easy
2–4 hours
Suitable for all fitness levels; minimal physical exertion required but ability to move carefully on deck recommended.
Experience St. Augustine’s stunning coastline from the water with St Augustine Sailing’s private charters. Perfect for celebrations, learning, or cruising under gorgeous Florida sunsets.
St. Augustine, Florida, is known for its rich history and stunning coastal views, and there’s no better way to experience this than with a private sailing adventure from St Augustine Sailing. Located in the oldest city in the United States, this company offers a unique glimpse of St. Augustine’s scenic waterways framed by lush maritime forests, historic landmarks, and abundant marine life. Whether celebrating a special occasion like a birthday, exploring the coast with friends, or learning the ropes with an introductory sailing course, St Augustine Sailing provides an intimate and memorable experience on the water.
The key feature of this adventure is the personalized private charters led by experienced captains like Dan, Lauren, and Roseanne, who bring professional hospitality combined with deep local knowledge. From smooth, leisurely sails during a picturesque sunset to engaging wine and food tastings aboard the boat, each trip is curated to maximize enjoyment and connection with the coastal environment. The routes often reveal views that land-based tours miss, including glimpses of dolphins and stunning, uninterrupted water vistas.
The natural beauty of the area includes salt marshes, sandy beaches, and estuaries that support diverse birdlife and marine species. Guests appreciate insights into local ecology and cultural history shared by captains during their sails, adding layers of understanding to the adventure. St Augustine Sailing stands out as a destination experience because they emphasize creating lasting memories, whether for a celebratory event or relaxed learning.
St. Augustine’s historical backdrop, including Spanish colonial architecture and coastal defenses, enriches the ambiance. Combined with the warm Florida climate—which averages in the high 70s to 80s during many sailing months—this outdoor experience is both educational and exhilarating. Whether you’re a first-time sailor or a seasoned adventurer, the company’s commitment to personalized service makes every journey one of discovery and delight on Florida’s beautiful Atlantic coast.
Sunset sails are popular; reserving in advance ensures a prime spot on the boat during golden hour.
Even smooth rides can cause discomfort for some; having tablets on hand helps ensure comfort.
Coastal breezes can cool off quickly after sunset; a light jacket or sweater is recommended.
While beverages may be available, fueling up beforehand keeps energy high for active trips.
St. Augustine is the oldest continuously inhabited European-established settlement in the continental U.S., founded in 1565.
St Augustine Sailing supports sustainable boating practices to minimize environmental impact and protect local marine ecosystems.
Protects eyes from glare off the water and enhances visibility.
summer specific
Keeps you warm against cool coastal breezes after sunset.
fall specific
Ensures safety when moving on wet, slippery boat surfaces.
Staying hydrated is important during sun and sea exposure.