St Petersburg, Florida

In 1914, the first commercial airline flight took off from downtown St Petersburg, Florida, making the trip across the bay to Tampa in 23 minutes. Although it was a major moment in aviation history, it really says more about the anything-can-happen-here spirit that still permeates the largest city on the peninsula between Tampa Bay and the Gulf of Mexico.

While most of the towns that line Florida’s west coast are cloaked in a uniform of sleepy sameness built around days at the beach, there’s an explosion of eccentricity occurring among the two dozen municipalities that share this peninsula — with St Petersburg as the spiritual leader. The city’s devotion to individuality has served as a magnet for artists, entrepreneurs and a sizable LGBT community. Wikipedia’s roots are here, as are the headquarters of the Home Shopping Network. It’s the kind of place where a divey sports bar and an organic café can coexist peacefully on the same street. In 2013, the city received hosting honours for the Blue Ocean Film Festival & Conservation Summit — a distinction it will share only with Monaco.

St Petersburg is also home to the largest collection of Salvador Dali’s artwork outside of Spain and enough independent galleries to rival a much bigger metropolis. St Pete Pride, the largest Pride event in the state, draws upward of 100,000 attendees to the downtown Grand Central District in June. And yes, the 56 kilometres of powdery, white-sand beaches from St Pete to Clearwater are great, too — some of the best in Florida.

As tempting as it is to head directly to the beach, it makes more sense to set up base camp in downtown St Petersburg for easy access to dining, nightlife, museums and a year-round calendar of outdoor events ranging from jazz and cinema to a Grand Prix race through the city’s streets. Arts and the waterfront meld beautifully on Beach Drive, site of two noteworthy hotel choices. The Birchwood, with its forest mural across a modernized Spanish Mission façade, has delivered a boutique-style boost to downtown; The Canopy, its Miami Beach–reminiscent rooftop lounge, and Birch & Vine, its indoor-outdoor farm-to-table restaurant, are both destinations unto themselves. The Vinoy Renaissance St Petersburg Resort is a pretty-in-pink bayfront icon dating to 1925, and while the hotel’s style is more old-school, its epic Sunday brunch is timeless.

Two of the city’s major museums also share this stretch of waterfront. The Chihuly Collection is like Willy Wonka’s factory for grownups, each room ablaze in a rainbow of blown-glass blooms and baubles. The Museum of Fine Arts packs in heavy hitters like Georgia O’Keeffe, Monet and Cézanne, which are rivalled by its glass conservatory with lovely water views. The Downtown Looper trolley covers this area free, and for 50 cents, the journey can be extended to the not-to-be-missed Dali Museum, a structure with architectural flourishes — geodesic dome jutting from its side, helical staircase — befitting the surreal artworks inside. There’s a special trolley route to cover the more than 40 galleries and studios that participate in St Petersburg’s Second Saturday ArtWalk.

For a whopping $2, the trolley system also travels to Pass-A-Grille, a refreshingly undeveloped stretch of sand at the southern tip of St Pete Beach. The LGBT sunbathing spot, Sunset Beach, is located west of downtown (via Central Avenue) toward the southern end of Treasure Island, between two jetties. It gets busiest on Sundays in the early to mid-afternoon, after which the crowd migrates to tea dance at the Flamingo Resort, the largest gay-owned and -operated resort in Florida; the sprawling complex includes multiple bars, a pool, and dance club. Gay bar/dance club/café Georgie’s Alibi has reigned for years as the city’s most popular LGBT nightspot.

Worth a drive

Rent a car for sampling some of the surrounding communities, like lesbian favourite Gulfport, on Boca Ciega Bay, where the private residences share the same jaunty colours as the shops overflowing with local arts and crafts. Continue 20 minutes south to 460-hectare Fort De Soto Park, one of the best spots for dolphin watching and kayaking.

Tarpon Springs, a 45-minute drive north of St Petersburg, houses the largest Greek community in the United States — picture barrel-chested men doing sponge-diving demonstrations and all the saganaki, grilled octopus and baklava you can eat. For the ultimate in tranquility, head to Honeymoon Island State Park and catch the ferry to Caladesi Island to experience the wild beauty of its nature trail and five-kilometre white sand beach.

For the most up-to-date travel information on gay St Petersburg, see our City Guide, Listings Guide, Events Guide and Activities Guide.

For more information, visit visitstpeteclearwater.com.

For the most up-to-date travel information on nearby gay Tampa, see our City Guide, Listings Guide, Events Guide and Activities Guide.