THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Discover an immersive sailing adventure in St. Augustine, Florida, where history meets the sea. Crew Sails offers hands-on trips that connect you to the coast’s beauty and maritime past.
Discover an immersive sailing adventure in St. Augustine, Florida, where history meets the sea. Crew Sails offers hands-on trips that connect you to the coast’s beauty and maritime past.
Book with St Augustine Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by St Augustine Sailing · St. Augustine, Florida
St. Augustine, Florida, known as the nation's oldest city, offers a unique blend of historic charm and scenic coastal beauty. Set on the Atlantic coast, this city captivates visitors with its colonial architecture, lush maritime landscapes, and warm, inviting waters. One of the best ways to explore St. Augustine’s coastal environment and soak in its rich nautical heritage is through Crew Sails, a premier sailing adventure company providing an authentic and hands-on sailing experience along these storied shores.
Crew Sails operates from the heart of St. Augustine, inviting adventurers to step aboard traditional sailboats that harness the steady Atlantic breeze. This trip stands out for its personalized vibe, where guests don’t passively observe but actively participate in sailing their vessel. Whether you’re a novice eager to learn the ropes or someone with sailing experience seeking a peaceful day afloat, Crew Sails crafts an experience tailored to your comfort.
The sailing routes glide past significant coastal landmarks, from the iconic St. Augustine Lighthouse to the shimmering Matanzas Bay. Along the way, sailors enjoy refreshing views of coastal marshlands, salt flats, and the vast stretch of Atlantic blue. The water here is famous for its clarity and calm, particularly in spring and fall, giving an excellent opportunity to spot local wildlife such as migratory birds and playful dolphins.
St. Augustine’s sailing history dates back centuries; these waters witnessed the voyage of Spanish explorers and the establishment of the oldest European settlement in the U.S. Crew Sails connects you to that legacy by using traditional sailing methods and locally maintained vessels, providing a link to maritime history alongside modern-day enjoyment.
For anyone fascinated by a blend of history, nature, and adventure, Crew Sails offers a rare glimpse into this coastal ecosystem while imparting sailing knowledge in a welcoming atmosphere. Their commitment to sustainable operation ensures that your time on the water leaves as light a footprint as possible, promoting the health of local marine habitats.
Whether you seek a morning cruise basking in the sunrise over Matanzas Bay or a sunset sail under warm Florida skies, Crew Sails promises a memorable outing that stands apart from typical sightseeing tours. Embrace the adventure, feel the wind in your hair, and chart your course through one of Florida's historic gem cities by water.
moderate.
2–4 hours.
Good physical condition recommended; moderate strength and balance needed for handling sails and staying steady on deck.
No prior experience is necessary. Crew Sails welcomes beginners and provides guidance to all guests.
Wear comfortable, layered clothing and shoes with good grip. Bringing sun protection like a hat and sunscreen is recommended.
Typically, guests bring their own snacks and beverages, but Crew Sails can advise on local provisions.
Boats generally accommodate small groups of up to 6 to 8 people for a personalized experience.
Children are welcome, but the trip requires vigilance and adhering to safety instructions; check with Crew Sails about age limits.
Trips are weather dependent. If conditions are unsafe, Crew Sails will reschedule or offer a refund.
St. Augustine is the oldest continuously inhabited European-established settlement in the continental U.S., founded in 1565, reflected throughout the city’s maritime culture.
Crew Sails practices eco-friendly sailing by minimizing fuel use and educating guests on preserving marine habitats.
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