Shared Brunch Sailing Cruise + St. Augustine Old Jail

Pair the charm of a scenic sailing brunch with one of St. Augustine’s most unique historical landmarks in this Shared Brunch Sailing Cruise + St. Augustine Old Jail package. With Tripster, you’ll enjoy exclusive savings and the ease of one booking for two amazing experiences.

On the water aboard a Shared Brunch Sailing Cruise. As you sail along the Matanzas River and historic bayfront, soak in picturesque views of the Castillo de San Marcos, the Bridge of Lions, and the charming city skyline. While you enjoy a delicious brunch menu and refreshing drinks, keep your eyes open for dolphins and seabirds that often accompany the cruise. This laid-back experience is the perfect way to relax, socialize, and take in the beauty of St. Augustine.

Once back on land, step into history with a guided visit to the St. Augustine Old Jail. Built in 1891, this well-preserved jailhouse provides a glimpse into what life was like for prisoners more than a century ago. Costumed interpreters share fascinating stories about the facility’s notorious inmates, the sheriff’s living quarters, and daily life in the Old Jail. Both educational and entertaining, it’s one of the city’s most popular historic attractions.

By booking with Tripster, you not only get package discounts but also save time with real-time availability and one easy checkout. No need to manage separate reservations. Tripster combines both attractions into one convenient experience, easy right? Yes, indeed.

This package is ideal for travelers who want to balance leisure and history. From sipping mimosas on deck to walking through the cells of a 19th-century jail, it’s an experience that highlights both St. Augustine’s charm and its fascinating past.

Book your Shared Brunch Sailing Cruise + St. Augustine Old Jail package today with Tripster, and enjoy an unforgettable day of history, scenery, and value in America’s oldest city.