Shared Day Sailing Charter Along the Bayfront + St. Augustine Old Jail

Sail into adventure and step back in time with this Shared Day Sailing Charter + St. Augustine Old Jail package. Tripster makes it easy to enjoy the beauty of St. Augustine’s bayfront and explore one of the city’s most fascinating historic landmarks.

All aboard a shared sailing charter along the bayfront, where you’ll glide across the sparkling waters of Matanzas Bay. From your spot on deck, you’ll see panoramic views of the Bridge of Lions, the Castillo de San Marcos, and the picturesque city skyline. With a friendly crew, gentle breezes, and the sunshine of Florida’s oldest city, it’s the ultimate way to relax on the water.

Dive into history at the St. Augustine Old Jail, built in 1891 and now listed on the National Register of Historic Places. Costumed guides bring the past to life with stories of notorious inmates, daring escapes, and the daily hardships of 19th-century prisoners. Explore restored cells, sheriff’s quarters, and artifacts for a fun, interactive history lesson that visitors of all ages will enjoy.

When you book through Tripster, you’ll unlock exclusive savings while simplifying your travel planning. Instead of juggling separate reservations, you can reserve both experiences at once, giving you more time to enjoy your trip.

This package is ideal for couples, families, and history lovers looking to combine scenic sailing and fascinating history in one unforgettable day.

Book your Shared Day Sailing Charter + St. Augustine Old Jail package today with Tripster, and discover the best of the Ancient City by land and sea!

Package Includes:

Shared Day Sailing Charter Along the Bayfront

Sail St. Augustine's historic bayfront on a small-group yacht cruise from Camachee Cove Yacht Harbor. Pass landmarks like the Castillo de San Marcos and spot dolphins along the scenic Tolomato and Matanzas Rivers. Led by a licensed captain, it's perfect for couples, families, and first-time explorers of Florida's Historic Coast.

Old Jail Museum

Tour the Old Jail Museum in St Augustine—an 1891 Romanesque landmark that looks more like a resort than a prison. Explore cells, gallows, and sheriff's quarters, get "booked" and try to escape during this immersive guided tour.

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Your package is based upon 2 adults. However, each product may classify different adults and children by different ages.
This package is subject to availability of tickets and rooms for selected travel dates.
Pricing is subject to amount of people chosen in the package, dates, show times, ticket selections, hotel and room selections, plus applicable taxes.

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This package is subject to availability of tickets and rooms for selected travel dates.
Pricing is subject to amount of people chosen in the package, dates, show times, ticket selections, hotel and room selections, plus applicable taxes.

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Shared Day Sailing Charter Along the Bayfront + St. Augustine Old Jail

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