Private Sailing Charter with Captain, BYOB

Discover the Charm of Charleston by Private Sailing

Imagine gliding across the shimmering waters around Charleston in a sleek private sailboat, with your own crew and the freedom to bring your favorite drinks. For $500 per group (up to six people), you can enjoy a 2.5-hour personalized sightseeing cruise, tailored to your interests. Whether you’re celebrating a special occasion, seeking a romantic sunset, or just want to see Charleston’s waterfront from a new perspective, this experience offers a relaxed, intimate way to absorb the city’s scenic beauty and historical sights.

What we love most about this trip is how flexible and personal it feels — you set the tone, whether it’s a leisurely afternoon or a sunset cruise that captures Charleston’s golden hour. Plus, the ability to bring your own snacks and drinks makes it feel like a private moment with friends or family, without the hassle of formal reservations or crowded tours. On the downside, the cost is per group rather than per person, which works out well for small parties but might seem steep if you’re traveling solo or as a couple looking for a shared experience.

This tour is perfect for travelers who value authenticity and comfort. Whether you’re celebrating a birthday, planning a romantic date, or organizing an anniversary, many reviews highlight how engaging and memorable the experience can be. If you love scenic views, historical sights, and a touch of laid-back luxury, then this sail is likely to be a highlight of your Charleston visit.

Key Points

• Private and Personal: Only your group sails together, offering intimacy and flexibility.
• Bring Your Own Drinks: Snacks or alcohol are welcome, creating a relaxed, personalized atmosphere.
• Iconic Sights: Pass by landmarks such as Arthur Ravenel Jr. Bridge, Fort Sumter, USS Yorktown, and Charleston Battery.
• Expert Captain: The crew provides insights on Charleston’s history and points of interest.
• Beautiful Views: Perfect timing around sunset offers incredible photo opportunities and golden light.
• Ideal for Celebrations: Great for birthdays, anniversaries, bachelor(ette) parties, or romantic dates.

A Detailed Look at the Experience

The Itinerary and Stops

The cruise begins at 33 Lockwood Dr, where your private boat awaits. Once aboard, the captain smoothly sets sail into some of Charleston’s most iconic waters. The main attraction is the chance to see the Charleston Battery, a historic waterfront promenade lined with stately mansions and lush parks. We loved how the boat glided past this area, providing a perfect view of the city’s elegant waterfront.

One of the most talked-about sights is the Arthur Ravenel Jr. Bridge. This impressive cable-stayed bridge, connecting downtown Charleston with Mount Pleasant, is an engineering marvel. During the cruise, you’ll get several opportunities to snap photos with the bridge as a stunning backdrop, especially during sunset when the light hits it just right. As one reviewer put it, “you will definitely have chances to take pictures with the bridge as a gorgeous backdrop.”

A visit to Fort Sumter is another highlight. Accessible only by boat, this historic site marks the beginning of the Civil War. The cruise offers a contemplative moment as you drift past this National Monument, imagining the echo of cannon fire that once echoed across the harbor. The captain may share some historical tidbits, making the view both scenic and educational.

The Sights and Their Significance

• Fort Sumter: A must-see for history buffs, and its boat-only access makes viewing from the water a special experience.
• The Ravenel Bridge: Besides its size and design, it’s an iconic feature of Charleston’s skyline, best appreciated from the water.
• Charleston Waterfront Mansions: The cruise offers views of beautifully preserved homes and the city’s historic waterfront, perfect for photos.
• St. Michael’s Church: One of Charleston’s oldest churches, recognizable by its tall steeple, it’s a steady fixture on the skyline and a reminder of the city’s enduring history.

The Experience and Atmosphere

The tour’s relaxed pace means you can truly enjoy the scenery and take in the sights at your leisure. Many reviews emphasize the friendly, knowledgeable captain (Will, in several reviews), who provides insights into Charleston’s history and landmarks. Several guests mention how engaging he was, especially with children — one review fondly recalls a captain teaching a young girl to drive the boat, which added a special touch.

The sunset cruises get particular praise, with guests noting how the “golden hour” bathes the city and water in warm light, transforming the views into magical moments perfect for photography or just quiet reflection. The comfortable boat and the opportunity to bring your own food and drinks make this feel like a private, laid-back gathering rather than a commercial tour.

The Practicalities and Value

At $500 per group, the experience offers significant value for those seeking exclusivity and flexibility. It’s especially appealing because your group isn’t sharing the boat with strangers, and you have control over the timing and what you bring onboard. The inclusion of bottled water and all fees makes budgeting straightforward. Keep in mind, gratuity isn’t included, so tipping your captain is customary if you feel they’ve enhanced your trip.

Booking generally requires planning about 38 days in advance, which is typical for popular boat tours. The duration of around 2.5 hours is just right for a relaxed experience — enough time to see the sights without feeling rushed.

Who Should Consider This Tour?

If you’re someone who loves scenic views with a side of history, this cruise is ideal. It’s perfect for romantic couples, families with kids, or small groups celebrating special days. It’s especially well-suited for those wanting to enjoy Charleston from the water without the effort of sailing themselves. If you’re looking for a private, flexible, and comfortable experience with beautiful photo opportunities and insightful commentary, this tour hits the mark.

However, if you prefer a more structured or educational tour with a larger group, or if you’re on a tight budget, you might want to explore other options. But for those wanting intimacy, customization, and stunning views, this sailing cruise is hard to beat.

Final Thoughts

This private sailing experience around Charleston is one of those moments that sticks with you — a blend of breathtaking scenery, relaxed atmosphere, and personalized service. The ability to bring your own drinks makes it a perfect setting for celebrations or special moments, while the knowledgeable captain ensures you don’t miss out on interesting sights or stories.

The value for the price is particularly notable given the exclusivity and flexibility it offers. It’s a way to enjoy Charleston’s waterfront at your own pace, with plenty of memorable photo opportunities and a chance to see landmarks from a perspective only the water can provide.

If you’re after an authentic, relaxed, and visually stunning way to experience Charleston, this cruise could very well be the highlight of your trip.

FAQ

Can I bring my own drinks and snacks?
Yes. One of the biggest perks of this tour is that you’re welcome to bring your own alcohol, snacks, or drinks, making it a flexible and personal experience.

How long is the cruise?
The cruise lasts approximately 2 hours and 30 minutes, including the time to travel to and from the sights.

What landmarks will I see?
You’ll cruise past Charleston Battery, Arthur Ravenel Jr. Bridge, Fort Sumter, USS Yorktown, and see waterfront mansions and St. Michael’s Church.

Is this a private tour?
Yes. This is a private experience for your group only, up to six people, offering a more intimate setting.

How far in advance should I book?
Most travelers book about 38 days ahead of their preferred date, which helps ensure availability, especially during busy seasons.

Are children welcome?
Yes, many reviews mention family-friendly trips, and kids seem to enjoy the boat ride, especially when Captain Will engages with them.

What is included in the price?
All fees, taxes, and bottled water are included. Gratuity is not included but is customary if you’re pleased with the service.

What should I wear?
Casual, comfortable clothing suitable for being on the water. Weather can vary, so consider bringing layers and sun protection.

Is there a cancellation policy?
Yes. You can cancel up to 24 hours in advance for a full refund. Cancellations within 24 hours are not refundable.

What if the weather is bad?
If weather conditions are poor, the tour may be canceled and rescheduled or fully refunded, ensuring safety and comfort.

This sailing cruise around Charleston offers a delightful mix of scenic beauty, historical sights, and relaxed fun. Whether celebrating, sightseeing, or simply seeking a quiet escape on the water, it’s a memorable way to see one of America’s most charming coastal cities.