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

Millionaire Gallery

Signed guitars, Hollywood wardrobe, and autographed sports and music pieces, built into shadowbox displays and certified by third-party authenticators. The Duval Street gallery opens in the afternoon and stays open into the evening.

Key West

Holle Fine Art Gallery

Holle represents Tom Everhart, the only artist Charles Schulz ever taught and legally authorized to paint Peanuts as fine art. The gallery sits on Duval and stays open until ten every night, so it fits into an evening rather than competing with your beach day.

Key West

Key West Art and Historical Society

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

Key West

Derubeis Fine Art of Metal Key West

Chris DeRubeis, acclaimed as the “Father of Conceptual Movement,” pioneers the signature style of Abstract Sensualism®, transforming metal into luminous, emotionally charged fine art that blends sculpture and painting in celestial abstraction.

Key West

Sunset Pier

Ocean Key Legacy Resort & Bar — iconic Key West destination featuring the famed Sunset Pier with cocktails, live music & nightly views.

Key West

Wyland Gallery of the Florida Keys

Wyland has painted more than a hundred life-size whale murals around the world and has run an ocean conservation foundation since 1993. His Key West gallery is on Duval, open until ten most nights and eleven at weekends.

Key West

7 Artists & Friends Gallery

Seven Key West artists went in together on one gallery a block off Duval, and the range inside is the fun part: watercolors and oils on one wall, photography and glass on the next, sculpture and hand made jewelry in between. Walk in off Simonton Street, or book the place to yourself by appointment.

Key West

Key West International Dance Company

Experience vibrant cultural dance and bold artistry with Key West International Dance Company!

Key West

Edward B. Knight Pier

Popular with residents and tourists alike, the Edward B. Knight Pier is dog-friendly!

Key Largo

REEF Ocean Exploration Center for Marine Conservation

Explore the REEF Ocean Exploration Center: inspiring ocean discovery and conservation!

Meetings Max
136
Total Space
4000 sq ft
Largest Room
2000 sq ft

South Florida Symphony Orchestra

South Florida Symphony Orchestra — orchestral concerts & classical performances in Fort Lauderdale, where artistry meets community connection.

Key West

Guild Hall Gallery

Twenty-seven local artists rent individual stalls across two floors here, and each one works the floor five hours a week, so the person selling you a painting is often the person who painted it. The gallery has occupied the same Duval Street building since 1976.

Key West

Backyards of Key West Gallery

Key West cottages, roosters, bar fronts and beaches, photographed around the island and then painted over by hand, stroke by stroke, on a tablet. Mark Baratto's gallery is tucked into the Shops at Mallory Square, across from Cuban Coffee Queen.