There’s always something happening in the Florida Keys & Key West, from festivals focusing on the area’s colorful history, artistic culture and quirky ambiance to events that celebrate the Keys’ underwater paradise. While this calendar lists selected highlights for 2012, a comprehensive schedule of events throughout the Keys can be found at www.fla-keys.com/
Feb. 18-19: Gardenfest Key West. Key West. South Florida’s top nurseries are to show bromeliads, orchids, fruit trees, palms, tropical flowers and natives at the Key West Tropical Forest & Botanical Garden’s annual plant sale. Other attractions include landscaping workshops, garden supplies booths, arts and crafts and docent tours. Visit www.keywestbotanicalgarden.org or call 305-296-1504.
Feb. 20-26: 28th Annual Winter Star Party. Big Pine & the Lower Keys. Approximately 600 astronomers from around the world gather to view southern constellations, comets and stars in the Lower Keys’ clear night skies — virtually the only place in the continental U.S. where they can be viewed. Lectures, programs and workshops round out the event. Visit www.scas.org/wsp.html for more information.
Feb. 25-26: Upper Keys Gigantic Nautical Flea Market. Islamorada. Hundreds of marine- and water sports-related vendors offer wares to thousands of buyers seeking deals on new and used boats, marine equipment, electronics, fishing tackle, nautical arts and crafts, dive gear and more. The event is held at Founders Park, MM 87. Visit www.
Feb. 25-26: Old Island Days Art Festival. Key West. The 47th 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. Visit www.keywestartcenter.com/
March 2-3: 6th Annual Sombrero Beach Run. Marathon. Come for the run and stay for the sun. A comprehensive race format includes a 15k Challenge, 10k Run and 5k Walk/Run, all set for 8 a.m. at Sombrero Beach. Runners from around the Keys, country and world participate in the weekend-long event organized by the Southernmost Runners Club. Other attractions include music, awards, raffles, prizes, food and entertainment. Visit www.sombrerobeachrun.com.
March 3: 50th Annual Conch Shell Blowing Contest. Key West. An island tradition that celebrates the historic importance of conch in the Keys, this unique contest features contestants in several age categories attempting to make “music” with fluted conch shells. Visit www.oirf.org or call 305-294-9501.
March 3: 36th Annual Marathon House & Garden Tour. Marathon. Tour beautiful homes and extraordinary gardens in the Marathon area, all selected for their uniqueness and reflection of Keys living. Each home is to be adorned with floral arrangements created by members of the Marathon Garden Club. Visit www.marathongardenclub.org or call 305-743-4971.
March 10: Woofstock Music Fair. Islamorada. A day of peace, paws and music comes alive as MarrVelous Pet Rescues and Adoptions hosts a family fun event at Islamorada’s Founders Park, MM 87. Join the “fur out” festival featuring local rescue groups, food, drinks, vendors, contests, demonstrations and more. Admission is free and leashed, well-behaved dogs are welcome. Visit www.keyswoofstock.com.
March 10-11: The Original Marathon Seafood Festival. Marathon. Gourmet delicacies from the waters of the Florida Keys, live music, a kids’ play area and an array of vendors highlight this annual weekend event that generally attracts more than 15,000 seafood lovers and families to Marathon Community Park, MM 49 oceanside. Visit www.marathonseafoodfestival.
March 24-25: Cuban Cultural Exposition & Hot Havana Nights. Key West. The Key West Tropical Forest & Botanical Garden presents Cuban-themed events including exhibits of art, crafts and artifacts, lectures, dominos and dancing lessons. Events culminate in a Hot Havana Nights gala with dining, dancing and more. Visit www.keywestbotanicalgarden.org or call 305-296-1504.
March 31-April 1: 21st Annual Florida Keys Island Fest. Islamorada. The annual event features music, art, food and fun. Island Fest hosts a world-class art show with 100 artists and crafters from around the state, great live music and a “Taste of the Islands” competition where the best Upper Keys restaurants compete for coveted awards. Visit www.islamoradachamber.com or call 305-664-4503.
April 8: Underwater Easter Egg Hunt. Key Largo. The Easter Bunny stars in the annual underwater egg hunt off Key Largo to benefit Kids in Special Situations, a local charity for needy children. The event, held each year on Easter Sunday, is hosted by Atlantis Dive Center on its 8:30 a.m. dive. Visit www.captainslate.com or call 305-451-3020.
April 15: 18th Annual Bay Jam. Islamorada. This music and art festival features local and guest artists performing on the shores of Florida Bay at the TIB Amphitheater at Founders Park, MM 87. Visit www.keysice.com or call 305-394-2765.
April 20-29: 30th Annual Conch Republic Independence Celebration. Key West. Parades, bed races, parties and a wacky “drag race” commemorate the founding of the Conch Republic on April 23, 1982, in response to a U.S. Border Patrol roadblock that halted traffic in and out of the Florida Keys. Visit www.conchrepublic.com or call 305-296-0213.
April 21: 31st Annual Seven Mile Bridge Run. Marathon. A field of 1,500 runners participates in this annual foot race across the longest segmental bridge in the world. Call 305-395-7040 or visit www.southernmostrunners.com/.
April 23: 17th Annual Taste of Key West. Key West. Scores of area restaurants present mouthwatering samples of their cuisine to benefit AIDS Help Inc. The culinary celebration takes place at the Truman Waterfront overlooking Key West Harbor. Visit www.aidshelp.cc/taste.html or call 305-296-6196.
April 26-29: Key Largo Conch Republic Days. Key Largo. This festival celebrates the Florida Keys’ independence from the mainland. Attractions include daily events at Key Largo restaurants, drink and food specials, contests and more. Visit www.keylargoconchrepublicdays.
May 2-6: Key West Songwriters Festival. Key West. The annual showcase of musical magic features America’s foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. Visit www.
May 10-13: Key West Paddleboard Classic. Key West. During this ocean paddleboard race, participants enjoy a challenging 12-mile course over crystal blue waters, circling Key West through scenic mangroves, passing by the Historic Seaport district and more. Visit www.keywestpaddleboardclassic.
May 12: Battle in the Bay Dragon Boat Festival. Marathon. In this high-action beach-launch competition, national and local teams propel colorful dragon boats along a 400-meter course parallel to Sombrero Beach. Races are free to watch. Visit www.battleinthebay.org or call 305-766-1053.
May 17-20: Key Largo’s Original Music Festival. Key Largo. Enjoy the entertainment, food and ambiance of Key Largo. Presented by the Upper Keys Business Group, the event features “on the water” venues, unique entertainers and local musicians. Visit www.
May 18-19: 10th Annual Harry S. Truman Legacy Symposium. Key West. Key West’s political history is highlighted in panel discussions, a reception and tours of the Little White House where Truman spent many working vacations during his presidency. Visit www.trumansymposium.com or call 305-294-9911.
June 6-10: Key West Pride. Key West. The 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. Visit www.pridefestkeywest.com.
June 7-10: Third Annual Key West Bacchanalia. Key West. At this food and wine event with a twist, join Keys celebrity chefs as they face off in culinary competition with a great cause in mind. Benefits support breast cancer research. Visit www.keywestbacchanalia.com or call 305-766-3356.
June 16: The Original FKCC Swim Around Key West and Swim Meet. Key West. This United States Masters Swimming-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 www.fkccswimaroundkeywest.com or call 305-809-3562.
July 12-15: Mel Fisher Days. Key West. 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 Señora de Atocha. Visit www.melfisher.org or call 305-296-6534.
July 14: 28th Annual Underwater Music Festival. Big Pine & the Lower Keys. A quirky concert broadcast underwater for divers, snorkelers and the occasional mermaid emphasizes reef preservation. The submerged songfest is held at Looe Key Reef in the Florida Keys National Marine Sanctuary. Visit www.lowerkeyschamber.com or call 305-872-2411.
July 17-22: Hemingway Days. Key West. The 32nd annual celebration of the legendary author’s work and lifestyle features literary readings, a short story competition, fishing tournament, Sloppy Joe’s Look-Alike Contest and more. A celebration will be held July 21 honoring the 113th anniversary of Hemingway’s birth. Visit www.sloppyjoes.com for look-alike events or www.hemingwaydays.net for all other events.
July 27 – Aug. 5: Key Largo Food & Wine Festival. Key Largo. Set on an island known for its bountiful tropical fruit, fresh snapper, tuna, mahi-mahi, shrimp and lobster, the nine-day festival incorporates gourmet wine dinners with cultural specialties, feasts and fiestas, palate-pleasing adventures and wines from around the world. Visit www.
Aug. TBA: Captain Tony Days. Key West. The late Captain Tony Tarracino was an American icon, saloonkeeper, boat captain, gambler, former mayor of Key West and inspiration for Jimmy Buffett’s “Last Mango in Paris.” The festival is a celebration of Tony’s life, featuring storytelling contests, street fairs, film showing and more. Call 305-296-0160.
Aug. 16-19: Tropical Heat. Key West. Tropical Heat offers four days of all-male revelry on the island city whose openness and respect for diversity have made it a world-renowned gay vacation destination. Visit www.tropicalheatkw.com or call 305-294-4603.
Aug. 30 – Sept. 3: Third Annual Key West Brewfest. Key West. Dozens of beers and micro-brews are on tap at this “tasty” event that benefits Key West Sunrise Rotary Club of the Conch Republic. Beer tastings, food and musical rhythms round out the weekend activities. Visit www.keywestbrewfest.com or call 800-354-4455.
Sept. 4-9: Womenfest. Key West. This festival for lesbians and their friends features parties and gatherings, sailing and snorkeling, live music, comedy performances and other activities. Visit www.womenfest.com or call 800-535-7797.
Sept. 13-16: Phil Peterson’s Key West Poker Run. Florida Keys. Motorcycle enthusiasts from around the U.S. are to travel the Keys’ scenic Overseas Highway from mainland Florida to Key West to raise money for charity. Stops are arranged throughout the Keys with a final celebration in Key West. Visit www.petersonsharley.com or call 800-545-2561.
Sept. 22: Conch Life Scramble. Islamorada. This wacky on-the-water charity golf tournament brings together four-person teams to enjoy a game of nine holes by boat. Proceeds benefit Keys charities. Visit www.conchlifescramble.com or call Lee Christine Young at 305-522-1590.
Sept. 22: Conched In Key West Bar Crawl – Key West. Join a the second annual Charity bar crawl and support Reef Relief. Bar hoppin’ around Key West for a great cause. Visit Facebook.com/KWCrawl for more information.
Sept. 26-30:Florida Keys Birding & Wildlife Festival. Marathon & Lower Keys. A celebration of the natural wonders of Florida wildlife takes place at the peak of the fall birding season. The event includes presentations and field trips focusing on education and conservation as they relate to Keys birds and wildlife, and an environmental fair. Visit www.keysbirdingfest.org or call 305-872-0774.
Oct. 5-7: Third Annual Conchtoberfest. Marathon. This Middle Keys event is full of food, beverage, vendors, music and entertainment for the entire family. “Conchtoberfest Nights” at local venues throughout Marathon lead up to main weekend events at Hawks Cay Resort. All events are open to the public. Visit www.conchtoberfest.com or call 305-289-4901.
Oct. 18-21: Key Largo Pirates Festival. Key Largo. Buccaneers and wenches can enjoy three days of piratical fun including a costume contest, walk the plank, rum tasting, booty hunt, pirate show, thieves market, underwater poker and more. Visit www.keylargopiratesfest.com or call 305-394-3736.
Oct. 19-20: Goombay Festival. Key West. 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. Visit www.goombay-keywest.org for more information.
Oct. 19-28: 33rd Annual Fantasy Fest. Key West. 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. Visit www.fantasyfest.net or call 305-296-1817.
Oct. TBA: Underwater Pumpkin Carving. Key Largo. Divers become underwater artists as they turn pumpkins into Halloween masterpieces beneath the sea in the Florida Keys National Marine Sanctuary. Visit www.amoray.com or call 305-451-3595.
Oct. 23: 30th Annual Headdress Ball. Key West. This “over the top” contest includes an extravagant show with lots of Key West razzle dazzle, as well as cash prizes for winners. The competition is “head and shoulders” above the rest with contestants judged from the shoulders up. Visit www.headdressballkeywest.com/ or call Rebecca Tomlinson at 305-294-4603.
Nov. 4-11: Key West World Championship Powerboat Races. Key West. High-speed powerboats continue Key West’s longstanding tradition in a challenge described as the Indianapolis 500 of powerboat racing. Visit www.superboat.com or call 305-296-6166.
Nov. 8: Key Largo Chamber of Commerce’s 31st Annual Cook-Off. Key Largo. The culinary competition is open to professional and amateur cooks and chefs, as well as young aspiring chefs. Categories include soups and chowders, appetizers, sides and salads, main dishes and desserts. Visit www.keylargochamber.org or call 305-451-4747.
Nov. 10: Key Largo Bridge Run. Key Largo. Enjoy the sunrise where the Atlantic Ocean meets the Gulf of Mexico during the morning race over part of the historic 18-Mile Stretch and the Jewfish Creek Bridge at Key Largo, gateway to the Keys. The race is an outreach of Key Largo Baptist Church. Visit www.keylargobridgerun.com for more information.
Nov. 21 – Dec. 31: Key West “Bight” Before Christmas Holiday Celebration. Key West. The harbor walk along the Historic Seaport at the Key West Bight, stretching from Greene Street to Grinnell Street, is to be festively lit from rooftops to the sea for the holiday season. Celebrate with holiday events, browse at unique island shops and galleries, and relax at waterfront restaurants and watering holes. The festivities are presented by the Key West Bight Preservation Association. Visit www.keywestchristmas.org or call 305-304-2633.
Nov. 21 – Dec. 2: Pirates in Paradise 2011. Key West. Historic Key West is transformed into a pirates’ stronghold with more than 150 pirate entertainers. Tall ships, sea battles, a lively pirate village and marketplace, arts and crafts, pirate sails, a living history encampment and nonstop entertainment celebrate Key West’s maritime history. Visit www.piratesinparadise.com or call 305-296-9694.
Nov. 24: Big Pine & the Lower Keys Island Art Festival. Big Pine & the Lower Keys. Highlights of this holiday event include live music by local entertainers, food, exhibits and booths featuring locally produced arts and crafts. Festivities traditionally take place on the grounds of the Lower Keys Chamber of Commerce, MM 31 oceanside. Visit www.lowerkeyschamber.com or call 305-872-2411.
Nov. 30 – Dec. 1: Key West Triathlon (TRIKW). Key West. The third annual Olympic distance and sprint triathlon event is to bring hundreds of top athletes to Key West. The event typically includes a fitness expo for athletes. Visit www.trikw.com or call 305-394-3469.
Dec. 7: Florida Keys Holiday Festival. Islamorada. This extravaganza traditionally begins with a tree-lighting ceremony at Founders Park, MM 87. Other attractions typically include a holiday parade featuring Santa, a 20-ton mountain of snow for mitten-clad munchkins, a holiday gift bazaar and a silent auction of ornaments decorated by local artists. Visit www.islamoradachamber.com or call 305-664-4503.
Dec. 7 and 15: Holiday Historic Lighted Inn Tours. Key West. Discover the holiday spirit and Key West’s architecture and history by touring several beautifully decorated historic inns each evening. Hosted by the Key West Innkeepers Association, the tours include culinary masterpieces by top island chefs. Visit www.kwholidays.com or call 305-295-1334.
Dec. 8: Key Largo Holiday Lighted Boat Parade. Key Largo. Each year, the waters of Blackwater Sound shimmer as decorated boats parade along the shoreline in celebration of the holiday season. Top spots for viewing and libations include Sundowners, Señor Frijoles, the Marriott Key Largo Bay Resort and Caribbean Club, MM 103-104. Visit www.keylargoboatparade.com or call 305-451-4502.
Dec. 8: Key West Lighted Boat Parade. Key West. Decorated and lighted boats are to cruise through Key West Harbor and the waters of the Historic Seaport. Musical guests are featured and the event is presented by the Schooner Wharf Bar. Visit www.schoonerwharf.com or call 305-292-3302.
Dec. 8: Boot Key Harbor Lighted Boat Parade. Marathon. Watch as dinghies, mega-yachts and anything in between turn the harbor into a sparkling procession along the parade route during this Middle Keys holiday kick-off event. The best viewing sites include Lazy Days South, Marathon Marina, Sombrero Dockside Lounge and Burdine’s Waterfront. Visit www.bootkeyharbor.com/
Dec. 15: Lower Keys Lighted Holiday Boat Parade. Big Pine Key. All boats are welcome to enter the parade including deep-sea cruisers, dinghies, kayaks and canoes. Santa and Mrs. Claus hand out candy to the kids. The best recommended viewing is from Pine Channel Causeway or Parrotdise Waterfront Bar & Grille, 183 Barry Ave. on Little Torch Key. The parade begins at 7 p.m. Call 305-923-5370.
Dec. 31: New Year’s Eve Fireworks on Blackwater Sound. Key Largo. The back bay is the setting for the annual New Year’s Eve fireworks extravaganza hosted by Sundowners, Señor Frijoles, Cactus Jacks, Gus’ Grille at the Marriott Key Largo Beach Resort and the Caribbean Club, MM 103-104. Visit www.keylargofireworks.com or call 305-451-4502.
Dec. 31: Key West New Year’s Eve Celebrations. Key West. The Southernmost City celebrates with a “conch shell drop” at Sloppy Joe’s Bar, 201 Duval St.; the descent of a super-sized red high-heel shoe carrying drag queen Sushi at the Bourbon St. Pub/New Orleans House complex, 724 Duval St., and the descent of a pirate wench from atop a tall ship’s mast in the island city’s Historic Seaport. Call 305-296-2388, 305-293-9800 and 305-292-3302, respectively.
(Lead photo from TCPalm.com)
- Get a Custom Caribbean Trip Plan & Itinerary! We'll help plan your trip based on your interests and our insider knowledge. Click here to learn more.
- See our recommended Travel Credit Cards. This is how we travel for free!
- Get your flight with Skyscanner (you'll never miss a cheap flight)
- Get your accommodation with Booking.com - They have great deals
- Love Pets and a Free Place To Stay? Definitely try Trusted Housesitters
- Need travel tips? Grab a Guide Book
- Need anything on Amazon, use this link, thank you!
- Get your travel insurance with World Nomads or AXA Travel Insurance
- Find our recommended Caribbean hotels, restaurants, charters, & tours here
- Need something else? Check out our list of favorite companies on our resources page