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.

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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

Conch Tour Train

Explore Key West's top sights and stories on the iconic Conch Tour Train!

Islamorada

Islamorada Art Gallery By Pasta

Marine-inspired art gallery & working studio in Islamorada.

The Lower Keys

Washed Up Key West

Washed Up Key West — sustainable hardwood art & furniture studio in Key West, where fallen trees become island treasures.

Islamorada

Coral Shores High School Performing Arts Center

The Coral Shores Performing Arts Center in Tavernier hosts live theater, concerts, and community performances in the Upper Florida Keys.

Key West

The Key West Amphitheater

The Key West Amphitheater — live music & concert venue in Key West, where island vibes meet high-energy performances.

Islamorada

Elena Madden Studio Gallery

Elena Madden paints water and light from memory, never from a photograph, in Conté crayon and acrylic layered until the surface seems to move. Her studio gallery sits in Islamorada's Morada Way arts district, and her 22-foot tarpon hangs in the lobby at Cheeca Lodge.

Key West

Art@ 830 Gallery

Hand blown glass, turned wood, ceramics and paintings on Caroline Street in the Historic Seaport, run by two artists who have been working in Key West for decades. Ask about Tony Gregory's Key West alphabet.

Islamorada

Jessica Ann Art Studio

Jessica Ann Art — original marine-life acrylic paintings in Florida Keys, where conservation meets Caribbean color.

The Lower Keys

Artists In Paradise Gallery

Artists in Paradise Gallery is a vibrant co-op gallery on Big Pine Key, showcasing original works by over 40 local artists, including paintings, pottery, glass, and fine crafts.

Key West

Archeo Gallery

Rugs hand-knotted in Afghanistan from nautical charts of the Lower Keys, African ceremonial art, and fish that swam in a Wyoming lake fifty million years ago. Archeo on Upper Duval calls it ancient art for modern living, and means it fairly literally.

Islamorada

Our Place in Paradise

Discover unique original art, pottery, and workshops in a welcoming Florida Keys gallery.

Key West

Historic Tours of America

Trolley + walking historic tours of Key West.

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.

Key West

Millionaire Gallery

Millionaire Gallery specializes in high-end photography and fine art from world-class photographers, with locations in the Keys and online sales.