Top St Augustine Sailing Tours

See St. Augustine from a new perspective with this leisurely sunset cruise. Climb aboard a boat for a scenic cruise including views of Castillo de San Marcos National Monument, the Bridge of Lions, and the St. Augustine Lighthouse. Sip beer or wine from the on-board bar with the Osprey, 21 and older option, or select the Island Breeze option for a family-friendly experience.

During St. Augustine’s Nights of Lights festival, the city is bathed in sparkling light. Choose the Sunset Tour to watch the sun set over the cityscape and see St. Augustine light up against the night sky, or the Evening Tour to enjoy the full nighttime display. Both tours offer live music and complimentary drinks, including beer, wine, margaritas, and hot chocolate, along with snacks, holiday cookies, and festive 3-D glasses that enhance the lights.

Discover a new perspective on St. Augustine—and enjoy a relaxing trip out on the water—on this sightseeing boat tour. Pick from multiple start times, head to the marina, and hop aboard. See highlights like the Bridge of Lions, Castillo de San Marcos National Monument, and National Shrine of Our Lady of La Leche, and learn the stories behind the sights from your captain’s narration.

Sail along St. Augustine’s picturesque coastline—and indulge in a number of generous wine samples—during this two-in-one tour. Make your own way to the dock, hop aboard the pontoon boat, and get comfortable: as you set off, you’ll see landmarks like the Castillo de San Marcos, the Bridge of Lions, and more. You’ll also taste six different wines, and will have access to the on-board bar.

Celebrate the holidays in St. Augustine with a nighttime boat cruise. Choose between two different vessels – one for adults only with an on-board bar, the other family-friendly and BYOB – and set on a scenic cruise to see the millions of white lights that make up the Nights of Lights Festival. Experience the magical atmosphere of the twinkling lights on the water.

St. Augustine is one of the oldest cities in the United States and is a spectacular sight when viewed from the water. Get a glimpse of the city’s historic district and surrounding area during this sunset boat tour. You’ll cruise around the banks of downtown St. Augustine, gazing at sites like the Bridge of Lions and the Castillo de San Marcos National Monument. You’ll also venture into the St. Augustine Inlet and see St. Augustine Lighthouse & Maritime Museum.

As the oldest continuously occupied colonial settlement in the United States, St. Augustine has a wealth of history within its city limits. See both historical sites and natural landscapes while on this shared sailing cruise. Climb aboard a luxury yacht and sail down the Tolomato River and Matanzas River. This small-group sailing tour passes by the St. Augustine Lighthouse and Bridge of Lions, as well as showcases spectacular sunset views.

Explore St. Augustine’s Bay Front from the water on this private 2-hour cruise aboard a luxury sailing yacht with space for up to six passengers. With a USCG-licensed captain at the helm, sail along the historic bay front. Look for wildlife, including dolphins, and admire the historic sites. Relax onboard, learn about sailing, or even take the helm.

Sunset is one the most beautiful times of day and many people like to take cruises to see sights from the water when the sun goes down. Kick up the fun with this St. Augustine Sunset Booze Cruise that allows you to see the sights at sunset and enjoy some drinks on the water, too. This cruise has room for up to 24 passengers and takes place in a unique cycle boat.