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It’s a big, rainbow planet we live on, but if you squirrel away all your pennies, max out your credit cards and use every long weekend as an excuse to travel, one lifetime may be enough to do it all. We sat down and dreamed up a list of queer experiences every LGBT person should have in their lifetime including a few novel ones that might not be on your gaydar yet, but are sure to tickle you, um pink. While a few are geared toward girls and a couple are just for the boys, most of the list is open to all. Grab your passport, call in sick and go do as many of these as possible right now!

Also: 8 LGBT-friendly destinations based on the colors of the Pride Flag

1. Have a cocktail at the Stonewall Inn: New York, NY
Nearly 50 years ago this Village taproom became the catalyst for a nationwide movement when its patrons, a group of drag queens, street kids and trangendered folk, fought back against police harassment. In June, President Obama made it a National Monument. Have a drink, hang with friends, soak up the moment and just try not to shed a tear.

Castro, gay, lgbt, California, San Francisco

The Castro Theater | Photo courtesy of Jason Heidemann

2. See a movie at the Castro Theater: San Francisco, CA
As the queer community assimilates, gayborhoods are becoming scarce, but the Castro district in San Francisco is still a rainbow-colored beacon and its best feature is its movie palace of the same name which opened in 1922 and whose sign is a city icon. See a camp classic, check out the leatherette ceiling and tap your feet along with the Mighty Wurlitzer organ.

mykonos-greece

3. Live like a Greek God: Mykonos, Greece
Ibiza, Sitges and Gran Canaria attract queer sun seekers by the thousands, but none quite touch the eternal fascination with the island of Mykonos thanks in part to the Ancient Greeks and their societal acceptance of homosexuality. Not that any of them enjoyed the hedonism of modern day Mykonos, a dizzying cornucopia of nightclubs, resorts and sun bathing in teensy swimsuits at famed Super Paradise Beach.

4. Get soaking wet with 20,000 gay women at the Dinah: Palm Springs, CA
This sun-drenched desert metropolis belongs to many including Hollywood A-listers, mid-century design fanatics and gay male sun seekers, but for one week annually the city turns Sapphic as party promoters Club Skirts turn the town into a nonstop party and music fest that is bar none the largest gathering of lesbians in the United States and has attracted the likes of Lea DeLaria and Lady Gaga among others.

Ipanemabeach-rio de janeiro-brazil

5. Soak up the sun with the girls and boys of Ipanema: Rio de Janeiro, Brazil
Captivating Rio is the place of every LGBT person’s dreams. This sunny city by the sea is hardly Brazil’s biggest (that distinction belongs to São Paulo), but LGBT Cariocans dance to the beat of their own Samba-infused rhythm day and night especially at Farme de Amoedo, an inviting stretch of gay beach in Ipanema. Pick up either a bikini or sunga and join the fun. You won’t be sorry.

6. Float away on on a queer cruise: Multiple locations
Whether you’re sailing the Sapphic seas, looking for a hot ship mate or gathering the kids for a getaway, at least once in your lifetime get your rainbow hands on deck and set sail on an Olivia, Atlantis or R FamilyVacations queer cruise. For one week these floating gayborhoods deliver our community to the most exotic places on earth—no homophobes allowed!

7. “Earn” a beaded necklace at Southern Decadence: New Orleans, LA
We’re not recommending anyone drop trou or lift their shirts in exchange for beads, but we are saying that shenanigans like these and lots more (way more, actually) go down at this legendary Labor Day weekend party in the Big Easy. Watch the French Quarter get overtaken by debaucherous steamy good times washed down with a hurricane or two (or five or six).

8. Harness your inner kink at Folsom Street Fair: San Francisco, CA
Shed your inhibitions (and just about every layer of clothing while you’re at it) and hit up this legendary street fair, the largest BDSM and leather fetish event of its kind in the world. It’s a spectacle unlike any other, but also one of the friendliest and most affirming displays of body positivity in the U.S. If you bump into a co-worker getting whipped by a dominatrix, just smile or look the other way.

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Cafe de Flore | Flickr CC: Karen Corby

9. Follow in the footsteps of James Baldwin: Paris, France
One of the most eloquent and provocative queer writers of all time, American novelist turned expat James Baldwin left quite a foot print on gay Paree and visitors to the City of Lights who trace his steps will take in numerous legendary haunts including café Les Deux Magots, Café Tournon, Le Select, Brasserie Lipp, Le Montana and Café de Flore among others. 

10. Pose for a selfie with Mickey Mouse at Gay Days: Orlando, FL
Gay Days started as a one-day event in which several thousand LGBT Floridians showed up at the beloved Orlando theme park wearing red shirts as a mark of visibility. Twenty-five years later (and still not sanctioned by Disney) it draws together an estimated 150,000 people for a week-long gathering that includes pool parties, A Taste of Gay Days and Miss Gay Days Pageant and is beloved by both a party crowd and same-sex families. 

paddle boarding, Key West, Florida Keys, naturism, lgbt

Nomadic SUP in Key West | Photo by Juan Pisani/I.c.e. Photography

11. Stand-up paddle board in the buff: Key West, FL
Just when you thought the Conch Republic was losing its quirky, queer charms (most gay resorts are long gone), along comes Nomadic SUP, a tour company led by out guide Cody White who leads private, naked standup paddle boarding tours for gay men and women (and even straight people!) deep in the heart of the secluded Florida mangroves. The hard part it turns out isn’t stripping down, it’s staying upright.

12. Drag out your night at the Dreamgirls Revue: Los Angeles, CA
Drag Race runner up and All Stars winner Chad Michaels plays mother hen to emerging queens in his native San Diego, but it’s mostly in Los Angeles where he produces and performs the Dreamgirls Revue, the longest running drag show in Southern California and a highly-entertaining one at that thanks to frequent appearances by other Drag Race alum and a newfound audience appreciation for the art form.

13. Find a dungeon with your name on it: Berlin, Germany
If you want to let your hair down, as in all the way down, look no further than Germany’s loose and libidinous capital city where bodies literally go bump in the night. No sexual fetish is too extreme and people of every gender identity and expression will find their desires catered to, especially at queer spaces like Lab.oratory—perhaps the most adventurous bar and sex club on earth at the moment. Isherwood is smiling in his grave.

Diana

14. Sail around Bahía de Banderas with lady Diana: Puerto Vallarta, Mexico
Sunbathing at Blue Chairs, joining the queue at Pancho’s Takos and strolling the Zona Romantica are all requisite PV experiences, but so is sailing the high seas with out tour operator Diana DeCoste who’s been setting the standard in cruising (of the maritime kind) for the past 17 years with a weekly excursion that includes snorkeling, secluded beach time and sunset cocktails—and always sells out well in advance.

15. Have a moment of silence at the Homomonument: Amsterdam, Netherlands
We can think of many ways to kill time in Amsterdam. The Dutch capital is deserving of its reputation as a breezy and tolerant mecca for people of all kinds as evidenced by its tolerance for sexual pleasure and drug use, but between cruising the canals and the bars, save a moment for reflection at the Homomonument, a canal side trio of triangles that commemorates people who have been persecuted due to their homosexuality.

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Pineapple Point | Photo by Jason Heidemann

16. Stay at a gay resort: Fort Lauderdale, FL
Who would’ve imagined a sun-drenched canal town best known for launching the gaudy, libidinous tradition known as spring break would reinvent itself as a high-end destination for gays and lesbians? Boasting some 15 LGBT-exclusive resorts (most clothing optional), laid-back Fort Lauderdale remains the quintessential weekend gaycation demanding only swimming, sunning, boozing and relaxing.

17. Idyll away the summer at IDA: Middle Tennessee
Imagine a 200-acre farm—in rural Tennessee of all places—that ebulliently wraps its arms around a community of queer, transgendered and gender non-conforming people in the form of work projects, art making and community building and that’s IDA (aka Idyll Dandy Arts). Come during summer and be treated to Idapalooza, a festival of music that brings in hundreds and helps pay for and maintain this vital safe space.

18. Time share a summer home with a half dozen besties: Fire Island, NY
Scorching summer heat sends New Yorkers fleeing their city in droves come June and it just so happens they have a quick getaway in the form of an idyllic sand bar where queers have gathered openly for more than 50 years. The Pines is geared toward the monied while Cherry Grove is funkier and more inclusive, but to experience either most folks cobble together big bucks for a summer time share—and it’s worth it.

Calypso Cabaret

Calypso Cabaret | Flickr CC: ecodallaluna

19. See a ladyboy cabaret: Bangkok, Thailand
Between gay karaoke and go-go bars, 24 hour saunas, sweaty nightclubs and friendly (wink, wink) massage parlors, rowdy Bangkok is Southeast Asia’s undisputed queer capital and famous among nightlife offerings are ladyboy cabarets in which  transgendered women (katoey in Thai) perform gender illusions to the tunes of popular gay divas. Check out the Vegas-style revues at legendary Calypso Cabaret.

20. Revel in the dark at the Sydney Mardi Gras Parade: Sydney, Australia
The Aussie sun is famously intense, but for one night annually it pales in comparison to the rainbow-tinged parade that is the high watermark for the annual Sydney Gay and Lesbian MardiGras. Watch as some 8,500 participants march proudly, ebulliently and often scantily down Oxford Street in a blur of glitter, sequins and breezy self-expression that epitomizes everything we love about the land Down Under.

21. Break a sweat at Atlanta Black Pride: Atlanta, GA
Summers in Georgia are notoriously sticky, but the heat brought at Atlanta Pride Weekend is thanks to the thousands of men and women of color who converge every Labor Day weekend to celebrate the largest Black Pride event in the United States. A mashing together of daytime activism and nighttime celebration, events are neatly divided by gender, but all come together for Sunday’s Pure Heat Community Festival.

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Britney Spears in Vegas | Flickr CC: ADRIANOVIAJANTE007

22. Mouth the words to every Britney Spears song: Las Vegas, NV
Credit Canadian superstar Celine Deon for planting herself in Vegas and turning the city into a destination hot spot for entertainers in their prime—not long past it. Elton John, Cher and others have stopped here for long residencies in the past decade, but today’s superstar du jour is Britney Spears and many a Sin City vacation is booked exclusively for a chance to get clamor for a piece of the blonde chart topper.

23. Discover your P-spot: Provincetown, MA
This teensy New England hamlet at the dangling end of Cape Cod is the very definition of queer paradise and is so inclusive that it devotes themed weeks to women, women of color, same-sex families, bears, party boys, leather folk and more. Stay at one of dozens of gay guesthouses, see a cabaret show (as in Miss Richfield 1981 or Dina Martina), hit up Herring Cove Beach and do at least one Tea Dance at the world famous Boatslip.

Sidetrack in Chicago

Sidetrack in Chicago | Photo courtesy of Monica Pedraja

24. Sing along to show tunes at Sidetrack: Chicago, IL
Bid adieu to the passengers aboard the Titanic with the launch of a thousand cocktail napkins, heckle Madonna’s Eva Peron or just sing your heart out at this legendary Monday night fixture where devotees of the Great White Way and up-and-coming talents alike gather with fanatical devotion to watch clips from Broadway shows both past and present. A more enjoyable night in a gay bar you will not have.

25. Meet Le Village people in the ultimate gayborhood: Montreal, Canada
The era of the gay ghetto is ending and that’s probably a good thing, but oh what joy it still is to walk down a street where gay businesses abound and hand holding is the norm. Although cities like Toronto and San Francisco boast enviable queer ‘hoods, there’s nothing quite like strolling Montreal‘s Rue Sainte-Catherine, a.k.a. the Village, in summer.

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Jason Heidemann

Jason Heidemann

Jason is an associate editor at Orbitz, a social media marketing consultant and a freelance cultural reporter for numerous publications. His works has been featured in the Huffington Post, Time Out, Passport, the Chicago Tribune, Chicago Magazine and many others.

3 thoughts on “25 LGBTQ vacations you must take before you die (NSFW)”

  1. A little US Domestically heavy – I’d suggest Jason travels a little more outside of the US – unless he thinks each of the “lands” at EPCOT counts as a visit abroad

  2. wow – you removed my post because I criticised the write for being too US domestic centric missing out many great places around the world outside of the US. this isn’t a travel blog it someone who can’t see beyond the US – shameful that you delete criticism – I guess because you know its true

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