Best Festivals and Events of the Florida Keys

Best of Florida Keys Festivals and Events

The Florida Keys are known to be quirky, offbeat, and always interesting. Here's some of the best festivals and events for January to June.


Key West Literary Seminar 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 is a culinary, wine and spirits celebration of savory events showcasing the flavors of Key Largo and Islamorada in the Upper Keys.

The Baygrass Bluegrass & Craft Beer Festival 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.

Florida Keys Seafood Festival 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.


Upper Keys Garden Walk 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.

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.


Conch Shell Blowing Contest 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.


Papio Kinetic Sculpture Parade and weekend 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 with colorful sculptural floats, tricycles with costumed riders and artistically decorated bikes.

38th Annual Conch Republic Independence Celebration 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.


Key West Songwriters Festival 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.

Key Largo Original Music Festival 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 includes five days of fun for Key West's LGBTQ visitors, friends and allies. 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.

For more: Florida Keys calendar of events
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January 4, 2020

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