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Key West Events and Entertainment


Plena Libre
Held in early January
Location: East Martello
Admission Charged
Put on your dancing shoes! The rhythms, sounds and island soul shake the town during the Founders Plena Libre outdoor festival at East Martello.

Sculpture Key West
Held mid January – late March
Location: Fort Zachary Taylor Historic State Park
Sculpture Key West is an annual exhibition of contemporary outdoor sculpture that takes place every winter at Fort Zachary Taylor Historic State Park in Key West.


Founders Society Annual Anniversary Gala
Held in early February
Location: Key West
Join the Founders Society as it celebrates its anniversary of bringing quality music, dance and theater to the Key West stage.


Key West Songwriters Festival
Held in mid May
Location: Key West

Showcases some of America's foremost performing songwriters, staged in audience-friendly island settings.

Dolphin Masters Invitational
Held in late May

Location: Key West
Annual fishing tournament with a large purse.


Tavernier Creek Marina Dolphin Rodeo
Held in early June
Location: Key West

Amateur Tournament Cash Prizes with a Jr. Angler Division

Pridefest Key West
Held early – mid June
Location: Key West
Event honoring diversity, openness and freedom in the city that is consistently recognized as one of the world’s top gay and lesbian vacation destinations.

Cuban American Heritage Festival
Held in mid June
Location: Key West
Showcases the culture and customs Cubans brought to Key West.

Key West Gator Club Dolphin Derby
Held in late June
Location: Key West
Event raises money for college scholarships.


Lower Keys Permit All-Tackle Tournament
Held early – mid July
Location: Islamorada

All-release tournament featuring trophies and prizes in fly, spin and artificial categories.

Geiger Key Dolphin Tournament
Held in mid July
Location: Key West
Modified release with four categories: combined weight, bull, cow and junior.

Hemingway Days Festival
Held in mid – late July

Location: Key West
Annual celebration of the legendary author’s work and lifestyle highlighted by the Sloppy Joe’s Look-Alike Contest.

Drambuie Key West Marlin Tournament
Held in mid – late July
Location: Key West
Catch-and-release tournament held in conjunction with Key West’s annual Hemingway Days Festival.

Reef Awareness Week
Held in late July
Location: Key West
Spearheaded by the organization Reef Relief, the weeklong event showcases North America's only living coral barrier reef with activities for all ages.


Key West Summer Food & Wine Festival
Held in early August
Location: Key West

Showcases the talents of Key West’s master chefs as well as the quality and diversity of the island’s culinary offerings.

Key West Fishing Tournament's Swordfish Tournament
Held in early August
Location: Key West

Key West Fishing Tournament’s Flats S.L.A.M. Tournament
Held in mid – late August
Anglers receive citations noting their catches and qualify for a variety of trophies.


Women Fest
Held in early September
A lesbian-oriented festival of art shows, sailing and snorkeling, comedy performances and other activities.

Annual Key West Poker Run
Held in mid September
Motorcycles cruise from Miami to Key West to raise funds for local charities.


Florida Keys Birding & Wildlife Festival
Held in early October
Location: Marathon and Lower Keys
A celebration of the natural wonders of Florida wildlife at the peak of the fall birding season. Presentations and field trips focus on education.

Goombay Festival
Held mid – late October
Location: Key West’s Bahama Village
Two-day street fair in Key West's historic Bahama Village.

Fantasy Fest
Held in late October
Location: All of Key West
Each year there is a different theme for this costumed, fun-filled event. Come enjoy the costume competitions, grand parade and wacky sights and sounds.


Key West Old Island Days
Held in early November
Location: Key West

Events include an art festival, crafts show, conch shell blowing contest and house and garden tours celebrating Key West culture and history.

Key West Offshore World Championship
Held in early November
Location: Key West
High-speed powerboats continue Key West's longstanding tradition.

Annual Talent Show
Held in mid November
Location: Tennessee Williams Theatre
The Founders annual talent show is a dream come true for many of the talented community performers. Watch as rising stars, both young and old, perform everything from show tunes to modern dance routines, rock n' rock, hip hop and magic tricks before a captivated crowd and prestigious panel of local celebrity judges.

Pirates in Paradise
Held late November – early December
Location: Key West
Historic Seaport and other venues throughout Key West are transformed into a pirates' stronghold with mock sea battles, a thieves' market featuring arts, crafts and more.


Key West Holiday Parade
Held in early December
Location: Old Town
Family-friendly parade through Old Town celebrating the holiday season.

Islamorada Fishing Club Sailfish Tournament
Held in early December
Location: Islamorada
First leg of the Florida Keys Gold Cup Sailfish Championship.

Key West Lighted Boat Parade
Held in mid December
Location: Key West Harbor
Event features decorated and lighted boats cruising through Key West Harbor and the waters of the Historic Seaport.

New Year’s Eve Key West Celebration
Held on New Year’s Eve
Location: Various locations in Key West
Southernmost City celebrates New Year's Eve with conch shell drop at Sloppy Joe's Bar, "wench" drop at Schooner Wharf Bar, and red high heel drop with drag queen Sushi at Bourbon Street Pub/ New Orleans House.

Arts & Entertainment

Tennessee Williams Theatre
Performing Arts Centers for Key West
5901 College Road

Key West, FL 33040
Call for performance schedule

Key West Pops Orchestra
Key West, FL 33041
Call for performance schedule
The Key West Pops Orchestra has three concerts per season filled with Pops music, Opera, and Broadway favorites to enrich the cultural performance of the Florida Keys residents.

The Waterfront Playhouse
310 Wall St
Key West, FL 33041

Call for performance schedule
The Key West Players have been presenting the magic of live theatre for over 65 years!

Key West Symphony Orchestra
1025 White St
Key West, FL 33041

The Key West Symphony is proud to be the center of cultural activities on beautiful Key West. Only in Key West can you swim with a whale in the morning and conduct the great masters that evening.

The Red Barn Theatre
319 Duval Street, Rear
Key West, FL 33040
Enjoy great live theater productions at the Red Barn Theatre in Key West, Florida. See live comedy, drama, musical theater, and cabaret shows in an intimate small theater. Great stage shows featuring the finest professional actors, dancers, singers and directors from Key West's own famous arts community, as well as visiting stars. Enjoy fabulous theatrical entertainment in a unique, casual, romantic Island setting.

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