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

SeaSister Island Gallery

Rachel Garreau came to Key West from Casablanca with thirty-six dollars, worked at Sloppy Joe's, spent five years as an art director, then sold her house to open her own gallery on Duval. It is full of work by Key West artists, and she is usually in it.

Key West

The Purple Cottage

Jennifer Resor cuts and kiln-fires glass in Key West, and because every piece is shaped and fired by hand, no two come out the same. Sold directly rather than through a storefront.

Islamorada

DeClues Custom Framing

DeClues Custom Framing is a custom picture-framing shop in the Upper Keys that builds new frames for artwork and photographs. It works alongside DePaula Gallery, with framing drop-off and pickup on weekday afternoons.

Key West

The Historic Armory

One of the few armories built in the South after the Civil War, and an unusual wood-frame one at that, this 1903 landmark on White Street has been on the National Register of Historic Places since 1971. Twelve artist studios fill the second floor and Fringe Theater performs on the first.

Islamorada

Windley Key Fossil Reef Geological State Park

Windley Key Fossil Reef Geological State Park — a unique blend of geology, history and nature trails in Islamorada.

Key West

Shrimp Boat Sound Studio

Shrimpboat Sound Studio — historic recording studio in Key West, where legends like Jimmy Buffett made music in a humble, iconic space.

Key West

San Carlos Institute

San Carlos Institute — Cuban heritage museum & cultural center in Key West, where history, art, and independence converge.

Key West

St. Paul's Episcopal Church Key West

Founded in 1832 and the oldest congregation in Florida south of St. Augustine, St. Paul's Episcopal Church is one of Key West's most treasured historic landmarks, offering weekly worship, an annual concert series, and five on-grounds wedding and event venues at 401 Duval Street — all while undergoing a breathtaking historic restoration for its 200th anniversary in 2032.

Key West

Key West Cooking Show

Key West Cooking Show: Dinnertainment blending history with flavor.

Key West

Red Barn Theatre

Red Barn Theatre — professional live theater in Key West, where big stories come alive in an intimate, historic space.

USCGC Ingham Maritime Museum

USCGC Ingham Memorial Museum — historic Coast Guard cutter & floating maritime museum in Key West, where legends of service meet immersive history.

Key West

Key West Impromptu Classical Concerts

Key West Impromptu — chamber music concert series in Key West, where world-class classical performance meets community spirit.

Islamorada

Michelle Nicole Lowe, Artist

Michelle Nicole Lowe painted the cover of the 2023 Keys Traveler, a watercolor marking two hundred years of the Florida Keys. She is a fifth-generation Conch whose great-grandfather sailed over from Green Turtle Cay, and she paints the fish, birds and old bridges she grew up around.

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

Comedy Key West

Experience top comedy shows and open mics in vibrant Key West! Laugh live now!