THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Discover a romantic boating escape with the Sweetheart - Sweet Dreams Package in historic St. Augustine, Florida. Perfect for couples seeking serene coastal views and intimate moments on the water.
Discover a romantic boating escape with the Sweetheart - Sweet Dreams Package in historic St. Augustine, Florida. Perfect for couples seeking serene coastal views and intimate moments on the water.
Book with St Augustine Sailing
Verified experiences and guided adventures in the surrounding area.
780 ratings
Operated by St Augustine Sailing · St. Augustine, Florida
Located along Florida’s historic northeast coast, St. Augustine offers an enchanting blend of old-world charm and natural beauty, making it a perfect destination for couples seeking a romantic outdoor escape. The Sweetheart - Sweet Dreams Package invites travelers to experience an intimate adventure on the water, framed by St. Augustine’s sparkling Intracoastal Waterway and Atlantic coastline. Known as the oldest continuously inhabited European-established settlement in the continental United States, St. Augustine not only tempts visitors with its centuries-old architecture and cobblestone streets but also offers tranquil coastal scenes that create the perfect backdrop for lovers looking to unwind.
This package delivers a uniquely serene boating excursion, ideal for romantic celebrations or simply a memorable day together. As the boat glides quietly through waters edged by bright mangroves and oyster beds, couples can soak in sights of native bird species such as osprey and herons, alongside occasional glimpses of playful dolphins. The gentle sound of the water and the warm Florida sun make every moment feel like a private escape.
What sets this experience apart is its seamless combination of comfort, privacy, and natural beauty, allowing you to reclaim time and space with your partner away from the usual hustle. The boat offers cozy seating and an intimate setup customized to celebrate your special occasion, be it an anniversary, honeymoon, or just a cherished day out. St. Augustine’s coastal geography here is characterized by soft sandy shores and salt marshes, offering a peaceful contrast to the busier downtown areas.
Beyond the water, St. Augustine is rich in history and culture, with landmarks such as the Castillo de San Marcos National Monument and centuries-old lighthouses that speak to the city’s strategic importance over the centuries. This local heritage adds an extra layer of depth to every visit, reminding guests of the stories that shaped this vibrant seaside community.
For visitors, the Sweetheart - Sweet Dreams Package offers a standout way to connect with nature while enjoying a distinctly personal journey in a region famed for its outdoor recreation options. Whether you’re launching from the city marina minutes away or exploring the surrounding beaches afterward, this boat charter encapsulates the beauty of Florida’s coastal wilderness with a romantic twist.
easy.
1–3 hours.
Suitable for all fitness levels; minimal physical exertion required as this is a boat charter
Yes, this boat charter is designed for adults and can accommodate various group sizes, but it’s especially popular among couples.
While the package does not include refreshments, guests are welcome to bring their own snacks and non-alcoholic beverages.
In case of inclement weather, the trip can be rescheduled or refunded based on availability and safety considerations.
The boat departs from St. Augustine’s main marina, located conveniently near downtown and accessible by car or hotel shuttle.
Pets are not permitted on this particular boat charter to ensure comfort and safety of all guests.
Yes, the package can be personalized with prior arrangement to celebrate events like anniversaries or proposals.
St. Augustine was founded in 1565 and boasts the nation’s oldest masonry fort, reflecting its Spanish colonial past.
Local operators emphasize eco-friendly practices to protect waterways, encouraging wildlife observation without disturbance.
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