easy
2–4 hours
Suitable for all fitness levels; minimal physical exertion required as the crew handles sailing duties.
Experience the magic of St. Augustine’s coast aboard a private sunset sail with St Augustine Sailing—perfect for celebrations or tranquil escapes. Discover dolphins, stunning views, and expert guidance on the water.
Situated in the charming coastal city of St. Augustine, Florida, St Augustine Sailing offers an exceptional private sailing experience that captures the essence of the area's rich maritime heritage. Known as the nation’s oldest city, St. Augustine boasts stunning views of the Atlantic coastline, historic sites, and unique natural surroundings that make each sail an unforgettable journey. This private charter is ideal for birthdays, celebrations, or simply a peaceful escape to experience the waters from an entirely new perspective.
What sets St Augustine Sailing apart is its intimate size and personalized service, making every trip feel customized and special. Their experienced captains, such as Dan and Lauren, bring local knowledge and a deep passion for sailing, providing educational insights on landmarks, wildlife, and the unique geography visible from the water. Guests might glimpse playful dolphins or enjoy breathtaking sunset skies, all while cruising smoothly across the tides.
The sailing vessels are well-maintained with comfort and safety in mind. Whether you are opting for a multi-hour introduction to sailing, a celebration brunch sail, or a relaxed sunset cruise, the crew ensures every detail is covered, from beverage options to the storytelling that enhances the whole experience. The ability to combine wine or food tastings with the outing adds a gourmet touch that complements the scenic views.
St Augustine Sailing offers a rare chance to experience coastal Florida’s calm waters in an intimate and exclusive way. The area’s unique blend of historical charm and diverse ecosystems, including estuaries and barrier islands, provide a stunning backdrop for exploration. This is not just a sail; it’s a chance to connect deeper with one of America's most historic waterfronts under the guidance of passionate and knowledgeable locals. Whether a seasoned sailor or a first-timer, this adventure creates lasting memories and a fresh appreciation for St. Augustine’s natural beauty and maritime culture.
Sunset sails are popular and fill quickly; reserve your spot in advance for the best experience.
Even on overcast days, UV exposure on the water can be strong—protect your skin and eyes.
Choose comfortable footwear with good grip to safely navigate the boat deck during your sail.
Evenings on the water can get breezy, so a lightweight layer is recommended during sunset trips.
St. Augustine was founded in 1565 and is the oldest continuously occupied European-established settlement in the continental U.S., which adds rich historical context to the sailing routes.
The operators practice environmentally responsible sailing and support local efforts to preserve the coastal ecosystems and marine life through mindful navigational practices.
Protects your skin from prolonged sun exposure during daytime sails.
summer specific
Keeps you warm against cool breezes during early morning or sunset trips.
fall specific
Provides safety and stability on wet boat surfaces.
Reduces glare and protects your eyes while sailing on open water.
all specific