Private Sailing Charter with Captain

Experience an exclusive sunset sailing charter in Charleston’s scenic Harbor. Marvel at the breathtaking beauty of the Holy City and discover iconic landmarks while enjoying the luxury of a stocked cooler and dedicated crew.

Duration: 2 hours, 30 minutes
Cancellation: 24 hours
Highlights
  • Charleston Harbor - The golden hour of sunset is our prime booking time!
    You’ll smoothly cruise past the iconic Charleston Battery, soaking up the timeless charm of downtown Charleston. Hold onto your hats because the fun’s just starting! As you sail past the peninsula, you’re in for jaw-dropping views of Charleston and learn why we call it “The…
What's Included
  • Bottled water included
  • All fees and taxes covered
What's Not Included
  • Gratuity
Additional Information

Set sail on an exclusive journey aboard “Esprit de Joy,” designed for groups of up to 6 guests for a 2.5-hour charter exploring the picturesque Charleston Harbor. The prime booking time is during the golden hour of sunset, allowing you to experience one of the most stunning sunsets. Alternatively, enjoy an afternoon sail with your friends and family….

Location
33 Lockwood Dr
Lockwood Drive
Rideshare: Get dropped off at The Harborage at Ashley River Marina, 33 Lockwood Drive, OR Pay $10 and park in the guest lot of The Courtyard by Marriott hotel (35 Lockwood Dr) adjacent to the marina. Walk to the sidewalk, turn right on Lockwood Drive, turn right into the marina, to gray building.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(57 Ratings)
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Rebeccau310
Jun 16, 2025
Amazing sunset cruise with Captain Will! - My husband and I booked a sunset cruise with Will and it was incredible! He was so friendly and truly passionate about sailing. He answered all our questions and chatted with us, but also gave us our space and time to spend alone. When we come back to Charleston, we’ll absolutely be only booking with Will.
Review provided by Tripadvisor
Brooke_g
May 25, 2025
My group of girlfriends... - My group of girlfriends and I had an amazing time on this trip! Thank you for everything! This is a “must” if you are visiting Charleston!
Review provided by Viator
Curiosity557896
May 25, 2025
A Great Time on the Harbor With Charleston Harbor Sailing - I have been on several trips with Charleston Harbor Sailing. It is one the most incredible ways to spend 3 hours in Charleston. I have entertained many out of town guests on The Espirit de Joy. I think it’s the absolute best way to see the beauty of the Charleston Battery, James and John’s Islands and all the sights including the Ravenel bridge! The sailboat is immaculate and Captain Will is a real pleasure. A must see!
Review provided by Tripadvisor
Justin_f
May 19, 2025
Great overall experience.... - Great overall experience. Sunset cruise has best lighting for photos. Want with 5 people in May. Great weather and evening to experience sailing. Would do again.
Review provided by Viator
Venture557128
May 16, 2025
A perfect afternoon - My daughter and I had a relaxing afternoon cruise with Will. We really enjoyed the sites and conversation. The route we sailed was a perfect way to sight see and to beat the May Charleston heat. Will was very accommodating. We came down when there was a lot of rain. We were able to reschedule with him and find a day that worked to take us out. Will is a very capable Captain. The sailboat is very comfortable and well maintained. I look forward to sailing with him again. I would not hesitate to book a charter.
Review provided by Tripadvisor
Q3367rlcaitlinm
May 9, 2025
Unforgettable Experience - My husband and I went out with Captain Will this weekend on the last evening of our honeymoon. Being able to enjoy the sailboat privately was such a romantic and unforgettable experience. Will was such a great person to talk with and offered to take all the photos we wanted anywhere on the boat, play whatever music we wanted and let us have privacy on the bow to enjoy the views when we wanted it. 100/10. Will be coming back!
Review provided by Tripadvisor
Stefanie_k
May 6, 2025
Took an awesome ride in... - Took an awesome ride in the bay with our captain, Will. Everything was great and Will was the ultimate host making sure we had everything we needed! Highly recommend this activity.
Review provided by Viator
E6604pndaniell
Apr 9, 2025
Great experience - Reserved this as part of our honeymoon. Well worth it! The view was incredible and we both really enjoyed it. Definitely 10/10
Review provided by Tripadvisor
Rachelle_a
Apr 4, 2025
Memorable family evening!! VERY kid friendly!! - WONDERFUL evening spent with Captain Will on the sunset cruise with my husband and two young children. Will really engaged with my 5 year old daughter and taught her how to drive the boat, which she was thrilled with, and created some really special family memories. We loved the flexibility of bringing wine and snacks onboard. It was overall just the most wonderful, memorable evening on our vacation and we are so thankful we did this!
Review provided by Viator
Todd_b
Mar 23, 2025
The Brewers - Will was our captain and he was a great host! Our family had a great time on the boat and he provided a lot of insight on the history of Charleston. We brought along a picnic dinner and he had plates and cups available for us. We would recommend this tour to anyone who wants to see Charleston from the water in a private sailing experience.
Review provided by Viator
From $500 (Per Group)
up to 6 guests
1 - Traveler
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).