St. Augustine: Shared Day Sailing Charter

If you’re seeking a relaxing way to see some of St. Augustine’s most iconic sights from the water, a 2-hour shared sailing charter might just be the perfect fit. This tour offers a chance to enjoy cozy sailing aboard a small boat with a professional crew, all while taking in views of historic landmarks like the Castillo de San Marco, the Bridge of Lions, and the St. Augustine Lighthouse. It’s an experience that promises both scenic beauty and a touch of maritime adventure—without breaking the bank.

What we love about this experience is the intimate group size—limited to just 6 participants—making it ideal for those who want a more personal, relaxed vibe. Plus, the chance to see St. Augustine’s architecture from the water, especially at sunset, delivers some truly breathtaking moments. The only thing to consider is that it’s a 2-hour tour, so if you’re looking for a deep-dive or extensive sightseeing, you might want to combine it with other activities.

This sailing experience suits travelers who appreciate authentic coastal vistas, small-group intimacy, and a flexible schedule. It’s especially appealing if you enjoy picturesque sunsets, tranquil sailing, and want a memorable way to see the city’s landmarks from the water.

Key Points

• Small group intimacy enhances the experience, with just 6 participants on each boat.
• Breathtaking views of St. Augustine’s landmarks from the water offer a unique perspective.
• Sunset sailing provides a particularly picturesque setting for photography and relaxation.
• Convenient amenities include free parking at the marina and flexible booking options.
• Additional costs for food and drinks; alcohol can be purchased onboard but red wine isn’t available.
• Weather-dependent; good sailing days mean clear skies and a gentle breeze.
• Accessibility is limited for non-swimmers and those prone to seasickness.
• Preparation essentials include comfortable shoes, hats, cameras, and sunscreen for a comfortable cruise.

You can check availability for your dates here:

An Authentic Look at the Sailing Tour

Embarking on this shared sailing charter in St. Augustine means slipping into a cozy vessel with a professional crew that’s attentive and ready to ensure your trip is smooth and enjoyable. The tour lasts just two hours, which is ample time to soak in the sights without feeling rushed. What sets this experience apart is the chance to see key landmarks from a vantage point most visitors don’t get—out on the water.

Itinerary Breakdown and Highlights

The tour departs from the marina, where you’ll arrive about 10 minutes early to meet your crew and get comfortably settled on the boat. Once underway, your crew will guide you around the harbor and provide commentary on the landmarks. Expect to see the Castillo de San Marco, the historic fortress that has guarded the city since the 17th century, from a fresh perspective—gliding past its sturdy walls with a gentle breeze.

Next, you’ll pass the Bridge of Lions, an elegant suspension bridge featuring striking architectural details. Watching it from the water, you’ll see its impressive span connect the downtown area to Anastasia Island, offering an excellent photo opportunity. The highlight for many is the St. Augustine Lighthouse, which guests will admire from afar, its tall white structure standing proud against the skyline.

What Makes the Experience Special

The breathtaking views are undoubtedly the star of this tour. Many reviews highlight how the sunset creates an almost magical glow over the city’s architecture and water. One guest noted, “Watching the sun sink behind the lighthouse with the city lights flickering on was an unforgettable sight.”

The small group setting, limited to 6 participants, fosters a relaxed and friendly atmosphere. It’s perfect for couples, friends, or families who want a more personalized experience. The crew’s professionalism is often mentioned as a strong point—they are knowledgeable, friendly, and attentive, ready to answer questions or share local stories.

Practicalities and Value

The price point of $137 per person is reasonable given the intimacy and quality of the experience. It includes the 2-hour sail, professional crew, and stunning views. Parking is free at the marina, which adds convenience—no need to hunt for a spot or pay for parking elsewhere.

You should plan to bring essentials like comfortable shoes, hats, sunglasses, a camera, and sunscreen. For those who like to toast the sunset, alcohol can be purchased before boarding (excluding red wine), but note that no alcohol is included in the price. Food and other drinks are also available for purchase, which makes it easy to customize your experience if desired.

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Weather and Timing Considerations

Since the tour depends on weather conditions, it’s advisable to check the forecast and dress accordingly. A mild breeze and clear skies are the ideal sailing conditions. Tours are typically offered in the morning and afternoon, with the sunset sail being particularly popular because of the stunning vista it provides. Keep in mind, the tour is not suitable for non-swimmers or those prone to seasickness, so plan accordingly.

Why This Tour Works Well

If you’re a traveler who loves authentic scenic views, then this sailing trip will delight you. It’s especially good for romantic evenings or peaceful afternoons when you want to escape the busy streets and enjoy a more tranquil experience. It’s also a fantastic way to capture unique photos of St. Augustine’s historic structures from a different angle.

The small group size tends to attract travelers who prefer a more personalized touch, and the flexible booking options—reserve now & pay later—make planning simple. Whether you’re celebrating a special occasion or just want a peaceful break from sightseeing, this sailing tour offers a quiet, scenic, and memorable slice of St. Augustine’s coastal charm.

The Sum Up

This shared sailing cruise offers a thoughtfully curated window into St. Augustine’s beauty from the water, with a focus on comfort, intimacy, and authentic views. It’s best suited for small groups, couples, and anyone who appreciates tranquil scenery and historic landmarks. The combination of professional crew, breathtaking vistas, and the potential for a beautiful sunset makes it a worthwhile addition to a Florida itinerary.

While it’s not a comprehensive sightseeing tour—focusing mainly on the city’s waterfront and key historic sites—it’s a perfect way to experience the city’s maritime atmosphere. If you’re looking for a relaxing, scenic, and intimate way to explore St. Augustine’s coastline and landmarks, this sailing charter is an excellent choice.

FAQ

How long is the tour?
The tour lasts 2 hours, giving you plenty of time to enjoy the scenery without feeling rushed.

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

Is parking available?
Yes, there is free parking at the marina, making logistics easier for travelers.

Can I buy drinks onboard?
Yes, alcohol (except red wine) and additional food and drinks are available for purchase during the tour.

Is this tour suitable for children?
The tour is limited to 6 participants and is best suited for those comfortable on the water. Non-swimmers and people prone to seasickness may want to consider their comfort level.

What should I bring?
Bring comfortable shoes, a hat, sunscreen, a camera, snacks, and sunglasses to enhance your experience.

Are pets allowed?
No, pets are not permitted onboard.

What if the weather is bad?
The tour is weather-dependent. Check the forecast and be flexible with rescheduling if needed, as safety and comfort come first.

Can I cancel or reschedule?
Yes, you can cancel up to 24 hours in advance for a full refund, offering some peace of mind if plans change.

Is this experience good for sunset viewing?
Absolutely. The sunset sail is highly recommended for those seeking especially stunning views as the sky turns to hues of orange and pink.

This sailing tour in St. Augustine offers an inviting way to see the city’s landmarks from a unique angle, combining scenic beauty with a relaxed, intimate setting. It’s perfect for those who want to savor the quiet majesty of the coast, especially at sunset, and enjoy a personal touch that larger tours often lack. Whether celebrating a special occasion or simply seeking peaceful seaside moments, this experience is bound to leave lasting memories.

You can check availability for your dates here: