Child joyfully interacting with a dolphin in the water.

Events

It's not just another day in paradise! You'll find doings and happenings up and down the Keys, nearly every day of the year. Check out the latest fun and frolic below.

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Key West

Aladdin and the Legend of the Lamp

May 16, 2026, May 17, 2026

May 16, 2026, at 7:00 PM & May 17, 2026, at 3:00 PM Experience an exciting celebration of dance as CoffeeMill Dance Studio presents their annual...

Key West

13th Annual Running of the Chihuahuas!

May 17, 2026

Get ready for one of Key West’s most adorable traditions—the 13th Annual Running of the Chihuahuas! Held at Rick’s Key West on Sunday, May 17, this...

Key West

Deep Waters, Hidden Histories: The Henrietta Marie and Its Afterlives

May 17, 2026

Join us at the Mel Fisher Maritime Museum in Key West for an evening of reflection, storytelling, and discovery centered on the Henrietta Marie — an...

Key Largo

Delicate Balance of Nature Lecture Series: How Part of the Atlantic Ocean Became a State Park with Elena Muratori

May 18, 2026

Before it became a world-renowned underwater destination, the coral reef off Key Largo faced an uncertain future. Join Elena Muratori, Park Services...

Islamorada

Golden Fly Tarpon Tournament

May 18 - 20, 2026

Golden Fly Invitational Tarpon Tournament is one of the Florida Keys’ most prestigious fly-fishing competitions, held annually in Islamorada during...

Marathon

Paint & Sip with Artists: Sandra Lee

May 20, 2026

Join a Paint & Sip at Marathon Yacht Club with artist Sandra Lee—$50 includes instruction and supplies to paint an 8x10 coral reef. Hosted by Keys...

Islamorada

May Immerse Yourself – 45 Years of DAN & Exhibit Opening

May 20, 2026

Celebrate a milestone in diving history at May Immerse Yourself – 45 Years of DAN & Exhibit Opening at the History of Diving Museum in Islamorada...

Key West

Harbor of History: A Key West Seaport Walking Tour

May 20, 2026

Explore the rich maritime history of Key West on the Harbor of History: A Key West Seaport Walking Tour with the Key West Art & Historical Society...

Islamorada

Grand Opening of Prescribed Pressure and May Immerse Yourself! 45 Years of Divers Alert Network

May 20, 2026

Join the History of Diving Museum for the grand opening of Prescribed Pressure and Immerse Yourself, celebrating 45 years of Divers Alert Network (DAN...

Key West

Sons and Daughters of Italy Key West Lodge 47th Birthday Party & Wine Tasting

May 20, 2026

Celebrate the 47th anniversary of the Sons and Daughters of Italy, Key West Lodge 2436, with an evening of Italian wine, antipasto, live music, and...

Key West

Writing Character from Setting with CJ Hauser (PEAR)

May 20, 2026, May 21, 2026

Wednesday & Thursday, May 20-21, 12 –1pm Explore the powerful connection between place and personality in this generative writing workshop with...

Key West

International Cuisine Day at Truman Waterfront Market

May 21, 2026

Enjoy a flavorful waterfront afternoon filled with international food vendors, food trucks, artisan goods, specialty treats, handmade crafts, and...

Key Largo

Upper Keys Humane Society Kitten Yoga

May 21, 2026

Stretch, relax, and unwind at Kitten Yoga with the Upper Keys Humane Society in Key Largo, where calming yoga meets playful, adoptable kittens. This...

Islamorada

Paint, Dip & Sip

May 22, 2026

Join Olive Morada for Paint, Dip & Sip, a relaxing evening of watercolor painting, light bites, beverages, and good company celebrating the launch of...

Key West

Once There Was a Railroad by Wayne Garcia

May 22, 2026

“Once There Was a Railroad” by master woodcarver Wayne Garcia brings the remarkable story of Henry Flagler’s Overseas Railroad to life through a...