Best 975 things to do in Cudjoe Key, FL

Private Overseas Highway road trip with time to explore Key West

Ride the Overseas Highway with a local guide and free time to explore Key West

Paddle mangrove tunnels, enjoy a picnic, and look for Key Deer

Toast Key West's sunset from a 45-foot catamaran with drinks included

Enjoy live songs from stage, screen, and radio with Miss Bouvee's adult-humor performance

Backcountry flats fishing for up to 4 anglers on the ShadowCaster

Join hands-on coral nursery care and reef restoration work in Key West

Walk Key West’s Hemingway haunts with three food tastings

Walk Hemingway’s Old Town haunts with a guide in 65 minutes

Brunch, drinks, and a swim stop aboard a Key West sail

Sunday sailing with brunch bites and bottomless mimosas

Sail into Christmas morning with brunch, mimosas, and Key West views

Watch Key West’s holiday boat parade from a 75-foot catamaran with drinks and passed appetizers

Celebrate Valentine’s Day with cocktails, passed appetizers, and a sail through Key West waters

Explore a preserved Civil War-era fort with one-day admission

Visit the Tennessee Williams Museum during daily open hours

Private fishing and island adventures with a captain

Fish reefs and offshore waters or mix in swimming, sandbars, and island hopping

Explore Boot Key Harbor with a champagne toast at sunset

Cruise by catamaran to Money Key for beach time and flat snorkeling

Twin 200 HP power for independent Florida Keys boating

Take the helm of a 22-foot pontoon with a 115-horsepower Suzuki engine

Set out with fishing and navigation gear aboard a 19-foot boat

Explore Marathon waters aboard a well-equipped 21-foot center-console boat