The Best Annual Festivals in Key West

Celebrate Island Life: Top Annual Festivals in Key West

At Blue Flamingo Resort Key West, we believe life’s a party — and on this island, there’s always something to celebrate. From legendary parades to food-filled weekends and music under the palms, Key West festivals keep the good times rolling. Whether you’re planning your first visit or returning for another sun-soaked escape, here’s your ultimate guide to the best annual events in Key West, plus insider tips on when to go, what to expect, and why Blue Flamingo makes the perfect home base for every celebration.

kick off the year with culture & music

January

Key West Literary Seminar

Every January, the Key West Literary Seminar brings together acclaimed authors, critics, and readers for panels, readings, and walking tours through Key West’s historic neighborhoods. It’s a quieter festival than some, but beloved by book lovers and those looking for a thoughtful, cultural escape during the slower season.

Mile 0 Fest

A boutique, five-day Red Dirt & Americana music festival that combines island vibes with serious musical talent. Past lineups have included Randy Rogers Band, Shane Smith & The Saints, American Aquarium, and more. Shows take place in outdoor venues like Coffee Butler Amphitheater on Truman Waterfront, and daytime “pop-up” sets happen at beach bars, pool stages, and even on music sails.

seafood & art season

February

Florida Keys Seafood Festival

Celebrate the island’s fishing roots with lobster, grouper, and conch fritters fresh off the dock — a family-friendly local favorite. The focus is on local fishermen and sustainable sourcing offering casual events with live music, kid zones, cooking demos, and a community feel.

Old Island Days Art Festival

Held on Stock Island just outside Key West, Old Island Days brings together local and regional Key West artisans — painters, sculptors, jewelers, mixed media makers, and coastal craftspeople. The festival is one of the longest-running in the Keys and attracts thousands of visitors a year.

MUSIC, FOOD & SUNSHINE

Spring

Key West Songwriters Festival

One of the signature music events in Key West, this festival features 50+ shows over multiple nights and draws more than 200 songwriters and performers to the island. Performances are held across listening rooms, bars, and outdoor stages.

Taste of Key West

Taste of Key West is a premier foodie event, where top restaurants, chefs, and wineries serve small-plate tastings, wine pairings, and chef demonstrations. This is one Key West food festival you will not want to miss.

loud and proud

Spring

Key West Pride

A full week of inclusive celebrations including a grand parade on Duval Street, sunset parties, drag shows, beach events, art shows, and community fairs. Key West Pride is one of the most celebrated LGBTQ+ events in Florida. As an LGBTQ+-friendly resort in the heart of the island, we welcome guests from all walks of life with open arms, colorful energy, and tropical flair. Our location puts you just minutes from the Key West Pride Parade route and downtown celebrations, while our pool parties, themed cocktails, and partner events with local LGBTQ+ organizations make it easy to keep the good vibes going long after the parade ends.

A Slice of Key West History

July

Key Lime Festival

Key West is home to the famous Key lime — this festival celebrates the region’s unofficial fruit with sweet, tart, tropical flair. From cocktail strolls to pie-eating contests and dessert showcases, the island’s love for key lime shines here. Visitors often seek out events hosted by the iconic “best key lime pie” spots during this time.

Hemingway Days

Hemingway Days is a long-standing tradition honoring Ernest Hemingway’s legacy in Key West. Pay tribute to Papa himself with Hemingway look-alike contests, a “Running of the Bulls” parody, literary readings, and fishing tournaments.

rum & island heat

August

Lobsterfest

While the prominence of Lobsterfest varies year to year, historically it was a four-day celebration of lobster season with street fairs, lobster brunches, live music, chef cook-offs, and special events throughout town.

Rum Fest

Rum Fest in Key West is all about tropical drinks, tastings, cocktail events, and celebrating Caribbean and island-inspired spirits. Expect rum flights, mixology classes, and beachside cocktail bars.

women & brew

September

WomenFest Key West

WomenFest is one of the longest-running lesbian and queer women’s music & arts festivals in the U.S. Expect themed parties, brunches, live music, wellness events, dance nights, pool gatherings, and community connections.

Key West BrewFest

This is a multi-day celebration of craft beer and local flavor. The main tasting event features over 60 breweries and 225+ beer varieties in one evening. Aside from the beachfront tasting, BrewFest includes pool parties, beer-pairing dinners, tap takeovers, and events at hotels & bars island-wide. At Blue Flamingo we host pool parties, samplings and other activities as a part of our annual involvement.

spooky season is here

October

Fantasy Fest

Key West’s most famous festival — ten days of parades, costume balls, street parties, themed events, body art, and more. Attendance can reach tens of thousands. As an added bonus, Blue Flamingo Key West is an official sponsor and hosts poolside events, DJ soirees, and festival-themed offerings during the Fantasy Fest season.

Goombay Festival

Goombay is a precursor to Fantasy Fest, rooted in Bahamian and Caribbean traditions, held in Bahama Village. Expect steel drums, island cuisine, dancing, and cultural performances that set the tone for the larger festival weekend.

Zombie Bike Ride

A quirky, fun bike ride where participants dress as zombies and pedal through town, often the night before Fantasy Fest’s big parade.

Halloween in Key West

No one does Halloween like Key West. Between Fantasy Fest, the Zombie Bike Ride, and nightly street parades, October turns the island into a non-stop costume party. Locals and visitors alike take over Duval Street — and at Blue Flamingo, the celebration starts poolside and goes well past sundown.

FIlm & FULL THROTTLE

November

Key West Film Festival

This festival draws indie filmmakers, critics, and cinephiles. Screenings, red-carpet premieres, panels, and social events are spread across theaters and outdoor venues.

Powerboat Offshore Racing

Have a need for speed? High-speed boat racing events often take place in Key West waters in November. These powerboat championships draw spectators to the waterfront and harbor, and Blue Flamingo sponsors events during these races including a locals party.

HOLIDAYS ARE HERE

December

Bight Before Christmas & Lighted Boat Parade

During the Key West “Bight Before Christmas” (or Harbor Walk of Lights) visitors and locals can watch the Lighted Boat Parade to see boats decked in holiday lights cruise past the waterfront — Key West’s tropical twist on the holiday season.

New Year’s Eve Shoe Drop & Fireworks

Ring in the new year with the famous “red stiletto drop” on Duval Street — a Key West classic. It’s a lively, fun event — perfect to celebrate with live music, fireworks, and the island’s festive spirit.

Where to Stay?

Whether you’re visiting for Fantasy Fest, Hemingway Days, or Lobsterfest, Blue Flamingo Key West is the perfect base to experience the island’s best events in comfort and style.

• Central Location: Minutes from Duval Street, Old Town, and all major festival routes. Blue Flamingo is your tucked away getaway close to it all yet with plenty of space to unwind.

• Tropical Oasis: Two pools, cabanas, lawn games and laid-back island energy — the perfect place to recover between festivities.

• Newly Renovated: Completely reimagined rooms including one-bedroom and ocean-view suites that blend coastal cool with modern comforts and amenities.

• Exclusive Offers: Keep an eye on our Special Offers page for festival-season deals and event-weekend packages.

Plan Your Trip

Start planning your stay today and join us for the best annual festivals in Key West. From parades to pool parties, there’s always something to do — and Blue Flamingo Resort is always ready to welcome you with open arms, a cold drink, and the island’s best vibes.

👉 Book your stay now at Blue Flamingo Resort Key West for your next Key West getaway.