Gay Florida: best Florida weekend getaways for gay travellers

Stretching towards Cuba on a series of tropical islands all linked to the mainland via the Florida Overseas Highway, find the Florida Keys, home to some of the most romantic getaways in Florida. Key West in particular is a gay favourite for its eccentricity and creative energy, pushed forward by literary residents both past and present. Once home to both Ernest Hemingway and Tennessee Williams, Key West’s population of gay nationals and ex-pats has boomed since the 1970s, and the island is now ripe with gay-owned hotels and B&Bs as well as an active gay nightlife centred around Duval Street.

It’s easy to guess why the region is nicknamed ‘the Floribbean’, blessed as it is with year-round sunshine and tropical beaches many lined with Caribbean-style villas and Cuban eateries. With such beautiful surrounds comes inevitable beach-bum hedonism centred in the city’s dive bars, but, to balance to books, Key West offers much in the way of culture in its literary festivals and art galleries, all served alongside performances and phenomenal sunsets on Mallory Square. Indulge in a weekend of water-sports, boat tours and partying, sampling Latin and Cuban culture along the way by way of a salacious food and music scene. Staying longer in the Keys? Discover our pick of the top 10 things to do in gay Key West.

Despite gaining a reputation in the past for its somewhat trashy nightlife and grittier spots, more recently, Tampa has undergone a complete make-over to show off a stylish and sophisticated side we never knew existed. Continued development has turned the Hillsborough Riverwalk into a glittering feat of urban design, while a transformed bar scene in the trendy GaYbor district now attracts many gay partygoers from across southwest Florida. Heading the Florida gay scene with countless drag show, cabaret and gay club offerings along Ybor Street, Tampa also organises regular LGBTQ+ events, such as the yearly Tampa Pride and Diversity Parade and the Tampa International Gay & Lesbian Film Festival.

Located on the west side of the Florida peninsula, Tampa is often wrongfully overlooked by travellers. Besides its wild nightlife, gay Tampa showcases a neat selection of museums, parks and cultural institutions all within reach of the gay St. Petersburg waterfront and the best gay beaches in Florida. Base yourself in Tampa for sightseeing around the National Historic Landmark District, exploring the redeveloped cigar factory buildings to find pop-up bars, boutique lofts and evermore locally-owned businesses bring community spirit to Tampa. After a full day of shopping and eating, head over to any of the 5 best gay bars in Tampa for a wild night to remember.

Just across Old Tampa Bay on the Gulf Coast is the beach city of St. Petersburg, going hand-in-hand with Tampa City and fostering a growing arts and culture scene focused on downtown. Now known as the gay capital of Florida or ‘Gay St Petes’ to locals, the city is constantly cultivating its LGBT+ credentials, now given a perfect score by the Human Rights Campaign’s Municipal Equality Index, which looks at the quality of life for LGBT+ people in cities around the world. While there is no official gay district, the whole of St. Petersburg can be considered gay territory, thanks to its swell of diverse gay-friendly neighbourhoods. Unofficially though, the historic Grand Central commercial district and nearby neighbourhood of Kenwood are quietly taking off as the go-to gay destinations, hosting all kinds of gay-friendly businesses (everything from antique stores and salons to bars and restaurants) in amongst 1920s’ Craftsman bungalows and a cheery, down-to-earth atmosphere.

While St Petersburg might be known as the newer, more downbeat gay capital, Fort Lauderdale stands as Florida’s largest and most diverse gay destinations, popular among gay travellers the world over. Letting your hair down in Fort Lauderdale is easy as it comes, between leisurely days on the sandy waterfront and wild nights in town. Stay centre-stage at the Ritz-Carlton or another of the best gay resorts in Florida to be close to the endless beach action, moving inland for sophisticated shopping and dining on Las Olas Boulevard or yachting through the Venice-like waterways that grid the entire city.

As for the city’s gay scene, Wilton Manors is the place to be with its huge assortment of gay bars and clubs visited by upwards of 1.1 million LGBTQ travellers each year. Besides the nightlife, the community at Wilton Manors is also a reason to stay, with more than 100 gay-owned businesses set up here, including a number of hotels and guesthouses. Visit during the month of February to get involved with Fort Lauderdale Pride, where live music, dance and partying comes studded with LGBTQ+ activism. At any other time of year, Fort Lauderdale remains active in gay rights awareness, being home to the Stonewall National Museum & Archives. Gain evermore insights into this gay paradise with our dedicated guide to Fort Lauderdale.

Taking a somewhat softer approach for a gay weekend getaway, we travel to the artsy city of Sarasota, around an hour south of Tampa by car. Sarasota offers more of the same paradise beaches that you’ll find elsewhere in Florida but with an added air of sophistication given from its population of affluent theatre-lovers, sailors and veterans. The rich history of Sarasota tells of Spanish colonial takeovers and the resulting Seminole Wars, where the territory was fought over by Native Americans, Spaniards, Brits and Settlers for many years. Until the Tampa railroad came in 1902, the Gulf was the only connection to the outside world, making sailing boats and steamships prized property until today. With the city becoming a popular winter anchorage point for America’s most affluent, Sarasota drew the attention of circus magnate John Ringling who relocated his circus here, also building a huge mansion, art museum and college with his riches, in turn helping Sarasota to grow into the arts hub it is today.

By day, tour the shops and restaurants on St. Armand’s Circle or rest up behind the secluded dunes that run along North Lido Beach below the beautiful 22-acre Lido Park. By night, experience the town’s lively theatrical heritage, either at a Sarasota Ballet performance or at McCurdy’s east end theatre for the Drag Queen Bingo Bonanza. Other LGBT-focused events around the city include outreach theatre at Asolo Rep, ‘Embracing our Difference’ festival, the Harvey Milk festival or the annual Sarasota Pride Fest held downtown in J.D. Hamel Park.

Home of both the Church of Scientology and Hooters, with a somewhat outdated approach to men’s fashion, Clearwater can be forgiven for its lack of exciting visuals thanks to its excellent selection of gay beaches and offbeat neighbourhoods. Split into two parts – between Clearwater proper and the upscale barrier island Clearwater Beach running just offshore – Clearwater as a whole is hard to dismiss. boasting year-round sunshine at its most bathed in during the rush of Spring Break when the young and the beautiful descend on the beachfront. Later in the year, LGBTQ+ Pride Month brings more big party vibes to the area, lasting the entire month of June and climaxing at the nearby St. Pete Pride Fest, Florida’s largest gay pride parade.

One of the best day trips in Florida, Clearwater Beach is perfect for a leisurely day of sunbathing and picnicking across the island’s parks and quartz-sand beaches, before moving into the city’s historic Grand Central District, for world-class museums, the largest concentration of Scientologists outside of Los Angeles, and surely a lively night of entertainment.

With the name alone able to conjure up visions of wide palm-lined boulevards connecting pristine beaches to poolside resorts, Miami maintains timeless appeal for gay travellers the world over. Though long-serving, Miami remains wholly cosmopolitan with the finest restaurants, boutiques and gay nightlife offerings found anywhere on earth. For the ultimate Florida gay beach experience, visit Miami Beach Island during one of the city’s LGBT events, such as White Party Week, Winter Party Festival or Miami Beach Gay Pride, when 12^th Street Beach becomes the go-to place for gay socialising. Outside of the festivals, however, both 12^th Street and South Beach remain beacons for the LGBTQ+ community, where the entire waterfront comes lined with bars, mega clubs and welcoming boutique hotels. Alternatively, for a no-holds-barred experience, try the clothing-optional Haulover Beach with its very own gay section between the 12^th and 16^th lifeguard towers.

As well as the location for partygoers, South Beach also doubles up as a classy place to stay with its collection of Art Deco residences and Mid-century hotels built on the waterfront. Discover Latino-influenced culture anywhere along the front or cross back over the bridge to Downtown Miami for a taste of urban lifestyles and commerce. The ultimate end to your Miami vacation however lies in nature, with an adventure out to the southernmost tip of the peninsula to get lost in the vast wilderness of the Everglades. Discover the full depths of Miami beyond its shores with Mr Hudson’s Miami travel guide. Those with the time on their hands can also consider taking the ultimate American Southeast road trip – from New Orleans to Key West.