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
  • 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 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
(64 Ratings)
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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
Cosmopolitan452635
Aug 15, 2025
A Highlight of Charleston - So appreciated sharing this experience with dear childhood friends. The Espirit de Joy is a beautiful craft. Captain Will is an expert, enjoyed hearing about some of his racing adventures. Embraced the breeze and sailing the open water especially nice coming from landlocked Colorado! Fascinating learning some history of Charleston area and viewing the architecture on the shoreline. Would highly recommend this excursion.
Review provided by Tripadvisor
Cassie_c
Jul 28, 2025
We had an amazing time! I... - We had an amazing time! I would do it again in a heart beat. Especially seeing the sunset on the water.
Review provided by Viator
Y1513cqstaceyl
Jul 27, 2025
Good vibes, great boat ride - Friendly captain. Beautiful views of the battery and historic forts. Good tunes. Relaxed vibes. Made for a great boat ride with my twin sister!
Review provided by Tripadvisor
Scott_s
Jul 2, 2025
Beautiful evening sail!... - Beautiful evening sail! Very relaxing and laid back experience! Great way to see the harbor! Fun trip.
Review provided by Viator
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
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).