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Where to eat, drink and be clothing optional in Key West

Where to eat, drink and be clothing optional in Key West

Visiting Key West feels like you’re in another world unto itself.

Maybe it’s the mix of city life and island vibes, a balance so difficult to get right yet one Key West pulls off with poise.

Maybe it’s the inspiring tropical landscape, a mix of deep green foliage, shimmering blue waters and bursts of color from flowers and buildings that rivals the universal rainbow flags just about everywhere in sight.

Or maybe it’s simply because in a state with an anti-gay reputation, Key West rises as a gay mecca where locals not only welcome but celebrate the LGBTI community.

I flew from New York City to Key West via Miami, and within minutes I was engaged in conversation with my friendly taxi driver.

The gist of our conversation was his explaining to me that he doesn’t even like visiting NYC, could never live there and that Key West will be his home for life. In 10 minutes or less he gave the rundown on what makes the island his first love.

At the top of the list were the people, the weather, and it’s location: Far away enough to feel secluded, yet close enough to visit the city if one so chooses. My response?

‘Alright Key West, show me whatcha got!’

Over the course of the next five days, I made fast friends with both locals and people from far away. The weather – clear skies and warm vibes – the water clear and beautiful, the nightlife vibrant and food was just about perfection everywhere we dined.

What’s not to like about Key West? I honestly never got a chance to find out…and we’re much happier for it.


Getting to Key West typically requires a connection via land or air through Miami or Fort Lauderdale. We’ve been told that depending on traffic, the scenic 4-hour drive is well worth it.

For those less worried about scenery and ready to frolic as fast as possible, a quick 40-minute flight connection from Miami via American Airlines/American Eagle or Delta is the best way to go. Southwest Airlines recently discontinued their direct Key West service.



Alexander’s Guest House
I first read about Alexander’s on TripAdvisor because, as they say, word of mouth is everything. The reviews were stellar and after checking in to the cozy guesthouse with their warm and friendly staff, it was not hard to see why.

Known as Key West’s premiere LGBT guesthouse, the grounds consisting of 17 rooms and suites instantly feel intimate, immaculate, traditionally cozy and well decorated. The staff and other guests make it feel like more like you’re at someone’s home than at a hotel. LOVED IT!

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Island House
Looking for the all-gay place to stay? Look no further than Island House, Key West’s Shan-Gay-La where skin is in, and the guests and staff are all full of smiles.

Boasting a round-the-clock café, bar, pool and health club, the place has been hailed as the world’s ultimate resort for gay men.

With it’s friendly staff and relaxed vibe, it’s the perfect place to shake off your shyness!


The Harbour View Cafe at Pier House Resort
In addition to the spectacular views of all the sailing and celebrating on the water, this al fresco dining experience served up one of the most delicious entrees I’ve ever eaten in the form of the Crispy Yellow Tail Snapper with Coconut Rice.

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Shor American Seafood Grill Hyatt Key West Resort
When in Key West, eating great seafood should be a top priority for most dining experiences.

I’m sure that Shor served up not only the best fish tacos we’ve had in many moons, but also one amazingly perfect margarita I’m told is made with all fresh squeezed juices.



Abbondanza Italian Restaurant
If by chance you’re not a seafood lover, I grieve for you, and I recommend Abbondanza for tastily authentic Italian cuisine that’s rich in flavor, substantial in portion and light on the wallet.

Sure, my entrée was fish, but the bruschetta, calamari and fried zucchini we ate as our starters were nothing less than marvelous.

Flaming Buoy Filet Company
My friends and had our final dinner together at this charming gay-owned and operated bistro per the referral of just about… everybody. The chef managed to put new spins on some classic dishes that were an absolute pleasure to the palette.

For my entrée, I opted for the Catch of the Day trio; at most seafood restaurants that would pretty much mean battered and fried. Here it consisted of Garlic & Lime Roasted Mahi Mahi, Lobster Thermidor and Red Curry Shrimp; each a different delight that complimented each other perfectly.




Bourbon St. Pub
This popular and the largest of Key West’s gay bars pays homage to the decadence of New Orleans with it’s seemingly dozens of delicious male dancers, cheap drinks and fun lively beats for some dancing on your own.

There’s also a garden bar in back, which like many places on the island is clothing optional.


Key West Legal Rum
As a Caribbean-born man, rum is practically part of my DNA. So I was pleasantly surprised that you can get a great selection of locally sourced, Key West made rum from Chef-Distiller Paul Menta’s Coco-Cola Factory turned Rum Distillery!

Take a tour, learn about the process, sample some of the full-flavored rums along with their homemade sodas and buy some to take home with you.



Jazz in the Garden
Off the beaten path, lies the Garden’s Hotel – one of Key West’s most highly acclaimed guesthouses. The grounds and its all-encompassing garden are among the most beautiful and inviting I’ve ever experienced.

Most Sundays, lots of locals (and those in the know) gather for ‘Jazz in the Garden’ until sunset. Live music and cocktails surrounded by nothing but beauty, art and a family of tortoises.


Wind and Wine
Weather permitting, hundreds of people gather in Mallory Square every day to watch the sunset and experience the liveliness of the street performers.

But the BEST way to experience a Key West sunset is by booking a spot on one of the Sunset Sailing cruises.

There are few things more gorgeous than watching the sun set on the water while sailing around the Keys on a schooner. A wide selection of wines and hors d’oeuvres is included in the booking, and the small group on our boat made it all the more intimate and beautiful.



At first, I thought Aqua was just another nightlife spot to enjoy a few drinks with friends and mingle.

But it’s so much more than a bar because of it’s phenomenal drag performers. These ‘girls’ put on a show that rivals performances on a certain televised Drag competition…

I dare you to take your eyes off them for even a minute.


Kayaking on Stock Island
The friendly (and very patient) folks at Lazy Dog Kayaks made my first foray at kayaking an unforgettable experience.

Even with strong winds, my friends and I each went at it solo on the seas navigating the mangroves, observing the native wildlife and getting one hell of a good workout doing it.


Sailing, snorkeling & sunbathing on The BLU Q
It was a picture-perfect day at sea on this all-male catamaran sailing excursion around the Keys. With an intimate group of 20-30 guys, it’s a great way to meet some locals, make new friends, eat, drink and relax at sea.

You can choose to go with or without the option of clothing if you’re a ‘balls to the walls’ kind of guy.


The Art of Chocolate & Wines 101
Whether you’re a novice or sommelier when it comes to wines, Lush Bar is sure to increase your knowledge about the craft of making chocolate and the art of pairing wines.

Host Mark Certonio gave us some hands-on schooling on how two of life’s most delicious joys are created, sourced and complimented. It’s truly a singular sense-ation to experience with friends and loved ones.


For a more personal taste of Key West, get in touch with travel correspondent and founder of Minoritees clothing brand Collin Spenceron Twitter.

For all the news on Key West, follow the tourism board on Facebook and Twitter, and for the latest and best on gay travel, follow Gay Star Travel on Facebook and Twitter.

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