Berlin, Chicago &… Provincetown?! Gays reveal their worst vacation experiences
When have you experienced trouble in paradise?

While gay vacation destinations vary in vibe and geography, they’re all supposed to be a great time. But that’s not always the case. Sometimes you put on your first speedo and immediately wish you were back home, away from inflated prices and egos.
As LGBTQ+ people, we are blessed to inhabitant many of the world’s most vibrant cities and stunning resort towns. We run the streets of New York and then ferry off to Fire Island. Cosmopolitan treasures such as Berlin and Barcelona are brimming with gays, as are oases like Palm Springs and Provincetown. You get the point: gay destinations are awesome! What nobody says here should be treated as gospel.
That said, we’re always down for some commiserating. It’s far more stimulating than sifting through another IG photo dump. We asked Queerty readers about when they’ve experienced trouble in paradise. Here’s what they had to say…
What was your most disappointing gay vacation destination and why?
How about we take this to the next level?
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“When we first moved to New England in 2002, we joined a Bear social group through an AOL chat room (yes, that long ago). They arranged a Winter gathering at a B&B in Provincetown from a Friday night through Sunday. We were kind of excited; this was our first outing since moving, and never stayed at a B&B. We were looking forward to meeting with the men and socializing for the two days.
“But one of the ‘leaders’ spent the entire weekend incessantly babbling about the NEXT thing coming (Bear Week), and we just could not let anyone get into the moment. Even in the hot tub, he just would not shut up about Bear Week. It was like, ‘Well, why did you coordinate this weekend?’ Were clawing our way out of there by the time we checked out on Sunday. We never met with them again. The B&B was superb, the company not so much.” — Rad in Rhode Island
I have an explanation as to why your group leader opted for a winter weekend in Provincetown opposed to Bear Week: $$$. Though Ptown was more affordable in the early 2000s–along with every other beach town–Bear Week has long been one of its marquee summer attractions. Still, a winter getaway in Provincetown can be gorgeous: it’s one of the most enchanting places in the U.S. We’re sorry to hear your experience was ruined! Two decades later, maybe it’s time for a return trip?
“San Francisco. Definitely not a walkable city AT ALL. Everything was ridiculously overpriced. Not a lot of friendly faces, even in the Castro. SF is a hard pass for me from now on.” — JB in St. Mary’s
While everyone is entitled to their opinion, we are scratching our heads a little bit at JB. San Francisco consistently rates as one of the most walkable cities in the country. It’s also a place where a lot of people take public transit, ranking third among U.S. cities in terms of percentage. SoCal may be all about car culture, but SF is not. That is, unless we’re talking about those driverless Waymos…

“People talk about West Hollywood being a gayborhood. When my husband and I went there, it felt more like a gay strip mall. Everything was so spread out. It wasn’t walkable. There was traffic everywhere. It looks cute in pictures but it felt like a suburb with palm trees and rainbow crosswalks.” — Lance in Seattle
Indeed, WeHo and especially neighboring Beverly Hills can seem like luxury strip malls. But for L.A., West Hollywood is actually pretty walkable. Though as Lance noticed, most people prefer to drive.
“Barcelona … there’s really not much for the gay traveler and for the straight traveler. A really overrated city!” — Jeff in Orlando
“Mykonos — used to be cool, now it’s just expensive and overrun.” — Andy in Ireland
Catalans and Mykonians might not lose sleep over Jeff and Andy’s complaints–locals in both places rail against overtourism. But there’s a Catch-22: tourists keep the lights on. There’s no easy exit from this particular trap.
“Berlin. While the city definitely has an intense, sexual side, between the constant reminders of the horrors of fascism and human atrocities on every corner and the intense aloofness of German men, the city really failed to live up to the hype. Especially as a more sober person, the magic really didn’t click for me or my husband. I could not feel sexy there.” — C in Washington D.C.
The hedonist capital of Europe, Berlin’s decadent energy isn’t for everyone. Before WW2, the Weimar Republic boasted the world’s first thriving gay scene, from iconic venues like the Eldorado to Magnus Hirschfeld’s Institute for Sexual Research. The city’s complicated, bruised history is the draw. Yes, Germans aren’t known for being warm and cuddly. But neither is the city itself. From overcast skies to to the long lines outside Berghain, the mood is dark.

“In 1998, friends kept pressuring me to go on an RSVP cruise, constantly gushing about how much fun they are. I finally gave in, and arranged passage on one going from Miami to Key West, then on to Cozumel, Mexico, and then back to Miami. It was only five days but it seemed like five months. To save money, I got a cabin with three other guys, one of whom snored, another who got up at 5:00 a.m. to go jogging, and another who partied until 3:00 am. I never got any sleep. It didn’t help that almost everyone started their day getting plastered at breakfast, nodding off into their scrambled eggs. I couldn’t wait for it to be over.” — Roger in Palm Springs, California
All aboard! RSVP Vacations has been hosting gay and lesbian cruises since 1985. Frankly, we’re impressed with the cabin-mate who woke up at 5:00 a.m. to go jogging and then got plastered at breakfast. We call that a full morning!
“Rehoboth Beach, Delaware. Incredibly crowded and expensive.” — Jason in Washington D.C.
Founded as a Methodist Meeting Camp in the 1870s, Rehoboth Beach has become a gay mecca. Like many of these areas–including Provincetown and Fire Island–Rehoboth used to attract more of an alternative crowd before the cost became prohibitive. It’s an old and depressing tale: gays with taste vitalize a place, and then get priced out.
“Ogunquit, Maine: weather was terrible and foggy even in summer, and it was not nearly as gay as I expected. The main gay bar was full of bachelorette parties. The beach was meh and the water was cold.” — Jake in L.A.
Maine is a lovely state. But Ogunquit is far from Ptown or Fire Island, even if the price is similar. Jake’s read is correct: Oguniquit is more gay-friendly than “gay, gay, gay.” Still, there are a lot of great sights to see. The Front Porch is an A+ piano bar. (But yeah, that Maine ocean water is frigid!)
“Key West was the worst. We went for New Years and thought we were going to celebrate in a gay mecca. But apparently, so did all the straight people. It was overrun with straight people enjoying the drag queen descending in the shoe. It was so not fun. Freakin’ straighties ruining everything.” — Craig in Weehawken, New Jersey
“Key West! The crowd was basically a Trailer Park full of straight people with WAY too many Tr*mp souvenirs lining Duval Street. Ugh. Plus, we were four of the 10 gays we encountered at the bars. It was a very disappointing Gay Boys Trip.” — Mark in Dallas
I just went to Key West for the first time myself and came away with a similar feeling (though I did have a great time). Back in the ’80s and ’90s, Key West was brimming with the weird and the queer. But now, the island is flooded with second home owners from Georgia and mainland Florida. City officials recently fining a lesbian couple over their rainbow fence doesn’t help matters, either.

“Chicago TBH. The gay strip was only two to three blocks long and there was no diversity.” — Harry in Brooklyn
As a relatively new Chicagoan, I can’t speak with authority about the city’s gay history. But in my 18 months here, I’ve found a vibrant and active queer scene in many neighborhoods. Then again, I have mostly stayed on the north side, and am a white guy in my mid-3s. Boystown has long been criticized for catering towards white, cis gays of a certain build and stature. I can’t say the reputation is unearned.
“It’s not a destination per se, but my first bathhouse experience did not live up to the hype. I found the vibe creepy and the leering men made me uncomfortable. My first and last visit!” — Mike in Baltimore
Hey, they say you gotta try everything at least once!
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