2 hours – Private Day Sail along Historic St Augustine Bayfront

Imagine gliding smoothly along the calm waters of St. Augustine’s historic bayfront, with the breeze in your hair and a stunning view of the city’s iconic landmarks unfolding around you. That’s precisely what this 2-hour private sailing tour offers — a chance to see the city from a fresh angle, on a luxurious yacht with your own licensed captain at the helm. Whether you’re celebrating a special occasion, seeking a romantic escape, or just eager for a unique adventure, this experience invites you to relax and soak in the sights from the water.

What we love most about this tour is the personalized nature — it’s just your group, up to six people, which means plenty of space to spread out, take photos, or even take the wheel if you’re up for it. Plus, the chance to spot dolphins and other wildlife adds a dash of unpredictability that keeps the trip lively. On the flip side, a potential consideration is the price — at $795 for a two-hour private cruise, it’s a bit of an investment, but for many, the exclusivity and views make it well worth it.

This trip is best suited for travelers who cherish intimate experiences and authentic scenery. It’s perfect for families, small groups of friends, or couples looking for a memorable, relaxing outing in one of Florida’s oldest cities. If you love scenic water views, a touch of adventure, and a chance to learn about local landmarks from the water, you’ll find this tour ticks those boxes.

Key Points

• Private 2-hour sailing along St. Augustine’s historic bayfront for small groups (up to six).
• Wildlife sightings, especially dolphins, are common during the cruise.
• The luxury yacht is USCG-licensed, ensuring safety and professionalism.
• You’ll see iconic landmarks like the St. Augustine Lighthouse and Castillo de San Marcos.
• The tour offers flexibility — relax, learn about sailing, or even take the helm.
• Cost is $795 per group, offering an exclusive experience for your party.
• The itinerary includes scenic views and visual highlights from the water, enriching your understanding of the city’s history.
• It’s a bookable experience that’s popular, often booked about 29 days in advance.
• Includes bottled water, restroom access, and a professional captain; gratuities are not included.

A Closer Look at the Experience

Setting Out from Camachee Cove Yacht Harbor

The adventure begins at 3076 Harbor Dr, where you meet your captain and crew. The boat, described as a luxury sailing vessel, promises comfort and style from the moment you step aboard. We love the fact that the tour is private, meaning no crowded group — just your party and the captain, creating a personalized atmosphere.

Once aboard, your captain, a USCG-licensed professional, will take charge, guiding you out of the marina and into the Tolomato River. Here, the scenery starts to unfold immediately — calm waters, lush waterfront homes, and the chance to spot dolphins at Porpoise Point, a well-known wildlife hotspot along Vilano Beach. One reviewer remarked, “We almost always see dolphins here,” which makes this a must-see for wildlife enthusiasts.

The Scenic Route Along Vilano Beach and Anastasia State Park

As you sail past Vilano Beach, you’ll notice the waterfront community known for dolphin feeding during tide changes — a charming, authentic sight that adds a touch of local color. The tour then passes Anastasia State Park, visible across the water, offering a picturesque backdrop to your cruise. The views from the boat give a broader perspective of the natural surroundings that shape this historic city.

Approaching the Historic Landmarks

Sailing deeper into the Matanzas River, the water views become more iconic. You’ll get a splendid vantage point of the St. Augustine Lighthouse, which looms in the distance. It’s a favorite photo stop for many, and the water’s perspective makes its grandeur even more impressive.

Further along, your captain points out the Great Cross atop the Nombre de Dios Mission. Built in 1966 and towering at 266 feet, it’s a striking symbol of faith and resilience visible from nearly every part of the cruise. As one reviewer noted, “You can see the Great Cross during the entire sailing,” emphasizing its dominance in the skyline.

Exploring Historic Fortifications and Bridges

The tour also features views of Castillo de San Marcos, the oldest masonry fort in the continental US. While you won’t dock there, the boat’s vantage point allows you to appreciate this 450-year-old structure from afar, offering insight into the city’s strategic importance.

Another highlight is the iconic Bridge of Lions, completed in 1927. Its artistic design, guarded by marble lion statues, makes it a picturesque sight — especially when the drawbridge opens for boat traffic. The views of this historic bridge from the water are particularly charming, and a great photo opportunity.

What’s Included and What to Keep in Mind

Your ticket covers bottled water, a restroom aboard, and a professional, licensed captain. It’s a completely private experience, meaning you’re only sharing with your group, making it ideal for celebrating, reconnecting, or simply enjoying a peaceful outing. Gratuities aren’t included, so if you’re pleased with your captain’s service, tipping is appreciated but optional.

The tour is generally well-reviewed, with travelers mentioning how peaceful and visually stunning the sail is. One noted, “It’s a beautiful experience to see the old city from the water,” highlighting how the water perspective adds depth to your understanding of the city’s layout and history.

Duration and Booking Considerations

At just about two hours, this cruise strikes a good balance — long enough to see key sights without feeling rushed. It’s quite popular, often booked about 29 days in advance, so planning ahead is a good idea if you want to secure your preferred date.

Prices may seem on the higher side, but considering the private nature and personalized experience, many find this to be a worthwhile splurge—especially if celebrating a special occasion or seeking a memorable outdoor activity.

Who Will Love This Tour?

This sailing trip is perfect for those who value intimate, scenic experiences. Families with kids might enjoy the wildlife viewing, especially dolphin sightings. Couples seeking a romantic escape will appreciate the privacy and the beautiful views of the historic city from the water. Small groups of friends looking for a fun and relaxing activity might also find this a highlight of their visit.

It’s less suited for travelers on a tight budget, given the $795 price point, but for many, the exclusivity, comfort, and unforgettable views justify the cost. If you’re someone who enjoys learning about local landmarks while feeling the wind in your hair, this tour hits the right notes.

Final Thoughts

This private sailing experience in St. Augustine offers a rare opportunity to see the city’s historic bayfront from a relaxed, luxurious perspective. The combination of stunning scenery, wildlife spotting, and the chance to learn about iconic landmarks makes it a well-rounded and memorable outing.

The personalized nature of this cruise ensures you won’t share your views with a crowd, and the professional captain’s guidance adds a layer of safety and local insight that enriches the trip. The views of the Great Cross, lighthouse, and fortifications from the water are particularly striking and provide a fresh appreciation of this storied city.

While it’s a pricier option, many travelers find the exclusivity and scenic beauty worth every penny. It’s especially suited for small groups who want an authentic, peaceful way to explore St. Augustine’s rich maritime history and natural beauty.

Frequently Asked Questions

What is the duration of the tour?
The tour lasts approximately 2 hours, providing enough time to enjoy the scenery and see multiple landmarks without feeling rushed.

How many people can participate?
The yacht accommodates up to six passengers, making it ideal for small groups, families, or couples wanting a private experience.

What is included in the price?
Your ticket includes a private yacht cruise, bottled water, a restroom onboard, and the services of a USCG-licensed captain. Gratuities are not included.

Can I take photos during the cruise?
Absolutely. The water views of the lighthouse, fort, and bridges offer great photo opportunities — just be mindful of your surroundings.

Is this experience suitable for children?
Yes, many reviews mention kids enjoying the wildlife and scenic views. Just keep in mind the length and the yacht environment.

How far in advance should I book?
Since the experience is quite popular and booked on average 29 days ahead, it’s wise to reserve early to secure your preferred date.

What if the weather isn’t good?
If weather conditions turn unfavorable, the tour can be canceled or rescheduled for another day. The company offers a full refund if canceled due to weather.

Are there any additional costs?
No, the listed price covers the entire experience for your group. Tips for the captain are optional.

Is this a guided tour?
Yes, your captain is knowledgeable about the area and provides commentary, pointing out landmarks and wildlife along the way.

In essence, this private sailing tour offers a blend of scenic beauty, wildlife encounters, and cultural sights — all from the comfort of a luxurious yacht. It’s a standout way to see St. Augustine from a perspective few visitors experience, making it a worthwhile addition to your trip.