Northeast · St. Augustine
76-foot replica blockade-runner schooner sailing out of the City Marina in St. Augustine. Day sails, sunset sails, and moonlight sails. The city's longest-running tall-ship daysail.
Schooner Freedom Charters runs crewed daysails on Matanzas Bay out of the St. Augustine City Marina, in the shadow of the Bridge of Lions. It’s the city’s longest-running tall-ship daysail operation.
Freedom is an authentic replica of a 19th-century blockade runner, the fast schooners that slipped out of hidden Florida ports past the Union blockade during the Civil War. She’s a double-masted, gaff-rigged, topsail schooner (76 feet sparred, 64 on deck), built in steel with aluminum spars by the naval architect Merritt Walters and Rover Marine in Norfolk, Virginia, in 1982. John and Sarah bought her in 2000, spent a year refitting her, and launched her as a St. Augustine charter in 2001; she’s a Class B tall ship licensed for 41 passengers.
The schedule runs day sails, sunset sails, and moonlight sails: a two-hour sail into the same Matanzas inlet the historic runners used, with the oldest city in the country as the backdrop.
Trips are seasonal and weather-dependent, so booking ahead is wise. Freedom was dry-docked for her Coast Guard inspection from September 21 to November 4, 2026, and sails again from November 5, with the Nights of Lights and sunset sails running November 21 to January 18, 2027; she also leads the Regatta of Lights parade on the bayfront in December. The boat is dog-friendly, and the owners’ son, Captain Jack, now takes the helm as well.
Northeast · St. Augustine
Sailboat rentals on Salt Run, the tidal lagoon inside Anastasia State Park, run by the park's concessionaire. Fourteen-foot Hobie Waves and single-sail Aqua Finns, reserved by phone. Previous sailing experience is required and renters must be over 21.
Crewed Northeast · Fernandina Beach
Private cruises on a Lagoon 410 catamaran from Amelia Island Marina, past Fort Clinch and the wild horses of Cumberland Island. Three-hour sunset sails and longer sightseeing runs, plus overnights to St. Marys and Jekyll, and to St. Simons and St. Augustine on request.
Daysail Northeast · St. Augustine
Atlantic Fury, a 65-foot sailing catamaran, sails from Beaches Marina on Vilano Beach into St. Augustine's harbor past the Castillo de San Marcos. Live-music sunset sails and dolphin-watch harbor sails by the seat, plus private charters. Their Island Cat is a power catamaran.