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 ambi- ance. 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) 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 and live entertainment.
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, including 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) 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 “Turtles & Sharks &
Mermaids” themed grand tasting is set for 5-7 p.m. Jan. 31 at the Key West Aquarium.
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 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.
Mote Marine Laboratory’s Ocean Fest: A Community Celebration (March 28; mote.org/oceanfest), 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 Florida Keys Island Fest (March 28-29; islamoradachamber.com) highlights nearly 100 artists and crafters, live music and a “Taste of Islamorada” competition for foodies. The 29th annual event takes place at Founders Park in Islamorada and admission is free.
The Papio Kinetic Sculpture Parade and weekend (April 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 April 4 with colorful sculptural floats, tricycles with costumed riders and artistically decorated bikes.
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.
The Stock Island Seafood Celebration (April 16-19) centers around what the Keys are known for — fresh seafood — on the Lower Keys island adjacent to Key West. Attendees can enjoy events including the main Shrimp Road Seafood & Craft Beer Festival April 18, a dog- and family-friendly fest at the Perry Hotel’s new waterfront event lawn with live music and free parking. The weekend includes seafood seminars, cooking classes and more.
Key West Paddle Classic (April 30 – May 3; lazydog.com), presented by Lazy Dog Adventures, includes a 12-mile Elite Race around the island held May 2, as well as 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 6-10; keywestsongwritersfestival.com) features America’s foremost performing songwriters and artists at dozens of concerts staged in intimate, audience-friendly settings. More than 50 shows and 200-plus country and pop hitmakers. Now in its 25th year, the festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs.
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/coralpalooza-2020) gives attendees the opportunity to plant a coral and help restore a reef during a weekend dedicated to World Oceans Day. Dive program participants will join Key Largo’s Coral Restoration Foundation Friday for a presentation and hands-on training, followed by a day of Keyswide reef restoration activities Saturday. Participants must be dive certified to engage in undersea plantings, but there are many activities open to others at a family-friendly day of land-based goings-on at the Exploration Center.