Rum Fest Key West

Key West's famous tropical heat, seafood, and world-class rum shine at Rum Fest Key West! Savor the best rums with sunset sails, sandbar trips, rum strolls, and delicious food and cigar events. Don't miss the rum cake competition, master classes, and grand tasting for an unforgettable experience!

1st Annual Just a Few Friends Key West

The inaugural event in Key West honoring Jimmy Buffett promises to be a vibrant celebration of island life and music. The streets will come alive with a Second line memorial walking parade, honoring the legendary musician's influence on island culture. Attendees can immerse themselves in a weekend filled with live music, beachside festivities, and a laid-back atmosphere reminiscent of Buffett's signature songs.

Fantasy Fest

Immerse yourself in a kaleidoscope of creativity and revelry at Key West's Fantasy Fest, a vibrant 10-day extravaganza bursting with costume-clad participants, lively parades, and endless libations. From dazzling street parties to royal coronation of the king and queen of Fantasy Fest, the event pulsates with excitement and boundless imagination, inviting attendees to unleash their inner fantasies and embrace the island's spirit of uninhibited fun. Join the festivities and embark on an unforgettable journey through a world of enchantment and celebration in the heart of Key West.

Key West Artisan Market

Higgs Memorial Beach Park 1000 Atlantic Blvd., Key West

Join the fun at the Key West Artisan Market on select Sundays! Discover local artisans showcasing colorful handmade crafts, unique jewelry, and delicious treats. Enjoy live music, tasty bites from local food vendors, and soak up the festive island vibes. It’s the perfect place to support creativity and find one-of-a-kind treasures!

Free

Key West Artisan Market

Higgs Memorial Beach Park 1000 Atlantic Blvd., Key West

Join the fun at the Key West Artisan Market on select Sundays! Discover local artisans showcasing colorful handmade crafts, unique jewelry, and delicious treats. Enjoy live music, tasty bites from local food vendors, and soak up the festive island vibes. It’s the perfect place to support creativity and find one-of-a-kind treasures!

Free

Key West Artisan Market

Higgs Memorial Beach Park 1000 Atlantic Blvd., Key West

Join the fun at the Key West Artisan Market on select Sundays! Discover local artisans showcasing colorful handmade crafts, unique jewelry, and delicious treats. Enjoy live music, tasty bites from local food vendors, and soak up the festive island vibes. It’s the perfect place to support creativity and find one-of-a-kind treasures!

Free

Key West Film Festival

The Key West Film Festival, a celebration of contemporary cinema, offers a rich blend of artistic vibrancy and cultural diversity in a historic island community. Through screenings, discussions, and workshops, it showcases Florida filmmaking talent while providing access to industry leaders and supporting emerging local student filmmakers.

Key West Artisan Market: Rock the Red Ribbon Edition

Higgs Memorial Beach Park 1000 Atlantic Blvd., Key West

Shop the Artisan Market for fine crafts, jewelry and more from talented local makers. Enjoy cocktails, coffee, food from vendor stalls and food trucks. This week's market supports World AIDS Day - all are invited to pick up and wear a red ribbon. Indigenous Park at 1801 White St. from 10 a.m. to 2 p.m.

Free

Waterfront Winter Wonderland

Coffee Butler Amphitheater 21 Quay Rd, Key West, FL

Enjoy Visits with Santa, live music performances, and festive celebrations throughout the season! Home to Key Wests only ice rink, we will also have thrilling carnival rides and fun for the whole family at Waterfront Winter Wonderland!

$10

Key West Artisan Market

Higgs Memorial Beach Park 1000 Atlantic Blvd., Key West

Join the fun at the Key West Artisan Market on select Sundays! Discover local artisans showcasing colorful handmade crafts, unique jewelry, and delicious treats. Enjoy live music, tasty bites from local food vendors, and soak up the festive island vibes. It’s the perfect place to support creativity and find one-of-a-kind treasures!

Free

Key West Artisan Market

Higgs Memorial Beach Park 1000 Atlantic Blvd., Key West

Join the fun at the Key West Artisan Market on select Sundays! Discover local artisans showcasing colorful handmade crafts, unique jewelry, and delicious treats. Enjoy live music, tasty bites from local food vendors, and soak up the festive island vibes. It’s the perfect place to support creativity and find one-of-a-kind treasures!

Free

Key West Artisan Market

Higgs Memorial Beach Park 1000 Atlantic Blvd., Key West

Join the fun at the Key West Artisan Market on select Sundays! Discover local artisans showcasing colorful handmade crafts, unique jewelry, and delicious treats. Enjoy live music, tasty bites from local food vendors, and soak up the festive island vibes. It’s the perfect place to support creativity and find one-of-a-kind treasures!

Free