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Events in the Florida Keys

Fantasy Fest

The grandaddy of all events takes in Key West, and is called Fantasy Fest. Nothing is more eagerly awaited than the opening of Fantasy Fest each October. This Halloween celebration combines elements of Mardi Gras and the Miami club scene, resulting in a wild party filled with costumes, parades, and rum runners (Captain Morgan sponsors). Parades of brightly-bedecked revelers flow down Duval and Whitehead Streets while other celebrants toss beads from balconies. You’ll have to make reservations far in advance for this party.

The Pirates in Paradise Festival takes over Key West’s historic seaport and Fort Zachary Taylor State Park & Beach and celebrates the official end of the hurricane season. Spanning November & December, this melee of pirate ships and buccaneers culminates in the Fort Taylor Pirate Feast & Shipwreck Ball. Other events include a pirate market, maritime art exhibits, a writer’s workshop, historic re-enactments, and more.

The Island Jubilee, also in November, is an arts & crafts festival in Key Largo’s Harry Harris Park. Live musical and theatrical performances.

The Key West Literary Seminartakes place each January, and features panels, readings, and literary parties (this is Key West, after all!). There's a theme each year, and the participants are respected members of their fields. Past themes were Travel Writing and Biography. They also sponser a Writer's Walk, which is a guided tour of famous literary sites in Key West. It's about a one-mile walk.

Other annual events include the Birding & Wildlife Festival in October, Florida Keys Jazz and Blues Festival (in April on Plantation Key, and in October on Islamorada), and the Florida Keys Heritage Festival in January. Marathon even sponsors a Florida Keys Renaissance Faire on Sombrero Beach in January. Don’t miss the daily Sunset Celebrations held at Mallory Square in Key West.

Key West also sponsors the Hemingway Days Festival in July. In the spirit of the Ernest Hemingway that Key West knew and loved, there are arm-wrestling contests, costume parties, and short-story competitions. Of course there's the Papa look-alike contest, where white-bearded man over a certain age show up and do their best to look Hemingway-like. The costume parties encourage people to dress up as Hemingway charaters...Key Westers love to dress up!

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5/11/2008 Florida Keys GLEE Green Homes Tour Tour houses built from alternative building materials, and renovated houses that are now energy- and water-efficient. Free and open to the public. Find out more information and sign up for tours at the GLEE Expo on May 10.

5/13/2008 - 5/24/2008 "Rompers, a collection of shorts" at Red Barn Theatre Celebrating short-attention-span theatre, the theatre at 319 Duval St. is proud to present short plays with an exciting mix of playwrights, directors and actors.

5/15/2008 - 5/18/2008 Marathon Offshore Grand Prix World-class, high-speed powerboats compete in the waters surrounding Marathon and the historic Seven Mile Bridge in the Middle Keys. The event also features live music by national talents.

5/16/2008 - 5/18/2008 Coconuts Dolphin Tournament Anglers are to compete in an event named for a Key Largo restaurant that serves up plenty of dolphin fish, known on most menus as Mahi Mahi.

5/16/2008 - 5/17/2008 Harry S. Truman Legacy Symposium: “Harry Truman and Immigration” Key West’s political history is highlighted in panel discussions, a reception and tours of the Little White House, where former President Harry Truman worked and relaxed during his time in office.w.

5/17/2008 - 5/22/2008 21st Annual Faro Blanco Invitational Tarpon Tournament Anglers are to tangle with silver kings in an event named for a famous Marathon resort, and which raises money for charities.

5/17/2008 - 5/18/2008 Keys Ultras - Prostate Cancer Benefit Races The inaugural year for the "Keys Ultras," there will be three individual ultra-marathon road races, between Key Largo and Smathers Beach, Key West. Proceeds benefit The Cancer Foundation of the Florida Keys.

5/18/2008 - 5/21/2008 14th Annual Outback Steakhouse Golden Fly Invitational Tarpon Tournament This prestigious fly tournament for large tarpon benefits both CCFA and college scholarships for Keys students.

5/21/2008 - 6/14/2008 "Naked Boys Singing!" at Waterfront Playhouse The international hit returns to the playhouse at historic Mallory Square.

5/22/2008 'Ray Of Light' Paintings On Display Redbone Gallery (mile marker 81.2) will feature the paintings of Don Ray from 5 p.m. - 8 p.m. Ray is well-known for dynamic underwater fish scenes in oil on canvas. Light refreshments will be served, the event is free and open to the public.

5/23/2008 - 5/25/2008 9th Annual Cuban American Heritage Festival The culture and customs Cubans brought to Key West are celebrated.

5/31/2008 Yamaha Dolphin Masters Invitational Experienced offshore captains are to lead the chase for the colorful and acrobatic dolphin fish and a hefty first prize.

6/1/2008 - 6/6/2008 Don Hawley Invitational Tarpon Tournament The world's best fly rod anglers are to pursue the mighty silver kings in one of the most storied tournaments in the Keys.

6/4/2008 - 6/5/2008 Islamorada Fishing Club Captain’s Cup Dolphin Tournament Anglers are to compete for a winner-take-all $25,000 jackpot for catching dolphin fish.

6/6/2008 - 6/8/2008 Big Pine & Lower Keys Dolphin Tournament Anglers in this 15th-annual event are to compete to catch dolphin fish, one of the most popular and best-tasting summertime fish off the Keys.

6/7/2008 - 6/15/2008 PrideFest Key West This festival honors diversity, openness and freedom in the city that is consistently recognized as one of the world's top gay and lesbian vacation destinations.

6/11/2008 - 6/13/2008 Ladies Invitational Tarpon Fly Tournament This fly tournament for tarpon is open to men and women. It benefits environmental scholarship funds.

6/13/2008 - 6/15/2008 Father’s Day Dolphin Derby Anglers are celebrate Father's Day by catching one of the most beautiful, best-tasting and fastest-growing fish in the sea, all to benefit the Marathon Youth Club.

6/14/2008 - 6/15/2008 Island Grill Blue Water Dolphin Tournament The event is to incorporate a one-day dolphin tournament with an optional Father/Son Fun Fish Father’s Day. Proceeds are to benefit Baptist Hospital’s Children’s Cancer Center.

6/14/2008 - 6/15/2008 Southernmost Swordfish Tournament This overnight swordfish challenge is to be part of the annual, season-long Key West Fishing Tournament.

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