Private Day Sail Along Historic Bayfront + St. Augustine Old Jail

Discover St. Augustine by both land and sea with the Private Day Sail Along Historic Bayfront + St. Augustine Old Jail package. With Tripster, you’ll enjoy exclusive savings and a seamless booking experience while exploring the oldest city in the U.S. from two unforgettable perspectives.

On the Private Day Sail Along Historic Bayfront, where you and your group will enjoy a personalized sailing experience along the Matanzas River. With a private captain at the helm, you’ll take in stunning views of the Castillo de San Marcos, the Bridge of Lions, and the charming downtown waterfront. Keep an eye out for Atlantic bottlenose dolphins, seabirds, and manatees in season. Whether you’re seeking a romantic outing or a family-friendly escape, this customizable sailing trip offers both relaxation and breathtaking scenery.

Step back in time at the St. Augustine Old Jail. Built in 1891, this historic landmark invites visitors to explore its preserved cells, gallows, and artifacts. Guided by costumed interpreters, you’ll hear fascinating stories about the prisoners who lived here and the sheriffs who enforced the law. Part museum and part immersive theater, the Old Jail provides a unique glimpse into St. Augustine’s past.

By booking this package through Tripster, you’ll unlock exclusive combo savings while simplifying your planning. Instead of juggling multiple reservations, Tripster offers instant confirmation, secure checkout, and verified guest reviews, so you can book with confidence and ease.

This package is perfect for couples, families, and history buffs who want to experience both the beauty of St. Augustine’s waterfront and the intrigue of its historic landmarks. From a private sail to the unforgettable atmosphere of the Old Jail, it’s a well-rounded way to explore the city.

Book your St. Augustine Old Jail + Private Day Sail Along Historic Bayfront package today with Tripster and enjoy a seamless blend of history, nature, and savings in America’s oldest city.