Sarasota proves that it’s not the size of the boat that matters most; this city of moderate proportions yields massive amounts of options. A destination rich in visual, performing, and culinary arts, it’s proud to be called Florida’s Cultural Coast® and the nation’s per capita arts capital for its arts organizations, according to Southern Living. For starters, there’s the Sarasota Opera, Florida Studio Theatre’s cabaret shows, The Players Theatre—famous for its Friday night drag shows and monthly Drag Queen Bingo—resident ballet company, orchestras, art galleries, and other classy diversions that draw a more mature, refined class of LGBT visitors. For a fast immersion into everyday high life, cross Sarasota Bay to St. Armand’s Circle, a historic district with over 130 fashionable shops and fine dining venues. Waterfront dining is available on either side of the bridge, not to mention romantic beach moments. Spend a day on Venice Beach; Crescent Beach in Sarasota’s Siesta Key, known for The World’s Finest, Whitest Sand™; or Longboat Key, a quiet, luxurious spot minutes from a full circle-back to St. Armand’s, to see what we’re talking about.

On the other hand, maybe it is the size of the boat, if you’re interested in the outstanding fishing Sarasota has to offer. Its healthy estuary in the Gulf Coast makes it a paradise for anglers, whether it’s salt- or freshwater fish you’re after from a charter boat, kayak, or even just from shore. Nature-lovers, be sure to also schedule some time to visit Myakka River State Park, whose 58 square miles of wetlands, prairies, hammocks, and pinelands are fantastic terrain to hike, canoe, kayak, or take an airboat or safari tram through for sightings of ospreys, bald eagles, and Florida’s signature gators. There are eight islands and keys to pick from as your launch point for any boat-related activity, but don’t feel too pressured—you can’t possibly choose wrongly.

Good to Know

  • Lively and actively expanding gay scene
  • Generally inclusive
  • Gay marriage legal since January 2015

Featured Resorts:

The Ritz-Carlton, Sarasota


An oasis of style and sophistication on Florida's Gulf Coast, The Ritz-Carlton, Sarasota offers 266 guest rooms over- looking Sarasota Bay, a marina and the city skyline. The hotel offers the best of both worlds: a city hotel in a relaxed resort destination.

Hyatt Regency Sarasota


Discover comfortable luxuries at Hyatt Regency Sarasota, where you'll find the perfect blend of location, pampering amenities and welcoming atmosphere. Situated on the private marina on Sarasota Bay, delight in the beautiful Gulf Coast weather as you swim through waterfalls gently splashing into the pool, or sip a glass of wine as you watch the beautiful sunsets. Stroll leisurely to downtown for the theater, shops and sightseeing, spend a day at the beach, or head to St. Arma ...

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