St. Augustine: Shared Day Sailing Charter

If you’re considering adding a touch of nautical charm to your St. Augustine trip, a shared day sailing might just fit the bill. This 2-hour cruise offers a laid-back way to enjoy some of the most iconic sights of the city, all from the comfort of a cozy sailboat. Whether you’re a seasoned sailor or just looking to unwind with gentle breezes and stunning views, this experience has something to offer.

What really makes this sail stand out is the chance to see landmarks like the Castillo de San Marco, the Bridge of Lions, and the St. Augustine Lighthouse from a perspective that’s both peaceful and visually striking. Plus, with small group sizes and a professional crew, it promises an intimate, friendly atmosphere. But, as with anything, there are a few things to keep in mind, like the need for good weather and some basic prep for comfort.

This tour is ideally suited for travelers who enjoy scenic views, relaxed outings, and don’t mind a bit of time on the water. It’s especially useful if you’re after a memorable experience without a lot of fuss — perfect for couples, small groups of friends, or even solo explorers wanting a peaceful escape from the busy streets.

Key Points

• Scenic water views of St. Augustine landmarks from a sailboat
• Small group setting limits to just 6 participants for a personalized experience
• Includes iconic sights like the Castillo de San Marco, the Bridge of Lions, and the Lighthouse
• Relaxed 2-hour cruise ideal for a quick but memorable outing
• Convenient amenities include free parking at the marina
• Food and drinks are available for purchase, with alcohol sold at the office

You can check availability for your dates here:

An Honest Look at the St. Augustine Shared Day Sailing

When you’re in a historic city like St. Augustine, there’s an undeniable charm in seeing its landmarks from the water, and this sailing tour leverages that perfectly. We loved the way the tour combines the beauty of the coast with a relaxed, no-pressure vibe—ideal if you’re not into the hustle of big boat tours.

How the Experience Unfolds

The tour lasts exactly 2 hours, giving you enough time to soak in the scenery without feeling rushed. You’ll board a small, cozy sailboat at the marina, where the friendly crew welcomes you and gets you settled. From there, the sails are raised, and you’re smoothly gliding past some of the city’s most famous sites.

The view of the St. Augustine Lighthouse from the water is a highlight, offering a perspective that’s often missed when exploring on foot. The lighthouse, perched high atop the coast, looks especially striking from the water, and many reviews mention how the sight feels like a postcard moment. You’ll also get good angles of the Bridge of Lions, a beautiful suspension bridge connecting downtown to Anastasia Island, and the historic Castillo de San Marco, which dominates the skyline.

The Comfort and Atmosphere

The boat is described as cozy, which means it’s perfect for small groups seeking an intimate feel. The limited group size—just six people—means you’ll have room to relax, chat with the crew, or take photos without crowds. Many travelers appreciate the professional crew, who are attentive without being intrusive, making the experience informative and enjoyable.

The Sights and the Sunset

What’s particularly appealing is the chance to watch the sunset over the city and the ocean. While the tour generally runs in the daytime, some options might include sunset sailing, which adds a beautifully golden glow to the landmarks and water. The tranquil setting and the gentle sway of the boat can make this a memorable, almost meditative experience.

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What’s Included and What’s Not

The price of $137 per person might seem a bit steep, but considering the small group size, the beautiful views, and the professional crew, many find it a good value. The tour includes all the essentials: the 2-hour sail, the crew’s expertise, and free parking at the marina.

If you want to enjoy drinks or snacks, you’ll need to purchase them separately at the office. Alcohol is available for purchase, but red wine isn’t served onboard, which might matter if you’re a wine lover. Food and extra drinks are also on offer, giving you the flexibility to enhance your cruise.

The Practical Side

Arriving 10 minutes early is recommended, so you can get familiar with the crew and settle in. The tour operates in the morning or afternoon, which works well for most schedules. Remember to bring sun protection, comfortable shoes, a camera, and perhaps some snacks—especially if you’re planning to extend your day with other activities.

Considerations and Downsides

The main considerations are weather-dependent conditions and the nature of small boats. If you’re prone to seasickness, this might not be your best choice. Also, since it’s a shared experience, if you’re looking for a private outing or have very specific sightseeing goals, this may feel limited in scope.

Who Is This Tour Best For?

This sailing experience caters well to those who want a gentle, scenic outing with a focus on views and atmosphere rather than adventure or extensive narration. It’s ideal for couples, small groups, or solo travelers who enjoy quiet, picturesque moments. Families with older children might find it enjoyable, but travelers with very young kids or non-swimmers should consider their comfort on a boat of this size.

Final Thoughts

If you’re after a relaxing way to see St. Augustine’s most recognizable sights, this shared day sailing ticks many boxes. It combines the beauty of the Gulf Coast with the charm of a small-group environment, creating an experience that’s both scenic and personal.

While the price might be on the higher side for a short tour, many find the quality of the experience and the gorgeous views worth it. The opportunity to see landmarks from the water, especially at sunset, offers a different perspective that’s hard to match with land-based tours.

In the end, this trip is best suited for those who want to slow down and enjoy the ocean breeze while taking in some of the city’s most photogenic sights. It’s a peaceful, scenic escape that adds a special touch to any St. Augustine visit.

FAQ

Is this tour suitable for children?
The tour is generally suitable for travelers who are comfortable on a boat. Families with older children might enjoy it, but non-swimmers or very young kids should consider their comfort level with being on a small vessel.

How long is the tour?
The sailing cruise lasts for 2 hours, providing a relaxed yet substantial experience.

What landmarks will I see?
You’ll get views of the Castillo de San Marco, the Bridge of Lions, and the St. Augustine Lighthouse, all from the water.

Can I buy food or drinks onboard?
Food and drinks are available for purchase at the office before boarding. Alcohol can be bought there but not red wine, and you can buy additional drinks or snacks if you wish.

Is parking free at the marina?
Yes, the tour includes free parking at the marina, which makes logistics easier.

What should I bring?
Bring comfortable shoes, sun protection, a camera, and possibly snacks or drinks for your comfort during the cruise.

If you’re looking for a peaceful, picturesque way to see some of St. Augustine’s most iconic sights, this sail offers a lovely, no-fuss option. Just keep an eye on the weather, and you’ll likely have a memorable experience that captures the city’s charm from a whole new angle.

You can check availability for your dates here: