Charleston: Private Daytime or Sunset BYOB Sailing Charter

Experience the Charm of Charleston from the Water with a Private Sailing Tour

Imagine gliding smoothly over the calm waters of Charleston Harbor, your favorite snacks and drinks in hand, while iconic landmarks drift past. For around $500, up to six people can enjoy a 2.5-hour private cruise aboard a beautiful 35-foot sailboat. Whether you prefer a daytime or sunset cruise, this experience offers a relaxed way to see the city’s waterfront from a fresh perspective. You’ll meet your USCG-licensed captain at Ashley Marina, hop aboard the graceful “Esprit de Joy,” and set off on a personalized voyage through one of South Carolina’s most photogenic harbors.

What we really love about this trip is how flexible and intimate it feels—you’re in control of what you bring, and the boat’s comfortable amenities make it easy to settle in. And the views are genuinely spectacular; from the Ravenel Bridge to Fort Sumter, you’ll get a front-row seat to Charleston’s maritime scenery. The only thing to consider is that this tour might be less suitable for very young children or those with mobility issues, given the boat’s size and the nature of sailing. But if you’re looking for a peaceful, scenic escape with a knowledgeable captain, this sail is a strong choice for couples, families, or small groups wanting a customized experience.

Key Points
– Private and customizable cruise experience for up to 6 guests
– Bring your own drinks and snacks — cooler and souvenir cups provided
– Iconic landmarks like Ravenel Bridge, Castle Pinckney, USS Yorktown, and Fort Sumter
– Flexible timing—choose between afternoon or sunset sailings
– Expert guidance from a USCG-licensed captain
– Ideal for those seeking a peaceful, scenic escape in Charleston Harbor

Exploring Charleston from the Water: What to Expect

This private sailing tour is designed for comfort and personalization. You’ll meet your captain at Ashley Marina, a convenient spot with free parking, located right near the Courtyard by Marriott Waterfront Hotel. It’s a straightforward walk to the boat, which is docked at the three-story gray building with a green roof. Once aboard the “Esprit de Joy,” a well-maintained 35-foot luxury sailboat, you’ll quickly settle in and start your adventure.

The cruise can be booked for either a 2.5-hour afternoon or sunset journey, making it easy to fit into your Charleston itinerary. The boat comfortably accommodates up to six guests, making it perfect for small groups or intimate family outings. The captain’s role is crucial—they’re not just there to steer but also to point out landmarks, answer questions, and enhance your experience with local insights.

You can check availability for your dates here:

The Itinerary: A Journey Through Charleston Harbor

As you cruise along the Charleston Battery, you’ll enjoy stunning views of the historic waterfront, including grand old homes and ships docked in the harbor. The captain will likely point out Castle Pinckney, a historic military fortress, and the Ravenel Bridge, a striking cable-stayed bridge that spans the Cooper River—an engineering marvel and perfect photo opportunity.

Next, your route may take you past the USS Yorktown Aircraft Carrier, a reminder of Charleston’s naval history, and toward Fort Sumter, where the Civil War began. Although the boat doesn’t stop, viewing these landmarks from the water offers a different perspective—more relaxed and less crowded than visiting on foot. It’s a chance to appreciate the scale and setting of these historic sites while listening to your captain’s commentary.

What’s Included and What’s Not

The tour price includes the private cruise, a USCG-licensed captain, bottled water, a cooler, and souvenir cups. You’re invited to bring your own snacks and beverages, making it a very relaxed, BYOB experience. The cooler keeps your drinks cold, and the souvenir cups add a nice touch—great for photos or as keepsakes.

What’s not included? No food is provided, so plan to bring your favorite snacks or small meals. There’s no hotel pickup or drop-off, so you’ll need to arrive at Ashley Marina, a short walk from parking. The tour is designed for a flexible, personal experience—no large groups, no rushing, just a peaceful sail with your chosen companions.

The Experience of a Sunset or Afternoon Cruise

Choosing between a sunset and afternoon cruise depends on what kind of atmosphere you’re after. An afternoon cruise offers more daylight for sightseeing and photography, perfect for capturing the vibrant waterfront and historic landmarks. The sunset option, however, provides a more romantic and tranquil setting, with the possibility of catching the city’s famous golden hour and the sky turning hues of pink and orange.

Many reviews mention how peaceful and beautiful these cruises are. One traveler described their evening as “so peaceful,” while another found their captain “phenomenal” and the experience “amazing.” The captain’s knowledge and friendly demeanor are often highlighted as a significant part of the appeal, making the journey not just visually stunning but also educational and engaging.

Why This Tour Offers Great Value in Charleston

For the price of $500, you get a personalized sailing experience that’s far more intimate and flexible than larger boat tours. The ability to bring your own drinks and snacks means you can customize your experience to your tastes, whether you’re celebrating a special occasion or just want a relaxing day on the water. The inclusion of bottled water, souvenir cups, and a cooler adds to the value—no hidden costs for basic amenities.

The small group size ensures that the experience remains relaxed and tailored—your captain will focus solely on your crew. The stunning views of Charleston’s landmarks from the water are hard to beat, especially with the captain pointing out details you might miss exploring on land. This tour is an excellent way to combine sightseeing with a touch of luxury, all in a setting that’s both scenic and peaceful.

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Who Will Enjoy This Experience?

This private sailing tour is ideal for couples seeking a romantic outing, families wanting a memorable adventure, or small groups of friends celebrating a special occasion. It’s perfect if you love being on the water, enjoy scenic views, and appreciate a knowledgeable guide who can enhance your understanding of Charleston’s history and sights.

It’s less suitable for young children under four or travelers with mobility issues, as the boat’s size and sailing nature might restrict ease of access. If you prefer a structured, large-group tour, or want food included, this might not be the best fit.

Final Thoughts

A private sail in Charleston Harbor offers a unique way to see the city’s waterfront—an experience that combines stunning scenery, expert commentary, and the flexibility to make it your own. Whether you’re watching a sunset or enjoying the afternoon light, the sense of peace and connection to the water is undeniable. The boat’s comfort, personalized approach, and scenic route make it a worthwhile addition to any Charleston visit.

If you’re after a relaxed, authentic experience with a focus on beautiful views and friendly guidance, this tour hits the mark. It’s especially appealing if you want to avoid the crowds, customize your outing, and truly enjoy the harbor’s scenic beauty at your own pace.

FAQ

How many people can join the cruise?
Up to six guests can enjoy this private sailing experience, making it perfect for small groups or families.

What is the duration of the tour?
The cruise lasts approximately 2.5 hours, available in the afternoon or at sunset.

Is there any food provided?
No, food is not included. You’re welcome to bring your own snacks and beverages, which you can store in the cooler on board.

What should I bring?
Comfortable clothes and shoes are recommended. Since it’s a boat, packed or layered clothing for variable weather might be wise.

Are drinks provided?
Bottled water and souvenir cups are included. You bring your own drinks, but the cooler helps keep them cold.

Is this experience suitable for children?
It’s best for children over age four, as the boat’s size and sailing conditions may not be ideal for very young kids.

Where do I meet the captain?
At Ashley Marina, located at 35 Lockwood Dr, Charleston. It’s a short walk from the parking lot at the Courtyard Marriott Waterfront Hotel.

Do I need to pay in advance?
Yes, reservations are made with the option to reserve now and pay later, providing flexibility in planning.

Can I cancel the tour?
Yes, you can cancel up to 24 hours in advance for a full refund.

Is it weather dependent?
Yes, like all sailing trips, tours may be affected by weather conditions, but the provider offers full cancellation options.

Whether you’re after a peaceful escape, stunning photos, or a memorable way to see Charleston, this private sailing tour offers a personalized, scenic experience that’s hard to beat.

You can check availability for your dates here: