Key West Events

Key West Pops Orchestra Presents “My Fair Lady” (Jan 24)
My Fair Lady stars Key West’s own talent Mike Mulligan.
Tennessee Williams Theatre
5901 College Road.
Stock Island, Key West, FL 33040
7:30 pm Tickets $30, $50, $75
Contact: (305)296-6059

Key West Food & Wine Festival (Jan 28 – 31)
Key West is famous for international restaurants and top chefs. This event invites the best on the island to showcase their culinary creativity specializing in the indigenous foods of the Florida Keys.
Contact: (305)292-1622

Master Chef Classic (Jan 31)
A chance to sample from the best local restaurants as they vie for top honors and the judges decide upon the winners competing in three categories; appetizers, entrees and desserts. Event will be at Westin Hotel on the Key West Harbor. Tickets available Jan. 8. This even benefits the MARC House programs for persons with developmental disabilities.
Contact: 294-9526, ext 25

Randy Roberts at Tennessee Williams Theatre (Jan 10th Feb 15th Mar 14th
Enjoy the magnificent, mulit-faceted talents of Key West’s Randy Roberts
3 times this season. “Both Sides Now (Jan 10th),” “That’s Entertainment” (Feb 15th),
“Not the Boy Next Door”(Mar 14th)
Tennessee Williams Theatre
5901 College Road
Key West, FL 33040
Tickets (305) 295-7676

Pridefest Key West (May 29 – June 6)
A festival honoring the Key West concept of “One Human Family” that embraces and honors diversity, openness and freedom in the little island city that is recognized as one of the world's top gay and lesbian vacation destinations. Come and celebrate with dance and cocktail parties, contests, shows, forums, street fair and the world famous Pride Parade along Duval Street. The Key West Business Guild is one of the nation's first gay and lesbian chambers of commerce, established in 1978, and Key West has been welcoming GLBT visitors and their friends long before then. Visit Key West’s own Gay and Lesbian Community Center (GLCC) and the only City Aids Memorial in the United States.
Key West Business Guild Office & Visitor Center
513 Truman Avenue
Key West, FL 33040

Tropical Heat 2010 ~ 5 Days of Men (Aug 19-22)
Organizers are planning ‘as we speak’ for this fever pitched events of adventurous adult fun for gay men and their friends. August is hot in Key West and the events are sultry. Stay Tuned to the website as plans are announced.

Womenfest (Sept 7 – 12)
Women from all over the globe to travel to Key West for Womenfest, the southernmost party for lesbians and their friends. Social activities and entertainment are staged at various locations around the island of Key West. This is the 22nd legendary event for women! Activities include pool parties, dances women only sunset sails and dolphin watching.

Fantasy Fest and Headdress Ball(Oct 22 – 31)
A week-long adult festival with entertaining costume events and contests each night that culminates with main event adult entertainment Carnival-style parade up Duval Street on the last Saturday night of the month. On Tuesday, the 26th, The Key West Business Guild sponsors the 28th “Headdress Ball’ event held in 2010 on Tuesday, 26, where glitz at it’s best showcases the most outrageous giant headdresses you’ll ever see accompanied with live entertainment and spectacular Key West Burlesque. Check with the Fantasy Fest web site for the announcement of the festival themes for 2010.

New Years Eve 2010 (Dec 31)
A Key West famous tradition that is broadcast on National Television on CNN at midnight - right from “Bourbon Street Pub” at 801 Duval Street. A saucy Key West drag queen named "Sushi," is “dropped” in a red shoe to bring in the New Year to ring in the New Year.
Contact: (305)294-9354

Recurring Gay Key West Entertainment Events

The Piano Bar
New York-styled Live Entertainment Daily from 5 PM.
1114 Duval Street
Key West, FL 33040
No Cover. Purchase of food or beverage required. Every afternoon at 5 pm the magic begins. This club brings in top pianists and singers from New York for frolic and fun. Open mic by request if you want to sing.
Contact: (305)294-5899

Pearl’s Patio Tropical Bar for Women
Where The Girls Are Happy Hour. Pearl's Patio is a tropical bar just for women. Located just behind the gates of Pearl's Rainbow, this is THE place for women to meet in Key West.
525 United Street. 5 to 7 PM Monday - Saturday.

Drag Show at 801 Bourbon Bar
Where the Drag Queens are every night.
801 Duval Street
Key West, FL 33040
Nightly, 9 PM & 11 PM.
Contact: (305)294-53


Really LIVE your
Key West vacation... island style...