THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Set sail on a romantic voyage in St. Augustine’s historic waters with the Sweetheart - Apple of My Eye Package. Discover coastal views, rich history, and tranquil moments crafted for couples seeking a memorable escape.
Set sail on a romantic voyage in St. Augustine’s historic waters with the Sweetheart - Apple of My Eye Package. Discover coastal views, rich history, and tranquil moments crafted for couples seeking a memorable escape.
Book with St Augustine Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by St Augustine Sailing · St. Augustine, Florida
Experience an unforgettable romantic escape with the Sweetheart - Apple of My Eye Package, a sailing adventure designed to capture the magic of St. Augustine, Florida’s oldest city and coastal treasure. This package offers couples the rare chance to glide across the shimmering waters of Matanzas Bay, savoring stunning views of historic landmarks and the Atlantic horizon under a gentle sea breeze.
St. Augustine, known for its centuries-old Spanish architecture and vibrant maritime culture, provides a unique backdrop for this intimate sailing experience. As you set sail from the heart of the city, the historic Castillo de San Marcos fort looms on the shoreline, a vivid reminder of Florida’s colonial past. The calm waters, dotted with mangrove-lined inlets and salt marshes, invite exploration and quiet reflection.
What makes this package stand out is its tailored romantic elements combined with immersive coastal scenery. Whether you’re celebrating an anniversary, honeymoon, or simply a special getaway, the Sweetheart package transforms an ordinary outing into a cherished memory. The experienced crew manages all the details, ensuring you can focus on each other and the mesmerizing views as your sailboat cuts smoothly through the water.
Perfectly suited to couples seeking a peaceful yet adventurous way to experience St. Augustine’s natural and historic charms, this sail combines tranquility with discovery. Expect to spot local wildlife such as herons and dolphins while cruising past timeless coastal landscapes framed by the city’s iconic lighthouse and picturesque waterfront homes.
This sail is more than just a boat ride — it’s a uniquely St. Augustine experience, blending history, nature, and romance on the open water. The Sweetheart - Apple of My Eye Package exemplifies the city’s enduring allure as a top destination for outdoor recreation lovers and romantic travelers alike. Set sail with this standout adventure and create stories that will last a lifetime along Florida’s storied Atlantic coast.
easy.
2–3 hours.
Suitable for all fitness levels; no strenuous activity required, just ability to get on and off the boat safely.
No, this package is designed for beginners and experienced sailors alike.
Specific package details vary, but many couples bring their own refreshments for onboard enjoyment.
Please check with the operator when booking, as policies can vary by season and reservation type.
Yes, this package is intended as a private romantic experience for couples.
Boarding may require stepping up onto the vessel; please inquire in advance for accommodation options.
Common sightings include dolphins, herons, egrets, and other coastal birds in their natural habitat.
St. Augustine is the oldest continuously inhabited European-established settlement in the continental U.S., founded in 1565.
Operators encourage eco-friendly practices to minimize impact on fragile coastal ecosystems and 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