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Key West, Florida City Info
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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

Location: Key West

Anglers receive citations noting their catches and qualify for a variety of trophies.




Women Fest

Held in early September

Location: Key West

A lesbian-oriented festival of art shows, sailing and snorkeling, comedy performances and other activities.


Annual Key West Poker Run

Held in mid September

Location: Key West

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.