January
Key West HALF MARATHON
Ready to run? Sign up for the annual half marathon in Key West and as a bonus perk, you get a special room rate at Havana Cabana!
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holidays & events
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January
Key West Seafood Festival
The Key West Seafood Festival is a family friendly event created to showcase local seafood and the Keys’ commercial fishing industry. Come out and enjoy live music, drinks, local-made artifacts and fresh seafood.
February
Mile 0 Fest
The annual Mile 0 Fest features some of the best Red Dirt & Americana acts on the planet. The festival includes 4 days of non-stop Americana and Red Dirt music, oceanfront at the beautiful and brand new Truman Waterfront Part Amphitheater.
February
Big Game Parties
Why just watch the game when you can experience it Flama Cabana-style? Grab your team and enjoy VIP or regular seating, game-day eats, and unbeatable vibes as we watch the big game on the big screen!
March
Nas Key West Southernmost Air Spectacular
Don’t miss the Blue Angels performing spectacular aerial maneuvers in their fighter jets. The viewing is admission free and held at the Naval Air Station Key West.
April
Seven Mile Bridge Run
Beginning in 1982 and held every year since, the Seven Mile Bridge Run attracts runners from all over the world. The bridge is shut down early morning as hundreds of runners race for the first place gold medal. Monies raised from this event benefit the local schools and youth groups.
May
Key West Songwriters Festival
Held every May for over 20 years, this festival attracts some of the area’s (and the nation’s) top songwriting talent. The festival is held over five days at various locations throughout Key West, and features over 50 shows.
June
Key West Pride Fest
The city of Key West is known for its laid back lifestyle and open and accepting atmosphere. That’s why each year hundreds of people come down to celebrate PRIDE week, where the community celebrates and reflects on the progress and improvement of the legal rights of the LGBT citizens.
July
Hemingway Days
Every July around Ernest Hemingway’s birthday, admirers of the famed author descend upon Key West to commemorate his legacy, through readings, tournaments, a lookalike contest and much more.
August
Lobster Fest
Lobster lovers -and those who like a good party – are welcome at this annual festival, which celebrates the beginning of lobster season in Key West. It all kicks off with a bar crawl on Duval; additional events include a lobster boil, a street fair and a delicious Sunday brunch.
September
Key West Women Fest
Just before the holidays start to rev up, Key West welcomes women from all over the world to celebrate the annual weeklong Womenfest. Filled with parties, nightly events and food and drink specials, Key West Womenfest celebrates the lesbian community.
October
Fantasy Fest
Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement!
THIS YEAR AT HAVANA CABANA:
DUCK DUCK BOOZE POOL PARTY
Don’t miss the duckie takeover at Havana Cabana on Monday, October 20 from 12pm to 4pm! We’re kicking off Fantasy Fest with a pool party like you’ve never seen before – complete with a pool full of rubber duckies, beverage samples, and swag. Duck floats, duckie bathing suits, duckie tutus, and creativity are highly encouraged
This event is FREE and open to the public! Learn more and RSVP here.
November
Graciasgiving
We celebrate GraciasGiving here at Havana Cabana! Join us this November for a special Cuban-themed menu, along with all-day football on our pool TVs.
November
Power Boat World Championship
The Key West World Championship is the final race of the Super Boat International offshore racing series; it takes place every November and features seven days of racing and other fun events. Make your way down to the Truman Waterfront to witness the action.
December
Lighted Boat Parade
Join visitors and locals at the Historic Seaport for the Annual Lighted Boat Parade! See boats of all sizes decorated in Holiday lights as they pass by. You’ll have a chance to cast your vote for your favorite decorated vessel!
December
Merry Flocking
It wouldn’t be Christmas without flamingos and mojitos! Join us this Christmas for a festive and merry holiday on the beach.
THIS YEAR AT HAVANA CABANA:
Celebrate the 12 Days of Mojitos with us! Plus poolside parties with live DJs, body painting, cigars, paint & sip activities, Santa photos, manicures and massages under our Tiki huts, jewelry pop-ups, & so much more!
December & January
New Year’s
Ring in the new year with us in Key West! We’ll be hosting our “Party Like a Flock Star” New Year’s Eve poolside party this year, featuring a live DJ, B12 shots and dining specials. There will also be a rehydration station prepped and ready to go if those cocktails start hitting a little too hard. Guests will also enjoy salsa dancing, Cuban Bingo, drinking contests, and then recover the next day with one of our hangover kits, put in every room.
