Artist painting a canvas in a sunlit studio with brushes in the foreground.

Arts & Culture

In The Florida Keys, creativity flows as freely as the tides. From galleries filled with local paintings and sculptures to theaters, dance, live music, and street festivals, the islands wear their artistry in full color. Key West has long lured writers, dreamers, and free spirits, while each destination brings its own twist—think outdoor art walks, history museums, and quirky roadside treasures. Whether you’re browsing studios or catching a play, culture here feels refreshingly unbuttoned, sun-soaked, and impossible to forget.

Filters
Keys Season Deals
Destination
Category
Key West

SeaSister Island Gallery

Discover high-end contemporary art from local and international artists in vibrant Key West.

Key West

Whimsy Key West

Whimsy Key West — custom illustration & whimsical art in Key West, where imagination becomes keepsake.

Key West

Tennessee Williams Museum

Tennessee Williams Museum — dedicated to the life and works of the famed playwright in Key West’s Little White House complex.

Key West

Fringe Theater

Experience unique, community-driven theater with local talent in Key West!

Key West

Gallery on Greene

Gallery on Greene is a premier fine art gallery in Key West’s Historic Seaport, specializing in representational works by renowned Key West and Cuban artists, with offerings spanning paintings, sculptures, and reproductions.

Weddings Max
100
Meetings Max
50
Total Space
2000 sq ft
Largest Room
2000 sq ft

Key West

Bug Ceramics Pottery Studio & Gallery

Bug Ceramics Pottery Studio & Gallery is Key West's first and only community pottery studio, tucked inside the Shops at Mallory Square, offering hand-building and wheel-throwing classes, walk-in pottery painting, private bachelorette and group events, and a gallery of handmade ceramics from local and international artists.

Key West

Key West Art and Historical Society

Explore two centuries of Key West history and art in a stunning historic landmark!

Key West

Yankee Freedom Dry Tortugas Ferry

Dry Tortugas National Park — remote Florida Keys paradise 70 miles west of Key West featuring historic Fort Jefferson, turquoise water, pristine beaches and world-class snorkeling.

Islamorada

The Hale Gallery

An Islamorada fine art gallery featuring rotating exhibitions from local and visiting artists.

Key West

Rams Head Presents

Rams Head Presents — live concerts & entertainment in Key West, where premium touring acts meet intimate island venues.

Key West

Sails To Rails Museum at Flagler Station

Explore Key West history from tall ships to railroads at Sails to Rails Museum!

Key West

The Birdcage Cabaret

The Birdcage Cabaret — live drag & variety cabaret in Key West, where glitz, music & bold performances light up the night.

Key West

Gingerbread Square Gallery

Key West’s oldest private art gallery, showcasing original works in a historic Victorian setting.

Key West

Ernest Hemingway Home & Museum

Explore the legendary Ernest Hemingway Home & Museum in beautiful Key West!