Gay Key West Guide: The Essential Guide To Gay Travel In Key West Florida 2018

Gay Key West Guide: The Essential Guide To Gay Travel In Key West Florida 2018

Gay Key West is a tropical sanctuary and crowning jewel at the end of Florida’s all-American Overseas Highway, home to an eclectic and edgy community that was “Out Before It Was In.”

Gay travelers are greeted in Key West by an accepting society that prides itself on being one of the first gay travel destinations globally to truly take off, as well as waving palm trees, turquoise waters and colorful conch houses. Gay Key West truly embraces it’s philosophy of ‘One Human Family,’ and allows gay locals and visitors alive to feel entirely at home anywhere they go here.

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It’s no secret that us gay boys – and girls – have been converging on Key West since the early 1970s when depressing real estate values, tropical warm and a laid-back lifestyle drew LGBT pioneers from across the US. Gay and lesbian guest houses pop’d up, hedonism prevailed, and a gay phenomenon took place – though we were arguably a little too clever for our own good.

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Today mass tourism and sky-high real estate prices have started to forced gay life further north to Fort Lauderdale, and many ‘hetero-friendly’ guest houses now stand where once fabled LGBT exclusive resorts stood. Yes, it seems like Key West – much like Austin, Oslo, and Auckland –  is on its way to being post-gay – but there is still plenty of energy and fire left for those still seeking a gay culture, nightlife, and indulgence only comparable to other legendary gay travel spots; Fire Island, Pattaya, Ibiza, Bangkok, Mykonos.

The wild gay annual events like Tropical Heat, Fantasyfest and Womenfest still draw in record crowds, the Duvel Street gay nightlife continue to expand, clothing option gay resorts remain fulled booked, and there are more drag shows than we could count. At times it still seems like gays outnumber straights in the Conch Republic… Yes, this legendary gay island is not done yet, and today Gay Key West’s still attracts hundreds of thousands of queers travelers every year looking for sun, sea, sand, and sex!

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Gay Key West Guide: The Essential Guide To Gay Travel In Key West Florida 2018

Naturally being gay does not define which attractions most of us will want to see in each destination and most queer travelers will simply want to check out the top things to see in Key West during the day! We found our favorite memories were watching the sunset from a relaxing cocktail bar, dancing till dawn with our queer family, or laying on any of Key West gay beaches. However, if you’re someone who can’t sit still, we have put together a few of our other things to do in this gay paradise that are sure to keep you busy!

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Top Highlights in Key West
  • Nancy Forrester’s Secret Garden – A quaint haven for reduced parrots run by an utterly devoted woman. Head down at 10 am for “Parrot 101” or visit later in the day to spend time with these mischevious orphans, play musical instruments, picnic or create art. A truly unique space that is well worth a visit.
  • Higg’s Beach – While gays will be welcomed at any beach in Key West, Higg’s Beach is the de facto gay beach in Key West for the local community to snorkel, admire the sunset or enjoy all the glorious eye-candy.
  • The Overseas Highway – Why fly to Key West when you can hire a car and drive the 181.9 iconic highway – built way back in 1928. It’s a full day trip but what better way to arrive at the tip of the continental US than driving this scenic All-American Road.

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  • Key West Garden Club – A free tourist attraction with colorful gardens and exotic plant. Set on the site of a Civil War Fort, this secluded Eden is one of Key West’s most tranquil – and undiscovered – spots.
  • 7 Artists & Friends – A 100% local art gallery representing many of Key West’s best artists. Sculptures, watercolors, photography, and whimsy: you’ll find it all here.
  • Duval Street & Old Key West – Wander the historic neighborhood of Key West, linger in galleries, admire the Bahamian and Spanish influenced mansions and enjoy a Cuban Coffee – perhaps with a cigar? Whats the rush…
  • Namaste Eco Excursions – Thousand’s of tourists daily are jam-packed onto tours for reef snorkeling Key West where they are taken to the nearest reef, dumped in the water without supervision in crazy numbers and cause extensive damage to the brittle coral and sea-life. We absolutely hate this and were determined to find another way. Thankfully we found LGBT friendly Namaste Eco, owned by insanely passionate Jeff Bowman who will not stop until you are infected with his passion and enthusiasm for everything under-the-sea. Discover comfortable and safe snorkeling destinations that are hand-picked for calm conditions, abundant ecology, great science, and few people! We cannot recommend these guys highly enough.

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  • Watersports Partyboat – A fun party-boat cruise which pairs water spots, BBQ lunch, drinks with plenty of sun and salt water. What more could you ask for?
  • Harry S. Truman Little White House – While today Trump might be holed up at Mar-a-Lago, here you can get an intriguing look into the winter White House of President Truman which was used for175 days during 11 visits.
  • Helicopter Flight – Surprisingly affordable, a bird’s eye view is the only way to get a proper view of the island and the iconic Overseas Highway which stretches off into the horizon.
  • Key West Haunted Pub Crawl – If you get sick of the gay nightlife then why not try exploring the spookier side of Key West – with alcohol of course! Visit a haunted mansion, a former more and discover why Key West’s original Spanish name was ‘Bone Island.

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  • Food Tour – We say this about every place we visit, but it bears repeating: you can’t truly know somewhere until you know it’s food! Key West is in the midst of a gastronomical rebirth, and you need an expert local foodie to help you navigate all too the islands’ edible delights. Or at least make sure to eat somewhere new every night, we are serious…There are more locally acclaimed restaurants and stands popping up than we can possibly keep track of!
  • The Ernest Hemingway Home and Museum – The most famous museum in Key West dedicated to the personal life and literary developments of the islands’ most famous writer. Ernest Hemingway. It’s very popular so try to visit during a weekday, and look out for the polydactyl cats—with extra toes- one of the more bizarre tourist attractions in Key West.
  • Miami and the Keys Explorer Pass – A popular tourist attraction pass that allows you to choose between 3-5 attractions across Miami and the Keys to enjoy at one low price.

Key West might be small – but it has plenty more to explore!

We recommend getting a full guidebook if you are staying for more than a night or two. It probably won’t have any information on Gay Key West – that’s what we are here for – but it will have useful tips and an exhaustive list of the best attractions across Florida to assist you on your fabulous adventure!

 

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Gay Annual Events in Key West
  • Gay Spring Break Key West – Every March thousands of hot, sexy men flock to gay Key West to relive their college days through epic parties, adventures, shows and events. For many years there was an official event, but now it’s more scattered with different bars and gay resorts in Key West offering their own activities. Still, that doesn’t stop all the boys heading down so be sure to book your accommodation far in advance during this peak time.
  • Key West Pride – The annual pride celebration of this tropical paradise held annually in June. Get lost in the magic of the island – and all it’s queer parties- while paying tribute to Key West’s One Human Family philosophy.
  • Tropical Heat Key West – What better way could there be to celebrate August, the hottest month in the Keys, than a 4-day event filled with all-male theme parties, pool parties, and adult-oriented entertainment promises. Tropical Heat promises to be hot, steamy and oh-so-scandalous, and it never disappoints.
  • Womenfest Key West – Held annually in September this is one of the world’s biggest gatherings of lesbians who come together in a celebration of themselves. And ladies, you deserve it! An epic clothing optional pool party, reek trips, roller derby, white party and stoplight party are just some of the event’s highlights. Though if you simply want to enjoy the atmosphere with a good margarita on a poolside chaise lounger, we wouldn’t blame you!

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  • Fantasy Fest 2018 – The biggest gay event in Key West taking place annually in October – we are not kidding when we say Fantasy Fest street festival rivals New Orleans Mardi Gras and Carnival in Rio De Janeiro in terms of debauchery and pleasure. A ten-day extravaganza that includes a parade, balls, costume competitions + parties, AIDS fundraisers, drag queen contests, body painting, pet parades and plenty of alcohol. The Headdress Ball is the ultimate gay event of the annual Fantasyfest and is absolutely not to be missed. Let your freak flag fly here – and book well, well in advance.

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Gay-friendly and Gay Hotels in Key West

On this glorious and extremely liberal island, you will not find any major accommodation that isn’t gay-friendly. After all being gay-friendly is about providing a non-judgmental and respectful environment in which all people are treated equally. In saying that, elegant design, helpful staff, and excellent value for money never hurt anyone. Some hotels in Key West have also gone above and beyond in recognizing + marketing to the LGBT community and given their popularity with gay travelers we would say it has paid off!

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Everybody likes to be surrounded by people with common interests and as such a there a few hotels in Key West favored by the gay jet-set. Most are located close to the bustling downtown – close to all the attractions by day and night – and each accommodation showcased here offers something unique and unforgettable. There are even 4 exclusively gay hotels in Key West if that is what you desire.

The following gay-friendly hotels in Key West are only the most recommended, but there are hundreds of other hotels in Key West if you don’t find quite find what you are looking for. Whether you want a fun and social hostel, a cheap but private place to crash after a night of partying or a chic luxury option to sip cocktails surrounded by fashionable people, Gay Key West as something for everyone! You could also view read about the best and most fabulous Key West Gay Resorts for your next Gaycation to help you get inspired.

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No matter where you choose to stay however it pays to book as far ahead as you can because occupancy rates in Key West are extremely high year-round with demand routinely exceeding supply. This trend goes into over-drive with special events, festival, and concerts when good Key West hotels are known to sell out months in advance.

Gay-Friendly & Gay Resorts Key West
  • Island House ☆☆☆☆ – Frequently named one of the best gay resort in this world, the legendary Island House in Key West draws in tens of thousands of men every year –  from all over the world and in all shapes, sizes, and ages. A true sanctuary for men offering plenty of those magical Key West moments with a fun pool, a popular bar, plenty of social activities and only a 10-minute walk from Duval Street gay bars. The most famous gay stay on the island with shared showers for the basic rooms, a sauna + gym and free Happy Hour drinks for all guests, every day! Our favorite Key West gay resort offering a little bit of everything – and even if they are full, you can still visit by purchasing an Island House Key West day pass for $30 valid from the time of purchase until 8 am the following morning [Photo ID is required.]

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  • Equator Resort ☆☆☆☆ – Tucked away in a quiet street of Old Town Key West, yet only 3 blocks from Duvel Steet is this fun male-only clothing-optional gay resort. A Lush, private setting complete with 2 heated pools 2 hot tubs, and 34 rooms converted from 5 historic properties. There is also complimentary Happy Hour daily for guests and guests of guest from 5:00 pm – 6:30 pm, perfect for meeting your new Key West gay family.
  • Ocean Key Resort ☆☆☆☆ – A classic island style resort enviably location on Sunset Pier with a full-spa, outpoll pool and hot tub. Splurge on one of the spacious sunset view suites for a view you will never forget. The Liquid Pool bar also offers one of the best pool parties in Key West with ultra VIP service, delicious drinks, and a tranquil oceanfront backdrop.

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  • The Marker Waterfront Resort ☆☆☆☆ – A luxurious waterfront resort with 3 outdoor pools, a relaxed restaurant, and the only newly built hotel to grace Old Town Key West in over 20 years. We loved the fusion of iconic conch architecture with eye-grabbing contemporary artworks, plus being able to just out onto the legendary Duval Street.
  • Hyatt Key West Resort ☆☆☆☆ – Always gay-popular, the Hyatt Resort in Key West offer 118 boutique rooms and somehow avoids the ‘cookie-cutter; resort feels. We loved the full spa with luxurious offerings, gym, heated pool, gorgeous rooms and the fun Blue Mojito bar.

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Gay-Friendly & Gay Hotels Key West
  • New Orleans Guest House ☆☆☆ – If you can’t stand to leave the gay nightlife of Key West for one night this male-only gay hotel is at the heart of Duval Street and part of the mainstay Bourbon Street Gay Pub. The rooms are nothing fancy, but you’ll get access to the pool, balcony overlooking Duvel Street and be just steps away from your room when you inevitably meet someone downstairs. Most of the property is clothing-optional, and the 15-man jacuzzi is steamy, to say the least.

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  • La De Ta ☆☆☆☆ – A adults-only hotel with large pool, polished hardwood floors and a boutique, grown-up vibe. Fun nightly cabaret theatre, decadent rooms and lower prices than most other hotels in the area.
  • The Gates Hotel ☆☆☆☆ – A newly opened designer hotel offering award-winning minimalist style, fabulous pool fun games, and bike rental. The unique rooms are super Instagrammable with exposed whitewashed beams and rustic platform beds, and we liked the Key West photography elegantly displayed throughout.

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  • Pier House ☆☆☆☆ – An elegant hotel extended out into the gorgeous ocean. Refined rooms offer rainfall showers and a central location, plus there is a private beach and heated outdoor pool, spa and gran. A rustic-chic option that is very gay-popular, but then…Where isn’t in Key West!
  • The Perry Hotel ☆☆☆☆ – A newly opened concept hotel on Stock Island offering an eclectic arrange of facilities, destination dining, and oh-so-cool rooms. Paying homage to the areas industrial past, we loved everything about this hotel, its staff, and its design – and they even offer a free shuttle drop-off near the Duvel Street gay area of Key West.

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Gay-Friendly & Gay Guest House Key West
  • Alexander’s Guesthouse ☆☆☆☆ – A immaculate LGBT guesthouse nestled inside a ( National Historic Register) 3-story Conch-Style home. A retreat for the soul with pool, Jacuzzi, beautiful decor and upscale rooms. Alexander’s is also the only gay guesthouse in Key West which caters to both men and women.
  • Cypress House ☆☆☆☆ – A LGBT-popular guest house (but not exclusive) where many of the staff are gay, but it is not clothing optional. A striking “conch mansion” with vintage decor, bright, and affordable prices.

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  • The Mermaid & The Alligator ☆☆☆☆ – The perfect gay-owned guesthouse in Key West with a mixed/ gay crowd. Dean and Paul have poured their soul into the 1904 mansion offering casual elegance and warm hospitality. Each room has a unique theme and is just gorgeous, but overall we would have to say we are loving the ‘the Royal Family on tour in the Bahamas’ vibes.
  • NYAH..Not Your Average Hotel / Hostel ☆☆☆ – If you’re just after the cheapest bed in Key West and don’t mind sharing a dorm then this is a funky adults only hostel in Key West with affordable shared rooms. Not only do you get access to a free continental breakfast, 3 outdoor pools, and 2 hot tubs, but your steps away from the Duvel Street gay bars. A life hack to explore Gay Key West on the cheap + you can meet other travelers here to go out and explore the nightlife with!
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Gay Nightlife in Key West Florida

With Key West being one of the most gay-friendly vacation destinations in the world, you would expect an incredible gay nightlife scene – and luckily Key West does not disappoint. Depending on your mood you can find anything here from a relaxed cocktail in an upscale bar to an all-night dance party surrounded by your queer family! There is also plenty of cruisy bars, sexy go-go boys, fab drag, fun events and something to cater for every taste. This is one of Florida’s most desirable and expensive destinations, however – and will cost you more than your typical gay beach holiday in Phuket or Puerto Vallarta.

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While gay life in Key West never stops, the LGBT nightlife scene here starts to get going when everybody heads to their favorite spot for the magical sunset and accompanying Happy Hours. Afterward, most gay bars and clubs are packed from 10 pm until into the early morning, with a mix of tourists and a few locals. Most the nightlife – gay or straight – is centered around Duvel Street, so if this is a priority, you should try to stay close by as ride-shares always have a premium later at night. Use our Gay Key West map at the end to help orientate yourself.

For many gay bars in Key West flip-flops and tank tops are the uniforms of choice – but some more upscale clubs and venues demand more. As Coco Chanel declared “luxury equals comfort,” so don’t get too caught up as later in the night plenty of t-shirts come off!

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Gay Clubs & Bars in Key West

  • 801 Bourbon Bar – A mainstay of gay life in Key West, this gay bar is the perfect place to head if you’re ever not quite sure where to go. Fun ‘Not Your Momma’s’ Bingo, karaoke, naught parties and Sushi, the Grande Dame of Drag who – along with the 801 Girls – present some of the finest drag shows in Key West.
  • Bar @ Island House Key West Resort – Between 5 PM and 6:30 PM daily this is the biggest gay party on the Key West with pumping music, cocktails and a free Happy Hour for all staying guests. If you’re just stopping by, there is a 2-4-1 Happy Hour on everything in the bar and it’s always packed! Not that it is quiet at any other time of day…

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  • Bourbon Street Pub – A infamous gay bar in Key West with sexy men, a very cruisy atmosphere and the New Orleans House, men’s clothing-optional resort upstairs. The weekly Saturday Key West gay pool party is the only place to be, but the bottomless drinks on Sunday Funday are also extremely popular. There is also a male-only clothing-optional garden bar, and you can probably imagine how cruisy this gets. At Bourbon Street Pub every night from 10 pm the Men of Bourbon take the stage (with occasional gay porn stars) to give a hot and steamy show, and you can purchase lap dances if you so desire. For our lesbian sisters, there is a Ladies Night is every Tuesday from 8 pm and is the closest things to a Key West lesbian bar. But it’s not that close…

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  • Bobby’s Monkey Bar – A local gay dive bar in Key West that is overlooked by most tourists. Small, smoky and much loved this is the place to chat with the bartender, get inside tips about gay life in Key West and perhaps dress up and have a go at the limitless karaoke selection. Bobby’s Monkey Bar would also love it if you bought a stuffed monkey to add to their collection.
  • 1 Saloon – “Calling all bears, cubs, otters and leather daddies + their admirers”…If this sounds like you then you’ll need to head to 1 Saloon which adjoins 801 Bourbon Bar. Kinky fun and the only leather gay bar in Key West. If you’re game, every Friday at midnight is Cock Shock – with prizes for the best couple, ink, chest, butt, and more.
  • Aqua Nightclub – A Key West LGBT nightclub famed for their talented drag shows performed by the Aquanettes. Upscale, classy and always raucous – If you’re looking for sophisticated style over cruisy go-go fulled fun this is the place to go. There is also the quaint Back Bar; here with a great selection of beers and specialty drinks favored by locals as a bit of a hidden gem.

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Mixed & Gay-Friendly Bars in Key West

  • Grand Vin Wine Bar – A small put favorite little wine bar with a shop and wine tasting. It was Key West’s first wine bar and has a cute little front porch where you can enjoy your beverage with a view of Duval Street.
  • Cabaret & Piano Bar @ La Te Da – Located on Duval Street, this fun hotel offers some of the best cabarets shows in Key West with drag divas and Broadway singers in the gorgeous Crystal Room. Ticks are required, but you can also stop by for the elegant By George Piano Bar. Always a fun mix of tourists and locals.

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  • Garden of Eden – A mixed/ gay-friendly clothing option bar in Key West for those brave enough to be tempted by a..unique experience. Located above the Bull & Whistle Bar
  • Caroline’s Other Side – A uber cool speakeasy hidden within a Caroline Street mansion. Marble bar, leather stools, and craft cocktails. We recommend the Adios Pantalones! [Watermelon Juice, High West Double Rye, Coconut Oolong Tea, Lemon Juice].
  • Rum Row @ The Gates Hotel – A pool bar/lounge concept in conjunction with First Legal Rum Distillery with fiery drinks and a delicious permanent food truck on-site. Part of the new modern, minimalist Gates Hotel.

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  • Virgilo’s Martini Bar – A dark spot for the best – and largest – Martini on the island. Dirty, please! There is also live music, $5 martinis every Monday from 7 pm and dancing most nights.
  • Fat Tuesday – The Key West location of this infamous New Orleans chain that got its start on Bourbon Street. We are not saying it’s classy, but the drinks are strong and the $4.50-weekday happy hour special is a great way to start the night. Don’t judge us!
  • Chart Room @ Pier House Resort & Spa – A throw-back to the Golden Age of Key West when legends such as Tennessee Williams and Jimmy Buffet hung out here, though things are considerably more upscale these days. Still, Chart Rooms tries hard to honor its routes with fun decor and photos, delicious drinks, and free popcorn + hot dogs.

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Cruising, Gay Saunas & Bath Houses in Key West

Even though Key West is a wildly popular gay vacation destination there is no gay bath house in Key West, and your nearest option for a traditional gay sauna is Miami, Tampa, Fort Lauderdale or Orlando. If your visiting from outside of the USA you should know that the sauna culture is not very prevalent in the USA and in no way as popular or as high-quality as you might find in international destinations such as Melbourne, Hong Kong, Bangkok, Munich or Paris.  Still, we never said there was no naughty fun to be had in Gay Key West…

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Instead of visiting a gay bath house, you can opt to stay in one of the thee raunchy clothing-optional gay resorts in Key West or try your luck with gay hook-up apps, in the clubs or visiting the gay beach in Kest.  For the easiest gay hook-ups in Key West, simply stay in a cruisy clothing optional gay resort/hotel. There are currently three options: New Orleans Guest House, Equator Resort, and the infamous Island House.

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Read more in our Gay Key West Hotels section, but suffice to say, there is plenty of casual fun to be had and your room only steps away. Even if you’re not staying, most gay resorts in Key West offer guest passes but we recommend getting the Island House Key West day pass for $30 [valid from the time of purchase until 8 am the following morning / Photo ID is required.]

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While none of the gay beaches in Key Beach are overly cruisy, you can frequently meet Mr. Right now. Try Higgs Beach, close to the historic district of Key West, or Smathers Beach near the airport. Being such a popular gay island destination, you can, however, meet members of the LBGT community on every beach here. Please be aware that while there is a topless sunbathing area at Higgs Beach, it is illegal to nude sunbath in Key West – in fact in most of Florida, so best to book a nude resort unless you want to spend a night in lock-up.

Gay sauna or not, in any sexual encounter, please take adequate precautions. No matter what your intentions are in Gay Key West, you should bring your own condoms and lube to play it safe. Take home a hot guy or a hot memory, not an STD.

Besides, you never know what other fun surprises your trip might have in store for you…

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Gay Key West Map

   

Further Things To Consider Before Any Gay Trip

 

Now you're all set and prepared to explore our big queer world, why not sort out everything else out all in one go? If necessary for your travel plans make sure you have brought proper travel insurance, protected your privacy by getting a secure VPN, compared all the top hotel booking sites to find just what you're after, reserved an unbeatable rental car price and - of course - booked the best flight deals!

 

Or maybe just forget it all and go for a last minute cruise or effortless tour instead?

 

Many gay travelers (including us) indulge in worldwide airport lounge access and pre-arrange airport transfers to take the stress out of travel. Naturally, we would never leave home without a more mainstream travel guide since we couldn’t possibly cover everything here!

Just add an adventurous attitude and plenty of smiles - they go a long way - and that about covers it all! Now go out, find your global rainbow family and don't forget to share your best gay stories with us on Facebook, Twitter, and Instagram...We'd love to hear from you!

  Queer In The World Gay Travel Guides