For one night only, 40+ local restaurants set up at Truman Waterfront Park for an open-air tasting with wines and craft beers. Admission is free, with food and beverage tickets available for purchase. The event runs 6–9 PM, timed perfectly for sunset views over the waterfront.

The 44th annual celebration of Key West’s playful “secession” from the U.S. in 1982. Ten days of parades, parties, pirates, bed races, and the Great Sea Battle in the harbor.

As the largest festival of its kind, the Key West Songwriters Festival celebrates its 30th anniversary this year and draws top talent from across the country. Spanning five days, the festival features 150+ artists performing at different venues throughout the island, including poolside at our resort. While the lineup hasn't yet been announced, the festival has helped launch the careers of artists like Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser, and Maren Morris. Expect five days and nights of live music and storytelling from veteran songwriters and the next big hit-makers.

A week of pool parties, drag shows, comedy nights, street fairs, and sunset sail cruises celebrating the island’s “One Human Family” spirit. The festival wraps with the Pride Parade down Duval Street, featuring a 100-foot section of Key West’s famous Sea-to-Sea rainbow flag.

Step into the world of Ernest Hemingway with five days celebrating his life and legacy. Now in its 45th year, the festival features a marlin fishing tournament, literary readings, the Lorian Hemingway Short Story Competition, and the iconic Hemingway Look-Alike Contest at Sloppy Joe’s Bar. Another highlight is the playful Running of the Bulls, where look-alikes parade with faux bulls down Duval Street. The festivities wrap with a Papa Birthday Bash and the Hemingway Rum Bar Stroll, a celebration that reflects Hemingway’s adventurous spirit and deep love for Key West.

Five days celebrating the island’s favorite citrus. Highlights include the Key Lime Pie Drop from the Key West Lighthouse, the World Famous Key Lime Pie Eating Championship on July 4th, the Key Lime Cocktail Sip & Stroll, mini pie baking classes, and rum tastings at the Key West First Legal Rum Distillery. So fun!

The 28th annual celebration of the opening of Florida's spiny lobster season with an island-wide party including the kickoff Lobster Boil, the Duval Street Fair with live music, and lobster prepared every way imaginable. The Key West Lobsterfest supports the Key West High School Scholarship Fund.

A five-day celebration of rum featuring tastings, live music, sunset sails, sandbar trips, culinary pairings, pool parties, and more held around National Rum Day (August 16). Photo credit: @the_rum_traveler from our 2024 pool party.

Labor Day weekend honors Jimmy Buffett in the place where it all began — five days of music, food, and island traditions. Photo credit: Nick Doll.

“The greatest gift Jimmy ever gave me was bringing me to Key West. And there’s never any place I want to be on Labor Day weekend, ever again for as long as I have breath, except for Key West.”
— Lucy Buffett

Key West’s biggest party of the year is a 10-day celebration of costumes, creativity, and imagination. Expect colorful parades, themed events, pool parties, quirky competitions, and nonstop fun, all leading up to the Masquerade March and the iconic Fantasy Fest Parade.

It’s the most festive time of year in Key West. Palm trees sparkle with lights, the Lighted Boat Parade glides through the Seaport, bikes and boats dress for the season, Santa sightings pop up around town, and the island closes the year with its famous New Year’s Eve drops. By land and sea, Key West becomes a tropical winter wonderland.