The Keys · Key Largo
Leopard catamaran fleet working the Keys out of Marina Del Mar in Key Largo since 1988, with further docks in Key West and on Stock Island. Bareboat or captained, by the day, the sunset or overnight, to the Keys and the Bahamas. Bareboat asks for time on a comparable catamaran.
Calypso has been chartering out of Key Largo since 1988, and the fleet is Leopards from 40 feet up to the 58-foot Vivo Per Lei and Lady Susan, a run of smaller cats behind them, and two monohulls for anyone who wants one under them: the 80-foot schooner Bloody Pirate, which takes up to 38 by day and 24 overnight, and the 52-foot ketch Pirates Choice, which runs the daily snorkel and sunset trips from Marina Del Mar. Docks are at Marina Del Mar in Key Largo, City Bight Marina in Key West, and Oceans Edge on Stock Island.
Bareboat qualification is by experience rather than certificate: the company asks for sailing experience on a catamaran of comparable size, then runs a mandatory orientation aboard, takes a float plan, and specifies what has to happen on return. A captain can be taken instead, and trips run as half days, sunset sails, full days or overnight, out to the Bahamas on the longer bookings.
One thing to know before browsing the fleet page: Calypso also operates the African Queen, the steamboat from the 1951 film, and she is a motor vessel, as is a power catamaran that has appeared in the fleet menu. Everything else in the lineup sails.
Featured Daysail The Keys · Marathon
Sirius is a Coast Guard inspected 36-foot sailing catamaran carrying 24 guests from Safe Harbor Marathon Marina, running two-hour sunset cruises by the seat and private charters. Capt. Dale Kamerzel has run the company since 2000. Siriusly Nauti is a motor boat.
Featured Daysail The Keys · Key West
Crewed daysails on Hindu, a 1925 gaff-rigged schooner designed by William H. Hand Jr. as a half-scale Grand Banks fisherman, later a WWII Navy patrol boat and Provincetown whale-watcher. Winter sunset and daytime sails out of the Historic Seaport.
Daysail The Keys · Key West
Year-round crewed sails on a 75-foot Key West-built catamaran from Sunset Pier at the foot of Duval Street. Nightly sunset cruises, Sunday brunch sails October to May and a Sunday swim-and-lunch sail in summer, private charters, food and drink in every fare.