In addition to the wonderful opportunities for outdoor activities like fishing, snorkeling, diving, sunbathing, and backroads tours, Key West is home to dozens of annual festivals, celebrations, and events that make a Key West vacation a good idea any time of year.
So while you’re making an itinerary that includes the well-known grilled lobster roll from Eaton Street Seafood Market and Restaurant and key lime pie from Kermit’s Key West Key Lime Pie Shoppe, check out this list of events that can make your Key West vacation even more memorable.
Food and Cultural Fun
Start the year off right with the Key West Food and Wine Festival, which fills five full days with home and garden tours and walking tours of the city that are centered around local culinary delights.
There are themed activities all over the city, such as making your own key lime pies, plus numerous food and wine pairings presented by local chefs.
If you miss the Food and Wine Festival, you can still enjoy home and garden tours during the annual Key West Home Tours event that’s held every spring. It showcases the architecture, landscapes, and history of Key West in a unique way.
In the fall, the Key West Film Festival highlights the essence of the Key West experience through films that center creativity, diversity, sustainability, and beauty.
It’s typically a four-day event, and you can attend film screenings and meet-and-greet events with the cast and crew of many of the films included in the festival. Area hotels often offer special packages, too, so be sure to mention why you’re in Key West when booking your rooms.
Sports Fun for All:
If you’re a runner, ring in the new year with Key West’s half-marathon and 5K each January. The weather is nearly always perfect, with mild temperatures and humidity.
There are several other runs held throughout the year, but perhaps the most popular is the Hemingway Sunset 5K run and walk. It’s part of Key West’s annual Hemingway Days. Runners and walkers of all ages and abilities are welcome to participate and join in the event’s after-party.
Key West is also home to many important annual sporting events that are exciting whether you’re a participant or a cheerleader. The Redbone Celebrity Tournament Series includes several charter fishing trips and events that support researching a cure for cystic fibrosis.
In particular, the SLAM event every September is popular for those who like to go out for tarpon and bonefish. The Southernmost Light Tackle Anglers Masters is a catch-and-release tournament.
Another catch-and-release tournament, the Key West Fishing Tournament, will consider entries over a period of eight months. It’s open to all ages, and there are dozens of recreational and sport fishing categories.
Each spring, the Key West Yoga and Wellness Festival includes a wellness marketplace within three days of classes, workshops, and educational programs.
Attendees can also book spa treatments as they learn more about the connection between body and mind in one of the most relaxing vacation destinations in the U.S.
Key West is fun for families, too, and many of the events that happen here welcome kids and their grownups. Ocean Fest is an annual event held in April, and programming includes touch tanks for kids, community art projects, and fishing clinics.
It’s hosted by the Mote Marine Lab at the NOAA Florida Keys Eco-Discovery Center and Truman Waterfront. The event also features a marketplace with food and craft vendors plus live music and performers.
If your family has a strong interest in marine conservation, consider planning your Key West vacation around the Key West Mermaid Festival, which happens in July. Programs and activities are centered around raising awareness of marine issues through education.
If parades are more your speed, don’t miss the Papio Kinetic Sculpture Parade in May. It’s a three-day event that honors Stanley Papio and his work; he was a well-known folk artist that called the Florida Keys home.
Attendees who line the parade route are treated to an outstanding display of floats and art bikes that roll down Duval Street in a human-powered display of creativity and ingenuity.
For a closer look at Papio’s work, view an exhibit of his work at the Key West Art & Historical Society’s Fort East Martello.
While a vacation in Key West is enjoyable at any time of year, booking your trip so that it coincides with festivals and sporting events can make your visit even more memorable.
It enhances your enjoyment of the natural beauty, culinary scene, and community that makes this island city so unique and welcoming to visitors.
While the shape and availability of these festivals and events can vary slightly over time, with activities continually updated, added, and revised for maximum participation and enjoyment, there’s no arguing that the welcoming nature of Key West shines through, whether you’re planning your first trip to Key West or you’re a regular visitor.
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