Immerse yourself in the heart of the action as the Battle of Key West Harbor takes center stage in our celebration. This epic and uproarious harbor battle brings together the Conch Republic’s Military Forces (Air Force, Army & Navy) and a colorful array of CR Privateers, facing off against their formidable opponent: a United States […]

Step into history at the Historic Seaport and witness the uproarious 'Tongue-in-Cheek' Surrender Ceremony of the US Coasties to the CR Armed Forces—a farce that's not to be missed! Experience the hilarity and excitement of this unique event, where laughter and entertainment are guaranteed. Best of all, admission is free for all to enjoy! For […]

Experience the epitome of fun with "The most fun you can have with your clothes on" at the zany bed race on Duval between Olivia and Southard. Gather your team and get ready to decorate your own bed to compete for prizes in this uproarious race. Arrive early to mingle with the teams and admire […]

Get ready for an electrifying night of amateur boxing in support of Key West PAL (Police Activities League)! (in front of Ricks.) Join as talented amateur boxers step into the ring to showcase their skills and determination. By attending this event, you're not only in for an exciting evening of sportsmanship and athleticism, but you're […]

Ahoy, matey! Prepare to embark on a thrilling adventure as we celebrate the pirate's life in style! Immerse yourself in the world of swashbuckling swordplay and sing along to captivating sea shanties. With live music, delectable food, and refreshing drinks, it's a pirate's paradise that you won't want to miss. Join us as we raise […]

Join at the local hotspot where community spirit thrives! Discover unique treasures from talented local artists, indulge in delicious offerings from specialty food vendors, and groove to the rhythm of live music—all in one vibrant setting. Best of all, admission is completely free! It's the perfect opportunity to support local artisans, savor mouthwatering delicacies, and […]

Set sail on a memorable adventure aboard a majestic schooner, sloop, or multi-hull vessel, and experience the beauty of the waters off Key West like never before. Our 'all-in-fun race series' pays homage to the rich tradition of the wreckers during the 1800s, adding an exciting and historical twist to your afternoon at sea. Feel […]

Immerse yourself in the captivating ambiance of a lush tropical garden, where every sip of wine is accompanied by the enchanting melodies of world-renowned jazz artists. It's the ultimate destination to unwind and indulge in an evening of exquisite music and fine wine. Best of all, this extraordinary experience comes to you completely free of […]

Experience the excitement of the race firsthand as you enjoy a BBQ dinner and live music while watching video highlights of the event. It's the perfect way to unwind and celebrate the achievements of the participants while enjoying delicious food and fantastic entertainment. Plus, don't forget about the coveted prizes awaiting the first-place finishers in […]