St. Augustine: Shared Day Sailing Charter

If you’re dreaming of a peaceful escape on the water in historic St. Augustine, this shared 2-hour sailing tour could be just what you’re looking for. While we haven’t personally been on this exact trip, reviews and detailed descriptions paint a clear picture of a cozy, scenic adventure that offers a fresh perspective of this charming Florida city.

What makes this experience stand out? First, the opportunity to feel the ocean breeze and the wind in your hair aboard a small, intimate sailboat. Second, the chance to gaze at iconic landmarks like the Castillo de San Marco, the Bridge of Lions, and the lighthouse from the water, providing a unique vantage point. Third, the relaxed, small-group setting ensures you’ll enjoy a personalized and peaceful cruise—far from crowded, tourist-heavy boat tours.

A possible drawback is that this tour is limited to those comfortable with being on the water and not prone to seasickness. It’s a short, 2-hour experience, so if you’re after a more extensive or active adventure, you might find it a bit brief. But overall, this tour is well-suited for travelers who love scenic views, a tranquil atmosphere, and snapping photos of St. Augustine’s historic sights from an angle few get to see.

This sailing tour appeals most to those seeking a relaxed, picturesque experience in the city, whether you’re celebrating a special occasion, traveling with friends or family, or simply craving a peaceful break on the water.

Good To Know

• Breathtaking Views: See iconic landmarks from a different perspective.
• Small Group Setting: Limited to six participants, ensuring a cozy, intimate experience.
• Expert Crew: Professional guides add a layer of safety and local insight.
• Convenient Parking: Free parking at the marina simplifies logistics.
• Flexible Booking: Reserve now, pay later with full cancellation options.
• Limited Duration: The 2-hour schedule is perfect for a quick escape but may leave some wanting more.

You can check if your dates are available here:

An In-Depth Look at the Experience

What the tour entails

This 2-hour shared sailing adventure begins at the marina, where you’ll arrive about ten minutes early to meet your crew and get ready for departure. The boat itself is described as cozy, suitable for a small group of up to six people—making the experience feel personal and relaxed. The professional crew, including knowledgeable guides, works to create a memorable outing, sharing insights about the sights and ensuring everyone feels comfortable on board.

The itinerary and sights

Once underway, you’ll cruise past several notable landmarks of St. Augustine. The Castillo de San Marco, a fortress with centuries of history, makes for an impressive sight from the water. You’ll also sail past the Bridge of Lions, a picturesque bridge connecting downtown to the beaches, and the St. Augustine Lighthouse, which is often visible from afar but takes on new significance when viewed from the water.

Many reviews mention the stunning views as a highlight. One reviewer noted, “Watching the sunset while the lighthouse glows in the distance was truly breathtaking.” This scenic backdrop makes the short trip feel more like a special occasion than just a boat ride.

The sailing experience

Feel the gentle sway of the boat as the crew handles the sails, giving guests a sense of the traditional sailing experience. The wind plays a major role, often providing just enough breeze to keep you comfortable and cool without feeling rough or unpredictable. Travelers have described the atmosphere as peaceful, ideal for snapping photos or simply soaking in the scenery.

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What’s included and what’s not

The tour price covers the 2-hour cruise, the professional crew, and free parking at the marina. Alcoholic drinks are available for purchase, except for red wine, and so are food and additional drinks—so bring your snacks, or buy a refreshing beverage onboard. Since the experience is designed to be relaxing, you might find it perfect for a quick break during your day exploring St. Augustine.

Practical considerations

Arriving 10 minutes early is recommended to greet the crew and settle in. Remember to bring comfortable shoes, a hat, a camera, sunscreen, and food or snacks if desired. The tour is not suitable for pets or non-swimmers, and those prone to seasickness may want to consider whether a short, calm cruise suits them. Also, wear shoes with non-marking soles to protect the boat.

Additional insights from reviews

Guests have said the small group size enhances the experience, making it more intimate and less crowded. Several reviews highlighted the friendly and attentive crew who shared interesting tidbits about the landmarks and navigated smoothly even in breezy conditions.

One reviewer commented, “The crew was fantastic—informative but not overbearing. It’s a perfect way to see the city from a different angle.” Others appreciated that parking was easy and free, removing a common hassle for visitors.

Why Choose This Sailing Tour?

This tour is ideal for travelers who want a calm, scenic escape without the need for extensive planning or physical activity. Whether you’re celebrating a special occasion, want quality time with family, or simply crave a peaceful moment on the water, this experience offers beautiful views with minimal effort.

The small group size ensures personalized attention, and the professional crew makes safety and comfort a priority. It’s a wonderful way to kick back, relax, and appreciate St. Augustine’s coastal charm from a fresh angle.

Who It’s Best For

• Sightseers wanting a different perspective of St. Augustine’s landmarks
• Couples or small groups seeking an intimate, relaxing experience
• Travelers interested in photos and scenic views
• Those who appreciate peaceful outdoor activities on the water
• Visitors with flexible schedules, as the tour runs in both morning and afternoon slots

Not suitable for non-swimmers or those prone to seasickness, and it’s not a long, active cruise—think of it as a breezy, laid-back sightseeing trip.

FAQ

How long is the sailing tour?
The tour lasts for 2 hours, providing enough time to enjoy the scenery without feeling rushed.

Is there parking available?
Yes, free parking at the marina makes logistics simple. We recommend arriving about 10 minutes early.

Can I bring my own food or drinks?
You are encouraged to bring food and snacks, and drinks are available for purchase onboard, except for red wine.

What should I wear?
Comfortable shoes with non-marking soles, a hat, sunscreen, and a camera are recommended. Bring layers if the weather is cooler.

Is this experience suitable for children or non-swimmers?
It’s best for non-swimmers and those comfortable on the water. Children over age five are likely fine, but always consider their comfort level with boat rides.

Are there any restrictions on alcohol consumption?
Yes, all alcohol must be bought in the office before boarding. Red wine is not available for purchase during the tour.

Final Thoughts

This shared day sailing tour in St. Augustine offers a peaceful, scenic way to see the city’s historic sights from the water. It’s perfect for those craving a short, tranquil escape amid stunning coastal views, all in an intimate, small-group setting. The experience’s highlights—like the breathtaking vistas of the lighthouse and fortress—are sure to leave a lasting impression.

While it may not satisfy those seeking a long adventure or high-energy activity, it delivers in relaxation and visual beauty. With professional crew, convenient parking, and flexible booking options, this tour is a smart choice for travelers looking to add a unique, scenic touch to their visit to St. Augustine.

In summary, if your idea of a perfect getaway includes gentle sailing, iconic sights, and a peaceful atmosphere, this tour is a rewarding way to enjoy the city’s charm from a different angle. It’s best suited for curious explorers, couples, and small groups eager for a quiet, picturesque cruise in historic Florida.

You can check if your dates are available here: