things to do in Key West, FL

Sip fine wines and craft beers on an intimate schooner sail as the sun sets off Key West’s coastline

Cruise to a Key West sandbar for independent paddling and floating fun

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

Watch the Powerboat Races from a captain-led spot on the water

Watch Race World Offshore action from a premier spectator boat

Sail Key West’s historic waterfront aboard a hand-built 86-foot schooner

Hoist sails and take the wheel aboard a 2-masted schooner

Explore Key West backcountry sandbars on a private charter for up to 6

Private 4-hour light tackle fishing charter for up to 4 guests

Choose your sandbar stops and explore Key West’s mangroves by private boat

Design your own sandbar escape among Key West’s mangroves

Build a flexible day of sandbars, mangroves, and island stops

Cruise Key West’s waterfront with local history narrated by a licensed captain

Private catamaran celebration with bubbly, wines, and party platters

Sail Key West on Schooner America 2.0 with complimentary soft drinks

Sail into the Key West sunset with drinks and hors d'oeuvres included

Sail Key West's night waters beneath the full moon aboard a 105-foot schooner

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

Sail Key West’s waters aboard a 105-foot schooner with Christmas brunch and drinks

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

See powerboat racing from above as a helicopter tracks the racecourse

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