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.
Key West Schooners is the wooden-boat side of the island’s day-charter waterfront: three hand-built schooners working from 201 William Street at the Historic Seaport. The lineup runs from a champagne sunset sail capped at 22 guests through windjammer day and sunset sails, a Bloody Mary morning sail, backcountry eco tours, and dolphin-watch trips, with drinks included and guests welcome on the halyards. The operation sails in family with Sebago Watersports, whose catamaran fleet covers the modern end of the same waterfront.
Each boat is a piece of maritime history in her own right. Appledore II is an 86-foot windjammer launched in 1978 to a Bud McIntosh design and sailed around the world by her builders, Herbert and Doris Smith, on an 18-month maiden voyage; she still splits her year the old way, Camden, Maine in summer and Key West in winter, making the 2,000-mile passage between homeports twice a season. Appledore Star is billed as the last Chesapeake bugeye ever built, the retirement project of Maryland shipwright James B. “Mr. Jim” Richardson, and her oyster-dragger shallow draft is what lets her work the mangrove islands on the eco tours year-round. Valora, a 43-foot schooner launched in 2018 by Boothbay Harbor’s Stimson boatbuilders to a design inspired by Commodore Ralph Munroe’s shallow-draft sharpies, handles the small-group dolphin sails and private charters, weddings included.
The pitch across all three is the same: real wooden ships, small passenger counts by party-boat standards, and trips where hoisting the main is part of the entertainment rather than an interruption to it.
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.