Date(s): June 6 – 8, 2025 Location: Sugarloaf Key, FL (Sugarloaf Marina, 17015 Overseas Hwy, Sugarloaf Key, FL 33042) Description: Reel in the fun at the 32nd Annual Lower Keys Dolphin Tournament, where anglers from across the islands gather for three days of competitive fishing, island-style festivities, and big-time prizes. With over $35,000 in cash […]
Date(s): June 13 – 15, 2025 Location: Stock Island Marina Village, 7005 Shrimp Rd, Stock Island, FL 33040 Description: Get ready to cast off for a cause at the Key West Gator Club Dolphin Derby, a fun and competitive fishing tournament with more than $15,000 in guaranteed cash prizes. Hosted just minutes from Boyd’s, this […]
Date(s): Saturday, June 14, 2025 Location: Higgs Beach, 1000 Atlantic Blvd, Key West, FL 33040ACTIVE.com+5Swim Around Key West+5swimaroundkeywest.com+5 Description: Ready to make a splash? Join the locals and fellow adventurers for the annual College of the Florida Keys Swim Around Key West—a beloved island tradition that’s equal parts challenge and celebration. Whether you're diving into […]
Date(s): June 22–29, 2025 Location: Various venues across Key West, FL Description: Celebrate love, resilience, and unity at the Key West Pride Festival 2025! This year's theme, “Still Rising,” honors the rich history and enduring spirit of the LGBTQ+ community. Immerse yourself in a week-long extravaganza featuring dance parties, historic tours, sailing excursions, beach gatherings, […]
Date(s): July 2–6, 2025Florida Weekly Key West+4Key West Concierge+4Dwell Key West+4 Location: Various venues across Key West, FL Description: Get ready to pucker up and party! The Key Lime Festival is back, bringing five days of zesty fun to the island. From pie-eating contests and pie-making classes to rum tastings and a 5K race, there's […]
Date(s): July 23–27, 2025 Location: Various venues across Key West, FL Description: Calling all fans of adventure, literature, and a good time—Hemingway Days is back! This annual celebration honors the legacy of Ernest Hemingway, who called Key West home during the 1930s. From the spirited Hemingway Look-Alike Contest at Sloppy Joe’s Bar to the whimsical […]
Date(s): August 13–17, 2025 Location: Various venues across Key West, FL Description: Raise your glass and toast to the tropics—Rum Fest Key West is back for another spirited celebration! This five-day festival showcases some of the finest rums from around the globe, offering a blend of tastings, competitions, and island adventures. Kick off the festivities […]
Date(s): August 29 – September 1, 2025 Location: Various venues across Key West, FL Description: Celebrate the life and legacy of Jimmy Buffett during Labor Day weekend at the second annual Just A Few Friends festival. This heartfelt tribute transforms Key West into a tropical playground filled with live music, island-style food, and unforgettable experiences. […]
Date(s): October 17–26, 2025 Location: Various venues across Key West, FL Description: Get ready to let your imagination run wild at Fantasy Fest 2025! This year's theme, "Bedtime Stories & Magical Monsters," invites you to step into a world where fairy tales and fantasy come to life. Over ten days, Key West transforms into a […]
Date(s): Sunday, October 19, 2025 Location: Fort East Martello, 3501 S. Roosevelt Blvd, Key West, FLLog in or sign up to view+9Zombie Bike Ride+9historickeywestvacationrentals.com+9 Description: Get ready to pedal into the undead! The annual Zombie Bike Ride is back, and it's bigger and better than ever. Join thousands of fellow ghouls and goblins for a […]
