KEY WEST EVENTS

May

Shell Key West Challenge

Annual Key West events for Shell employees and friends, sportfishing on big boats to benefit charities such as the Diabetes Research Institute

Yamaha Dolphin Masters Invitational

First Prize is big, very big.

June

Southernmost Swordfish Tournament

This is part of the Key West Fishing Tournament (see March listings) and features an all-night contest for swordfish. Register from 4 to 7 pm then lines in a 8pm, lines out at 5 am. Weigh-in and breakfast at the marina in the morning.

Annual Swim Around Key West

Each year a group of die-hard ocean swimmers swim a circle around the actual island of Key West, competing for prizes or just to finish. The event is carefully coordinated to emphasize safety, and all entrants must have an accompanying boat or kayak. There's a celebratory dinner after the last swimmer finishes and the year's winner gets his or her name printed on that year's T-shirt. It's a total of twelve and a half miles starting and ending at Smather’s Beach on South Roosevelt at the Bertha Street Boat Ramp.

PrideFest

This annual event features social events, parties, pageants, street fairs, and a parade over one week of celebration of gay pride. Each year there's a new theme with a kickoff party to start the week of fun and celebration. There's even an hisotrical exhibit at the new GLCC to trace the history of gays and lesbians in Key West.

Annual Harry S Truman Legacy Symposium.

All things Truman: workshops, reception, and a symposium at the Tennessee Williams Theater.

July

Fourth of July in Key West

Even though we seceded from the Unites States in the early 1980s, we still celebrate the Fourth of July with fireworks. You can see them from almost anywhere in Key West, but they do it at White Street Pier. If you have a boat, get out on the ocean and have a great time. If not, head for the beach or a rooftop.

Hemingway Days

July 17 to the 22nd Key West goes all out for its favorite famous resident, Ernest Hemingway. Hemingway lived in Key West from 1928 to 1939 and For Whom the Bell Tolls during that time. He hung out at Sloppy Joe's Bar and did lots of sportfishing. He lived hard and played hard and Key West loves him for that. Hemingway Days's main events are Ernest Hemingway Lookalike Contest, Arm Wrestling Contests, and Running of the Bulls down Duval Street.

Lobster Mini Season

This is the chaotic start of the lobster season, a chance for amateurs to get some lobster before the commercial guys get in there with their superior methods. It lasts for 48 hours (hence the mini season) and you must have a special lobster permit on top of your regular fishing permit from the State of Florida's Fish & Wildlife Commission.

Green Parrot Bar’s Off-The- Wall Sidewalk Art Show

Casual, low-key art show at the Green Parrot Bar, where there's no cover.

Celebrate Mel Fisher's Discoveries at the Schooner Wharf Bar

Mel Fisher discovered the Atocha, the Spanish shipwreck containing tons of precious gold, in the 1980s. His favorite bar was the Schooner Wharf Bar. They celebrate Mel, another favorite historical Key West citizen, with a homemade bikini contest, a trivia game, and drinks.

August

Lobsterfest

The official start of lobster season is this week, and Key West goes all out to celebrate it with Lobsterfest the second weekeend in August. Street fair on Saturday.

Battle of the Bars

Every year local bartenders get together and perform silly relay races to compete for their bars. It benefits Big Brothers/Big Sisters of Monroe County.

September

Womanfest

During the first week in September Womenfest is a celebration of lesbian life, including parties, art shows, cruises and lots of other activities.

Key West Poker Run

This is a motorcycle event, involving the beautiful stretch from Miami to Key West. Participants ride and make pit stops at local establishments for cards. Bring your Harleys.

Schooner Wharf Bikini Fashion Show

This is held at Schooner Wharf Bar 202 William Street. Mid September.

October

Goombay

Goombay is the official start of Fantasy Fest, taking place in Bahama Village. Caribbean music and food vendors line Petronia Street for two days.

Fantasy Fest

The ultimate week-long extravaganza featuring costumes, parties, and adult fun. Go here for the complete run down.

November

December

More Key West Events
Click the Links to Learn more
January Key West House and Garden Tours Tour fine homes and gorgeous gardens of Key Wet! February March Key West Fishing Tournament Kickoff Winter is over, and the warm weather fishing season begins! Key West Fishing Tournament, March through November A full season of fishing tournaments in Key West! Conch Shell Blowing Contest Only in Key West- a contest for making music with conch shells! April Robert Frost Poetry Festival Robert Frost fans convene in Key West. Taste of Key West Sample great food from the restaurants of Key West. World Sailfish Championship Big boats go offshore to get sailfish in deeper water and compete for prizes. May Key West Songwriters Festival Tons of singer songwriters from all over attend every year for concerts at local bars and restuarant June Key West Dolphin Derby Pridefest Key West This annual event features social events, parties, pageants, street fairs, and a parade over one wee July August September October November Key West Power Boat Races These big cigarette boats with jet engines come to Key West each year for the big races. December Halleluja Chorus at United Methodist Church The Key West Christmas season gets going with Handel's Messiah. New Year's Eve in Key West Ring in the New Year on Duval Street in Key West! Art in the Park Art in the Park in Key West is free for everyone. Browse fine arts from Key West's finest! Lighted Historic Inn Tour Tour Key West's historic inns on a nighttime tour. Key West Christmas Parade Annual Holiday Parade on Duval Street in Key West. Key West Lighted Boat Parade Another great annual Holiday tradition in Key West. Pirates in Paradise Festival Pirate fans, gather in Key West for Pirate sails and more. Annual Dachshund Walk Key West's newest tradition, dachshunds and owners gather and parade. Florida Keys Art Guild Outdoor Art Festival Free art show in Bayview Park in Key West.

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