Make your Valentine feel as special as he or she is! Make memories in Key West by starting aboard the Key West Express. Visitors are drawn to the southern charm and Caribbean influences of this laid-back island city, only 4 miles long by 1.5 miles wide. During the day or at night, the island is alive with sidewalk cafes, world-class restaurants, fishing, watersports, shopping, performing arts, musical entertainment and galleries before the island gathers each evening at Mallory Square for the world renown sunset celebration.
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The party atmosphere is always present in Key West, the ultimate place to ring in the new year. Key West is one of the few cities that is ALWAYS featured on the live national news feeds. There are certainly many reasons for its allure and popularity. First off it’s WARM!!! Imagine welcoming in the new year wearing shorts and flip-flops…. You can’t get any better than that!
Photo Credit: fla-keys.com
What began as part of a 19th century plan to help protect the southeastern coast of the United States, became Ft Zachary Taylor or just "Fort Zach" for short.
January 28 - February 1, 2026
The annual Key West Food and Wine Festival has been recognized by the Travel Channel as one of the top 5 food and wine events that you must attend. This series of wine and food themed venues showcases a diverse range of wines and inventive cuisine, hosted by their passionate creators at iconic island locations.
Celebrate your romance with Seashells, Sunshine & Sand. Some people dream of this day forever and should be one of the most memorable moments of your life. Whether your dream wedding includes
glistening tropical waters with sand between your toes, sophisticated sunset elegance at a five-star resort or anything in between, America's Caribbean Island Paradise offering year round weather, breathtaking water views and an abundant array of options will make your special day exactly as you imagine. Make memories at Smather’s beach, Higg’s beach, Fort Zachary Taylor historic state park or the gazebo overlooking the Atlantic Ocean at West Martello Tower & Gardens.
Photo Credit: HemingwayHomeEvents via Instagram by @irismoorephoto
You can even forgo the traditional wedding and broadcast your nuptials digitally, as some have taken to social media to live-stream their wedding, for those that are far and away and could not attend personally. Not only can you invite and and everyone, you want, but you'll also have virtual remembrance as well.
Fort Myers Beach hosts the largest sand sculpting event in the state. Considered a "Must See" experience and one of the TOP TEN best sand sculpting competitions in the world by USA Today and CNN Travel.
November 2-9, 2025
Each year, the Superboat International event gathers thrill seekers from all corners of the globe to witness the heart-pounding offshore racing action, showcasing the fastest and most powerful boats on the water. Participants and onlookers alike are immersed in the exhilarating roar of these incredible engineering marvels.
Closer to Havana than Miami, Key West has a long history of trade with Cuba and the rest of the Caribbean. Everything from sponges to seafood and ivory was brought into Key West. Arguably the most famous import was tobacco. Along with this tobacco came the elusive Cuban Cigar.
This 10 day mostly, free event features the unique opportunity to experience the voices, back stories, and personalities of some of the most influential and internationally-recognized singer-songwriters at some of the most famous venues across Captiva, Sanibel, Historic Downtown Fort Myers and Fort Myers Beach!
