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Experience a romantic sailing adventure in historic St. Augustine, Florida. The Sweetheart – Puppy Love Package offers couples a peaceful, scenic journey on gentle waters surrounded by natural beauty and coastal landmarks.
Experience a romantic sailing adventure in historic St. Augustine, Florida. The Sweetheart – Puppy Love Package offers couples a peaceful, scenic journey on gentle waters surrounded by natural beauty and coastal landmarks.
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 the historic coastal city of St. Augustine, Florida, on the Sweetheart – Puppy Love Package, a uniquely intimate sailing adventure designed for couples seeking romance and tranquility on the water. Known as the nation’s oldest city, St. Augustine’s charming waterfront and calm Atlantic waters set the perfect backdrop for a serene and memorable day afloat. This experience offers a blend of gentle ocean breezes, scenic views, and cozy luxury on a classic sailboat, elevating your visit to an unforgettable chapter of your Florida trip.
St. Augustine’s coastline is renowned for its gentle tides, making it an ideal location for a relaxing sail. As your crew guides the sailboat out from the marina, you’ll glide past historic lighthouses, sandy beaches, and the lush mangroves that flourish along the shoreline. The unique ecology of the area, including native coastal palms and occasional sightings of dolphins or manatees, enhances the intimate ambiance. The water surrounding St. Augustine is a network of protected inlets and bays, offering smooth sailing perfect for those less experienced at sea.
What sets the Sweetheart – Puppy Love Package apart is its focus on privacy and comfort tailored specifically for couples. Whether airing your vows, celebrating an anniversary, or simply sharing peaceful moments together, the package promises personalized attention. The experienced crew ensures a smooth journey, with options to pause in quiet coves for a refreshing swim or to bask under the warm Florida sun. Guests typically enjoy light refreshments on board, creating a serene floating retreat from the bustle of town.
As a part of the local outdoor recreation scene, this sailing adventure complements St. Augustine’s reputation for blending history, culture, and nature. Established in 1565, the city reflects Spanish colonial heritage with cobblestone streets and centuries-old architecture visible from the waterline, painting a unique picture of old and new. The Sweetheart package offers a calm escape while being perfectly positioned to view these cultural landmarks from a fresh perspective.
Choosing this sailing experience supports small, locally operated water activity providers committed to sustainable tourism practices. Care is taken to minimize environmental impact on the fragile marine habitats of Northeast Florida.
Whether you’re seasoned sailors or first-time adventurers, this package offers an ideal paced, romantic outing against the backdrop of one of America’s most storied shores. A few hours of drifting with the tide and a warm breeze, framed by local beauty and history, makes this adventure an ideal booking for couples visiting St. Augustine seeking both relaxation and connection.
easy.
2–3 hours.
Minimal physical effort required; suitable for all fitness levels
No prior sailing experience is necessary; the experienced crew handles navigation and safety.
The package includes a private sailing trip, light refreshments, and personalized service for couples.
Pets are not allowed on this sailing package to ensure comfort and safety for all guests.
Cancellations made 48 hours in advance receive a full refund; please confirm with the provider for exact terms.
Yes, the vessel is equipped with a restroom for guest convenience during the trip.
Bring layered clothing, sunscreen, a hat, and a waterproof camera to make the most of your outing.
St. Augustine is the oldest continuously inhabited European-established settlement in the continental U.S., founded in 1565.
Local operators follow guidelines to protect coastal habitats and reduce boat disturbance to marine wildlife.
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