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Experience a 2-hour small group sailing tour along St Augustine’s historic bayfront, enjoying wildlife sightings and stunning city views aboard a luxury vessel.

The Shared Day Sail along Historic St Augustine Bayfront offers an intimate and scenic way to explore one of Florida’s most charming coastal cities. Priced at $129 per person, this 2-hour small group cruise departs from 3076 Harbor Dr, providing a relaxed and memorable experience for families, couples, and friends alike. With a maximum of 6 travelers, this tour ensures personalized attention and a peaceful atmosphere, making it ideal for those seeking a calm escape on the water.
What truly sets this tour apart is its blend of wildlife spotting, historic city views, and the chance to interact directly with the USCG licensed Captain. The cruise is not just about the scenery — it’s also about creating lasting memories through a mix of adventure, education, and relaxation. While the tour is accessible to most, guests should be comfortable climbing a few steps onto the vessel. This sailing experience promises an authentic way to enjoy St Augustine’s bayfront from the water.

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This tour begins at 3076 Harbor Dr, where guests meet the crew and board a luxurious sailing vessel. The two-hour itinerary takes you from the dock into the serene waters of the Tolomato River, passing through areas where dolphins are often seen near Porpoise Point. As the boat glides along, the watercraft offers a peaceful way to observe local wildlife and enjoy the gentle sea breeze.
The cruise then continues down the Matanzas River, revealing spectacular views of St Augustine’s historic skyline. From the water, travelers get a different perspective of notable landmarks and the city’s famous bayfront. This route is especially engaging for wildlife enthusiasts and those interested in scenic cityscapes, with the chance to witness dolphins in their natural habitat during the trip.

One of the standout features of this tour is the opportunity to interact with the USCG licensed Captain. Guests can learn a little about sailing or even take the helm, adding an element of hands-on fun to the experience. Whether you prefer to relax and enjoy the views or engage actively, the crew is welcoming and eager to enhance the cruise with personalized attention.
Guides and captains like Captain Kim, Captain Chuck, and Captain Allen receive praise for their professionalism and friendly demeanor. In particular, the chance to have Captain Allen let guests try steering the sailboat creates a memorable highlight that sets this tour apart from typical sightseeing trips. The focus on interaction makes this sail both educational and relaxing, catering to a variety of preferences.
The tour’s route offers frequent sightings of dolphins, especially as the vessel approaches Porpoise Point. The presence of these intelligent marine mammals adds a lively touch to the cruise, and spotting them is often regarded as a special highlight of the experience.
Along With dolphins, the waters are teeming with other wildlife, including various bird species, which guests can observe from the vessel. This focus on nature makes the tour especially appealing to nature lovers, providing a peaceful setting where wildlife viewing is a natural part of the journey.

From the water, this sailing tour provides a unique vantage point of St Augustine’s historic bayfront. Passengers see the city’s famous landmarks from the water, enhancing their understanding of its geography and history. The views include famous sites and the charming layout of the old port area.
The calm waters and unobstructed vistas make for excellent photo opportunities. Whether you’re capturing the city skyline or the lush shoreline, these scenic views are a significant part of what makes this tour worthwhile.
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Participants should be able to climb a few steps onto the vessel, which might be a consideration for some guests. The tour is designed for most travelers, with most being able to participate comfortably.
Guests should plan to bring bottled water, which is included, and dress for the weather with light, breathable clothing. The tour runs in good weather, and if canceled due to poor conditions, a full refund or rescheduling is offered. Most bookings are made about 18 days in advance, emphasizing the popularity of this experience.

The tour departs from 3076 Harbor Dr in St Augustine, a straightforward meeting point accessible by car or local transportation. The mobile tickets make booking simple and convenient. The activity generally lasts around 2 hours, fitting neatly into a day’s itinerary, whether as a standalone activity or part of a broader exploration of the city.
Potential guests should confirm their reservation at least 24 hours in advance to ensure availability. The small group size guarantees a more intimate experience, making it suitable for those looking to avoid crowded tours.
This tour enjoys a perfect rating of 5.0 out of 5 based on 4 reviews, highlighting its consistent quality. Past participants describe the experience as “Memorable,” “Incredibly relaxing,” and “fantastic views.” Captains like Kim, Chuck, and Allen are praised for their professionalism and friendliness.
The reviews emphasize the spectacular boat, beautiful day, and the opportunity to steer as major highlights. The overall positive feedback suggests that this sailing adventure delivers on its promise of an enjoyable, scenic, and engaging experience.
Guests benefit from a full refund if they cancel at least 24 hours in advance, making booking less risky. If canceled due to bad weather, guests are offered an alternative date or a full refund. The tour’s reliance on good weather is typical for sailing trips, so checking the forecast before booking is advisable.
The Shared Day Sail along Historic St Augustine Bayfront represents a perfect way to enjoy the city’s scenic beauty and wildlife in a relaxed setting. The combination of stunning views, wildlife encounters, and captain interaction makes this experience stand out among water-based activities in the area.
Ideal for small groups seeking a peaceful escape, this tour offers a personalized, educational, and scenic journey on the water. For those who appreciate beautiful boat rides and a chance to see dolphins and the city from the bayfront, this sail delivers genuine value and memorable moments.
“Captain Kim was amazing, the boat was spectacular, and the views were out of this world. At this price point you'd be hard pressed to find a better…”
How long is the sailing tour?
The tour lasts approximately 2 hours, providing ample time for wildlife viewing and city scenery.
What is the maximum group size?
The tour is limited to 6 travelers, ensuring an intimate experience with personalized attention.
Are food or drinks included?
Bottled water is included in the price, but no other food or drinks are provided.
Can I interact with the captain?
Yes, guests are encouraged to interact with the USCG licensed Captain and may even try steering the sailboat.
What should I wear?
Guests should wear comfortable, weather-appropriate clothing and be prepared for outdoor conditions.
Is the tour accessible for everyone?
Participation requires the ability to climb a few steps, which may not suit everyone with mobility issues.
What if the weather is bad?
The tour is weather-dependent; if canceled due to poor conditions, guests receive a full refund or reschedule.
How do I book?
Most bookings are made 18 days in advance with a mobile ticket, and free cancellation is available up to 24 hours before the tour.
What landmarks will I see?
You’ll enjoy views of St Augustine’s historic sites from the water, including the bayfront and nearby landmarks.
Is this tour suitable for families?
Yes, the relaxed pace and wildlife viewing make it an excellent choice for families, couples, and friends alike.