St. Augustine was built facing the water, and the Schooner Freedom is the most romantic way to see it from that side. She is a 76-foot schooner built in the traditional style and billed as the city’s only tall ship, and she sails from the St. Augustine Municipal Marina just south of the Bridge of Lions. A typical sail lasts around two hours and covers Matanzas Bay: the crew raises the sails, the engine goes quiet, and the ship slides past the bayfront seawall, the coquina walls of the Castillo, the Vilano bridge and out toward the St. Augustine Inlet, with the black-and-white lighthouse on Anastasia Island in view. Dolphins are common in the bay and frequently surface alongside, and pelicans and ospreys work the channel. The crew mixes sailing with stories of the bay’s history, from the Spanish treasure fleets to the pirates who raided the town. Day sails suit families and photographers; sunset sails, the most popular, time the return for the light going gold behind the old town; and the company also runs special sailings such as full-moon sails. In winter, the Sunset Night of Lights sails are the headline: the ship leaves in the late afternoon and comes back into the bay as more than three million white lights switch on across the city and the Bridge of Lions, a view you cannot get from land. Seating is on deck, open to the sky, and the atmosphere is relaxed rather than party-boat.
Booking: sailings are scheduled daily in good weather and sell out on weekends, holidays and every evening of the Nights of Lights season, which runs November 21, 2026 through January 18, 2027; book Nights of Lights sails as early as you can. Tickets are sold through the operator, Schooner Freedom Charters, at the City Marina, 111 Avenida Menendez; the official county tourism listing links to their booking site. Private charters are available for groups and celebrations. Ask about the current food and drink policy when booking. Sailings depend on wind and weather, and the crew will reschedule if conditions are unsafe.
What to bring: layers, always. Even on warm days it is breezier on the water, and winter evening sails during Nights of Lights can be properly chilly once the sun goes down; a jacket, hat and blanket are not overkill. Bring sunglasses and sunscreen for daytime sails and a camera with low-light capability for the lights. The deck can be wet and is not fully accessible, so travelers with mobility concerns should call ahead.
Why it is worth it: most St. Augustine sightseeing happens at street level, in crowds. From the bay, the city reorganizes itself into the view the Spanish designed it for: the fort guarding the inlet, the town tucked behind it, the lighthouse marking the way in. It is the most couple-friendly two hours in town and a good choice for families with children old enough to sit still for a sail. Combine a sunset sail with dinner on the bayfront or Aviles Street afterward, and leave your car in the marina area or the Historic Downtown Parking Facility.
What to expect
The experience
A two-hour sail on a 76-foot schooner around Matanzas Bay — past the Castillo and toward the inlet and lighthouse — with day, sunset and seasonal Nights of Lights sailings.
Best time
Sunset for the light; Nights of Lights evenings (Nov 21, 2026 to Jan 18, 2027) for the city lit up from the water.
How long
About two hours.
Tips
Book Nights of Lights sails early. Bring layers, especially in winter. Ask about food and drink policy when booking. Sails depend on weather.
Quick picks
- Best for
- Couples and anyone who wants to see the old city from the water.
- Families
- Good for kids who can sit for two hours; watching the crew raise the sails and spotting dolphins are the hooks.
- Couples
- A sunset or Nights of Lights sail, then dinner on Aviles Street.
- Pair with
- The Castillo by day and a bayfront dinner after the sail.
- Time needed
- Two hours plus check-in.
Good questions
Where does the Schooner Freedom sail from?+
The St. Augustine Municipal Marina at 111 Avenida Menendez, just south of the Bridge of Lions.
How long is a sail?+
About two hours. Day, sunset and special sailings run on a published schedule, weather permitting.
When are the Nights of Lights sails?+
During the 2026-2027 Nights of Lights season, November 21, 2026 through January 18, 2027. They sell out quickly, so book early.
Will we see dolphins?+
Often. Bottlenose dolphins are common in Matanzas Bay, though sightings are never guaranteed.
What should I wear?+
Layers and non-slip shoes. It is breezier on the water than in town, and winter evening sails get cold after sunset.
