those that want to we're there in that section every night. We don't require you to sit at the same table with the same people. So, we actually, like when you move, move around, mix it up. Meet new people every night.
And if we see two people sitting at a table for six, we'll ask if you want to sit, you know, we'll try to group people together. Again, you don't have to, but it's really about making those relationships and giving people a chance to talk.
Sometimes people aren't used to inviting themselves to an empty seat in the table, so that's what we see as our job is trying to facilitate that. But yeah, all those questions, that shouldn't be stressful. It's your vacation, it's your holiday. You work really hard, particularly if you're an American.
You work ridiculously hard for very few days off, and we want to make the most of those. We want to make sure that you go home with memories and friends and don't regret a minute of it. And I always say that the cure for post-cruise depression is having your next one booked.
It doesn't have to be right away, but just having it on the calendar makes you feel a whole lot better because you come off that cruise ship and the next few days, you're like, I have to pay for all my meals and I only get one entree? And nobody's making my bed?
And my cabin steward, who I was sure loved me, is already forgotten about me and moved on to someone else?
So, you know right away it's like, it could be six months from now or a year from now, or two, but start planning the next one, because it gives you something to look forward to.
Episode Closing (52:49)
Rob Loveless
And connecting it back to the tarot, The Empress in reverse. Again, this is telling us that we might be feeling blocked or cut off from loving ourselves.
And like Chumley talked about today, obviously, today we are seeing more body positivity, which is great, but back in the 80s and 90s, even the early 2000s there was not as much body inclusivity within the LGBTQ+ community.
And as a result, it could feel very isolating and causing us to not prioritize our self-love. But with The Empress being number three, that's tied to community, and that's just exactly what Chumley's Bear Cruises does.
It creates a sense of community that prioritizes inclusivity, self-care, and self-love.
So, whether you're somebody who identifies as a bear or a chaser or somewhere in between in the LGBTQ+ community, just make sure that you're putting kindness out there, that you're channeling that feminine energy of The Empress that really is nurturing ourselves and nurturing others, so that way, we can create a welcoming community.
And as we prioritize self-love and self-care, it's also really important that we find those spaces where we feel genuinely accepted in the LGBTQ+ community.
And if you feel like you're having trouble finding those, maybe take the step to create that space. Because remember, even if you feel like you don't see a ton of you out there, you are not alone.
There are others out there that are probably feeling the same way you do and might be encountering the same struggles.
So, by creating that inclusive community, we can find those like-minded people within the LGBTQ+ community where we feel genuinely accepted and loved.
Connect with Chumley (54:10)
Rob Loveless
Chumley, thank you so much for coming on today. These bear cruises sound like so much fun.
So, for all the listeners out there, can you tell them where they can learn more about Chumley's Bear Cruises and connect with you?
Chumley Singer
Yeah, absolutely. We have, of course, a Chumley's Bear Cruise, Chumley's Bear Cruise's Facebook page. There's our public group, but also www.bearcruises.com, that's our website.
That's where all the information, that's the best place to start. And we're waiting for you to join us, Rob. You'll fit right in.
Rob Loveless
Awesome, sounds great. I'm looking forward to it. I'm due for a vacation, so I might have to check that out.
Chumley Singer
All right, sounds good.
Rob Loveless
And once you're done listening to this, check out Chumley's Bear Cruises. It sounds like so much fun. Maybe even book a cruise. I mean, who doesn't love a vacation? Especially a little fun in the sun.
Connect with A Jaded Gay (54:56)
Rob Loveless
And for the podcast here, you know the drill. If you have any questions or feedback, please reach out to me, rob@ajadedgay.com.
Please remember to rate, review. and subscribe. Five stars only. I greatly appreciate it.
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And remember: every day is all we have, so you gotta make your own happiness.
Mmm-bye.
Outtake (56:21)
Rob Loveless
So, with all that in mind, what can? Sorry, I'm losing my spot here.
This is, FYI, this is one of the first episodes I've recorded in a few weeks because there's been a lot of schoolwork.
So, I'm a little rusty. I'm stumbling more than I normally do.
Chumley Singer
No problem. No problem.
