2 Hr Shared Day Sail Along Historic Bay Front

Experience the Charm of St. Augustine from the Water

If you’re dreaming of a relaxing way to explore the historic charm of St. Augustine, this 2-hour shared day sail stands out as a fantastic option. For $149 per person, you’ll hop aboard a luxury sailing yacht with a small group of just six people, led by a USCG-licensed captain. You’ll cruise down the Tolomato and Matanzas Rivers, passing the historic bay front and catching sight of iconic landmarks and local wildlife.

What makes this sail truly special are a couple of standout details: first, the intimate group size means plenty of room to relax and enjoy the scenery without feeling crowded. Second, the opportunity to see dolphins in their natural habitat adds a memorable touch—many reviews highlight dolphin sightings near Porpoise Point.

One potential consideration is that the tour is weather-dependent. Since it’s a water-based experience, rough weather could lead to cancellations or rescheduling, so checking the forecast before booking is wise.

This tour is perfect for travelers who enjoy a leisurely, scenic outing with a touch of luxury and a focus on natural beauty. Whether you’re celebrating a special occasion, seeking a romantic escape, or simply want a unique perspective on St. Augustine’s historic waterfront, this sail offers a genuine, up-close experience.

Key Points

• Small-group intimacy keeps the experience personal and relaxed.
• Wildlife sightings, especially dolphins, add excitement and a natural element.
• Expertly guided by a USCG-licensed captain, ensuring safety and local knowledge.
• Flexible onboard options for bringing your own beverages or snacks.
• Ideal for all ages, including first-time sailors and seasoned boaters.
• Weather-dependent, so check the forecast before planning your day.

A Deep Dive into the 2-Hour Historic Bay Front Sail

When we think about St. Augustine, we often picture its cobblestone streets and historic architecture. But seeing the city from the water gives a fresh perspective—one that’s both soothing and enlightening. This shared sailing cruise offers exactly that, gliding smoothly along the Tolomato River and Matanzas River, giving you a panoramic view of the bay front’s historic landmarks.

What to Expect from the Itinerary

Your adventure starts at the St. Augustine Sailing dock, located at 3076 Harbor Drive. From there, a USCG-licensed captain takes the helm of a luxurious sailing yacht, designed for comfort and stability. As the boat gently leaves the dock, it’s your chance to settle in and unwind.

One of the highlights is the approach to Porpoise Point, where dolphin sightings are common. Many travelers quote the thrill of spotting these playful creatures—”Loved this experience and I will always remember how special it was,” one reviewer shared about their sail with Captain Dale. Keep your eyes peeled and your camera ready, as these sightings can be both frequent and close.

As the boat continues its course, you’ll enjoy beautiful views of historic sites from the water, including the old city walls, fortifications, and waterfront buildings. The calm waters and gentle breeze create an ideal setting to relax, take photos, or just soak in the scenery.

Wildlife and Scenic Highlights

The dolphin sightings are a major draw, and many reviews emphasize their frequency and proximity. The area around Porpoise Point is known for sightings, and it’s common to see these intelligent animals swimming alongside the boat or leaping out of the water.

Beyond wildlife, the views of St. Augustine’s historic bayfront from the water are truly striking. The mix of colonial architecture, coastal landscapes, and lively waterfront activity makes for an engaging backdrop, especially at different times of day.

The Experience on Board

Onboard, you’re invited to relax and enjoy. The yacht is well-maintained, comfortable, and designed for a small group, which means a personalized experience. The crew is happy to share insights about sailing and local landmarks, adding an educational element to your trip.

You can opt to bring your own beverages and snacks—think wine, beer, or a charcuterie board—to elevate the experience. The boat’s crew can prepare your drinks or snacks ahead of time if you call in advance.

What Reviewers Love Most

Most travelers rave about the intimate atmosphere and beautiful scenery. One traveler said, “Always a first time even at 80!” describing how a relaxed, scenic sail can be enjoyed at any age. Others mentioned the delicious onboard food and refreshing mimosas, which add a touch of luxury to the outing.

The professionalism and friendliness of the crew, especially captains Kevin, Dale, and George, is frequently praised. One reviewer remarked, “Captain George, an around-the-world sailor, was very friendly and capable,” emphasizing the skill and hospitality of those at the helm.

Considering the Price and Value

At $149 per person, this experience offers excellent value for a private, scenic cruise. Given the small-group setting, personalized service, and the chance to see wildlife firsthand, many travelers find it well worth the cost. Plus, the option to bring your own drinks or order special snacks means you can tailor the outing to your preferences without extra fees.

Who Will Love This Tour?

If you’re seeking a relaxed, scenic break from walking around historic streets, this sail offers a peaceful escape. It’s especially suited for couples, small groups of friends, or families wanting a memorable experience on the water. It’s also a fantastic way for first-time sailors to enjoy a gentle cruise with expert guidance.

Travelers interested in wildlife will appreciate the dolphin sightings, while history buffs will enjoy seeing St. Augustine’s landmarks from a different vantage point. Plus, if you’re celebrating a special occasion or simply want to treat yourself to a luxurious yet laid-back outing, this cruise hits the spot.

Practical Details and Tips

• Duration: Approximately 2 hours, making it a manageable addition to your day.
• Group size: Limited to six, ensuring plenty of space and personal attention.
• Meeting Point: 3076 Harbor Drive, easily accessible and well-organized.
• Weather: Since the tour depends on good weather, check the forecast before your trip. Cancellations due to weather are fully refundable or can be rescheduled.
• Beverages and Snacks: Plan ahead if you’d like to bring drinks or order a charcuterie board—contact the staff in advance to prepare.
• Children and Accessibility: Most travelers can participate; service animals are welcome.

Frequently Asked Questions

Can I bring my own drinks onboard? Yes, you’re encouraged to bring your own beverages like wine, beer, or canned cocktails. Just give the crew a call beforehand so they can have your items cold and ready.

What if the weather turns bad? The tour is weather-dependent. If conditions aren’t suitable, the trip may be canceled or rescheduled. They’ll offer a full refund if canceled due to poor weather.

How many people are on the boat? The group is capped at six guests, offering an intimate and relaxed atmosphere that’s perfect for conversation and enjoying the scenery.

Are children allowed? Most travelers can participate, and it’s suitable for a range of ages. Check with the provider if you have specific questions about children.

How do I book and pay? You can book online with a mobile ticket, and payment is handled during the reservation process. The tour is often booked 64 days in advance, so plan ahead.

Are drinks and snacks included? No, but you can bring your own or arrange ahead of time to have snacks like a charcuterie board or drinks waiting onboard.

Final Thoughts

This 2-hour shared day sail offers more than just a boat ride—it’s a chance to see St. Augustine from a fresh perspective, combining scenic beauty, wildlife encounters, and personalized service all in a relaxed, luxurious setting. The small-group size ensures you’re not just another face in the crowd but rather part of an authentic, memorable experience.

Ideal for those who enjoy nature, history, and luxury without pretension, this cruise delivers a peaceful yet engaging escape. Whether you’re celebrating a special day, seeking a romantic outing, or simply want a different view of the city’s storied waterfront, this sail is likely to leave you with lasting memories.

In essence, this cruise is all about blending comfort, discovery, and tranquility—perfect ingredients for a memorable day on the water in historic St. Augustine.