Where to Stay and Eat in Key West

5 Out Travelers. 1 Gorgeous Destination. This is OUT in Key West.

Last year, OUT sent newlyweds Kit Williamson and John Halbach on a romantic getaway to our favorite gay mecca. This year, the pair are back in Key West, and they brought some friends. Join Kit and John with their pals, Adrian Anchondo, Stephanie Frosch, and Anna Campbell for some glorious Florida sunshine, island adventure, and endless Key Lime Pie. Follow along as Kit, John, Adrian, Stephanie, and Anna take you OUT in Key West. 

Whether you’re looking for rest and relaxation or a place to bring the party home, Key West has the perfect lodging for you. No matter what you’re in the mood for, a memorable meal is always just around the corner here. This is where to stay and eat in Key West.

ENJOY A BOOZY BRUNCH AT AZUR RESTAURANT

Azur

This Mediterranean dining experience is open for brunch every day from 9:30 a.m. to 3 p.m. and serves dinner from 5:30 to 10 p.m.

John’s Tip: Key West is famous for key lime pie, so if you’re at AZUR for brunch definitely try their take on it: the key lime pie French toast. We’ve tried the delicious key lime treats all over the island and this French toast is definitely a favorite. Also, the bottomless mimosas are huge, and they keep them coming. AZUR is the perfect start to your Sunday Funday.

Kit’s Tip: Take a minute to chat with the staff. We had a great time talking with the owner and his fiancé; they were celebrating their wedding at the restaurant that very weekend! Key West has a small-town feel, and part of the fun is getting to know the locals.

SAMPLE COCKTAILS & SHARE TAPAS ON THE TERRACE AT POINT5

Point5

Located upstairs from Nine One Five on Duval Street, this tapas restaurant and lounge is open nightly from 6:00-12:00am.

Kit’s Tip: Upstairs from 915 on Duval Street, Point5 is an incredible spot to stop for dinner in Key West. There were a lot of great vegetarian options. I had the Tortelloni De Casa with shaved black truffle, ricotta, and pecorino cream sauce.

John’s Tip: Not only was the food great (my favorite was the Lobster Ravioli), the cocktail menu was fantastic too. Highlights for our group included the 915 Cocktail which is St. George chili vodka, prickly pear liqueur, agave nectar, and lemon juice, and the Island Old Fashioned with Flor De Caña seven-year rum, chocolate bitters, simple syrup, and orange twist.

PLAN A ROMANTIC DATE AT THE LITTLE PEARL

Littlepearl

Nestled in the heart of Old Town and away from the bustling downtown area, sits an excellent spot for fresh, local catch and innovative cuisine with a tropical twist.

John’s Tip: When I’m in an ocean town like Key West, I get a craving for sea food. The menu looked so good that it was hard to decide what to order, but I ended up going with the Spiced Tuna Tartar “Brûlée” and the Seared U-10 Diver Scallops with roasted sweet corn puree, shiitake mushroom bacon, corn succotash, and chorizo oil.

Kit’s Tip: For dessert we tried the key lime pie and the Moscato & Ginger Poached Pear with vanilla gelato and salted caramel, and it was all amazing.

ENJOY SOME PRIVACY WHEN YOU STAY AT ALEXANDER'S GUEST HOUSE

Alexanders

A lovingly restored Key West conch house built in 1902, boasting beautiful, original pine floors and stately windows, Alexander’s Guest House caters to a co-ed crowd of gays, lesbians, and allies.

Stephanie's Tip: Take advantage of everything this guesthouse has to offer! Your stay at Alexander's isn't limited to only your room. Soak up some sun at their resort style pool, or lounge in a hammock while overlooking the gorgeous Key West sunset. 

MAKE NEW FRIENDS WHEN YOU STAY AT ISLAND HOUSE

Island House

This all-male, clothing-optional resort features a bar and restaurant, gym, video room, pool, and multiple hot tubs that are all open 24 hours a day.

Adrian’s Tip: Out Traveler calls the Island House the best gay resort in the world, and it's no wonder they do because it has everything you could ask for. They’ve got a gym, two hot tubs and a pool right next to their very own restaurant and bar (It's open all night!). The grounds are beautiful, and so are the men. This is a clothing optional resort so you won’t have to worry about those pesky tan lines. 

Make sure you check out their pool parties on Wednesdays and Sundays, where you can get a free shot and win some prizes.  

TAKE A DIP IN THE POOL WHEN YOU STAY AT THE EQUATOR RESORT

Equator

This all-male, clothing-optional resort is located within walking distance of Duval Street.

Kit’s Tip: If you’re looking for a place to hang out at a pool, Equator Resort is the perfect spot. They actually have two pools, two hot tubs, and a bar on the property. And it’s clothing optional, if you’re feeling adventurous.

John’s Tip: Equator was the perfect home base for us. We loved our room and the pools were perfect. It’s within walking distance of everything, so it was easy to get around with Equator as our starting point.

Find all this and more waiting for you out in Key West. Plan your adventure here, and streamline your travel by flying directly to Key West International Airport from a variety of connecting cities, including Newark, NJ, Charlotte, NC, Atlanta, GA, Miami, FL, and more.

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