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.
Hindu Charters runs crewed daysails aboard the schooner Hindu out of the Historic Seaport at Key West Bight. On a Key West waterfront thick with catamaran party boats, Hindu is the rare genuine tall ship: a hundred-year-old wooden schooner you can sail on for a couple of hours.
The boat’s history is the draw. Hindu was built in 1925 by Hodgdon Bros. in East Boothbay, Maine, to a William H. Hand Jr. design, a half-scale take on a 19th-century Grand Banks fishing schooner, and launched as the yacht Princess Pat. She picked up the name Hindu on a later voyage, served in the U.S. Navy’s coastal patrol during World War II, and in 1946 went to Al Avellar of Provincetown, who used her to help pioneer New England whale watching. She now splits her year between Provincetown summers and Key West winters, and recently returned to service after a multi-year, ground-up restoration.
Winter trips are the classic Key West lineup of sunset sails and daytime harbor sails, all crewed, with guests welcome to help hoist the gaff-rigged sails or just settle in on deck. The sunset sail runs adults-first (charcuterie and wine, no kids’ pricing); families are pointed at the day sail instead.
Two booking notes: the operator’s site covers both the Provincetown summer season and the Key West winter season, and the same family runs a second, very different Key West boat year-round, the 75-foot catamaran Argo Navis.
Daysail The Keys · Key West
Year-round crewed sails on a 75-foot Key West-built catamaran out of the Historic Seaport. Sunset cruises, Sunday brunch sails, day trips, and private events, with food and drink included in every ticketed trip.
The Keys · Key Largo
Cottage-and-sailboat package on the bayside of Key Largo. Stay in one of the rental cottages, sail one of the included Catalina sloops day-by-day inside Florida Bay. No bareboat resume required for the sub-25-foot fleet.
Daysail The Keys · Key West
Three wooden schooners sailing from the Historic Seaport. Champagne sunset sails and windjammer day sails on the 86-foot Appledore II (Key West winters), backcountry eco tours on the bugeye Appledore Star, dolphin sails and private charters on the 43-foot Valora.