Sunset Tasting Cruise + St. Augustine Old Jail

Pair breathtaking waterfront views with rich history in this Sunset Tasting Cruise + St. Augustine Old Jail package. With Tripster, you can enjoy an evening of relaxation on the water and step back in time at one of the city’s most iconic landmarks, all while saving money and simplifying your travel plans.

On your evening aboard a sunset tasting cruise along the St. Augustine bayfront. Sip and savor curated beverages while you sail past historic sights like the Bridge of Lions, the Castillo de San Marcos, and the city’s glowing skyline. As the sun dips below the horizon, you’ll enjoy a relaxing, social atmosphere with unmatched views of the Ancient City.

The adventure continues with a visit to the St. Augustine Old Jail, built in 1891. Listed on the National Register of Historic Places, this unique attraction offers a fascinating look at 19th-century prison life. Guided by costumed interpreters, you’ll tour original cells, see the sheriff’s quarters, and hear true stories of the notorious inmates who once lived there. It’s an engaging, interactive experience for visitors of all ages.

By booking both experiences together through Tripster, you’ll unlock exclusive savings and enjoy the convenience of one simple reservation. No need to juggle separate tickets, because this package is designed to make your trip smooth and stress-free.

This combo is perfect for couples, families, or anyone who wants to blend a scenic evening cruise with St. Augustine’s rich history.

Book your Sunset Tasting Cruise + St. Augustine Old Jail package today with Tripster and make the most of your time in the nation’s oldest city.