FLORIDA KEYS — There’s always something happening in the Florida Keys & Key West, from eclectic festivals focusing on the area’s colorful history, artistic culture and notable cuisine to events that celebrate the Keys’ unique environment, underwater adventures and quirky ambiance.
While this listing contains selected highlights for the first six months of 2019, a comprehensive and frequently updated year-round calendar of Keys events can be found at fla-keys.com/calendar.
Uncorked … The Key Largo and Islamorada Food and Wine Festival (Jan. 10-20;floridakeysuncorked.com) is a culinary, wine and spirits celebration of savory events showcasing the flavors of Key Largo and Islamorada in the Upper Keys. The festival highlight is the Grand Tasting scheduled Jan. 19 at Islamorada’s Postcard Inn Beach Resort and Marina.
The 37th Key West Literary Seminar (Jan. 10-13; kwls.org), headquartered at Key West’s San Carlos Institute and founded in 1983, explores a different literary theme each year. The 2019 theme, “Under the Influence,” explores the nature of literary influence with readings, discussions and lectures by highly regarded contemporary writers and authors.
The Island Boat Show (Jan. 11-13; http://islandboatshow.com/, billed as the Keys’ “premier boat show,” is to be held at Hawks Cay Resort on Duck Key and Island Christian School in Islamorada. Planned attractions include boats, auction items, food and drink, vendors and fishing seminars.
The Florida Keys Celtic Festival (Jan. 12-13; floridakeyscelticfestival.com) at Marathon Community Park celebrates Celtic musical groups, Irish and Scottish dancing and Highland athletics. Also included in the fun are beverage booths, Celtic merchandise, a Kilts in the Keys event and children’s activities.
The 15th annual Big Pine & Lower Keys Nautical Expo (Jan. 12-13; lowerkeyschamber.com) attracts marine enthusiasts seeking gear at this outdoor “pop-up” showcase for all things nautical. The Lower Keys Chamber of Commerce organizes and benefits from the event.
The 59th annual Key West Home Tours (Jan. 18-19; keywesthometours.com) provide glimpses and tours of unique private homes in the southernmost city in the continental U.S. Tour proceeds benefit the Old Island Restoration Foundation’s grants, scholarships and Oldest House Museum. Tours also are scheduled Feb. 15-16 and March 15-16. During the January tours, Conch Train transportation between showcased homes is available for an additional cost.
The 36th annual Art Under the Oaks (Jan. 19; sanpedroparish.org/index.php/art-under-the-oaks), held at San Pedro Catholic Church gardens on Plantation Key in the Upper Keys, is a day of fine art, original crafts, food and fun for the entire family. Live entertainment and raffles also are among the attractions.
The 14th annual Florida Keys Seafood Festival (Jan. 19-20; floridakeysseafoodfestival.com) is a family-friendly event in Key West’s Bayview Park that features fresh Keys seafood caught, prepared and served by local fishermen and their families. Presented by the Florida Keys Commercial Fishermen’s Association, it also includes celebrity chef demonstrations, hands-on eco activities, live entertainment and a boat show.
The Key West Half Marathon & 5k Run (Jan. 20; keywesthalfmarathon.com/) attracts several thousand runners and walkers eager to experience a scenic 13.1-mile flat course in subtropical Key West. Now in its 21st year, the race is acclaimed as one of the United States’ leading winter half-marathons.
The Kelly McGillis Classic International Flag Football Championship & World Challenge Game (Jan. 22-29; iwffa.com) in Key West is expected to draw some 1,500 women and girls representing 32 teams from the U.S., India, Afghanistan and other countries for flag football events. The World Challenge Game is scheduled Jan. 27 at 6 p.m. at Wickers Field. The popular event is named for McGillis, the “Top Gun” movie actress and former Key West resident.
The 10th annual Key West Food and Wine Festival (Jan. 23-27;keywestfoodandwinefestival.com) is an eagerly anticipated “flip flops required” event in the island city. Attendees can indulge in gourmet galas and tastings, a tropical garden tour with wines and locally inspired treats, and only–in–Key West activities highlighting the city’s culinary scene. A Sunset Grand Tasting at the U.S. Coast Guard Cutter Ingham Museum is set for 5-7 p.m. Jan. 25.
The 25th annual Master Chefs Classic (Jan. 27; masterchefsclassic.com) blends a culinary competition for local chefs with tastings in the appetizer, entrée and dessert categories for 450 attendees. A Key West tradition, the event takes place at the Margaritaville Resort & Marina pier overlooking Key West Harbor.
Mile 0 Fest Key West (Jan. 29 – Feb. 2; mile0fest.com), in its second year, offers a star-studded lineup for fans of the growing Red Dirt and Americana music genres scene. Events are headquartered at the Key West Amphitheater at Truman Waterfront Park and scheduled artists include the Mavericks and Ray Wylie Hubbard.
The 25th Annual Pigeon Key Art Festival (Feb. 2-3; pigeonkeyartfestival.com) at Marathon Community Park attracts scores of art lovers to view creative artwork in the mediums of pottery, painting, glass, sculpture, photography, jewelry and more; live music, Keys cuisine and historical elements also are featured. The Pigeon Key Foundation benefits from the celebrated event.
The American Legion Riders Coral Head Music Festival (Feb. 16-17;coralheadmusicfest.com) is a weekend of fun and music by national and regional bands and entertainers including Vince Neil and John Cafferty. Proceeds from the event, held at the Marathon Community Park Amphitheater in the Middle Keys, benefit area charities.
The Sombrero Beach Run (March 2; sombrerobeachrun.com), in its 13th year in Marathon, attracts several hundred racing circuit runners for a weekend of running and sunning. The event is at Sombrero Beach, at the end of Sombrero Beach Road at mile marker 50. Awards are to be given to overall finishers in a 5k walk and 5k and 10k runs.
The Conch Shell Blowing Contest (March 2; oirf.org) has been a Key West tradition for more than half a century. Held at the Oldest House at 322 Duval St., this unique challenge celebrates the historic importance of conch in the Keys and features contestants from toddlers to seniors attempting to make “music” using fluted conch shells.
The Original Marathon Seafood Festival (March 9-10; marathonseafoodfestival.com) lures thousands of seafood lovers to the Middle Keys to savor lobster, stone crab, shrimp, fish and other Keys-harvested seafood. Additional attractions at the family-friendly feast include musical acts, an open-air boat show and vendors displaying artisan wares.
The Naval Air Station Key West 2019 Southernmost Air Spectacular (March 30-31;airshowkeywest.com) at Boca Chica Field, just north of Key West in the Lower Keys, showcases the Blue Angels U.S. Navy Flight Demonstration Squadron. This year’s theme is “Women in Aviation,” focusing on the “Future of Flight.” As well as the Blue Angels, scheduled performers include the Misty Blues All Woman Skydiving Team, wing-walker Ashley Shelton and the VFC-111 Sun Downers U.S. Navy Reserve Adversary Squadron. Gates open at 9 a.m. with activities throughout both days; the Blue Angels are scheduled to fly daily at 2:30 p.m.
Key West Yoga and Wellness Fest (April 4-7; keywestyogaandwellnessfest.com) combines the pursuit of mind, body and spirit wellness with the best of Key West. Guests can attend individual events or get a three-day VIP festival pass with VIP access to festival events, a celebration and goodie bag.
Seven Mile Bridge Run (April 6; 7mbrun.com/) attracts a field of 1,500 runners to Marathon each year to compete on a course traversing one of the world’s longest segmental bridges, the centerpiece of the Florida Keys Overseas Highway.
The Florida Keys Island Fest (April 6-7; islamoradachamber.com) highlights nearly 100 artists and crafters, live music and a “Taste of Islamorada” competition for foodies. The 28th annual event takes place at Founders Park in Islamorada and admission is free.
Mote Marine Laboratory’s Ocean Fest: A Community Celebration (April 13; mote.org), at the Florida Keys Eco-Discovery Center on Key West’s Truman Waterfront showcases the Keys’ marine environment. Florida-based Mote Marine Laboratory’s family-friendly event features marine-themed games, music, food and vendors.
The Marathon Pentathlon (April 13; themarathongames.com/) at Crane Point Hammock Museum & Nature Trail, includes five sequential events: a 1-mile foot race, 0.5-mile swim in Florida Bay, 1-mile standup paddleboard race, 1-mile kayak race and longest golf drive. Participants are capped at 45 per event.
The 37th Annual Conch Republic Independence Celebration (April 19-28; conchrepublicdayskeywest.com) commemorates the Florida Keys’ symbolic 1982 secession from the United States and rebirth as the independent and eccentric Conch Republic. Events typically include a parade, mock battle at sea with tall ships and a bed race billed as “the most fun you can have in bed with your clothes on.”
The Papio Kinetic Sculpture Parade and weekend (May 3-5; papioskineticparade.com) celebrates the legacy of the late Key Largo folk artist Stanley Papio, a renegade metal sculptor, with offbeat events in Key West. The highlight is a people-powered “mobile sculpture” parade May 4 with colorful sculptural floats, tricycles with costumed riders and artistically decorated bikes.
Key West Paddle Classic (May 4; lazydog.com), presented by Lazy Dog Adventures, includes a 12-mile Elite Race around the island, a 4-mile open race, paddleboard clinics and kids races. The event features multiple race divisions to challenge participants.
The Key West Songwriters Festival (May 8-12; kwswf.com) features America’s foremost performing songwriters and artists at dozens of concerts staged in intimate, audience-friendly settings. Typically included are more than 50 shows and 200-plus country and pop hitmakers. The festival celebrates 24 years with five days and nights of musical magic.
The Key Largo Original Music Festival (May 16-19; keylargooriginalmusicfest.com) treats music lovers to live performances with pop, rock, blues, folk and Nashville country artists at “on-the-water” venues in the Upper Keys.
Key West Pride (June 5-9; keywestpride.org) includes five days of fun for Key West’s LGBTQ visitors, friends and allies on the island known for its accepting “One Human Family” atmosphere. Events typically include pool parties, late-night drag shows and soirees, the finals of a renowned cocktail competition, on-the-water adventures, a street fair, pageants and a colorful parade.
The FKCC Swim Around Key West (June 15; swimaroundkeywest.org) is a 12.5-mile endurance swim, open to individuals and relay teams, around the island of Key West through Atlantic Ocean and Gulf of Mexico waters. Organized by Florida Keys Community College, it’s billed as the only sanctioned, insured and U.S. Coast Guard–permitted race around Key West. Associated events include shorter open-water swims.
Florida Keys visitor information: fla-keys.com or 1-800-FLA-KEYS
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