Top St Augustine Sailing Tours

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.

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.

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.

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.

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.