The Keys · Marathon
Bareboat and captained charters from Keys Fisheries Marina, gulfside Marathon at mile marker 49. 27- to 36-foot Catalina and Irwin cruisers and a Beneteau 51, by the day or in three-day, two-night packages within 50 miles, Key West included; a checkout stands in for paperwork.
Florida Keys Sailing rents its cruising fleet bareboat from Keys Fisheries Marina, the working-waterfront dock on the gulfside of Marathon at mile marker 49: a Catalina 27 and a Catalina 30 for day rentals and weekend packages, an Irwin 34, and a four-cabin Beneteau Oceanis 51 with generator and air conditioning for a crew that wants the big boat. The standard bareboat package runs three days and two nights, boarding at nine on the first morning and back at the dock by five on the third afternoon, with longer stays added by the day and dockage at the marina included. Navigation limits are 50 nautical miles from the dock, which reaches Key West.
Qualifying is by demonstration rather than certificate: the operator requires a checkout of the vessel and a signed bareboat agreement, and says a day rental might call for a demonstration of competent sailing skills. Private day sails on the same Catalinas run with a USCG-licensed captain aboard for up to six, half or full day, with sailing lessons folded in and no experience needed. The ASA school that shares the fleet has its own listing.
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. Public sunset cruises and Sunday brunch sails, private daysails and events, with food and drink included in every fare.