THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Discover the beauty of Florida's waters with a private sailing and portrait adventure in St. Augustine. Perfect for capturing memorable moments amid historic scenery and stunning coastlines.
Discover the beauty of Florida's waters with a private sailing and portrait adventure in St. Augustine. Perfect for capturing memorable moments amid historic scenery and stunning coastlines.
Book with St Augustine Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by St Augustine Sailing · St. Augustine, Florida
Experience the maritime charm of St. Augustine with 'Sail In Style: A Nautical Portrait Experience,' an exclusive sailing adventure tailored for those eager to embrace the open waters and capture unforgettable moments. As you glide across the scenic waterways aboard a beautifully maintained vessel, professional photographers will guide you through creating stunning portrait sessions against the backdrop of historic landmarks and sparkling Intracoastal waters. This trip isn't just about sailing—it's about embracing the nautical lifestyle, capturing breathtaking images, and creating cherished memories. Whether you're celebrating a special occasion or simply seeking a unique way to explore the coast, this adventure offers an intimate glimpse into Florida's rich maritime heritage. The crew at St Augustine Sailing ensures a comfortable, safe journey with personalized attention and expert guidance. Prepare to relax, have fun, and leave with professionally crafted portraits that reflect your adventurous spirit and love for the sea. Perfect for families, couples, or solo travelers, this experience combines the thrill of sailing with the artistry of portrait photography, all set in the enchanting surroundings of St. Augustine.
easy.
2–3 hours.
Suitable for all fitness levels; comfortable seating available onboard
Dress comfortably with light layers, and wear non-slip shoes suitable for boat decks.
Yes, the vessel is equipped with clean restroom facilities for guests' convenience.
Yes, bring your favorite non-alcoholic beverages; snacks are available upon request.
Absolutely, children over age 5 are welcome, but parental supervision is recommended at all times.
Weather decisions are made for safety; rescheduling options are available if conditions are unsafe.
No previous sailing or photography experience is required — guidance is provided throughout the trip.
St. Augustine is the oldest European-established settlement in the United States, dating back to 1565, and boasts a rich maritime history reflected in its preserved ships and harbor landmarks.
St. Augustine Sailing is committed to sustainable practices, including low-impact boat tours and protecting local wildlife 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