THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Discover the beauty of St. Augustine from the water during a private sunset sail along its historic bayfront. Enjoy stunning views, local wildlife, and a peaceful evening on the water with personalized service from St Augustine Sailing.
Discover the beauty of St. Augustine from the water during a private sunset sail along its historic bayfront. Enjoy stunning views, local wildlife, and a peaceful evening on the water with personalized service from St Augustine Sailing.
Book with St Augustine Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by St Augustine Sailing · St. Augustine, Florida
Experience the magic of St. Augustine from an entirely new perspective with the Private Sunset Sail Along Historic Bayfront. This exclusive boat tour offers a unforgettable opportunity to witness the city's stunning coastline as it bathes in the golden hues of evening. As you glide smoothly across the calm waters, enjoy panoramic views of historic landmarks and the vibrant Florida sunset. The intimate setting allows for personalized interactions with knowledgeable crew members from St Augustine Sailing, who share captivating stories of the bay's history and marine life. Perfect for couples celebrating special occasions or groups seeking a peaceful escape, this sunset sail combines scenic beauty with tranquility. Whether you're relaxing on deck or capturing breathtaking photos, this experience creates lasting memories. The gentle sea breeze, spectacular views, and the chance to spot local wildlife like seabirds and dolphins make this adventure truly unique. End your day with a sense of calm and wonder, as the sky transforms into shades of orange and pink. In every way, this private sunset sail promises a peaceful voyage filled with scenic splendor and fascinating tales from Florida’s oldest city.
easy.
1.5–2 hours.
Suitable for most fitness levels; no strenuous activity required
Yes, St Augustine Sailing offers beverage options, and you are welcome to bring your own snacks and drinks.
Children of all ages are welcome, but keep in mind the tour duration and suitability for younger kids.
Tours can be canceled or rescheduled with at least 24 hours' notice; please check specific policies at booking.
Please contact St Augustine Sailing in advance; most boats are accessible but may have limitations.
Pets are not typically permitted, but it's best to check with the company for specific accommodations.
Dress comfortably in layers, with sun protection in summer and warmer clothing in cooler months.
St. Augustine is the oldest city in the U.S., with a history dating back to 1565, making its harbor rich with stories of exploration and maritime adventure.
St Augustine Sailing prioritizes eco-friendly practices by minimizing waste and respecting marine ecosystems during tours.
St Augustine Sailing operates premium sailing experiences and certified sailing courses in historic St. Augustine, Florida. The company offers a diverse lineup of public and private excursions — from shared brunch sails and sunset tasting cruises to intimate private dinner charters and wedding packages aboard luxury yachts. Educational offerings include ASA 103 Basic Coastal Cruising, Basic Keelboat prep classes, and hands-on day sails on 21–22-foot boats and larger Jeanneau models. Each experience blends local maritime history, coastal wildlife viewing, and elevated hospitality. Professional skippers and trained crew lead all trips, delivering safety briefings, navigation expertise, and attentive service. On private dinner and tasting cruises, guests enjoy chef-prepared courses, sommelier-curated flights, and tailored menus served onboard. Photography-focused sails provide short portrait sessions against landmarks like the Lighthouse and Historic Bayfront. St Augustine Sailing prioritizes safety and instruction for learners and recreational sailors. Courses emphasize seamanship, heavy-weather operation, docking skills, and practical boat handling on 30–45-foot auxiliary-powered catamarans. Short introductory sessions give beginners the confidence to handle sails and basic lines. For weddings and private events, the company offers packaged options including on-yacht ceremonies, dockside Marriage Knot services, bouquets, photography, wedding cake, and charcuterie boards for small to mid-size groups. Vessel maintenance, certified instruction, and transparent booking policies support reliability and repeat business. Located in downtown St. Augustine’s marina district, the operator leverages local knowledge of tides, wildlife patterns, and historic routes to create memorable, trustworthy coastal adventures for couples, families, learners, and food-and-wine enthusiasts. Bookings are available year-round with flexible cancellation policies online.
Book with St Augustine Sailing