Events & Calendar

A special evening celebrating the life and works of Key West's most famous literary resident. Local actors perform scenes from Williams' greatest plays, interspersed with readings of his poetry and personal letters. A reception follows in the theatre lobby.

Shakespeare's beloved comedy gets a tropical twist in this enchanting Waterfront Playhouse production. Set against a moonlit Florida Keys backdrop, the play follows four young lovers and a group of amateur actors as they navigate love, magic, and mischief in an enchanted forest. Directed by Danny Weathers.

A group exhibition exploring the intersection of land and sea through mixed media, featuring twelve Keys-based artists working in collage, assemblage, and found-object sculpture. Opening reception April 3rd from 6–8 PM with live music and complimentary refreshments.

An evening celebrating independent filmmakers with connections to the Florida Keys. The showcase features five short films and one feature-length documentary exploring island life, marine conservation, and the creative spirit of the Keys. Q&A with filmmakers to follow.

Stroll through Islamorada's vibrant gallery district on the third Thursday of the month. Participating galleries include Rain Barrel Village, Portside Studio & Gallery, and more. Enjoy complimentary wine, meet the artists, and discover original works inspired by island life.

Tennessee Williams' Pulitzer Prize-winning masterpiece returns to Key West, the city where much of it was written. This intimate Red Barn Theatre production brings raw emotion and Southern Gothic intensity to the historic venue. Performances Thursday through Sunday.

Artists set up easels throughout Key West's historic district to capture the island's vibrant architecture, lush gardens, and waterfront vistas. Watch painters at work, then view the finished pieces at a reception and sale from 5–7 PM at the Key West Art Center.

Oscar Wilde's sparkling comedy of manners comes to the Middle Keys. This community production features a talented local cast delivering Wilde's witty dialogue and satirical jabs at Victorian society. A delightful evening of laughter and clever wordplay.

A series of literary readings in the lush gardens of the Hemingway Home. Local and visiting authors read from their latest works, followed by a discussion on the enduring influence of Key West on American literature. Wine and light bites included.

Gallery owner and artist Christine Scarsella presents her latest series of luminous abstract paintings exploring the play of light on water. The opening reception features live acoustic music, wine, and a chance to meet the artist in her intimate gallery space.

The Keys Community Concert Band teams up with local jazz musicians for a free sunset concert on Mallory Square. Enjoy smooth jazz, Latin rhythms, and island grooves as the sun dips below the Gulf of Mexico. Bring a blanket or lawn chair.

A contemporary dance performance inspired by the coral reef ecosystem of the Florida Keys. Dancers from South Florida collaborate with Keys-based choreographers to bring the underwater world to life through movement, projected imagery, and an original score.

An intimate evening of original music performed in the round by singer-songwriters from throughout the Lower Keys. Each artist shares stories behind their songs in this popular monthly gathering. Acoustic sets under the stars with a potluck dessert table.

A two-day celebration of LGBTQ+ artists and allies featuring visual art exhibitions, live performances, poetry readings, and interactive workshops. Over 40 artists and performers from across South Florida come together for one of the Keys' most colorful cultural events.

The annual Marathon Seafood & Arts Festival pairs the freshest local catch with juried fine art and craft vendors from throughout the Keys. Enjoy live music on two stages, children's art activities, culinary demonstrations, and a silent auction benefiting arts education.