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Events & Festivals in Key West

Events in Key West are epic, and we pride ourselves on welcoming guests to our budget-friendly Key West Motel year-round for events that draw visitors from around the globe. There is always something exciting happening on Duval Street, located practically right outside our door. Imagine yourself at the incredible festivals for which Key West is famous.

January to May

The Annual Seafood Festival includes samplings of grilled lobster, fried fish and stone crab claws. At the Key West Literary Seminar, readers from all over the world meet the best writers and listen to readings and lectures. Run around the entire island in the Key West Half Marathon, ranked #3 in Runner’s World Bucket List: 10 Destination Half Marathon’s. The annual Key West Food & Wine Festival includes 30 events ranging from extravagant walk-around tastings to educational food and wine seminars. The Old Island Days Art Festival brings together 100 fine artists. Each year participants in The St Patrick’s Day Bar Stroll visit several local waterholes in an effort to raise money for local Key West charities. The Conch Republic celebrates Independence Day every April with its theme - a "Sovereign State of Mind", seeking only to bring more "Humor, Warmth and Respect" to the world at large. The Key West Art & Historical Society provides family fun at the Kinetic Sculpture Parade. The Key West Songwriters Festival brings in over 200 performers and is the largest celebration of its kind.

June through September

Key West Pride is an annual event that welcomes the LGBTQ community to Key West’s open and accepting One Human Family philosophy. The annual Swim Around Key West provides the unique opportunity to swim individually or with a team for 12.5 miles around the island of Key West. The VFW Fishing Tournaments are year-round and provide an opportunity for fishing competition and saltwater trophies. Fun, food and fireworks can be expected at the annual July 4th celebration. An annual celebration of the Pulitzer Prize-winning author, Ernest Hemingway, Hemingway Days includes a look-alike contest, museum exhibits and other events to commemorate his life and accomplishments. The Drambuie Key West Marlin Tournament is a world-class fishing extravaganza. One of the biggest 4-day parties of the summer is the annual Lobsterfest celebration. For the beer lovers, Brewfest is the annual celebration on Labor Day weekend that includes beer dinners, brunches, happy hour parties, pool parties, seminars and a signature tasting festival. Womenfest draws thousands of ladies for a wide range of activities and events during four days of revelry and fun.

October through December

Support the Special Olympics Florida-Monroe County chapter with the 2 mile paddleboard race in the annual Stand Up Paddle (SUP) Invitational. Historic Bahama Village hosts the Goombay Festival and features eclectic cuisine, music and street vendors. The world famous Fantasy Fest directly follows Goombay and includes 10 days of events, parties, costume contests and the biggest parade of the year. Parrot Heads are fans of Jimmy Buffet, and Key West attracts about 3,500 of them each year at the Parrot Heads in Paradise festival. The Super Boat Races attract the most competitive racing teams in the world. The race course, on the Gulf side of the island, is 6 miles of fury, as super boats reach top speeds as high as 180mph. Race week includes a boat parade, exciting races 3 times a day, and a Duval street party. The Key West Film Festival is an annual celebration of film and filmmakers. And the holiday season wouldn’t be the same without Holiday Fest, a month-long schedule of events, including the lighting of the harbor walk, holiday light tours, The Nutcracker performance, holiday parade and more.

When you stay with us at Southwinds Motel, many of these events are just a short walk while you enjoy people-watching and the unique ambiance of Key West. For a memorable stay in exciting Key West, call our budget-friendly motel today.
Contact our concierge to book today at info@keywestsouthwinds.com.