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 at sunset is our most popular booking time!
    Enjoy a smooth cruise past the iconic Charleston Battery, absorbing the timeless allure of downtown Charleston. Get ready for excitement as the journey begins! As you sail past the peninsula, you’ll be treated to breathtaking views of Charleston and discover why it’s…
What's Included
  • Bottled water
  • All Fees and Taxes
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 friends and family.
Be…

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
(70 Ratings)
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1 star
Rob
Apr 22, 2026
Fantastic Sail! - Fantastic sail with Captain Will! Very relaxing sail on a beautiful vessel. We had a great time!
Review provided by Tripadvisor
Timdz9658oe
Apr 11, 2026
What an awesome experience - Will took us on a great sunset sail. He did a great job. And made it very special for us. He knows what he’s doing.
Review provided by Tripadvisor
Jim_h
Mar 29, 2026
Jim & Michele H. - Captain Will is awesome! He’s a very experienced sailor - definitely ask him about his history. He makes the entire sail relaxing and focused on our total experience - it was an amazing time on the water - highly recommended!
Review provided by Viator
Angela_h
Mar 28, 2026
Cold but great day out on... - Cold but great day out on the boat. Captain Will was super friendly and knowledgeable. Def recommend this tour.
Review provided by Viator
Robin_m
Mar 14, 2026
Perfect afternoon sailing... - Perfect afternoon sailing around Charleston with the family. Captain Will did a great job. Such an amazing activity for our weekend getaway.
Review provided by Viator
Andrewbd4951dg
Feb 16, 2026
Dream like - What an awesome experience this was. The captain was very knowledgeable and definitely knew a lot about his boats. 10/10 would recommend everyone to do if your visiting Charleston and get great views of the lovely city.
Review provided by Tripadvisor
Sambelk
Nov 4, 2025
Private Charter with Capt Will. - This was a great experience. Will was a great host and while cool in November we were prepared and thoroughly enjoyed ourselves. We caught the 5:20 sunset and saw the waterfront all the way up to the aquarium and the Yorktown. Dolphins entertained and we arrived back at dock right on time. We highly recommend this for your small group
Review provided by Viator
Megan_s
Nov 3, 2025
We had such a lovely time... - We had such a lovely time sailing around the harbor with Charleston Harbor Sailing! Captain Will was fantastic — friendly, knowledgeable, and made the entire experience so enjoyable. The boat was beautiful and well-kept, and the views of Charleston from the water were unbeatable. Highly recommend this for both visitors and locals looking for a fun and relaxing way to enjoy the city!
Review provided by Viator
Madison_b
Sep 27, 2025
10/10 recommend! So... - 10/10 recommend! So relaxing and captain Will was amazing! We even got to see dolphins along the way.
Review provided by Viator
Shelby_b
Aug 16, 2025
We had a great experience... - We had a great experience with Captain Will. Very relaxing and the perfect evening activity for our girls trip.
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).