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304 North Cardinal St.
Dorchester Center, MA 02124

Enjoy a 2-hour shared sailing experience along St. Augustine’s historic bay front, guided by a USCG-licensed captain, with wildlife sightings and scenic views.

A 2-hour shared day sail along St. Augustine’s bay front offers an intimate and relaxing way to see the city from the water. The tour is priced at $149 per person and is ideal for those seeking a scenic escape with small-group comfort—limited to six travelers—and the expertise of a USCG-licensed captain. The experience includes gentle sailing down the Tolomato River and Matanzas River, with plenty of opportunities to spot dolphins and enjoy views of iconic landmarks.
This cruise suits anyone who loves beautiful waterways, wildlife, and a laid-back atmosphere. It’s especially perfect for families, couples, or small groups seeking a personalized, no-hassle adventure. The luxury sailing yacht provides a peaceful setting to relax, learn about sailing, or even take the helm if you wish. Keep in mind, the tour lasts approximately 2 hours, making it a manageable yet memorable outing in St. Augustine.

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The 2-hour yacht cruise begins at St Augustine Sailing on Harbor Drive. From this convenient starting point, the vessel slips away from the dock and heads toward the Tolomato River—a peaceful waterway perfect for spotting local wildlife and taking in the scenery. As the yacht glides along, the captain often points out historic sites visible from the water, giving a fresh perspective on the city’s storied past.
The duration allows for a leisurely experience that balances wildlife observation, scenic views, and onboard comfort. The small group size enhances this sense of intimacy, making it ideal for conversations and shared moments. The luxury sailing yacht ensures a smooth ride, whether you’re relaxing on deck or listening to the captain’s commentary.

During the cruise, the yacht sails down the Tolomato River, then continues along the Matanzas River toward the Bay Front. This route provides sweeping views of St. Augustine’s historic waterfront, with landmarks visible from the water that are impossible to see from land alone.
The Matanzas River is known for wildlife, and sightings of dolphins near Porpoise Point are common. The captain keeps a keen eye on the water, making sure passengers don’t miss these playful marine mammals. The route offers a relaxed pace, giving plenty of time to appreciate the scenery and observe local wildlife in their natural habitat.

One of the highlights of this cruise is the opportunity to see dolphins in their natural environment. As the yacht approaches Porpoise Point, the chances of spotting these playful marine creatures increase significantly. The captain’s experience ensures that wildlife sightings are frequent and natural, adding a touch of excitement to the tranquil voyage.
Aside from dolphins, the waters may reveal other marine life and seabirds, creating a lively and engaging experience for those interested in nature. The focus on wildlife makes this sailing tour especially appealing to families or anyone who appreciates animals in the wild.

This cruise offers a different perspective on St. Augustine’s historic sites. From the water, the city’s famous landmarks—including forts, churches, and old city walls—are visible in a way that complements visits on land. The coastal scenery allows passengers to appreciate the city’s charm from a relaxed, water-level vantage point.
While the tour doesn’t specify exact landmarks, the overall view of the bay front is a significant part of the experience. These scenic vistas are perfect for photography and provide a sense of the city’s maritime history, all from the comfort of a luxury yacht.
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Guests are welcome to enhance their sailing experience by bringing alcoholic beverages, such as beer, wine, or canned cocktails. It’s recommended to plan ahead and contact the operator to ensure your drinks are cold and ready onboard.
Plus, the tour offers the option to order snacks, like a charcuterie board, which can be waiting on the vessel for your arrival. This personalized touch makes the cruise ideal for celebrations, romantic outings, or casual get-togethers. The availability of bottled water is included, ensuring hydration during the journey.

The meeting point for this cruise is at St Augustine Sailing located at 3076 Harbor Dr in St. Augustine. The activity begins directly from this dock, with no complicated transfers needed. After the 2-hour sailing, the tour concludes back at the same location, simplifying logistics for participants.
Most travelers find this central location convenient, especially given its proximity to other city attractions. Parking options and easy access make it straightforward to start your water adventure without fuss.

This tour offers full flexibility with free cancellation available up to 24 hours before the scheduled start time. If weather conditions are unfavorable, the tour can be canceled or rescheduled, ensuring safety and comfort.
In cases where the minimum number of six travelers isn’t met, the tour may be canceled, but an alternative date or a full refund is always offered. Confirmation is received immediately upon booking unless the reservation is made within a day of the trip, in which case, it’s provided as soon as possible.
The small-group size and luxury yacht set this experience apart from larger boat tours. The focus on wildlife sightings, especially dolphins, and the scenic views of the historic waterfront make it a memorable outing. The professional, USCG-licensed captain enhances safety and offers informative commentary about the surroundings.
While the 2-hour duration keeps it manageable, the tour’s quality compensates for its brevity. Plus, options to bring food and drinks allow customization, making the cruise suitable for celebrations or simply relaxing away from crowds.
This experience appeals most to those who value personalized, intimate excursions in a luxury setting. It’s ideal for couples, families, or small groups seeking a peaceful cruise with wildlife viewing and scenic vistas.
Because it’s accessible to most travelers and includes most amenities, it suits both first-time sailors and seasoned water enthusiasts. The 2-hour length also makes it a perfect add-on to a day of exploring St. Augustine’s land attractions.
The 2-hour shared sailing experience along St. Augustine’s historic bay front offers a relaxed, scenic, and personalized way to enjoy the city’s waterways. The luxury yacht and small group size ensure comfort and intimacy, making it suitable for special occasions or casual outings.
Wildlife sightings, especially dolphins, and stunning waterfront views of historic landmarks create a memorable backdrop for this cruise. The option to bring food and beverages adds flexibility, allowing guests to customize their experience.
While the tour’s short duration might not satisfy those seeking a full-day adventure, it provides a perfect snapshot of St. Augustine from the water—peaceful, scenic, and charming. This cruise is best suited for those who appreciate quiet elegance and nature, offering a genuine taste of the city’s maritime beauty.
“I had never been on a sailboat. It was my 80th. So relaxing and just beautiful. Sailboat was beautiful with our great Captain Kevin. Food was delic…”
Can I cancel this tour if the weather is bad?
Yes, the tour is canceled if the weather is poor, with options for a full refund or rescheduling.
Is there a minimum number of participants?
Yes, a minimum of six travelers is required. If this isn’t met, the tour may be canceled with a full refund or alternative date.
Can I bring alcohol or snacks onboard?
Yes, guests can bring their own alcoholic beverages and snacks. It’s recommended to contact the operator in advance to arrange for cold storage or special requests.
What is included in the price?
The $149 per person fee includes the guided sailing and bottled water. Alcohol and snacks are not included but can be brought or ordered separately.
Where does the tour start and end?
The tour begins and ends at St Augustine Sailing, located at 3076 Harbor Dr.
How long is the tour?
The sailing lasts approximately 2 hours.
Is the tour suitable for children or people with mobility issues?
Most travelers can participate, and service animals are allowed, but specific accessibility info is not provided.
Is the experience suitable for first-time sailors?
Absolutely, the small group size, professional captain, and relaxed pace make it ideal for beginners.
Are there opportunities to learn sailing?
Yes, passengers can relax or even take the helm if they wish, providing a chance to learn about sailing firsthand.
What makes this tour different from other boat rides in St. Augustine?
Its small group size, luxury yacht, and focus on wildlife viewing and scenic waterfront landmarks set it apart from larger, more commercial options.