Exploring St. Augustine from the Water: A Private Day Sail Review
If you’re considering a way to see the historic charm of St. Augustine from a different perspective, a private day sail along the bayfront is a great choice. I haven’t personally been on this specific cruise, but the glowing reviews and detailed itinerary suggest it’s a memorable, calming experience that offers more than just sightseeing.
What really catches my eye about this tour? First, the personalized nature of it—you’re on a yacht just for your group, which means plenty of space to relax or get involved. Second, the chance to spot wildlife like dolphins and enjoy incredible water views of landmarks like the lighthouse and Castillo de San Marcos. One thing to keep in mind is the price point—$795 for up to six people—so it’s an investment, but one that seems well worth it if you love being on the water in a peaceful, intimate setting. This tour is ideal if you’re after a relaxed, scenic experience with personalized service, especially if you’re traveling with friends or family who appreciate nature and history.
Key Points
- Private, intimate experience on a luxury sailing yacht designed for groups of up to six.
- Wildlife sightings, especially dolphins, are common, adding a magical touch.
- Stunning water views of historic sites like the lighthouse and Castillo de San Marcos.
- Relaxed pace with options to learn sailing, take the helm, or just soak in the scenery.
- All-in-one price simplifies budgeting for a memorable waterway adventure.
- Convenient meeting point at Camachee Cove Yacht Harbor with included amenities like bottled water and restroom.
An Honest Look at the 2-Hour St. Augustine Bayfront Sail

Let’s break down what you can expect from this private sailing experience. The tour begins at 3076 Harbor Dr. in St. Augustine, a well-equipped marina at Camachee Cove Yacht Harbor. The boat is a luxury sailing yacht with enough space and comfort for your group, guided by a USCG-licensed captain. The 2-hour duration is perfect for a laid-back taste of the city’s waters, without feeling rushed, and you can expect a smooth, relaxing ride.
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Starting at Camachee Cove Yacht Harbor
Once you board, the captain will set course to gently slip from the dock and head down the Tolomato River. The experience begins with anticipation and a chance to unwind as you leave the busy marina behind and enter the quieter waters of the Intracoastal Waterway. As the boat begins to glide along, you’ll start noticing the natural beauty of the area, with frequent dolphin sightings at Porpoise Point near Vilano Beach. One review captures this perfectly: “Porpoise Point at Vilano Beach is a beautiful waterfront community and bounded by the intracoastal waterway. This area is known for seeing dolphins as they feed during tide change.”
Sighting Dolphins and Wildlife
Watching dolphins dance by the boat is often a highlight, and this tour seems to deliver just that. The guides are experienced at looking for wildlife, and most guests report seeing these playful creatures during the sail. It’s one of those moments that make the trip feel special and connected with nature. Besides dolphins, you’ll be passing locations like Anastasia State Park, which you can glimpse from the water, giving a sense of the city’s natural surroundings.
Historic Landmarks from the Water
One of the tour’s strengths is the opportunity to photograph or simply admire iconic sites like the St. Augustine Lighthouse and Castillo de San Marcos. The lighthouse is visible in the distance as you cruise down the river, offering a stunning backdrop for photos. The fort, built by the Spanish, is also nearby, and you get a panoramic view that’s quite different from walking around the city streets.
The Great Cross and Nombre de Dios Mission
Another notable feature along the route is the Great Cross, erected in 1966 and towering 266 feet high. It’s visible throughout the sail, providing a striking visual anchor and a reminder of the city’s spiritual history. The tour offers a scenic perspective that’s unlike any you’d get from land—there’s a certain peacefulness in looking up at such a structure from the water.
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The Bridge and Its Artful Design
As you approach the bridge connecting downtown to Anastasia Island, you’ll notice its unique design—flanked by white marble lion statues and completed in 1927. It’s a beautiful piece of engineering and art, and from the water, it offers a different appreciation for its craftsmanship. The bridge is a drawbridge, opening for boat traffic, so your captain might adjust the course accordingly if it’s an active day for maritime movement.
What It’s Like Onboard

Guests consistently praise the comfortable luxury of the yacht and the professionalism of the captain. The crew is described as friendly and knowledgeable, eager to share insights about the waterway, local wildlife, and landmarks. Many reviews highlight how the experience isn’t just about sightseeing but also about relaxing—an ideal way to unwind while enjoying the scenery.
Learning and Participating
For those interested in sailing, there’s an opportunity to learn — and even take the wheel if you like. This makes the experience engaging rather than passive, especially for those with a curiosity about boats or sailing. One reviewer mentioned how Nuri, a crew member, made the experience fun and educational, with the added bonus of seeing military training exercises, which was an unexpected treat.
The Relaxation Factor
Many guests comment on how peaceful and stress-free the cruise is. The boat’s amenities, like bottled water and on-board restrooms, ensure comfort during the short trip. The scenery, wildlife, and gentle movement of the yacht combine to create a calming escape from the city streets.
Is This Tour Worth the Price?

At $795 for up to six people, this sail isn’t the cheapest option around, but it’s a value-rich experience. You’re paying for the exclusivity and comfort of a private yacht, along with the personalized attention of a licensed captain. Considering that many reviewers found it to be a “wonderful afternoon,” and appreciated the chance to see the city from a new angle, it seems like a worthwhile splurge if you value private, scenic time on the water.
It could be especially suitable for a special occasion or a leisurely day with friends or family. The reviews echo this sentiment, with guests describing it as a peaceful, beautiful, and engaging experience that’s perfect for celebrating something or simply enjoying a tranquil day.
Who Would Love This Experience?

If you’re seeking a relaxed, scenic cruise with the flexibility to participate, this is a great pick. It’s ideal for small groups who want to avoid crowded tours and prefer a personalized touch. Nature lovers will enjoy dolphin sightings and the chance to see landmarks from a different perspective. It’s also suitable for those interested in a bit of sailing experience or just a peaceful escape on the water.
While it’s not specifically marketed as family-oriented, the friendly atmosphere and scenic views could make it a lovely outing for older children or teens who enjoy nature and boats. But, overall, it’s best suited for adults or groups looking to indulge in a luxurious, calm cruise.
Final Thoughts

This private day sail offers a blend of comfort, scenic beauty, and a touch of adventure. You’ll enjoy peaceful waters, wildlife sightings, and stellar views of some of St. Augustine’s most recognizable landmarks—all from the quiet comfort of a luxury yacht.
The experience’s strength lies in its personalized approach and the chance to see the city’s waterway through a different lens. Whether you’re on a romantic getaway, celebrating a special occasion, or simply want a break from the hustle and bustle, this tour promises a memorable, relaxing outing.
If you love being on the water and want a flexible, intimate experience with good chances of dolphin sightings and stunning views, this cruise hits the mark. Just keep in mind the price, and plan accordingly for a special treat rather than a budget activity.
2 hours – Private Day Sail along Historic St Augustine Bayfront
“Peaceful morning sail and a beautiful add-on brunch. Communicative and easy to work with. Thanks Captain Chris!”
FAQ

Is this a group or private tour?
This is a private tour, so only your group will participate, making it ideal for personalized experiences and flexibility.
How long is the cruise?
The cruise lasts approximately 2 hours, offering a relaxed pace with plenty of time to enjoy the scenery.
What is included in the price?
The cost covers the yacht captain, bottled water, and restroom on board, ensuring comfort during your trip.
Can I learn to sail during the trip?
Yes, guests interested in sailing can participate and even take the helm, if they wish, during the cruise.
What landmarks can I see from the water?
You’ll get views of the St. Augustine Lighthouse, Castillo de San Marcos, Great Cross, and the Bridge of Lions with its lion statues, plus surrounding water views.
Is this experience suitable for children?
While not specifically marketed as family-friendly, older children and teens who enjoy boats and wildlife might appreciate the trip. Always check with the operator if you have concerns about younger kids.
If you’re after a peaceful, scenic, and personal water experience in St. Augustine, this private sail could be just what you need. Enjoy the views, the wildlife, and the gentle sway of the boat—you might find it’s one of those moments to cherish.
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