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Your 2025 Key West Calendar

There’s really never a bad time to visit Key West. Great weather and colorful events go on year round, and there’s always something interesting for visitors to partake in. With that in mind, here are just a few of the things you can look forward to on your visit to Key West this year.

Key West Food and Wine Festival

Photo // Jeremy Ball

Notably advertised as “flip flops required,” this Key West staple has 30 unique and tasty gustatory events over 5 days. Tastings run the gamut from fancy to casual, while cuisine seminars help to educate visitors about Key West’s thriving culinary scene.  Key West Food and Wine Festival

When: January

Check out: Top Things To Do in January 2025 Key West 

Florida Keys Seafood Festival

a man cooking hot dogs on a grill

This family-friendly event was created to showcase local seafood and the Keys’ commercial fishing industry by providing the freshest seafood available. Each year our fishermen and women are proud to offer the community a variety of seafood at reasonable prices. This years dates are February 15th & 16th.

When: February 

Check out: Top Things To Do in February 2025 Key West 

 

Experience the Taste of Key West

a group of people walking on a beach

This open-air event promises an assortment of beverages and palate-pleasing plates. Restaurants and food vendors from across the Lower Keys and Key West donate their staffs’ time and extraordinary culinary talents to create delectable small plates. Foodies can stroll edibles and drinkables, ranging from seafood, tropical and Caribbean flavors, to European dishes, vegetarian offerings, and desserts. Taste of Key West gates open at 6PM for general admission.

When: March 

Check out: Top Things To Do in March 2025 Key West 

Conch Republic Days

a man carrying a large umbrella

The Conch Republic’s Annual birthday party means 10 days of nonstop festivities. Try your hand at the conch blowing competition, attend the Independence Celebration Parada Party, and close it all out with an epic pig roast and pirate costume competition. An unforgettable week in Key West!  Conch Republic Days

When: April 

Check out: Top Things To Do in April 2025 Key West 

Key West Songwriters Festival

a group of people standing in front of a crowd

Join us for one of the best events of the year! Key West’s Annual Singer Songwriters Festival is the largest of its kind in the world. Enjoy 5 days and nights of musical bliss, as you see and hear countless musicians at various locations throughout the island. Venues include beaches, boats, bars, resorts and historic theaters and the best part is most of the shows are FREE! Check here for more information.

When: May

Check out: Top Things To Do in May 2025 Key West 

Key West Pridefest

Photo // Misterbnb

What better way to celebrate the power of diversity than a party in what is consistently recognized as one of the world’s top gay and lesbian vacation destinations? Take your pick of shows, parties, forums, street fests, and the unforgettable Pride Parade along Duval Street!  Key West Pridefest

When: June

Check out: Top Things To Do in June 2025 Key West

Key Lime Festival

Photo // Fla-Keys.com

Are you a fan of Key Lime pie (who isn’t)? Embrace your passion by joining us to celebrate the fruit that inspired one of the most famous deserts in the world! For the ambitious, there’s even a Key Lime pie-eating contest where they can test their chops against experienced locals. Key Lime Festival

When: July

Check out: Top Things To Do in July 2025 Key West 

 

 

Key West LobsterFest

a lobster on a wooden surface

Lobster season is finally open again on August 6th! Ok, so it’s only been 4 months, but it feels like ages since we’ve indulged on the Caribbean tails. What better way to celebrate than the Annual LobsterFest, a 4 day festival in early August where you’ll find Lobster cooked every way imaginable. Head to Duval for the street fair and get lobster wasted!

When: August

Check out: Top Things To Do in August 2025 Key West 

 

Key West BrewFest

What better way to spend the Labor Day long weekend than by partaking in the annual Key West BrewFest which offers nearly 200 beers and microbrews on tap, great food, and pool parties, all to benefit the Rotary Club of the Conch Republic. Key West BrewFest

When: September

Check out: Top Things To Do in September 2025 Key West 

 

Fantasy Fest

Moving Skeleton Float operated by paraders

Photo // FantasyFest.com

A world-famous costume festival, Fantasy Fest is billed as “an annual 10-day party in paradise for grown-ups”. Participants and visitors can enjoy a parade with large-scale floats, a pet costume competition, a street fair with some amazing local food, and performances by island-style bands.  Fantasy Fest

When: Late October

Check out: Top Things To Do in October 2025 Key West 

 

Key West Super Boat World Championship

Photo // Andy Newman/Florida Keys News Bureau/HO

Those with a need for (aquatic) speed will surely enjoy the annual Key West Super Boat World Championship, features powerboats what is known internationally as the “Indianapolis 500 of powerboat racing”. A portion of the course runs through Key West Harbor, where racers regularly reach speeds over 140 mph and onlookers are close enough to get a real sense of the speed involved. Key West Super Boat World Championship

When: November

Check out: Top Things To Do in November 2025 Key West 

Key West New Years Eve

Photo // The Key West Citizen, Rob O’Neal

New Year’s Eve is always fun, but no place does it quite like Key West! From the free concert on Sunset Pier to the iconic lowering of the conch shell at midnight, it’s a great way to kick off your new year! Key West New Years Eve. 

When: December 31

Check out: Top Things To Do in December 2025 Key West

 

And remember, when you’re planning your vacation to Key West, don’t forget to contact Key West Food Tours for the opportunity to eat like a local and visit a variety of authentic establishments!