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Calendar of Events for Key West

March 01 - Jun 30, 2014, in Key West
Key West Art & Historical Society presents: Marky Pierson, Night Visions in Technicolor 
Emerging local artist and graphic designer Marky Pierson is to exhibit new paintings and designs focusing on three distinct categories: 'Conch Night' Series featuring the Hemingway House, Custom House and Curry Mansion; 'Squishy Femme' Series explores soft, squishy and everything womanly; 'Graphic Design' Series features graphic posters of iconic Key West images and large format paintings inspired by vintage tourism posters. Custom House Museum is located at 281 Front Street, and open daily 9:30 a.m. to 4:30 p.m.
Contact: 305-295-6616
April 01 - Sep 30, 2014, in Key West
Key West Art & Historical Society presents: Key West or Bust, A History of Tourism 
The Florida Keys have historically been an alluring travel destination for travelers around the world. With the onset of the Great Depression in the 1930s, tourism in Key West was the lynchpin in warding off bankruptcy. This exhibit explores the history of tourism in the Florida Keys from the 1920s until the 1980s while focusing specifically on transportation, accommodation, travel brochures and postcards. Custom House Museum is located at 281 Front Street, and open daily 9:30 a.m. to 4:30 p.m.
Contact: 305-295-6616
April 06 - Nov 30, 2014, in Key West
Key West Fishing Tournament 
More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes. 
Contact: Rob Harris 305-587-6718; Doris 305-295-6601
June 01 - Sep 30, 2014, in Key West
Key West Art & Historical Society presents: Will Fernandez 
For longer than a decade, Will Fernandez has been one of Key West's most enchanting artists. He paints and sculpts almost entirely from memory and makes his works quite humorous and whimsical. In this exhibition, he displays a number of his impressionistic-style paintings, as well as a selection of his distinctive sculptures in stone, wood, clay and more. Custom House Museum is located at 281 Front Street, and open daily 9:30 a.m. to 4:30 p.m.
Contact: 305-295-6616
June 11 - 15, 2014, in Key West
Key West Pride 
Key West shows its Pride every day, and this is your chance to be a part of the celebration! This five day celebration includes a film festival, dance parties, drag shows, bike tours, clothing-optional pool parties, water excursions, a street fair, Pride Pageants, and a 'Pride in Our Community' Parade down Duval Street. 
Contact: Guy Ross 305-294-4603
June 13 - 15, 2014, in Key West
Fifth Annual Key West Bacchanalia 
A food and wine event with a twist - enjoy a Grand Tasting Village, Celebrity Cook-off, Burger Wars, Bulldogs BBQ, seminars, dinner and mixology competitions and more! A spectacular three-day fiesta of food, spirits and wine. Enjoy celebrity chefs, Bravo TV Top Chef stars, world-renowned mixologists, and some of the best rums, spirits, wine, beer and food from local restaurants, in one of the Keys' premier foodie events.
Contact: Aga and James Hilferty 305-766-3356
June 14, in Key West
Key West Island Swim: FKCC Swim Around Key West 
Long distance solo swimmers and relay teams of two to six people, with or without fins, can compete in this United States Masters Swimming-sanctioned even, a 12.5-mile swim clockwise around the island of Key West. The clockwise route around the island takes swimmers through the waters of the Atlantic Ocean and Gulf of Mexico, ending where they began at Smathers Beach. Open for all age groups. A swim meet is held June 15. 
Contact: Lori Bosco 305-809-3562
June 20 - 22, 2014, in Key West
Key West Gator Club Dolphin Derby 
A grand prize of $5,000 cash is to be awarded the boat team with the largest aggregate weight in dolphin during the derby's two fishing days, with teams allowed to enter one qualifying fish each day. Second- and third-place teams will earn $2,500 and $1,000, respectively. Individual anglers can compete for trophies, prizes and cash totaling more than $15,000 in the tournament's divisions for male, female and junior participants. 
Contact: Greg Oropeza 305-304-1348
July 10 - 13, 2014, in Key West
Mel Fisher Days 
This annual celebration brings together Mel Fisher fans and treasure-hunting enthusiasts in a celebration of the anniversary of Fisher's discovery of the shipwrecked Spanish galleon Nuestra Senora de Atocha.
Contact: 305-296-6534
July 13 - 16, 2014, in Key West
Del Brown Permit Tournament 
Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well. 
Contact: Loren Rea 305-360-6969
July 15 - 20, 2014, in Key West
Hemingway Days 
The 34th annual celebration of the legendary author's work and lifestyle features literary readings, a theatrical premiere, short story competition, fishing tournament, Sloppy Joe's Look-Alike Contest and a pre-birthday "party" commemorating Ernest's July 21st birthday. 
Contact: (305) 296-2388 (Look-Alike); 294-0320 (literary)
July 16 - 19, 2014, in Key West
Drambuie Key West Marlin Tournament 
Anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West's annual Hemingway Days, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total. 
Contact: Tim Greene 305-304-0317
July 19, in Key West
Hemingway 5K Sunset Run & Paddleboard Race 
This is the original and oldest ongoing 5K Run in Key West and takes place as part of the the annual Hemingway Days Festival. The race course is a scenic flat course that runs past Key West's most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point and the famous Green Parrot Bar! The Lazy Dog Paddle Board Race will take place before the 5K and kicks off at 6PM. The 4 mile paddle board challenge will start at the Beach by the Southernmost Beach Cafe. Visit website for more details. 
Contact: Barb Wright at 305-240-0727
August 14 - 17, 2014, in Key West
Tropical Heat 
Tropical Heat offers All Male-All Adult fever-pitch revelry on the island whose openness and respect for diversity have made it a world-renowned gay vacation destination. The festival includes more than a dozen intriguingly decadent events ranging from drag shows to themed pool parties and gatherings at island clubs.
Contact: 305-294-4603; 800-535-7797
August 28 - Sep 01, 2014, in Key West
Fifh Annual Key West Brewfest 
More than 150 beers and micro-brews are on to be tap at this "tasty" annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event are some of the great activities on tap.
Contact: 800-354-4455
September 04 - 07, 2014, in Key West
Womenfest Key West 
Womenfest offers a wide range of activities guaranteed to appeal to a broad range of interests. Golfing with palm trees and iguanas, clothing-optional pool parties, a sizzling dance club scene, and women-only water excursions that range from jet skis to dolphin watching all promise to pique the interest of the more adventurous while film, live music, and special comedy shows offer the opportunity to enjoy paradise at a slower pace. All of this on a tropical island that is "close to perfect but far from normal." 
Contact: 800-535-7797; 305-294-4603
September 05 - 07, 2014, in Key West
Robert James Sales S.L.A.M. Celebrity Tournament 
In the first of three tournaments in the annual Redbone Celebrity Tournament Series, also called The Trilogy, anglers target tarpon, permit and bonefish to achieve the coveted "flats grand slam." The event raises funds for the fight against cystic fibrosis. 
Contact: Susan Ellis 305-664-2002
September 18 - 21, 2014, in Key West
42nd Annual Phil Peterson's Key West Poker Run 
It's an All-American event as motorcycle enthusiasts from around the U.S. travel the Keys' scenic Overseas Highway - designated Florida's only All-American Road - from mainland Florida to Key West to raise money for charity. Winner takes all, and can win a new Harley-Davidson Motorcycle or cash. Stops are arranged throughout the Keys with a final celebration in Key West. Keys-wide events planned for the entire week. 
Contact: Drew Peterson 305-235-4023
October 09 - 13, 2014, in Key West
SoMo Marathon & Half Marathon 
Presented by Pat Croce's Rum Barrel, this event is one of a kind! Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half promises just that- 26.2 or 13.1 miles of ocean and gulf views, as well as iconic Key West landmarks. A full weekend of events include the race and a Sunday Paddle Board race for the Special Olympics of Monroe County. 
Contact: 305-766-5284
October 17 - 26, 2014, in Key West
35th Annual Fantasy Fest 
This outrageous 10-day costuming and masking celebration features flamboyant costume competitions including one for pets, promenades, street fairs and a grand parade that stars marching groups, island bands and lavish floats. More than 40 masquerade contests, themed parties, parades and other spectacles are to challenge the creativity of mask and costume designers. 
Contact: 305-296-1817
October 17 - 18, 2014, in Key West
Goombay Festival 
Held in Key West's historic Bahama Village neighborhood, the lively Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets.
Contact: Bob Oberle 305-304-2643
October 20, in Key West
Heroes and Villains 5k Run/Walk 
Be super, be evil, be AWESOME and get your run on! Dress up as your favorite Superhero or Super Villain and run, walk or fly to the finish line. Prizes are awarded for most creative, best group, scariest and funniest characters. Winner medals and awards are to given for overall male and female winners, masters (40+) male and female winners. Register online. Race starts at 6 p.m. The race begins and ends at The Reach, A Waldorf Astoria Resort and ends with a luau. Come for the run, stay for the fun!" ? 
Contact: Beth Moyes 305-747-8563
October 21, in Key West
32nd Annual Headdress Ball 
This "over the top" contest includes an extravagant show with lots of Key West razzle dazzle, and is a competition "head and shoulders" above the rest with contestants judged from the shoulders up! Major cash prizes including a $1,500 grand prize. Tickets sell out quickly! Held at the Southernmost on the Beach, 508 South Street. 
November 02 - 09, 2014, in Key West
34th Annual Key West World Championship Races 
Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and conclude in November for the famous Key West World Championships. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West's longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power. 
Contact: 305-296-6166
November 07 - 10, 2014, in Key West
Third Annual Key West International Latin Arts Festival 
Experience "Vientos del Alma," a celebration of traditional Latin American cultural arts featuring dance and percussion workshops, artists' exhibits, poetry readings, wine tastings, culinary surprises and a spectacular theatrical concert. Vientos del Alma (Winds of the Soul) highlights include: InnerNacionalSound's Christian Monz√≥n and Valerie Carr, renowned Miami-based Tango Times dance luminaries Roxana Garber and Oscar Caballero and an outstanding international line-up of local and visiting musicians, folk dancers and thrilling performers. Visit website for details and tickets; events to be held at San Carlos Institute. 
Contact: 305-394-0808
November 12 - 16, 2014, in Key West
Third Annual Key West Film Festival 
Showcasing films that exhibit excellence in storytelling, the festival's lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the Tropic Cinema and San Carlos Institute. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers. 
Contact: 941-527-9385; 305-295-9112
November 28 - 30, 2014, in Key West
This annual event comprises three days of artistry throughout historic Old Town, with spotlight events rotating among the island's multiple cultural districts. Highlights include live mural painting, gallery openings and showcases, performance art, theater and musical performances. 
Contact: Marky Pierson 305-619-2275
December 04 - 07, 2014, in Key West
TRIKW Swim-Bike-Run in Paradise 
The Key West Triathlon and Expo expects to host a maximum of 1,000 participants and some of the sport's best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances. 
Contact: Doug Bradshaw 305-797-8361
December 31, in Key West
New Year's Eve Shoe Drop Celebration 
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. 
Contact: Bob Oberle 305-304-2643
CALL US 1-(800) 797-8787

Key West Vacation Rentals 1075 Duval St Suite C19 Key West, Florida 33040 +1 (305) 296-9292

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