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

The Key West Amphitheater

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

Key West

Magie Ruley-Island Inspirations

Bright, tropical acrylic art by Key West painter Maggie Ruley — bold colors, island scenes, and happy vibes.

Key West

Key West Theater

The Key West Theater — performing arts & live events in Key West, where historic charm meets world-class entertainment.

Key West

Key West Pottery

Key West Pottery is a hands-on studio offering locally made ceramics, coastal pottery gifts, wheel-throwing classes, and a chance to create your own piece in island style.

Key West

Gingerbread Square Gallery

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

Key West

Key West Ghost Tours: Southernmost Shadows and Ghosts

Discover Key West’s haunted history with a chilling walking ghost tour through cursed graveyards, eerie historic sites, and stories of restless spirits in the heart of Old Town.

Key West

The Historic Armory

The Armory — historic 1903 arts & performance center in Key West, where preservation meets creative community.

Key West

Key West International Dance Company

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

Key West

Art@ 830 Gallery

multidisciplinary gallery & studio in Key West, where vibrant creative expression meets immersive local art experiences.

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

Key West Gallery

Key West Gallery features collections from world-renowned and emerging artists in fine art, limited editions, and VIP consultation services in the heart of Key West.

Key West

Suenami Art

Experience vibrant coastal seascapes, marine wildlife and tropical wave art by Susan Gillingham — an acclaimed South Florida artist blending Caribbean flair with ocean passion

Key West

Randy Roberts LIVE!

Randy Roberts — performance magic & illusion shows in Key West, where spectacle meets island enchantment.

Key West

Shade Ceramics and Shutter Photography

Shade & Shutter Key West is a serene, artisan gallery where handcrafted ceramics meet evocative nature photography.

Key West

Alex Vega Key West Firehouse Museum

Explore Key West's historic firehouse museum with unique artifacts and fun tours!

Meetings Max
25