THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Set sail from St. Augustine on a private 2-hour sunset charter that melds historic coastal views with tranquil waters and enduring maritime tales. Discover why this intimate sailing adventure is a top pick for exploring Florida’s oldest city by sea.
Set sail from St. Augustine on a private 2-hour sunset charter that melds historic coastal views with tranquil waters and enduring maritime tales. Discover why this intimate sailing adventure is a top pick for exploring Florida’s oldest city by sea.
Book with St Augustine Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by St Augustine Sailing · St. Augustine, Florida
There’s a unique kind of magic in St. Augustine, Florida, the nation’s oldest city, where history meets salty breezes and shimmering coastal waters. The 2-hour Private Sunset Sailing Charter offers an intimate escape on the Atlantic, allowing you to glide over gentle waves while the sun dips behind the horizon in a blaze of fiery color. As one of the city’s premier water activities, this trip is tailored for travelers who want a personalized, serene introduction to St. Augustine’s spectacular seascape. Your private charter vessel leaves from the historic downtown waterfront, a short stroll from centuries-old cobblestone streets and the iconic Castillo de San Marcos — the oldest masonry fort in the continental United States, built in the 1600s.
The sailing experience centers on the graceful dance between wind and water. With an expert captain at your helm, you’ll navigate past scenic landmarks like the St. Augustine Lighthouse and the picturesque Matanzas Bay, absorbing the coastal ecosystem’s diversity. This area is known for its sandy beaches and mangrove-lined shorelines, home to egrets, dolphins frequently spotted breaching nearby, and occasionally manatees.
What makes this private charter stand out in the St. Augustine landscape is its exclusivity and flexibility; the open deck lets you soak in panoramic views and fresh salt air during the climactic sunset hour without the distractions of a larger tour group. It’s perfect for couples seeking a romantic outing, families wanting a memorable adventure, or solo travelers eager to connect with the water’s rhythms.
St. Augustine’s waters are calm enough for novice sailors, making this trip accessible regardless of prior experience. Alongside the natural spectacle, your captain provides engaging insights into the region’s maritime history and ecology, enriching your evening with stories of early explorers and local conservation efforts.
Book a sunset sail here and you tap into more than a pretty view: you find a fresh angle on Florida’s Atlantic coast wrapped in historic charm and natural beauty, a must for visitors who appreciate both culture and outdoor adventure.
easy.
2 hours.
No special fitness required; suitable for all ages and abilities
No, this private charter is designed for all experience levels, and your captain will handle navigation.
The private boat comfortably seats small groups, typically accommodating up to 6 guests.
Wear comfortable layers including a windbreaker, and sun protection is recommended before sunset.
Guests can bring their own beverages and snacks; confirm specifics with the operator when booking.
Dolphins, egrets, and occasionally manatees are often spotted near the shoreline during the sail.
Yes, the gentle waters and calm conditions make this sailing trip family-friendly.
St. Augustine’s coastal waters have been central to American colonial maritime trade and defense since the 16th century.
Local operators support efforts to protect coastal habitats and minimize pollution, ensuring sustainable marine tourism.
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