THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Experience a romantic afternoon sailing the historic coastal waters of St. Augustine, Florida. The Sweetheart - Head Over Heels Package offers couples a serene, intimate journey that blends maritime heritage with personalized comfort.
Experience a romantic afternoon sailing the historic coastal waters of St. Augustine, Florida. The Sweetheart - Head Over Heels Package offers couples a serene, intimate journey that blends maritime heritage with personalized comfort.
Book with St Augustine Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by St Augustine Sailing · St. Augustine, Florida
Set sail from St. Augustine, Florida, and immerse yourself in an intimate sailing adventure designed to celebrate romance on the water. The Sweetheart - Head Over Heels Package offers couples a unique chance to explore the historic waters of the nation’s oldest city aboard a comfortable, expertly managed sailboat. St. Augustine’s coastal charm and gentle sea breeze provide the perfect backdrop for an unforgettable escape. St. Augustine itself is a blend of old-world architecture and natural coastal beauty, with rich Spanish colonial history and scenic waterfront views along Matanzas Bay and the Intracoastal Waterway. This package specializes in creating a tranquil, private experience for couples, with opportunities to glide past iconic landmarks such as the Castillo de San Marcos and Fort Matanzas from a fresh perspective on the water.
What differentiates this sailing trip is its focus on creating a heartfelt connection amid the soothing rhythm of the sea. The calm coastal waters are ideal for beginners and casual sailors seeking a serene outing rather than a high-adrenaline adventure. The Sweetheart package typically includes attentive service from a skilled captain who navigates while you relax and enjoy the scenery, making it an effortless experience to cherish. Sunset sails elevate the atmosphere, letting you watch the sky transform over the historic skyline as the orange hues reflect off the gentle waves.
The sailboat itself is designed for comfort and intimacy, with cozy seating areas ideal for couples looking to unwind. Whether it’s a proposal, anniversary, or just an escape from the everyday, this package offers a special way to make memories while surrounded by some of Florida’s most picturesque coastal waters. Beyond the water, St. Augustine’s cobblestone streets, quaint cafes, and oceanfront parks await exploration, offering the perfect complement to your sailing experience.
This trip stands out as a uniquely tailored romantic outing in a region better known for its history and beaches, combining the charm of sailing with personalized attention and local knowledge. Ideal for visitors wanting a peaceful, scenic experience that highlights St. Augustine’s maritime heritage without the crowds or complexity of larger charters. If you’re dreaming of an easy yet elegant escape on a sailboat, this package is a standout choice worth booking.
easy.
1–2 hours.
Suitable for all fitness levels; minimal physical effort required.
No prior sailing skills are needed; the captain handles all navigation and sailing duties.
Policies vary but typically light snacks and non-alcoholic beverages are allowed; confirm with the operator.
Yes, this package offers private experiences specifically tailored for couples.
Check the operator’s booking platform for specific refund guidelines and cancellation windows.
Pets are generally not permitted due to safety and comfort concerns.
Accessibility can be limited due to the boat’s layout; contact the provider to discuss individual needs.
St. Augustine is the oldest continuously inhabited European-established settlement in the continental U.S., founded in 1565.
Operators emphasize eco-friendly practices such as minimizing fuel use and promoting wildlife respect to protect coastal ecosystems.
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