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 2020, a comprehensive and frequently updated year-round calendar of Keys events can be found at fla-keys.com/calendar.
The Orange Bowl Swimming Classic (Jan. 3; jacobsaquaticcenter.org) brings hundreds of college swimmers from around the U.S. to Key Largo for an open-to-spectators sprint-style meet that features several fast-paced swimming events. College teams compete following a monthlong winter training session at Key Largo’s Jacobs Aquatic Center.
The 38th annual Key West Literary Seminar (Jan. 9-12; kwls.org), founded in 1983 and headquartered at Key West’s San Carlos Institute, explores a different literary theme each year. The 2020 theme, “Reading Between the Lines: Sports & Literature,” focuses on writing that examines why sports matter so much and explores the roles sports play in social issues, personal transformation and cultural change.
Uncorked … The Key Largo and Islamorada Food and Wine Festival (Jan. 9-19; 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. 18 at Islamorada’s Postcard Inn Beach Resort and Marina.
The Florida Keys Celtic Festival (Jan. 11-12; 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 kickoff and children’s activities.
The Big Pine & Lower Keys Nautical Expo (Jan. 11-12; lowerkeyschamber.com) attracts marine enthusiasts seeking gear at this outdoor “pop-up” showcase for all things nautical. More than 90 vendors are expected to participate. The Lower Keys Chamber of Commerce organizes and benefits from the event.
The Baygrass Bluegrass & Craft Beer Festival (Jan. 17-19; baygrassbluegrass.com/), features three days of traditional bluegrass, old time, soulgrass, “newgrass” and Americana bands performing in Islamorada. Attendees can enjoy satellite events at small local emporiums and an all-day waterfront main event with 10 bands and two stages.
The Florida Keys Seafood Festival (Jan. 18-19; floridakeysseafoodfestival.com
The Key West Half Marathon & 5k Run (Jan. 19; keywesthalfmarathon.com/) attracts several thousand runners eager to experience a scenic 13.1-mile flat, fast course in subtropical Key West. Now in its 22nd year, the race is acclaimed as one of the United States’ leading winter half-marathons. An associated 5k is scheduled for those who prefer a shorter challenge.
The Kelly McGillis Classic International Flag Football Championship & World Challenge Game (Jan. 21-27; iwffa.com) in Key West is expected to draw some 1,500 women and girls representing 32 teams from the U.S. and countries around the world for flag football events. The popular event is named for McGillis, the “Top Gun” movie actress and former Key West resident.
The Island Boat Show (Jan. 24-26; islandboatshow.com/, billed as the Florida Keys’ premier boat show, is to be held at Hawks Cay Resort on Duck Key. Planned attractions include 40 boat brands, auction items, food and drink, vendors and fishing seminars.
The 26th annual Master Chefs Classic (Jan. 26; 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.
The Key West Food and Wine Festival (Jan. 26 – Feb 2; keywestfoodandwinefestival.com
The Upper Keys Garden Walk (Feb. 15; gardenclubupperkeys.org/) is a unique self-guided tour that showcases beautiful private garden properties in the Upper Keys. The event also is to include a tea party with an art show, Garden Market, vendors and more.
The American Legion Riders Coral Head Music Festival (Feb. 15; coralheadmusicfest.com) features fun and music by national and regional bands and entertainers including The Outlaws and Night Ranger. Proceeds from the event, held at the Marathon Community Park Amphitheater in the Middle Keys, benefit area charities.
The Winter Star Party (Feb. 17-23; scas.org/winter-star-party) draws some 650 astronomers and astro-imagers from around the world 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.
The Sombrero Beach Run (March 7; sombrerobeachrun.com), in its 14th year in Marathon, attracts several hundred racing circuit runners for a weekend of running and sunning. The event is held at Sombrero Beach, at the end of Sombrero Beach Road at mile marker 50. Awards are given to overall finishers in a 5k walk and 5k and 10k runs.
The Conch Shell Blowing Contest (March 7; oirf.org) has been a Key West tradition for 58 years. Held at the Oldest House at 322 Duval St., this unique challenge celebrates the historic importance of the conch mollusk in the Keys and features contestants from toddlers to seniors attempting to make “music” using fluted conch shells.
The Original Marathon Seafood Festival (March 14-15; 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, raffles, prizes and vendors offering artisan wares.
Seven Mile Bridge Run (March 28; 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 38th Annual Conch Republic Independence Celebration (April 17-26; conchrepublicdayskeywest.com, conchrepublic.fun) 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 along Key West’s Duval Street, a mock battle at sea with tall ships, sunset sailing cruises, parties and the Great Conch Republic Drag Race.
Earth Day Festival at oTHErside Adventure Park & Keys Cable (April TBA; facebook.com/KeysCable/), is a festival of earth-centric activities and events including organic food, music and vibes presented by Otherside Boardsports and Keys Cable Adventure Park, located in Marathon. Attendees can enjoy artisan cocktails with fresh pressed juices, local food and eats, eco-conscious and earth-inspired pop-up apparel shops offering goods including waterwear for a plastics-free ocean — swimwear and board shorts made of recycled plastic bottles. Among other planned event highlights are a fashion show, terrarium station, wakeboarding and more.
The Key West Songwriters Festival (May 6-10; keywestsongwritersfestival.com
The Key Largo Original Music Festival (May 14-17; 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 3-7; gaykeywestfl.com/pride/) 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.
CoralPalooza (June 6; coralrestoration.org/
The College of the Florida Keys Swim Around Key West (June 20; 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 The College of the Florida Keys, 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.
Mystery Fest Key West (June 26-28; mysteryfestkeywest.com) draws bestselling mystery and suspense authors, aspiring writers, true crime experts and fans to America’s southernmost city. Attendees can meet and learn from some of the country’s most notable authors, collect signed books and enjoy workshops, panels and presentations on aspects of mystery writing.
Florida Keys calendar of events: fla-keys.com/calendar
Florida Keys visitor information: fla-keys.com or 1-800-FLA-KEYS