St. Augustine: Shared Day Sailing Charter

Imagine gliding smoothly across the waters of Florida’s oldest city, feeling the wind in your hair and catching breathtaking views of historic landmarks from a fresh perspective. That’s exactly what you get with the St. Augustine Shared Day Sailing Charter — a two-hour cruise designed for those who want a relaxing, scenic escape without breaking the bank. Whether you’re a first-time visitor or a seasoned traveler craving a different vantage point, this small-group sailing adventure offers a refreshing way to experience St. Augustine.

What we love about this tour is the opportunity to see the city’s famous landmarks from the water, especially the St Augustine Lighthouse and the Castillo de San Marco. The intimacy of a small group—limited to just 6 participants—means more personalized attention and a cozy atmosphere. Plus, the outdoor setting allows you to truly enjoy the refreshing ocean breeze and stunning sunset views.

One consideration? If you’re prone to seasickness or aren’t comfortable on boats, this experience might not be ideal. Also, keep in mind that alcohol (except red wine) is available for purchase onboard, but no drinks are included in the price, so plan accordingly.

This sailing tour is perfect for couples, small groups of friends, or families seeking a leisurely, authentic way to see St. Augustine’s waterfront. It’s especially appealing if you love being outdoors, enjoy photography, or simply want a peaceful break from touring on land.

Key Points

• Intimate Experience: Small group size ensures personalized attention and a more relaxed atmosphere.
• Iconic Sights: Offers outstanding views of landmarks like the St Augustine Lighthouse, Castillo de San Marco, and Bridge of Lions.
• Flexible Schedule: Usually available in the morning and afternoon, providing options for different plans.
• Value for Money: At $137, it’s a reasonably priced way to enjoy the city from a unique perspective.
• Convenient Parking: Free parking at the marina makes logistics easier.
• Weather Dependent: The experience is highly weather-dependent; calm seas and sunshine make for the best trip.

You can check availability for your dates here:

A Detailed Look at the Sailing Adventure

For many travelers, the real charm of a sailing tour lies not just in the sights but in the experience itself. The 2-hour cruise aboard a cozy sailboat is designed to maximize comfort and scenic viewing, with the professional crew managing the boat and ensuring everyone feels engaged.

Starting Point and Logistics: Arriving at the marina 10 minutes early is recommended to meet your crew and settle in. Parking is free, which is a practical bonus when navigating busy coastal areas. Once aboard, the small group (limited to six guests) creates a friendly, intimate setting that’s perfect for conversation or quiet reflection.

The Itinerary: As the boat gently departs the marina, you’ll soon be gazing at the city’s waterfront from a perspective few get to enjoy. The sail typically takes you past notable landmarks—the Bridge of Lions, an elegant span connecting historic neighborhoods; the imposing Castillo de San Marco, guarding the city since the 17th century; and the St Augustine Lighthouse, perched high on Anastasia Island.

What makes this special: Watching these landmarks from the water offers a different appreciation that land-based tours can’t quite match. The way the lighthouse silhouette contrasts against the sky at sunset, or how the Castillo appears commanding from the water, adds depth to your understanding of St. Augustine’s history and architecture.

Onboard Experience: The crew is described as professional and friendly, creating a welcoming environment. Many reviews mention the “breathtaking views” and the relaxed ambiance. An onboard commentator might share tidbits about the landmarks, but the focus remains on enjoying the scenery and the gentle rhythm of sailing.

Photography Opportunities: If you’re into capturing memories, this tour is ideal. The views of the lighthouse, the historic skyline, and the bridge are perfect for photos, especially at sunset when the lighting softens and casts a warm glow.

Sunset and Beyond: While the main tour is 2 hours, many find that the sunset view alone makes it worth the price. Watching the sun dip over the city and ocean while aboard a sailboat is a memorable highlight.

What’s Included and What to Bring

The tour includes everything you need for a smooth experience:

• A 2-hour sailboat cruise with a professional crew
• Breathtaking views of St. Augustine’s landmarks
• Free parking at the marina

However, food and drinks are not included, though beverages—including alcohol—are available for purchase (excluding red wine). You’ll want to bring:

• Comfortable shoes for moving around comfortably
• A hat and sunscreen for sun protection
• A camera to capture the scenic moments
• Snacks or drinks if desired

Important tips: Arrive at least 10 minutes early to check-in. Wearing shoes with non-marking soles is required, and spray tanning products should be avoided, as they can stain the boat or your clothes. Smoking and pets are not permitted onboard.

Authenticity and Value: What Travelers Say

Reviews often highlight the stunning views as the best part of the experience, with many noting that seeing landmarks from the water adds a new layer of appreciation for St. Augustine’s historic charm. One guest said, “The views of the lighthouse and the city skyline were simply breathtaking, especially at sunset.”

Others appreciate the small-group format, describing it as “more personal and relaxing than large tour boats,” ideal for meaningful conversations or quiet reflection. The crew gets high marks for professionalism and friendliness, making guests feel comfortable and engaged.

Some travelers mention the weather’s impact—sunshine and calm seas enhance the trip, while choppy waters or overcast skies might diminish the experience. It’s worth checking the weather forecast before booking.

For those concerned about cost, many find the $137 price reasonable given the quality of the experience, especially considering the opportunity to see the city’s most iconic sights from a peaceful, outdoor setting. The inclusion of free parking at the marina adds convenience, reducing logistical worries.

Who Should Consider This Tour?

This sailing adventure suits those who value authentic, scenic experiences over scripted tours. It’s perfect for travelers who:

• Love being outdoors and near water
• Want a unique view of St. Augustine’s landmarks
• Prefer small, intimate group settings
• Are flexible with timing (morning or afternoon options)
• Don’t mind spending time on a boat for a relaxed 2-hour experience

Not ideal for non-swimmers or seasick-prone visitors, as the boat’s stability and open water setting might cause discomfort. Pets and smoking are not allowed, aligning with the focus on a clean, safe environment.

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The Sum Up

The St. Augustine Shared Day Sailing Charter offers a refreshing alternative to land-based sightseeing. For a reasonable price, you get a personalized, scenic cruise that showcases the city’s most iconic landmarks from a unique water perspective. It’s a fantastic way for travelers to enjoy the outdoors, capture memorable photos, and experience the historic waterfront in a leisurely, relaxed setting.

If your idea of travel includes beautiful views, peaceful sailing, and small-group camaraderie, this tour will likely be a highlight of your visit. It’s especially appealing if you’re eager to combine sightseeing with the serenity of being on the water, away from crowds and traffic.

While it’s weather-dependent and not suitable for everyone, those who love a gentle sail and panoramic views will find this experience well worth the modest investment.

Frequently Asked Questions

Is this tour suitable for children or families?
Yes, families can enjoy this experience, especially those with older children who are comfortable on boats. The small group size and peaceful ambiance make it a family-friendly outing.

Do I need any sailing experience?
No, you don’t need prior sailing knowledge. The crew handles the boat, and the focus is on enjoying the sights and the breeze.

What should I wear?
Comfortable shoes with non-marking soles, a hat, and sunscreen are recommended. Bring a camera and any snacks or drinks you might want.

Can I bring alcohol or food onboard?
You can purchase alcohol (excluding red wine) at the marina before boarding. Food and additional drinks are available for purchase but are not included.

What if the weather is bad?
Tours are weather-dependent. You might find cancellations or rescheduling if conditions are unsafe or unpleasant.

How long in advance should I book?
Since the experience is small-group and popular, booking a few days ahead is advised, especially during peak seasons.

Is parking easy to find?
Yes, free parking is available at the marina, simplifying your logistics.

Are pets allowed?
No, pets are not permitted onboard, maintaining a safe and clean environment for all guests.

What is the best time to take this tour?
Mornings and afternoons are usually available, but many find that sunset cruises offer particularly stunning views.

This sailing tour is a wonderful way to add a relaxed, scenic dimension to your visit to St. Augustine. Whether you’re seeking iconic photo moments or simply a peaceful break on the water, it offers true value for those looking to experience the city from a different angle.

You can check availability for your dates here: More Great Tours Nearby