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
(48 Ratings)
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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
Mark_d
Mar 22, 2025
Nice relaxing trip and a... - Nice relaxing trip and a great sailing day overlooking all areas of Charleston and surrounding areas
Review provided by Viator
Juliefr7393xq
Feb 14, 2025
Get out on the water to really experience Charleston - We had a great sail with Captain Will and Charleston Harbor Sailing! We saw dolphin and a College of Charleston sailing race. What a great way to experience Charleston!
Review provided by Tripadvisor
Paulja3638ov
Feb 8, 2025
Unforgettable Birthday - Booked a sunset cruise as a surprise for my wife’s birthday. Everything was incredible, the weather, the sunset, the sailing itself. Captain Will was great, very personable and knowledgeable of the area and the history. Highly recommend! Can’t wait to come back.
Review provided by Tripadvisor
Kelly_c
Nov 9, 2024
5 star experience! - Absolutely fantastic sailing experience with Will! Would book this again & again ... 5 star experience!
Review provided by Viator
Gary_c
Nov 7, 2024
Highly recommended. Beautiful boat, great views (dolphins!). Pro captain. Worth the $$ - We're a "young" couple in our 50s celebrating our birthdays and we're very happy with this boat charter. Captain Will was a pro, calm and knowledgable. There was good communication regarding the booking leading up to the departure date and there was no issue finding Will at the Harborage location. The boat was beautiful as were the views, and a few dolphins came right up close! Will provided lots of interesting facts about the area when asked - but he also gave us space to enjoy our time as a couple. This experience was so much better than being on some ship with 50 other people clamoring for space. We'd highly recommend this experience to others visiting Charleston.
Review provided by Viator
Rick_h
Nov 6, 2024
The weather was perfect! ... - The weather was perfect! The boat captain was pleasant and knowledgeable. He really made our time memorable.
Review provided by Viator
Daisy_b
Oct 1, 2024
Fantastic - We had a wonderful 29th anniversary sail. Will was a great captain. Charleston was a beautiful place for a sail. I highly recommend doing it.
Review provided by Viator
T1113wlmegant
Sep 11, 2024
The best sunset cruise experience! - We had the absolute best time ever on our sunset cruise! Our captain Will was so knowledgeable, gracious, and caring with his time and expertise. He was just the cherry on the top of the best night of or vacation. The Esprit de Joy was a beautiful, clean, and perfect size boat for our small group of six. We highly recommend this experience!
Review provided by Tripadvisor
Select Date and Tickets
up to 6 guests
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April 2025
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