Calendar

Dec
1
Fri
Key West Holiday Fest
Dec 1 – Dec 31 all-day

Each year a wide range of seasonal celebrations takes place throughout Key West during the month of December. Events include the lighting of the Harbor Walk of Lights, tours of historic decorated inns, a holiday parade and much more.

Dec
31
Sun
New Year’s Eve Shoe Drop Celebration
Dec 31 all-day

The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below.

As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.

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Jan
24
Wed
Key West Food & Wine Festival
Jan 24 – Jan 28 all-day

Top chefs and restaurateurs display culinary creativity Key West Food & Wine Festivaland the Keys’ indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively “Old Town Uncorked,” neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting.

Feb
1
Thu
Cuda Bowl
Feb 1 – Feb 3 all-day

Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. Prizes and trophies are to be awarded for top angler and guide in light tackle spin and fly divisions.

Feb
28
Wed
Sunset Green Event Lawn presents: Michael McDonald
Feb 28 all-day

With a career that encompasses five Grammys, numerous chart successes and personal and professional accolades, as well as collaborations with some of the world’s most prominent artists, Michael McDonald remains an enduring force in popular music. Hailing from St. Louis, McDonald arrived in Los Angeles in the early 1970s, honing his talents as a studio musician before becoming an integral part of Steely Dan. In the mid-‘70s McDonald was invited to join the Doobie Brothers as the band redefined their sound with McDonald serving as singer, keyboardist and songwriter on such Top 40 singles as “Takin’ It To The Streets,” “It Keeps You Runnin’,” “Minute By Minute” and “What A Fool Believes.” Sunset Green Event Lawn is a brand new multipurpose event space located at The 24 North Hotel in Key West. Tickets on sale Dec. 8 at 12 noon.

Mar
12
Mon
March Merkin Invitational Permit Tournament
Mar 12 – Mar 15 all-day

A charity flats-and-fly-only tournament with a twist – in addition to catch and release, anglers earn extra points for tagging their caught fish. Held at the Key West Yacht Harbor Marina on Stock Island.

Capt. Don Gable guided Mike Dawes to the 2011 Championship

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Mar
14
Wed
Key West Theater presents: Mike Love
Mar 14 all-day

Meet Mike Love. No, not one of the Beach Boys! One of reggae music’s rising stars. Born and raised in Oahu, Hawaii to a musical family that spans generations, Mike Love brings a multitude of influences to the table, all tied together by the common goal of making the world a better place. Doors open 7 p.m., show starts 8 p.m.

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Mar
15
Thu
Fringe Theater presents: Vincent Zito’s Bernstein on Broadway @ The Studios of Key West, 533 Eaton Street
Mar 15 – Mar 16 all-day

Conductor Vincent Zito leads a stellar cast in celebration of the 100-year anniversary of the birth of the beloved American composer, Leonard Bernstein. Performances by Bobby Nesbitt, Susie Speidel, Susan Powell, Richard White, Jono Mainelli and Vincent Zito. Two nights only! Shows 7 p.m., at The Studios of Key West, 533 Eaton Street

Mar
16
Fri
58th Annual Key West House & Garden Tours
Mar 16 – Mar 17 all-day

Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and interior design that complements each. February and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. Tickets are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Apr
19
Thu
Fringe Theater presents: Conch Republic Re-Visited, by Gayla Morgan & Monnie King
Apr 19 – Apr 28 all-day

Ever wonder just how the Conch Republic was born? Four actors tell the tale in this fast-moving comedy that is filled with music, confetti, and flags – which actually IS a lot like how the Conch Republic WAS born! Find out why we seceded where others failed! Shows 7 p.m., 4/19-22, 4/24-28 at The Studios of Key West. 533 Eaton Street.

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