The subtropical island of Key West will welcome revelers to its annual Pride celebrations June 1-5, with a jam-packed schedule that features several dozen Pride events. The festivities showcase the diversity and equality that help make the continental United States’ southernmost city a top vacation destination for LGBTQ visitors from around the world.
Divers and ocean enthusiasts can celebrate the 20th “sink anniversary” of the third-largest vessel ever intentionally scuttled to become an artificial reef — the retired 510-foot Navy Landing Ship Dock Spiegel Grove, which lies off Key Largo — with events May 15-17 and a contest to win a Keys trip to dive the famous wreck.
In April 1982, the Florida Keys symbolically “seceded” from the United States and were reborn as the independent Conch Republic. Today the republic is internationally acclaimed as the Keys’ irreverent alter ego — and this month, the 40th annual Conch Republic Independence Celebration commemorates the historic action with a roster of rollicking events.
In Key West each April, “drag racing” takes on a whole new meaning — as exotic drag queens don quirky sporting attire, lavish wigs and towering high heels to vie for victory in the Conch Republic Drag Race. The offbeat competition is scheduled April 16 on Duval Street (appropriately dubbed Key West’s “main drag”).
Key West’s 40th annual Conch Republic Blue Ribbon Bed Race is scheduled to “blanket” the island’s famed Duval Street April 23. The zany event, billed as “the most fun you can have in bed with your clothes on,” features decorated beds on wheels that are propelled along Duval by teams of costumed runners.
History lovers can experience Presidents' Day Weekend events in Key West at the Harry S. Truman Little White House, Florida’s only presidential museum, including a theatrical production on Truman starring the 33rd president’s oldest grandson. “Give ‘Em Hell, Harry!” is scheduled Feb. 18-19, followed by a Feb. 21 picnic on the museum grounds.
Each spring, the Tennessee Williams Birthday Celebration honors the openly gay playwright who lived and wrote in Key West from 1949 to 1983. The 2022 commemoration includes showings of films adapted from Williams’ plays, curator-led tours of Key West's Tennessee Williams Museum, writing competitions, theatrical presentations and a birthday reception (complete with cake).
Known for creative, colorful, sometimes quirky artwork and a rich diversity of handcrafted artisan wares, the Florida Keys are internationally recognized for artistry inspired by stunning seascapes, landscapes and a light-drenched subtropical color palette. This season, the Keys feature fresh-air strolls that explore the matchless talent and fascinating work of skilled local artists.
Celebrating its 38th year of delighting audiences, Key West’s Headdress Ball is set for Saturday, Feb. 26, at the Coffee Butler Amphitheater. The glamorous LGBTQ gala typically features about 25 contestants showcasing huge and elaborate original masks, cowls, bonnets and other headgear — with top Florida Keys talents staging dazzling entertainment between headdress presentations.
Attendees at the Key West Food and Wine Festival can enjoy gourmet galas and tastings, art and wine experiences, wine dinners, seminars and activities that spotlight the Florida Keys’ culinary scene and talented chefs. Equally appealing are the glimpses the festival offers into the island chain’s unique heritage, culture and warmly welcoming vibe.