Top St Augustine Sailing Tours

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.

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.

Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories on the sea. Our cruise is perfect for all water-lovers: families, couples, and friends. Some guests interact with the USCG licensed Captain, learn a little about sailing, or take the helm. Others relax and enjoy the trip. No matter your preference, this cruise will be a highlight of your vacation.

Explore St. Augustine’s Historic Bay Front from the water on this small-group day cruise on a luxury sailing yacht. With a USCG-licensed captain at the helm, sail down the Tolomato River, Matanzas River, and along the bay front. Look for wildlife, including dolphins, and admire the historic sites. Relax onboard, learn about sailing, or even take the helm.

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.

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.

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.

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.

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting that allows guests to fully immerse in the beauty of the holiday lights without the crowds or noise of typical boat tours. Our yachts offer a more personalized, relaxed atmosphere with comfortable seating, and the option to book private charters. You’ll also be guided by experienced USCG captains who know the waters and the best vantage points to view the city’s spectacular light display. Whether you’re celebrating a special occasion or seeking a peaceful, romantic evening, our tailored sailing experience ensures you enjoy the Nights of Lights in comfort and style.

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.

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.