THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Join a private sunset sailing experience in St. Augustine and witness stunning coastal views as the sky transforms at sunset. Perfect for a romantic evening or small group celebration, this boat tour promises an unforgettable adventure on the water.
Join a private sunset sailing experience in St. Augustine and witness stunning coastal views as the sky transforms at sunset. Perfect for a romantic evening or small group celebration, this boat tour promises an unforgettable adventure on the water.
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 a sunset like never before with the Shared Sunset Sailing Charter in St. Augustine, Florida. As the sun begins to dip below the horizon, join St Augustine Sailing aboard a private boat tour designed for relaxation and breathtaking views. This unique sailing trip offers an intimate atmosphere where you can unwind and enjoy the vibrant colors painting the sky, all while gliding over calm waters past historic landmarks and scenic coastal spots. The crew's friendly demeanor and expert navigation ensure a safe and comfortable experience, making it perfect for couples, friends, or small groups seeking a memorable evening. Throughout the voyage, you'll have the chance to snap stunning photos of the sunset, spot local wildlife, and listen to stories about St. Augustine’s rich maritime history. Whether celebrating a special occasion or simply escaping into nature, this activity guarantees a peaceful retreat with the bonus of spectacular sunset vistas. Bring along your favorite beverage, sit back, and savor the tranquility of this personalized sailing adventure, leaving with unforgettable memories of St. Augustine’s stunning coastline and fiery skies.
easy.
2–3 hours.
Suitable for most fitness levels; no strenuous activity required
It's recommended to book at least a week in advance, especially during peak seasons, to secure your preferred date and time.
Please contact St Augustine Sailing directly to discuss accessibility options, as some boats may have limited accessibility.
You are welcome to bring your own beverages; alcohol consumption is permitted but please do so responsibly.
Dress comfortably in light layers, and bring a jacket if it gets cool after sunset.
Yes, you can bring snacks or light refreshments to enjoy during the sail.
Yes, children are welcome, but please ensure they are supervised at all times for safety.
St. Augustine is the oldest city in the US, founded in 1565, with a rich maritime history reflected in its coastal waters and historic landmarks.
St. Augustine Sailing is committed to eco-friendly practices, including responsible wildlife viewing and minimal impact sailing methods.
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