things to do in Cudjoe Key, FL

Join Key West's holiday flotilla aboard a decorated schooner with drinks, bites, and onboard festivities

Sing along with live holiday music aboard a festively lit schooner

Join Key West schooners in a monthly race to Sand Key Lighthouse

Sail into Key West sunset views with holiday treats aboard a 105-foot schooner

Glide over shallow seagrass flats on a clear paddleboard

Set your own pace on the water

See the Florida Keys' bridges, islands and turquoise waters from above

Cruise or fish the Keys with GPS-guided local routes

Cruise the Keys on a 23-foot dual-hull World Cat for three days or more

Fish the flats and backcountry on a 6-hour private charter

Fish the flats and backcountry on an 8-hour private charter

Target tarpon twice in one day with morning and evening sessions

Private sunset tarpon charter that departs around dusk

Start the day with a family-friendly Florida Keys morning on the water

Private, light-tackle fishing in the calm Florida Keys backcountry

Watch Key West’s changing sunset colors from a private 26-foot boat

Choose backcountry waters or weather-dependent deep-sea fishing from a 26-foot Intrepid

Explore a Key West sandbar by boat

Follow pirate clues to hidden Key West sandbar treasure

Look for dolphins as the sun sets over Key West waters

Watch the Key West sunset and look for dolphins from the water

Cruise the Historic Seaport as the sun sets

Explore on a 250 HP, fishing-ready boat with delivery and pickup included

Bring your group aboard for fishing, snorkeling, or a day on the water