Charleston: Private Daytime or Sunset BYOB Sailing Charter

A brief overview

Imagine drifting along Charleston Harbor on a sleek, private sailboat with your own crew and unobstructed views of some of the city’s most iconic sights. This charter experience promises a personalized way to see the historic waterfront, whether during a breezy afternoon or a romantic sunset. With up to six guests, it offers an intimate setting that combines comfort, scenic beauty, and the chance to relax with your favorite snacks and drinks.

What makes this tour particularly appealing? First, it’s completely private, giving you control over the pacing and sights. Second, it’s BYOB, meaning you can bring your preferred beverages to enjoy at your leisure. Lastly, the knowledgeable USCG-licensed captains ensure a smooth, safe journey while pointing out the highlights along the way.

A potential consideration? The tour lasts only 2.5 hours, so it’s perfect for a quick escape but might leave those looking for a longer experience wanting more. Still, for most travelers seeking a snapshot of Charleston from the water, this experience hits the mark. It’s especially well-suited for couples, small groups, or families wanting a memorable, customizable outing.

You can check availability for your dates here:

Key Points

• Private & customizable: Up to six guests, choose between daytime or sunset cruise.
• Beverage flexibility: Bring your own drinks, enjoy bottled water, and use provided souvenir cups.
• Iconic landmarks: View the Ravenel Bridge, Castle Pinckney, USS Yorktown, and Fort Sumter.
• Expert guidance: USCG-licensed captain ensuring safety and local insights.
• Scenic routes: Cruise past The Battery, admire Charleston’s historic waterfront and skyline.
• Value: At $500 for a private group, it offers a personalized experience at a reasonable price considering the intimacy and exclusivity.

What to Expect on Your Charleston Sail

This charter begins at 33 Lockwood Dr, at the Ashley Marina. Once there, you’ll meet your captain, board the “Esprit de Joy”, a 35-foot luxury sailboat equipped for comfort and style. From the moment you step aboard, you’re set for a relaxed, scenic cruise designed to showcase Charleston’s waterfront icons.

The Itinerary & Highlights

Start at the marina: The meeting point is straightforward, with free parking at the Courtyard by Marriott Waterfront Hotel. After a quick check-in, you’ll step onto the boat, which comfortably accommodates up to six people—perfect for an intimate experience.

Sailing along the Charleston Battery: As you glide past the historic shoreline, your captain will point out homes with colorful facades and explain their significance. You can expect to see Fort Sumter, the site where the Civil War began, and Castle Pinckney, a crucial defense fort from the 19th century.

Iconic landmarks: The sail then takes you past the Ravenel Bridge, a striking cable-stayed bridge connecting Charleston to Mount Pleasant. Many reviewers mention how impressive it is to see this engineering marvel up close from the water.

Wildlife and scenic views: Guests frequently mention seeing dolphins and pelicans during their cruise, adding a lively and natural element to the experience. One reviewer noted, “We saw lots of wildlife, including dolphins and pelicans,” which enhances the feeling of being connected to nature even in a historic harbor.

Sunset or afternoon: The sunset cruise is particularly popular, with guests describing it as “the perfect evening” and “a calm, breathtaking experience.” The changing light and cooler temperatures make for a romantic and serene outing.

Snacks and drinks: You’re encouraged to bring your own food and beverages. The boat’s cooler is available for storage, and bottled water, plastic champagne flutes, and souvenir cups are provided—adding a little extra fun and style to your sipping experience.

Ending the cruise: The sail concludes back at Ashley Marina after approximately 2.5 hours, leaving you with lasting memories and plenty of photo opportunities—like capturing the skyline at sunset or the bustling harbor.

Why this experience works for travelers

What truly sets this charter apart is the personalized touch. Unlike large, commercial cruises, this private sail offers a tailored journey where your interests and pace take precedence. It’s perfect for small groups or couples wanting an exclusive, quiet escape.

The knowledgeable captain, often praised for his attentiveness and insights, adds educational value without feeling like a formal tour. As one reviewer shared, “Will was amazing,” and that kind of attentive service makes all the difference.

On top of that, the scenic route—covering key landmarks and offering wildlife sightings—makes it an engaging experience that appeals to history buffs, nature lovers, and those simply seeking stunning views. The option to choose a sunset cruise adds a romantic touch, with many describing it as “the most beautiful time of day to be on the water.”

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Navigating the cost and value

At $500 for a group of up to six, the price might seem steep at first glance. However, when you consider you’re getting a custom private experience, with the flexibility to bring your own drinks, and the exclusivity of a small group, the value becomes clearer.

Compared to larger commercial cruises, which can cost significantly more per person and require sharing the space with dozens of other travelers, this private charter offers a much more relaxed and intimate environment. Plus, with the boat comfortably accommodating everyone, there’s plenty of room to spread out and truly enjoy the views.

The experience’s appeal

Several reviewers highlight how memorable and enjoyable the trip was. For instance, one noted, “This was our favorite part of our trip,” emphasizing how special the experience felt. The chance to sit on the bow during a gust of wind and snap photos was described as “thrilling,” indicating the fun and interactive nature of the ride.

The calm, scenic nature of the cruise also makes it suitable for a variety of travelers—whether planning a romantic date, a family outing, or a small gathering of friends. Because the tour is BYOB, it allows for a personalized celebration—think champagne, craft beer, or even non-alcoholic options.

Practical details

Duration: 2.5 hours, perfect for fitting into a busy day or as a highlight of a longer trip. Starting times vary, so checking availability is recommended.

Meeting point: The parking at Courtyard by Marriott Waterfront Hotel is free, and directions are straightforward. The meet-up involves walking to the Ashley Marina, where you’ll find the gray building with a green roof—the starting point for your adventure.

Group size: Up to six guests, ensuring plenty of space and personal attention.

Inclusions: The experience includes a private cruise, a licensed captain, bottled water, a cooler, and souvenir cups—adding value and convenience.

Exclusions: Food and hotel transfers are not included, so plan to eat before or after your cruise.

Age restrictions: Not suitable for children under four, but ideal for older kids and adults seeking a relaxed, scenic outing.

FAQs

Can I bring my own drinks?
Yes, you’re encouraged to bring your own beverages and snacks. The boat has a cooler for storage, and bottled water is provided.

How long does the cruise last?
The cruise lasts approximately 2.5 hours and includes scenic stops along Charleston Harbor.

Is this experience private?
Absolutely. The cruise is for your group only, with a maximum of six guests, allowing for a personalized and relaxed experience.

Are there any age restrictions?
Yes, the tour isn’t suitable for children under 4 years old to ensure safety and comfort for all guests.

What landmarks will I see?
Expect to see the Ravenel Bridge, Castle Pinckney, USS Yorktown, Fort Sumter, The Battery, and other historic waterfront sights.

Is parking available at the meeting point?
Yes, free parking is available at the Courtyard by Marriott Waterfront Hotel, located at 35 Lockwood Dr.

Do I need to pay upfront?
You can reserve your spot now and choose to pay later, offering flexibility in your travel planning.

What should I wear?
Comfortable clothes and shoes are recommended, especially since you’ll be on the water and possibly exposed to the sun or wind.

Can I book for a sunset or daytime cruise?
Yes, both options are available, and many guests prefer the sunset for its romantic light and cooler temperatures.

What if I need to cancel?
Cancellations are free if made at least 24 hours in advance, allowing for flexible planning.

Final thoughts

This private sailing charter in Charleston offers a fantastic way to see the city’s waterfront in a relaxed, intimate setting. With knowledgeable guides, stunning vistas, and the flexibility to bring your own drinks, it’s a memorable experience that combines comfort, beauty, and personalization.

It’s best suited for small groups, couples, or families who value exclusivity and scenic beauty. If you’re looking for a special way to explore Charleston from the water—without the crowds or rigid schedules—this tour ticks all those boxes.

While the ride is relatively short, the quality of the experience and the personalized service make it a worthwhile investment. Whether you’re celebrating a special occasion, seeking a peaceful afternoon, or simply want a different view of the city, this sailing adventure is likely to leave you with lasting memories—plus plenty of great photos!

You can check availability for your dates here: