2 hours – Private Sunset Sail along Historic Bay Front

Discover the Charm of a Private Sunset Sail in St. Augustine

If you’re looking for a relaxing way to see St. Augustine from a new perspective, a private sunset sail along the historic bay front might just be your perfect match. This two-hour trip offers a peaceful escape on the water, away from the usual crowds, with plenty of opportunities to enjoy the scenery, wildlife, and a beautiful sunset. Whether you’re celebrating a special occasion, planning a romantic evening, or just want a quiet, intimate experience on the water, this tour delivers.

What we love about this experience is the personalized touch of a private vessel—you’re not just another face in a group—and the chance to spot dolphins and porpoises in their natural habitat. The views of iconic landmarks like the Castillo de San Marcos and the Bridge of Lions make it a memorable way to soak in the city’s charm. However, keep in mind that the price per group is $795, which might feel steep if you’re on a tight budget, but for the exclusivity and tailored experience, it could be worth it.

This tour is best suited for couples, small groups, or families who appreciate serenity and scenic beauty. If you’re someone who loves a relaxed, luxurious vibe and values thoughtful service, you’ll likely enjoy every minute of this sail. But if you’re after an active, high-energy adventure or traveling with very young children, this might not be the best fit.

Key Points

• Private setting offers a customized experience away from crowds.
• Wildlife sightings, including porpoises, add a lively touch.
• Stunning views of St. Augustine’s landmarks from the water.
• Comfortable two-hour cruise, perfect for a relaxing evening.
• Includes bottled water for guests, with optional beverages and snacks you can arrange in advance.
• Ideal for small groups, couples, or families seeking a peaceful, scenic outing.

An In-Depth Look at the Sunset Sail Experience

The Itinerary: What to Expect

This tour begins at Windward at Camachee Cove Yacht Harbor, where you’ll meet your captain and crew. Once onboard, you’ll set sail along the Tolomato River, leaving the dock behind and heading into the waterway. The crew encourages guests to keep an eye out for dolphins and porpoises—and many travelers have praised the chances of wildlife sightings, making this a lively and engaging experience, especially for nature lovers.

Your cruise then continues along Vilano Beach, a beautiful waterfront community. The area is well-known for its scenic intracoastal waterway, and you’ll get a good look at Porpoise Point. As you cruise further, Anastasia State Park comes into view across the water, offering a glimpse of the northern part of this lush, protected area.

As the boat moves into the Matanzas River, you’ll be close enough to snap some fantastic photos of the St. Augustine Lighthouse, an iconic landmark silhouetted against the setting sun. The lighthouse’s striking presence is a highlight for many guests, providing a picturesque backdrop for your photos.

One of the tour’s key features is the passage under the Bridge of Lions, with its distinctive white marble lion statues guarding each side. Built in 1927, the bridge is an architectural delight and a symbol of this historic city. Seeing it from the water adds an extra layer of charm to the experience.

What’s Included and What’s Not

Your ticket includes bottled water and the expertise of a professional yacht captain. This means you can relax knowing you’re in good hands, and you’ll stay hydrated while soaking in the views.

However, the tour does not include alcoholic beverages or snacks. You’re encouraged to plan ahead if you want to enjoy wine, beer, or canned cocktails—just give the team a call beforehand so beverages are cold and ready on the boat. Likewise, you can pre-order a charcuterie board to enjoy during the sail, making the experience even more special.

The Experience Provider: What to Know

Operated by St. Augustine Sailing Enterprises, this tour is designed for small, private groups. The boat can accommodate up to six guests, making it an intimate event perfect for couples celebrating, small families, or friends. Confirmation is quick, especially if booked at least a day in advance, and the tour is flexible with cancellations—free up to 24 hours beforehand if plans change.

Why This Tour Might Be Worth It

At $795 per group, you’re paying for exclusivity and personalized service, which many guests feel justifies the cost. The reviews are glowing—one even called it a “wonderful first time on a sailboat,” praising the captain’s skill in capturing the wind and making everyone feel comfortable. That sense of care and expertise is a big part of what makes this experience memorable.

Beyond the gorgeous views, this sail provides a peaceful, quiet environment ideal for unwinding. It’s especially suited for those seeking a romantic outing or a serene escape from the busier parts of town.

How the Views Make a Difference

Many people, including one reviewer who took his wife for her birthday, appreciated how the sail brought the city’s landmarks into a new light. Seeing the Castillo de San Marcos and the Bridge of Lions from the water, especially at sunset, transforms them from simple sights into living, breathing parts of the landscape. It’s a chance to slow down and take in the scenery without distraction.

Wildlife Sightings: What You Can Expect

Guests frequently mention porpoise and dolphin sightings as a highlight. These playful creatures often make appearances along the route, adding a lively element to the trip. One reviewer noted the captain’s effort in trying to catch the wind, which not only made for a smooth sail but also kept the experience engaging.

The Sunset Moment

As the sun dips lower, the sky lights up with warm hues—reds, oranges, and purples—creating an idyllic setting. This isn’t just a scenic cruise; it’s a chance to pause and appreciate the natural beauty of the coast, framed by historic landmarks in the distance.

Who Should Consider This Tour?

This tour is ideal for small groups, couples, or families who love a relaxed, scenic experience. It caters well to those who want a quiet, intimate outing with personalized attention, rather than a crowded or commercial feel. If you’re someone who values comfort, beautiful views, and wildlife encounters, this sail will likely hit the mark.

That said, if you’re traveling with very young children or prefer high-energy activities, you might find this experience a little slow-paced. It’s more about serenity and appreciation of the scenery than adventure or physical activity.

Final Thoughts: Is It Worth It?

For those longing for a peaceful, picturesque way to enjoy St. Augustine’s coast, this private sunset sail offers a special slice of tranquility. The ability to customize your experience, combined with the stunning backdrop of landmarks and wildlife, makes it a worthwhile splurge, especially for a romantic getaway or a memorable celebration.

The fact that it’s a private tour means fewer crowds and a more tailored experience, which can really elevate a simple sunset ride into something memorable. The knowledgeable captain and crew make a difference, ensuring you’re comfortable and that you get the most out of your time on the water.

While the cost may seem high, many guests find the exclusivity, views, and relaxed atmosphere justify the price. If you’re after a scenic, quiet evening with the chance for wildlife sightings and great photo opportunities, this sail is likely to deliver.

FAQs: Practical Questions about the Sunset Sail

How long is the tour?
It’s approximately 2 hours, giving you plenty of time to relax and enjoy the scenery without feeling rushed.

Where does the tour start and end?
The tour begins at Windward at Camachee Cove Yacht Harbor and returns there at the end, making it easy to coordinate with your plans.

What’s included in the price?
Bottled water and the services of a yacht captain are included. You can arrange for alcoholic beverages and snacks in advance for an additional fee.

Is this experience suitable for children?
While most travelers can participate, it’s not specifically tailored for very young kids. It’s more suited for small groups, couples, or families with older children who can enjoy a peaceful boat ride.

Can I cancel if my plans change?
Yes, cancellations are free if made at least 24 hours before the scheduled start time. Cancellations less than 24 hours in advance aren’t refunded.

What should I bring?
Bring layers for changing weather and possibly a camera for photos. If you want drinks or snacks, plan ahead and pre-order.

Are there any hidden costs?
No, but remember that alcoholic beverages and snacks are optional extras you can pre-arrange.

How many people can fit on the boat?
This private tour is designed for groups up to 6 guests, ensuring a comfortable and intimate experience.

What’s the weather policy?
The tour is weather-dependent. If canceled due to poor weather, you’ll be offered a different date or a full refund.

In the end, this sunset sail offers a peaceful, scenic, and personalized way to experience St. Augustine from the water. If you’re seeking a tranquil escape with gorgeous views and wildlife, it’s definitely worth considering.