A Gay Slice of Key West

A Gay Slice of Key West

By Denny Patterson

If you have never been to Key West before, then you are in for a real treat. This unique tropical island is the vacation destination people visit in order to escape their worries and troubles. There is plenty to see and experience because the island is small, and nothing is very far away from where you are staying. Explore the crystal-clear waters with a sailing excursion or savor a Key West sunset at Mallory Square. Grab a cold drink along Duval Street and listen to a local band or pick up a souvenir. Key West is the place to experience a taste of Caribbean culture without ever leaving the United States. Depending on your agenda, this vacation can be fun, relaxing, romantic, or wild. Make the most of Key West because you are bound to come back. Listed below are just a couple of Key West’s most prominent highlights.

Attractions & Things to Do

Duval Street

The hub for sightseeing, attractions, cuisine, and shopping, Duval Street is full of activity that should be visited by every tourist. This 1.25-mile stretch is a beautiful confluence of art, culture, history, heritage, and exuberant celebrations. In addition, it is one of the few places in the world that touches two bodies of water. Its northern end meets the warm Gulf of Mexico while the south end spills into the royal blue waters of the Atlantic Ocean. Duval Street proudly shows its cultural ties to the Bahamas and Cuba, both of which influenced its architecture.

Key West Gay Trolley Tour

(800) 535-7797

This tour was developed by the Key West business guild to offer insight into Key West’s flourishing gay and lesbian culture. Throughout the 70-minute tour, participants will see where literary greats like Tennessee Williams and Elizabeth Bishop lived, locate the original site of the great gay club, the Monster, and learn about the impact the LGBTQ community has had on the area’s culture, politics, and economy. Key West would not have a rich history without the LGBTQ community. The tour costs $20 and takes place every Saturday at 11:00AM, starting and ending at 511 South Street.

Key West Ghost Tours

(305) 29-GHOST (305-294-4678)

Did you know that Key West is one of the top ten most haunted cities in America? If not, you do now. Many may find Key West to be strange during the day, but once the sun sets, the restless souls of the island’s frightful and tragic past begin to stir. Participants will travel down the narrow, dark streets of Old Town, filled with 19th century wooden houses that hold onto the secrets of their former inhabitants. Some of the tours other haunted stops includes the Key West Cemetery which is the final resting place of approximately 100,000 people, Captain Tony’s Saloon where a ton of famous Key West icons like Ernest Hemingway frequented, and a visit to one of the most haunted toys ever to exist – Robert the Doll. Reservations are required because space is limited. This tour may not be suitable for children under 13.

Sunset Watersports

(855) 3 SUN FUN (855-378-6386)

Sunset Watersports is the oldest and largest watersports company in Key West. Located on Smathers Beach for over 20 years, the company originally started out just as a place for people to experience parasailing. Its popularity grew which resulted into expanding to five different locations with 11 different trips and activities. In addition to parasailing, Sunset Watersports offers wave runners, snorkeling, dinner cruises, boat rentals, dolphin excursions, and the “Do It All” pass which is considered the #1 watersports trip in Key West. Participants will spend the day on a $2 million yacht and enjoy all 11 watersports activities. Come rested because this trip is guaranteed to wear you out. Exhausting, but well worth it.


Aqua Key West

(305) 294-0555

If you are looking for the best drag show in town, then Aqua Key West is the place to be. Offering entertainment seven nights a week, this places hosts drag shows, karaoke, and late-night dancing. In addition to the main show bar, Aqua offers areas that provide a little peace and quiet in a lovely outdoor setting. Perhaps you may be up for a game of pool. This hot spot is great for a night on the town. Make sure to make a reservation.

Bourbon Street Pub

(305) 294-9354

Bourbon Street Pub is Key West’s most popular gay bar featuring music videos, male dancers, drink specials, live performance five nights a week, and garden & pool bar happy hour. Opening in 1995, this spot has become a staple for the area’s LGBTQ community. Make sure to check out their website for upcoming events, and which male porn star may make a guest appearance to get your blood pumping.

Little Room Jazz Club

(305) 741-7515

In the mood for some jazz? The Little Room Jazz Club features an eclectic variety of musicians from around the world with live jazz performances every night starting at 8:30PM. This establishment offers some of the best live local entertainment, reasonably priced beer, wine & cocktails, and an atmosphere unlike any other bar on Duval Street.

The Green Room

(305) 741-7300

Located in the heart of the Key West bar district, The Green Room provides patrons with a fresh experience never before seen in Key West, featuring organic frozen cocktails and a full bar executed with environmental sustainability, efficiency, and customer experience at the center of it all. Great musician, friendly staff, and an amazing atmosphere, this bar is a popular nightlife spot to be enjoyed by all.


Key West Key Lime Pie Co.

(305) 517-6720

In the Florida Keys, key lime pie is the most iconic dessert. With the first being made in the early 20th century, it was named after the small key lime fruit that naturally grows throughout the region. If you are planning a trip to Key West, then the Key West Key Lime Pie Co. must be on your to-do list. Come in and enjoy a traditional or extra tart key lime pie, or perhaps a fabulous frozen chocolate-dipped bar. This establishment also offers a pie-making class where you can go behind-the-scene and make your own mini key lime pie right in their kitchen. Even better, you can order a slice of pie online and get it shipped anywhere in the continental U.S.

Latitude’s Restaurant

(305) 292-5300

Looking for an evening of fine dining?  Located on the private island of Sunset Key, Latitude’s Restaurant provides fresh and flavorful cuisine with breathtaking views of the Gulf of Mexico. It was named the #1 Best Overall Restaurant in Key West by OpenTable in 2016, and one of the 100 Most Romantic Restaurants in America for 2017. An ever-evolving work of art type menu incorporates locally sourced fresh fish and tropical fruit, and cuisine is based on what is in-season and includes daily fresh catch. Luxuriate while dining in the Ernest Hemingway Room, where photos of the author, fisherman, and former Key West resident adorn the walls or outdoor dining where you will find yourself watching a magnificent sunset.

Mangia Mangia

(305) 294-2469

In Key West, Mangia Mangia is famous not only for their fresh homemade pasta, but also for creating a nourishing meal that envelops your senses. From spaghetti topped with green-lipped New Zealand mussels in a garlic marinara sauce to linguine with clams in shallot, Mangia Mangia offers a variety of delicious pasta dishes full of flavor and delight. Located on the corner of Southard and Margaret right in the heart of the Old Town.

The Flaming Buoy Filet Co.


The Flaming Buoy Filet Co. makes a statement and provides local cuisine that you can only find in Key West. A combination of retro supper club, sassy corner bistro, and highly personal whim this establishment was founded by Fred Isch, and his partner Scot Forste. Every recipe is an interpretation of something they ate at their respective family tables. Local additions, seafood, and tropical fruits, every bite is a party for the taste buds.


Hotels & Resorts

Equator Resort

(305) 294-7775

This all male, clothing optional resort meets all your needs and expectations to experience a relaxed and private escape. Beautifully designed and landscaped, this high-end post modern Caribbean hot spot invites guests to enjoy a secure and exclusive all male experience. From island views to poolside views, the Equator offers numerous accommodations. Included in each night satay are: complimentary continental breakfast with fresh locally baked pastries, complimentary happy hour with selections of frozen drinks, beer, wine, and liquor options, complimentary Wi-Fi, and nine complimentary adult male channels in each room. The Equator Resort is only three blocks from Duval Street.   

Island House Key West

(305) 294-6284

An 8-minute walk from the Key West Bight Ferry Terminal, this buzzing resort for gay men is less than a mile from restaurants and bars on Duval Street. Inspired by Ernest Hemingway’s Havana home, the rooms feature tropical style and original art. All offer ceramic tile floors, and complimentary Wi-Fi and flat-screen TVs offering premium adult channels, plus iPod docks. Freebies consist of limited parking, and regular happy hours. There’s a poolside cafe/bar, a heated outdoor pool and a clothing-optional sundeck, as well as hot tubs, and a health club offering a gym with a sauna and a steam room. An erotic lounge shows videos 24 hours a day.

New Orleans House Key West

(305) 293-9800

This lively adults-only guest house catering to gay men is only minutes away from several Key West attractions. The 11 unfussy rooms have free WiFi and cable TV, as well as mini-fridges, microwaves, and coffeemakers. A 1-bedroom apartment and a cottage provide pull-out sofas. Freebies include happy-hour drinks, entry into partner nightclubs, and continental breakfast served on a balcony. There’s a clothing-optional pool with a sundeck, plus a bar and a hot tub. Minimum-stay rules may apply.

The Perry Hotel Key West

(305) 296-1717

Named one of the 2 Best-Designated Hotels by Architectural Digest and 2017 Winner of the Gold Key Award for Best Upscale Lobby, The Perry Hotel offers an experience like no other in Key West. The new waterfront hotel is exclusively located at one of South Florida’s deepest water marinas. Each room is pet friendly and features water views. The rustic, chic décor is warm and inviting and will make guests not want to check out. Lounge poolside in a cabana or hop on the shuttle to downtown Key West. Enjoy world class dining and allow the Perry Hotel to turn your dream vacation into a reality.

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