11 Ways to Enjoy the Florida Keys and Key West

Key West is an international gay mecca, attracting more than 250,000 visitors to this top LGBTQ+ vacation destination that celebrates openness and pride! But the beach town vibe and welcoming vibe extend to the Florida Keys, too! 

So if you’re eager to get away to a warm-weather vacation spot this winter or any other time during the year, you should consider a relaxing, digital detox vacation. For travel inspiration, here’s a list of ways you can explore and enjoy not only Key West, but also The Lower Keys, Marathon, Islamorada, and Key Largo. Plan for your island vacation now, you’ll thank us later!

1. Celebrate Diversity 
The Florida Keys salute diversity and openness, and the subtropical island of Key West is internationally known as a top LGBTQ vacation spot. The city of Key West proudly adopted “One Human Family” as its official philosophy in 2000 — a move soon followed by Monroe County, which encompasses the entire Florida Keys island chain. Recognizing that all people are created equal, the all-inclusive destination is renowned for its welcoming and accepting attitude.

2. Stay in an LGBTQ+ Resort or Hotel  
Key West features several properties that specifically cater to the LGBTQ+ community — complete with pools, Jacuzzis, clothing-optional sundecks, full-service bars, and complimentary happy hours. Other accommodations are known for their warm welcome to all guests and include a wide array of hotels, motels, inns, and waterfront resorts.

3. Discover Local LGBTQ+ History
The Tennessee Williams Museum, located at 513 Truman Ave., memorializes the iconic playwright who called Key West home from the late 1940s until he died in 1983. Williams lived in Key West as an openly gay man with his partner Frank Merlo and had a pivotal influence on the island’s literary culture. The museum features one of the largest permanent collections of Williams memorabilia currently on display for the public.

4. Dine at an LGBTQ-Owned and Operated Restaurant
From upscale gourmet restaurants to casual seafood spots, Key West and the Keys are known for culinary excellence. Among Key West’s landmark restaurants are Azur, featuring Mediterranean specialties and wonderful brunches on a shaded terrace or in an intimate dining room, and The Flaming Buoy Filet Co., a blend of retro supper club and sassy corner bistro. Both are gay-owned and -operated, providing top-rated cuisine and warmly personal service.

5. Experience Key West’s Vibrant Nightlife
Key West offers fantastic nightlife with many LGBTQ bars, shops, and entertainment venues — including several located around the 700 block of Duval Street near the island city’s permanent rainbow crosswalks. Premier LGBTQ events are held each year that attract visitors from around the world: Key West Pride, Tropical Heat, Womenfest, and the Headdress Ball among others.

6. Take an Instagram-Worthy ‘Southernmost’ Selfie
Key West’s red, black and yellow Southernmost Point marker isn’t picturesque, but hundreds of visitors take their photos beside it every day. Why? Because the buoy replica marks the southernmost spot in the continental United States. Overlooking the Atlantic Ocean on Whitehead Street, its brightly-painted body bears lettering that proclaims it’s just 90 miles from Cuba. 

7. Spend a Lazy Day on Fort Liz Taylor Beach
Key West is home to several public beaches including the locals’ favorite at Fort Zachary Taylor Historic State Park (affectionately nicknamed Fort Liz Taylor Beach by the LGBTQ community). Taylor stayed in Key West frequently during her years with Richard Burton — whose adoptive father, playwright Philip Burton, numbered among the island’s famous residents. The beach is a perfect place to swim and snorkel in crystal-clear waters, and the park provides numerous amenities.

8. Dive into an LGBTQ Watersports Adventure
Blu Q Gay Sailing Adventures offers a fantastic portfolio of scheduled watersports activities. Passengers can enjoy several different clothing-optional excursions including the all-male Sail, Snorkel & Paddle trips — as well as all-welcome sunset sails. Some trips include visits to remote islands and sandbars, sailing across the clear shallow waters of the backcountry, and viewing stunning scenery of mangroves and marine life. Dolphins, stingrays, and turtles occasionally appear to give passengers a true aquatic welcome.

9. Find the Ideal Place to Watch the Sunset 
Venture out and enjoy one of Key West’s world-famous sunsets. While many spots offer breathtaking sunset views, virtually everyone MUST experience the Mallory Square Sunset Celebration. The iconic waterfront gathering takes place each evening beside Key West Harbor, where crowds enjoy the talents of energetic street performers, view artisans’ handmade wares, and applaud the sun setting over the water.

10. Ring in the New Year ‘Island Style’
New Year’s Eve celebrations in Key West generally include balmy weather and a warmhearted “One Human Family” welcome for visitors eager to swap their heavy winter clothes for shorts and tank tops. In typically offbeat style, revelers can choose from several zany takeoffs on New York City’s traditional Times Square ball drop — including the “drop” of a drag queen in a giant-sized red fiberglass high heel. Drag queen and resident celebrity Sushi (aka Gary Marion) stars in the festivities while suspended high above the Duval Street crowds at the Bourbon St. Pub complex.

11. Tie the Knot in Paradise
Key West weddings may be religious or civil and take place at a church, on the Monroe County Courthouse steps where the Florida Keys’ first same-sex marriage was held, or elsewhere on the island. They can range from a simple exchange of vows to a full ceremony with music by an organist or classical ensemble.

Experienced gay and lesbian wedding specialists are experts in finding just the right attire, flowers, music, wedding rings, catering, cakes, photographers, videographers, decorators, transportation, and officiants.

And once the knot is tied, Florida Keys honeymoons can be spent in a luxury oceanfront resort, an intimate island suite, or a lovingly restored historic guest house. Romantic activities might include commandeering the wheel of a tall ship, chartering a sailboat, or hiring a seaplane for a truly memorable day trip to the Dry Tortugas.

For more information on what to see in do, check out the Florida Keys and Key West website for more travel inspiration.