Key West’s calendar is just like the island itself—eccentric, historic, celebratory, and deeply tied to the water. From world-class songwriting and culinary festivals to quirky historic look-alike contests and high-octane boat races, here is your month-by-month guide to celebrating in the Conch Republic.
A prestigious four-day gathering of world-renowned authors and avid readers for discussions, readings, and workshops.
Mid JanActive
Key West Half Marathon & Runfest
A scenic, flat winter race routing through historic Old Town and along Smathers Beach.
Late JanMusic
Mile 0 Fest
A massive, boutique festival bringing the best of Red Dirt and Americana music to beachfront stages and the amphitheater.
WeekendsHistory
Old Island House Tours
Historic home tours opening private, beautifully preserved Key West residences highlighting unique architectural heritage.
Jan – FebCulinary
Key West Food & Wine Festival
A multi-day culinary celebration featuring waterfront tastings, winemaker dinners, and neighborhood wine strolls.
FEB
February
Mid FebCulinary
Florida Keys Seafood Festival
A family-friendly local tradition celebrating the island’s fishing heritage with fresh stone crab, conch fritters, and lobster.
Mid FebHistory
Presidential Family Weekend
Hosted annually over Presidents’ Day Weekend, the nation’s largest gathering of presidential descendants features panels and family cookouts.
WeekendsHistory
Old Island House Tours
Self-guided viewings of historic private homes supporting local preservation.
Late FebCulture
Key West Art & Craft Fair
A premier, juried outdoor event at Truman Waterfront Park to browse high-quality handmade works.
MAR
March
WeekendsHistory
Old Island House Tours
The final weekends to tour beautifully preserved, historic private Key West residences.
Late MarCulinary
Taste of Key West
An open-air evening at Truman Waterfront Park showcasing small plates and pairings from dozens of local restaurants.
Local Tip
March brings spectacular weather! We highly recommend booking outdoor and waterfront dining reservations well in advance.
APR
April
Late AprFestival
Conch Republic Independence Celebration
A hilarious 10-day festival honoring Key West’s playful 1982 “secession” from the U.S., complete with drag races and mock sea battles.
Local Tip
Don’t miss the famed Drag Races on Duval Street during the Independence Celebration—it’s a high-heeled local favorite!
MAY
May
Early MayMusic
Key West Songwriters Festival
The largest festival of its kind in the world, bringing more than 100 top-performing songwriters to intimate acoustic stages across the island.
JUN
June
Early JunFestival
Key West Pride
A weeklong, vibrant celebration of diversity featuring sunset cruises, pool parties, and a grand parade down Duval Street.
Mid JunCulinary
Truman Tropical Fruit Festival
A free, family-friendly event on the lush grounds of the Little White House to sample fresh exotic fruits and themed cocktails.
JUL
July
Early JulCulinary
Key Lime Festival
A quirky celebration of the island’s signature citrus, featuring cocktail strolls and a legendary pie-drop championship.
Mid JulCulture
Hemingway Days
A celebration of Ernest Hemingway’s literary legacy, highlighted by the world-famous Look-Alike Contest at Sloppy Joe’s Bar.
AUG
August
Mid AugCulinary
Key West Lobsterfest
Marking the opening of the spiny lobster season with massive street fairs, live concerts, and open-air lobster boils.
Local Tip
August has the warmest waters of the year—making it the ideal time to book a backcountry snorkeling charter or sandbar trip!
SEP
September
Early SepFestival
Womenfest
One of the country’s longest-running festivals celebrating lesbian and queer women with themed gatherings and live music.
Local Tip
September is historically quieter on the island, making it the perfect time for uncrowded beaches and enjoying the relaxed local vibe.
OCT
October
Late OctFestival
Fantasy Fest
Key West’s wildest annual event—a legendary 10-day adult masking and costume festival featuring themed balls and an extravagant parade.
NOV
November
Early NovNautical
Race World Offshore Championship
High-octane powerboats race at speeds over 100 mph through the harbor, drawing massive crowds to the waterfront.
Mid NovCulture
Key West Film Festival
A fast-growing cultural event showcasing contemporary independent films, documentaries, and intimate director Q&As.
Late NovFestival
Holiday Fest Kickoff
The island rings in the Key West Holiday Fest, a month-long celebration kicking off with the Harbor Walk of Lights.
DEC
December
Early DecFestival
Key West Holiday Parade
Held the first Saturday of December, spectators line Truman Ave and Duval St to cheer on marching bands and creatively decorated floats.
Mid DecNautical
Lighted Boat Parade
Holiday festivities culminate with a maritime-style lighting of the Historic Seaport featuring a dazzling illuminated boat procession.
Planning Your Trip?
Whether you’re coming down for Fantasy Fest, the Hemingway Days, or just looking to relax by the water, our team can help you find the perfect vacation home close to the action.
