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2013 is just a couple weeks away, can you believe it! If you are hitting Key West and the Florida Keys next year for a vacation, here are some special events that might be worth checking out.

While this calendar lists select highlights for 2013, a full schedule of events throughout the Keys can be found at

2013 Events for Key West & The Florida Keys

Jan. 3: Orange Bowl Swimming Classic. Key Largo. Some of the best college swimmers in the country, and perhaps future Olympians, compete each year at Jacobs Aquatic Center, mile marker (MM) 99.6 oceanside, in a free-to-attend event that is part of the celebration surrounding the annual Orange Bowl college football game in Miami. Visit or call 305-453-7946.

Jan. 4-5: Ragnar Relay Florida Keys Race. This 199-mile race takes runners throughout the Florida Keys to the southernmost island in the continental U.S. on a route beginning in Miami and ending in Key West. Visit

Jan. 10-20 (workshops Jan. 13-17): 31st Annual Key West Literary Seminar. Key West. The seminar’s 2013 topic is “Writers on Writers,” offering workshops, panel discussions, readings and receptions that feature some of contemporary literature’s leading writers. Visit or call 1-888-293-9291.

Jan. 10-19: Uncorked … the Key Largo and Islamorada Food & Wine Festival. Key Largo and Islamorada. Enjoy a multisensory experience as Key Largo and Islamorada’s culinary experts “step up to the plate” to present nearly 30 tasty food, wine and spirits events. Savor the flavors of the Keys in 10 days of culinary events, cooking demonstrations, themed wine dinners, food and wine pairing classes, progressive wine dinners, art and wine shows, and the festival finale, “A Grand Tasting.” Visit or call 305-394-3736.

Jan. 12: No Name Race. Big Pine & the Lower Keys. Join a 5k walk and run that benefits the Monroe County Domestic Abuse Shelter. The race begins at 8 a.m., covers 3.1 miles and is based at the Old Wooden Bridge Guest Cottages & Marina on Big Pine Key. Visit or call 305-743-5452.

Jan. 17: Third Thursday Art Walk. Islamorada. Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans who are spotlighted in galleries at Morada Way between MM 81 and 82 as well as “culinary art” and live music 5-9 p.m. Free admission. The Art Walk is held the third Thursday of each month. Visit

Jan. 18-19: 53rd Annual Historic House Tours.Key West. Presented by the Old Island Restoration Foundation, the house and garden tours offer a rare opportunity to see inside some of Key West’s magnificent, charming and tropical residences that reflect the varied tastes and originality of their owners. Additional tours are scheduled Feb.15-16 and March 15-16. Visit or call 305-294-9501.

Jan. 19: Art Under the Oaks. Islamorada. This art show at the San Pedro Church features arts and crafts in many mediums, as well as food vendors and live music, from 9 a.m. to 4 p.m. Visit or call 305-664-5574.

Jan. 19: Florida Keys Seafood Festival. Key West. This family-oriented feast features fresh local Keys seafood, drinks, marine-related crafts, youth activities and live music. The free-admission annual event is held at Bayview Park. Visit or call 305-872-9026.

Jan. 19-20: Big Pine Key Nautical Flea Market. Big Pine & the Lower Keys. All things nautical are to be displayed and sold at the free-admission event that also includes live music, food and beverages. The seafaring sale takes place on the grounds of the Lower Keys Chamber of Commerce, MM 31 oceanside. Visit or call 305-872-2411.

Jan. 20: Key West Half Marathon. Key West. In its 15th year, this run attracts more than 1,000 annual participants and has been recognized by Runners World magazine as one of the 10 great half-marathons of the winter season. The 13.1-mile course through Old Town Key West passes Key West landmarks and includes the scenic waterfront. Visit or call 305-240-0727.

Jan. 20-25: Key West Race Week 2013. Key West. Elite racing yachts and crews from around the world compete for class championships in one of the most prestigious regattas on the international sailing circuit. Visit or call 781-639-9545.

Jan. 24-27: Key West Food and Wine Festival. Key West. Top chefs and restaurateurs showcase their culinary creativity and the Keys’ indigenous cuisine in a tasty schedule of events for food lovers. Attendees also can participate in food-related adventures during the savory celebration. Visit or call 800-474-4319.

Jan. 26-27: Islamorada Fine Art Expo. Islamorada. Sponsored by the Morada Way Arts District, the event includes a “meet and greet” with artists and a high-end juried show within the Morada Way Art District. The expo features remarkable fine art and handcrafted items, music, food and performance art surprises. Visit .

Jan. 26-27: 28th Annual Key West Craft Show. Key West. More than 100 juried artisans and crafters gather to display their talents at a popular show on lower Whitehead Street in historic Old Town Key West. Visit or call 305-294-1241.

Jan. 26-27: 4th Annual Key Largo Stone Crab & Seafood Festival. Key Largo. Full of fresh conch, local stone crab and other seafood, entertainment and fun for the entire family, the festival includes cooking demonstrations, eating and costume contests, a kids’ play area, arts and crafts vendors, music and more. Visit or call 305-451-4502.

Jan. 27: Key West Master Chefs Classic. Key West. Local restaurants vie for top honors in three categories: appetizers, entrees and desserts. Attendees sample the culinary treats while judges pick the winners. The show is held 4-7 p.m. at Westin Key West Resort & Marina. Visit

Feb. 4-10: 29th 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

Feb. 8-10: Civil War Heritage Days. Key West. Colorful Civil War re-enactments and tours of Key West’s historic Civil War-era Fort Zachary Taylor highlight the journey into the island’s past. Visit and click “Events” or call 305-292-6850.

Feb. 23-24: 19th Annual Pigeon Key Art Festival. Marathon. Artists and craftspeople are to exhibit their work at Marathon Community Park, MM 49 oceanside. The event also features live music and food. Attendees can use their ticket stubs toward a tour of historic Pigeon Key, a tiny island where Florida Keys Over-Sea Railroad workers lived in the early 1900s. Visit or call 305-509-0345.

Feb. 23-24: Upper Keys Gigantic Nautical Flea Market. Islamorada. Hundreds of marine and water-sports 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 or call 305-394-3382.

Feb. 23-24: Old Island Days Art Festival. Key West. The 48th 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 or call 305-294-1241.

March 1-2: Seventh Annual Sombrero Beach Run. Marathon. 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 event organized by the Southernmost Runners Club. Other attractions include music, awards, raffles, prizes, food and entertainment. Visit

March 2: Conch Shell Blowing Contest. Key West. An island tradition for more than 50 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make “music” with fluted conch shells. Visit or call 305-294-9501.

March 2: 37th Annual Marathon House & Garden Tour. Marathon. Tour beautiful homes and extraordinary gardens in the Marathon area that reflect Keys living. Each home is to be adorned with floral arrangements created by Marathon Garden Club members. Other attractions include an art show at the club, MM 50 bayside. Visit or call 305-743-4971.

March 6-10: Song Man, Dance Man. Key Largo. Presented by Key Players with the Friends of Key Largo Cultural Center, Jon Peterson stars in a rollercoaster ride through the lives of seven show business icons: Fred Astaire, Gene Kelly, Donald O’Connor, Bobby Darin, George M. Cohan, Anthony Newley and Sammy Davis Jr. Show times are at 8 p.m. at Murray E. Nelson Government & Cultural Center, MM 102.

March 9-10: 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

March 16: Woofstock Music Fair. Islamorada. A day of peace, paws and music comes alive as MarrVelous Pet Rescues and Adoptions hosts a free family fun event at Islamorada’s Founders Park, MM 87. Join the “fur out” festival featuring local rescue groups, food, drinks, vendors, contests and demonstrations. Leashed well-behaved dogs are welcome. Visit

March 23-24: Naval Air Station Key West Southernmost Air Spectacular. Key West. The U.S. Navy flight demonstration team Blue Angels and other military and civilian aerial performers are to fill the skies at this free-admission, family-friendly event. Visit

April 4-7: Second Annual Brew on the Bay. Key Largo. Presented by the Rotary Club of Key Largo, the craft beer festival includes a home brew competition, more than 80 craft beers from around the world featured in an unlimited tasting with food, music and entertainment along the waterfront. Visit

April 7: 19th Annual Bay Jam. Islamorada. This music and art festival stars local and guest artists performing on the shores of Florida Bay at the Capital Bank Amphitheater at Founders Park, MM 87. Visit or call 305-394-2765.

April 13: Cuban Cultural Exposition & Hot Havana Nights. Key West. The Key West Tropical Forest & Botanical Garden presents a celebration of the Cuban contribution to Keys culture in dance, music and food. Highlights include a renowned Cuban band, Tropicana-style revue, artwork by Cuban and émigré artists and a taste of the island 90 miles from Key West. Visit or call 305-296-1504.

April 13: 32nd 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. Visit or call 305-395-7040.

April 13-14: 22nd 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 or call 305-664-4503.

April 19-28: Conch Republic Independence Celebration. Key West. Parades, bed races, parties and a wacky “drag race” commemorate the founding of the Conch Republic April 23, 1982, in response to a U.S. Border Patrol roadblock that halted traffic in and out of the Florida Keys. Visit or call 305-296-0213.

April 21: Race Around the Rock. Key West.A new 15k run in Key West, the event has a 7 a.m. start time. The course is a flat, fast course beginning at the foot of Margaret Street. Enjoy the island city’s scenic waterfront and see a piece of Key West history while running through Old Town. Visit

April 29: 18th 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 or call 305-296-6196.

April 21-28: 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

May 1-5: Key West Songwriters’ Festival. Key West. The annual showcase of musical magic features a large roster of America’s foremost performing songwriters. Dozens of concerts are staged in intimate, audience-friendly island settings. Visit

May 2-5: Humphrey Bogart Film Festival. Key Largo. The inaugural event is to screen a rotating selection of Bogie classics centered around a theme of “Film Noir,” a genre in which Bogart excelled during the 1940s and 1950s. Also planned are a formal Bogart Ball, an outdoor screening of “Casablanca,” a display of Bogart memorabilia, tours on the fully restored African Queen and question-and-answer sessions with the star’s son, Stephen Bogart. Visit

May 11: Battle in the Bay Dragon Boat Festival. Key West. Catch the adrenaline rush and enjoy close-up views as boats race along a 400-meter course parallel to the quay in the submarine basin at Truman Waterfront. The Awakening the Dragon Ceremony kicks off the event at 8:15 a.m. and race action begins at 9 a.m. with qualifying heats. Highlights include a Flower Ceremony featuring breast cancer/survivor teams and a 2,000-meter endurance race. Races are free to watch. Visit

May 15: Shipwrecks of the Keys & Underwater Archeology. Islamorada. Presented by the Florida Keys History of Diving Museum, this informal educational program is part of a monthly Immerse Yourself in Diving History lecture series exploring humankind’s attempts to explore, understand and venture under the sea. Visit

May 16-19: 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 or call 305-394-3736.

May 17-18: 11th 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 or call 305-294-9911.

June 5-9: 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. Events typically include pool and dance parties, comedy and film, a street fair, contests, a pride parade and more. Visit

June 23: FKCC Swim Around Key West. Key West. This United States Masters Swimming-sanctioned event is a 12.5-mile swim clockwise around the island of Key West that is open to all age groups. Individual swimmers and relay teams can compete. Other attractions include a swim meet. Visit or call 305-809-3562.

July 4: Independence Day Fireworks. Throughout the Florida Keys. Key Largo offers fireworks at Blackwater Sound, where viewing is best at bayside restaurants around MMs 103-104; Islamorada’s Founders Park is the site of an old-fashioned “Spirit of Islamorada” celebration; Marathon’s Sombrero Beach hosts a family-friendly extravaganza; the Lower Keys’ fireworks display is set for Sugarloaf Airport, MM 17 bayside, and Key West’s luxurious Casa Marina Resort & Beach Club is the site of a picnic celebration and fireworks. Visit for complete regional listings and individual event details.

July 11-14: 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 or call 305-296-6534.

July 13: 29th 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 or call 305-872-2411.

July 16-21: Hemingway Days. Key West. The 33rd annual celebration of the legendary author’s work and lifestyle features literary readings, a short story competition, marlin fishing tournament, Sloppy Joe’s “Papa” Hemingway Look-Alike Contest and more. A celebration will be held July 21 honoring the 114th anniversary of Hemingway’s birth. Visit for look-alike events or for all other events.

July 20: Hemingway 5K Sunset Run & Paddleboard Race. Key West. The oldest ongoing 5k run in Key West, the event is to be held at 7:30 p.m. The course is a flat, fast 3-mile course starting at the Southernmost Point in the continental United States. A 3.5-mile paddleboard race is scheduled as well. Visit or call 305-204-0727.

Aug. 16-17: Anything that Floats Race. Key Largo. Grab your oars and anything that floats and enjoy this wacky, family-friendly on-the-water race of vessels crafted from items around the house. A fireworks show is to follow on Blackwater Sound, MM 104 bayside. Visit

Aug. 29 – Sept. 2: Fourth Annual Key West Brewfest. Key West. More than 150 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 or call 800-354-4455.

Aug. 30 – Sept. 1:Heroes Welcome Tribute Weekend. Duck Key. Each fall Hawks Cay Resort hosts an annual Heroes Welcome program to honor military, fire and rescue, law enforcement and medical personnel. Planned attractions include an All-American barbecue, heroes tribute and country music concert. Visit or call 1-888-313-5749.

Sept. 3-8: Womenfest. Key West. Thousands of singles, couples and groups of women flock to Key West each year for this renowned celebration for lesbians and their friends. Activities generally include dance parties, poolside gatherings, sailing and snorkeling, live music, comedy performances and more. Visit or call 800-535-7797.

Sept. 19-22: 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 or call 800-545-2561.

Sept. 21: Conch Scramble Par-Tee on the Water. Islamorada. This wacky on-the-water charity golf tournament brings together four-person teams to enjoy a game of nine holes by boat. Participants “drive” biodegradable golf balls toward floating greens (without any sand traps) and proceeds benefit Keys charities. Visit

Sept. 25-29:Florida Keys Birding & Wildlife Festival. Marathon & the Lower Keys. A celebration of the natural wonders of Florida wildlife takes place at the peak of the fall birding season. The event includes field trips focusing on education and conservation relating to Keys birds and wildlife, nature photography, hikes, kayak excursions and a family-fun environmental fair. Visit or call 305-872-0774.

Oct. 11-13: Key West Marathon. Key West. The weekend event includes a Friday fitness expo and Saturday morning 26.2-mile marathon. The scenic, flat course takes runners through Key West, across Stock Island and on to Rockland Key, allowing a rare opportunity to view both the Atlantic Ocean and Gulf of Mexico. Paddling, snorkeling and other water-based activities are planned Sunday. Call 305-394-4065 or email [email protected].

Oct. 17-20: Key Largo Pirates Festival. Key Largo. Buccaneers and wenches can enjoy three days of piratical fun including a costume contest, walk the plank challenge, rum tasting, booty hunt, pirate show, thieves market, underwater poker and more. Visit

Oct. 18-19: 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

Oct. 18-27: 34th 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. The 2013 festival theme is “Super Heroes, Villains … & Beyond!” Visit or call 305-296-1817.

Nov. 3-10: 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 or call 305-296-6166.

Nov. 14: Key Largo Chamber of Commerce’s 32nd Annual Cook-Off. Key Largo. The culinary competition is open to professional and amateur cooks and chefs, as well as young aspiring chefs. Categories for judging and public sampling include soups and chowders, appetizers, sides and salads, main dishes and desserts. Visit or call 305-451-4747.

Nov. 8-9: Key Largo Bridge Run. Key Largo. Enjoy the sunrise where the Atlantic Ocean meets the Gulf of Mexico while racing 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

Nov. 27 – 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 Key West Bight Preservation Association presents the festivities. Visit or call 305-304-2633.

Dec. 14: 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 or call 305-872-2411.

Dec. TBA: 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 on each scheduled evening. Hosted by the Key West Innkeepers Association, the tours include culinary masterpieces by top island chefs. Visit or call 305-295-1334.

Dec. 6-8: Christmas in the Keys. Marathon. An event full of food, beverages, regional vendors, music and entertainment for the entire family kicks off the Middle Keys holiday season. The fun is headquartered at Hawks Cay Resort, located on Duck Key. Highlights include a lighted boat parade, delicious treats and cocktails, Christmas-themed competitions and photos with Santa in his casual Keys attire. Visit .

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 or call 305-664-4503.

Dec. 7: 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, MMs 103-104. Visit or call 305-451-4502.

Dec. 7: Boot Key Harbor Lighted Boat Parade. Marathon. Watch as dinghies, mega-yachts and vessels in between parade through the harbor during this Middle Keys holiday happening. The best viewing sites include Lazy Days South, Marathon Marina, Sombrero Dockside Lounge and Burdine’s Waterfront.

Dec. 14: 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. 14: Schooner Wharf Bar & Galley 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 holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport. Visit or call 305-292-3302.

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 Bay Resort and the Caribbean Club, MMs 103-104. Visit or call 305-451-4502.

Dec. 31: Key West New Year’s Eve Celebrations. Key West. The Southernmost City typically 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.

Florida Keys events calendar:
Florida Keys visitor information: or 1-800-FLA-KEYS
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About the Author: RumShopRyan

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty. To learn more, visit our About Us Page.