The Keys · Key West
74-foot topsail schooner built 1982–83, long the unofficial flagship of the Conch Republic and, since 2023, flagship of Key West. Currently laid up at a Key West boatyard and not sailing. Her nonprofit is fundraising a full restoration.
Say it up front: the Wolf is not sailing. She is hauled out at a boatyard on Stock Island, needing major hull and deck restoration, and her nonprofit is raising the money to bring her back. This page stays in the directory because the boat matters, and because the day she splashes again, Key West gets its flagship back.
The Wolf is a 74-foot steel gaff-rigged topsail schooner to Merritt Walter’s Norfolk Rover design, built in Panama City between 1982 and 1983 by master builder Willis Ray and Captain Finbar Gittelman, who sailed her into Key West on her first voyage in 1984 and never really left. For four decades she was the working symbol of the island’s self-mythology: flagship of the Conch Republic, lead vessel of the Great Sea Battle reenactment from 1984 to 2023, head of the Pirates in Paradise fleet for fifteen years, and since 2023 the official flagship of the City of Key West itself. Certified for 44 passengers, she ran day sails and charters between the ceremonial duties, and underneath the theater did serious work: youth leadership sail training, Coast Guard licensure training, humanitarian voyages.
Captain Finbar died in 2024, and the restoration is now the way the town keeps faith with the boat he built. Anyone who wants to see a topsail schooner working Key West Harbor again knows where to send the check.
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 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.