2 hours – Private Day Sail along Historic St Augustine Bayfront

A Private 2-Hour Sail Along St. Augustine’s Historic Bayfront: A Closer Look

Imagine gliding quietly along the bayfront of St. Augustine, the oldest city in the U.S., on a beautifully maintained luxury sailing yacht. This private experience, costing $795 for up to six people, offers a vivid perspective of the city’s famed coastline. Led by a USCG-licensed captain, you’ll get to see iconic landmarks like the St. Augustine Lighthouse and Castillo de San Marcos from the water, while possibly spotting dolphins and other wildlife.

What we love most about this tour is how flexible and personal it feels — whether you want to relax, learn a bit about sailing, or even take the helm yourself, this experience adapts to your mood and interests. Plus, the chance to see dolphins at Porpoise Point makes it a memorable wildlife encounter.

A potential consideration is the weather — as with any outdoor water activity, a day with poor weather could lead to rescheduling or cancellation. But overall, this tour is best suited for groups seeking a tranquil, tailored way to explore St. Augustine’s coastal charm — great for families, couples, or friends looking for a relaxed, scenic adventure.

Key Points

• Private and customizable experience for up to six guests
• Wildlife viewing, especially dolphins at Porpoise Point
• Excellent views of historic landmarks from the water
• Educational and engaging with opportunities to learn sailing or take the helm
• Relaxing and intimate, ideal for romantic or family outings
• Weather-dependent, so check forecast before booking

An In-Depth Look at the 2-Hour Private Sailing Tour

Setting the Scene: What’s Included and Who Will Enjoy It?

This private day sail in St. Augustine offers a taste of the city’s seafaring past with a modern luxury twist. For $795, your group—up to six people—gets exclusive access to a beautifully appointed sailing yacht. The experience is perfect whether you’re after a peaceful escape, a bit of adventure, or a memorable photo opportunity of the city’s skyline from the water.

The tour is led by a USCG-licensed captain, ensuring safety and expert navigation. Alongside bottled water and restroom facilities onboard, this setup makes the experience convenient and comfortable—no need to worry about logistics or bringing extra supplies.

The Itinerary: From Marina to the Historic Bayfront

The adventure begins at Windward at Camachee Cove Yacht Harbor. As the boat eases away from the dock, you’ll instantly notice the tranquil beauty of the Tolomato River. The captain will steer you southward, passing the charming waterside communities of Vilano Beach and Porpoise Point.

One of the highlights is the likely sighting of dolphins—a common occurrence at Porpoise Point, especially during tide changes. Multiple reviews highlight how remarkable this wildlife viewing is; one guest mentions, “You will almost certainly see dolphins in this area,” which adds a special touch to the experience.

Across the water, Anastasia State Park is visible, offering a scenic backdrop and a sense of the natural beauty surrounding St. Augustine. The boat will then approach the St. Augustine Lighthouse, providing excellent photo opportunities and a chance to appreciate this iconic structure from a unique vantage point.

Key Landmarks and Scenic Stops

• Great Cross at Nombre de Dios: Towering 266 feet, this stainless-steel cross is visible throughout the sail and symbolizes the city’s spiritual roots. It’s an impressive feature that adds a sense of place and history to the views.
• Castillo de San Marcos: Built by the Spanish to defend Florida, this oldest masonry fort in the U.S. is a striking sight from the water, giving you a fresh appreciation for its strategic importance.
• The Bridge of Lions: Completed in 1927, this elegant drawbridge is famous for its marble lion statues guarding the entrance. It opens for boat traffic during the day, and watching it in action can be a fun highlight.

What Our Guests Say

Guests consistently praise the tour for its peacefulness and stunning scenery. One reviewer mentions, “Peaceful morning sail and a beautiful add-on brunch,” highlighting how the experience can be tailored for serenity and indulgence. Another notes, “The view of the old city from the water is lovely,” emphasizing the visual value of this perspective.

Many appreciate the opportunity to learn about sailing or even take the helm, making it more interactive than just a scenic cruise. The crew’s professionalism and friendliness shine through in reviews, with descriptions of captains being “wonderful explaining things to the kids” and making everyone feel at home onboard.

Practical Considerations

The duration of just two hours is ideal for those wanting a short, relaxing escape without dedicating an entire day. Since it’s a private tour, the experience can be more flexible and personalized, which is a big plus for families or couples.

Booking on average 23 days in advance indicates this experience is in demand, especially during peak seasons. It’s worth planning ahead, especially if you’re traveling during busy periods.

Is It Worth the Price?

At nearly $800 for a private tour, it might seem steep at first glance. However, considering the exclusivity, personalized service, and the chance to see wildlife and historic landmarks from a unique vantage point, many will find the value justifies the cost. The tour’s small group size makes it an intimate experience, perfect for creating lasting memories.

Who Should Consider This Tour?

If you’re looking for a peaceful, scenic, and personalized way to experience St. Augustine’s coast, this sail is an excellent choice. It’s especially suitable for those who enjoy nature, history, or sailing—or all three. Families with kids, couples seeking a romantic afternoon, or groups of friends wanting a special outing will appreciate the relaxed, flexible vibe.

This tour is less suited for travelers seeking a high-energy or loud adventure, or those who prefer large-group excursions. Also, keep in mind the weather can affect plans — a clear day will give you the most stunning views and wildlife sightings.

Frequently Asked Questions

How long is the tour?
The tour lasts approximately 2 hours, providing enough time to relax, take in sights, and enjoy some wildlife watching without feeling rushed.

What’s included in the price?
You get the private sailing experience with a USCG-licensed captain, bottled water, restroom facilities onboard, and the exclusivity of a private group.

Can we bring children?
Yes, this experience is suitable for families, and reviews mention explaining sailing and landmarks to kids, making it engaging for all ages.

What if the weather is bad?
The tour is weather-dependent. If canceled due to poor conditions, you’ll be offered a different date or a full refund. Planning on a clear day is recommended for the best experience.

Is this tour suitable for seniors or those with mobility issues?
While the tour involves boarding a boat and being on the water, the yacht is designed for comfort. However, accessibility details aren’t specified, so it’s best to check if you have specific needs.

How far in advance should I book?
Most travelers book about 23 days ahead, especially during peak seasons, to secure availability for their preferred date.

Can I learn to sail during this trip?
Yes, you’ll have opportunities to learn about sailing or even take the helm, making it more interactive and educational.

Is there a specific meeting point?
Yes, the tour begins at 3076 Harbor Dr, St. Augustine. The captain or crew will meet you there, ready to set sail.

Final Thoughts

This private sailing tour along St. Augustine’s historic bayfront offers an elegant blend of relaxation, scenic beauty, and personalized service. It’s perfect for those who want a quieter, more intimate way to see the city’s waterways and landmarks, with the added thrill of wildlife spotting.

Families, couples, or small groups looking for a special experience will find this trip ticks many boxes — gorgeous views, learning opportunities, and a peaceful escape from the busy streets. While it’s a bit of an investment, the exclusivity and unique perspective on St. Augustine’s coast could make it well worth it.

Ultimately, this sail captures the essence of what makes St. Augustine special: its history, its natural beauty, and its welcoming, laid-back charm. It’s a memorable way to connect with the city’s maritime spirit, making it a definite highlight for your visit.