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October 01 to October 31, in Florida Keys

Fantasy Fest Parade
Fantasy Fest’s 2009 pre-parade activities are to begin at noon on Halloween with the open-air Duval Street Promenade. Promenade vendors are to offer masking and costuming finery and accessories as well as food and libations. At 7 p.m., parade grand marshall Bridget Marquardt and the parade’s participants are to unleash their inner “Villains, Vixens, and Vampires” as they depart from a lineup area at the intersection of Southard and Whitehead streets.

November 05 to November 08, in Key West

18th Annual Meeting of the Minds More than 3,000 fans of the legendary singer, songwriter and bestselling author Jimmy Buffett will flock to Key West to celebrate their hero’s music and the lifestyle it promotes. Visit 'Parrotheads in Paradise' web site for details.

November 07 to November 14, in Florida Keys

Bubbafest Bike Tours New in the Florida Keys, join a biking and resort camping experience, from Key Largo to Key West. Lodging, meals and plenty of sunshine, scenery and memories included. Event limited to first 125 participants. Visit Web site for details. Contact: Bubba (321) 759-3433 Email: bikerbubba@aol.com

November 08 to November 15, in Key West

Key West World Championship Race High-speed powerboats continue Key West’s longstanding tradition in a challenge described as the Indianapolis 500 of powerboat racing. Contact: (305) 296-6166

November 21, in Key West

WomanKind’s 9th Annual Survivors Reunion Concert The Survivors, a tropical fusion band popular in Key West during the 80s, return from around the country to perform for one night. Guests can dance in the sand on Higgs Beach and enjoy a BBQ dinner. Band to play from 6:30 p.m. to 10 p.m. Tickets $20 in advance, $25 at the door. Call for details. Contact: 305-295-8255 Email: mspringer@womankindkeywest.org

November 29 to December 06, in Key West

Pirates in Paradise 2009 Historic Key West and Fort Taylor transform into a pirates' stronghold with over 150 pirate entertainers. Tall ships, sea battles, arts and crafts, pirate sails, a living history encampment and nonstop entertainment! Contact: (305) 296-9694   December 04 to December 05, in Key West FKCC Keys Chorale Holiday Concerts This annual event will feature the Magnificat by Monteverdi, and Laud to the Nativity by Respighi. The second half of the concert will feature holiday favorites for the entire family. Showtime 8 p.m. Friday, Saturday 2 p.m. matinee at Tennessee Williams Theatre. Call for ticket prices. Contact: (305) 295-7676   December 05, in Key West Key West Holiday Parade Local leaders, civic clubs and churches share their holiday spirit by parading through historic Key West. Contact: (305) 809-3700 December 11 to December 12, in Key West Historic Lighted Inn Tours Discover the history and holiday spirit of Key West by touring beautifully decorated historic inns. The tours include creative offerings by local chefs, artists, writers and performers. Contact: (305) 295-1334 December 12, in Key West Key West Lighted Boat Parade Decorated and lighted boats cruise through Key West Harbor and the waters of the Historic Seaport. The Gerald Adams Elementary School Steel Your Heart Band kicks off the festivities at 6:00 pm with a set of holiday tunes and standards on stage at Schooner Wharf, followed by the high energy Robert Douglas Band with Raven Cooper. Sponsored by Schooner Wharf Bar. Contact: (305) 292-3302 December 18 to December 19, in Key West Historic Lighted Inn Tours Discover the history and holiday spirit of Key West by touring beautifully decorated historic inns. The tours include creative offerings by local chefs, artists, writers and performers. Contact: Contact: (305) 295-1334 December 30, in Key West Key West Pops Orchestra presents: Home For the Holidays Alumni vocal and instrumental soloists are set to return to the Pops for this 7:30 p.m. performance at St. Paul's Episcopal Church, 401 Duval Street; including Clinton Curtis, Daniel Curtis, Ralph Garcia, Stephanie Leone, Lina Robles, Carmen Rodriguez and Joe Lowe. Tickets $20, students & military $15, kids under 12 free. Contact: (305) 296-6059 Email: info@keywestpops.org December 31, in Key West Key West New Year's Eve Celebrations The Southernmost City celebrates with a conch shell drop at Sloppy Joe's Bar, 201 Duval St.; a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St.; and a pirate wench descending from a tall ship mast in the island city's Historic Seaport. Call (305) 296-2388, (305) 293-9800 and (305) 292-3302. January 07 to January 10, in Key West 28th Annual Key West Literary Seminar The seminar’s 2010 topic is “Clearing The Sill of the World,” a celebration of 60 years of American poetry in honor of Richard Wilbur. Contact: (888) 293-9291 January 09 to April 24, in Key West Sculpture Key West 2010 Outdoor sculpture exhibition at Fort Zachary Taylor State Park and West Martello Tower. Cutting edge sculptures made by artists from around the world. Contact: 305-295-3800 Email: info@sculpturekeywest.com January 16, in Key West 5th Annual Florida Keys Seafood Festival A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. Free admission; hours open from 11 a.m. - 9 p.m. Bayview Park at Truman Avenue and Eisenhower Drive. Contact: Vicki 305-872-9026 or Dawn 305-292-4501 Email: vickigale@bellsouth.net January 16 to April 16, in Key West Sculpture Key West This stunning art exhibit showcases the work of leading contemporary sculptors at West Martello Tower, Fort Zachary Taylor State Park and the Key West Tropical Forest & Botanical Garden. Visit Web site for more information. January 18 to January 22, in Key West Premier Racing presents: Key West 2010 Nearly 300 racing yachts compete for class championships in this international midwinter sailboat regatta. Contact: (781) 639-9545 January 22 to January 24, in Key West Hog's Breath King Mackerel Tournament Anglers are to use fast boats to target the voracious king mackerel, also known as kingfish, for cash prizes. Contact: (305) 296-0364 Email: lee@murraymarine.com January 23, in Key West Anne McKee Artists Fund Auction Nearly 100 artists are to exhibit and auction their work to raise money for the fund that provides project-based grants to Keys artists. Artwork includes original paintings, sculpture, photography, fiber art, ceramics and more. East Martello Museum, 3501 S. Roosevelt Blvd. Email: info@annemckeeartistsfund.org January 30 to January 31, in Key West 25th Annual Key West Craft Show Juried artisans and crafters display their talents at a popular show on lower Whitehead and Caroline Streets in historic Old Town. Contact: (305) 294-1241 Email: kwartctr@earthlink.net February 12 to February 14, in Key West Civil War Heritage Festival Re-enactments, military parades, sea battles with schooner ships, and more await for this unique historical event. Contact: 305-292-6850 February 25, in Key West Friends of the Key West Library Bi-annual Fund Raiser A catered affair with entertainment, to be held at the Studios of Key West, from 6 p.m. to 7:30 p.m., cost $100 per person. Call for details. Contact: Brewster Chamberlin 305-293-0713 Email: smithchamberlin@aol.com February 27 to February 28, in Key West Old Island Days Art Festival The 45th annual juried fine art show is set on lower Whitehead Street in historic Old Town. The highly acclaimed show features oil paintings, watercolors, sculpture, photography and other offerings by artists from around the United States. Contact: (305) 294-1241 April 10 to April 17, in Florida Keys Bubbafest Bike Tours New in the Florida Keys, join a biking and resort camping experience, from Key Largo to Key West. Lodging, meals and plenty of sunshine, scenery and memories included. Event limited to first 125 participants. Visit Web site for details. Contact: Bubba (321) 759-3433 Email: bikerbubba@aol.com April 28 to May 02, in Key West Key West Songwriters’ Festival The 15th-annual showcase of musical magic features America’s foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. Contact: (305) 304-0814 May 13 to May 16, in Florida Keys Marathon Community Theater presents: Deathtrap The longest running comedy-thriller on Broadway, Deathtrap is a story where everyone has a hidden motive. Just when you think you have it figured out, the rug flies right out from under you. Showtime 8 p.m., matinee 3 p.m. Contact: (305) 743-0408 May 29 to June 06, in Key West Pridefest Key West 2010: Diversity In Paradise 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. Contact: (305) 292-3223 June 12, in Key West The Original FKCC Swim Around Key West Sponsored by the Bone Island Masters Club, this USMS-sanctioned event is a 12.5 mile swim clockwise around the island of Key West. Age groups 18 through 65 and older can register. Visit Web site for details. Contact: Lori Bosco (305) 809-3562 Email: aqualb@aol.com