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 Holy City,” - all right from the heart of the harbor. You won't want to miss iconic sights like Castle Pinckney, Ravenel Bridge, USS Yorktown, and Fort Sumter. Whether you are commemorating a birthday, a significant milestone, a team retreat, or a romantic date night, our aim is to craft an unforgettable experience for you. We've got you covered with plastic champagne flutes and souvenir cups that you can take home as cherished mementos. Our dedicated captain is here to ensure every moment on board is nothing short of extraordinary.
Fort Sumter holds significant historical importance as the site where the American Civil War began. Located in Charleston Harbor, this National Monument is accessible only by boat and offers a glimpse into the events that shaped the nation’s history. As we trim by, we invite our guests to imagine the echoes of the cannon fire that reverberated across the harbor.
The Arthur Ravenel Jr. Bridge, also known as the Cooper River Bridge, is an engineering marvel that spans the entire Cooper River, connecting downtown Charleston with Mount Pleasant. During our time together, you will definitely have opportunities to take pictures with the bridge as a gorgeous backdrop.
This waterfront seawall is a stunning sight from our sailboat and it will be the first landmark you will see as we embark on our journey. You’ll be able to see the beautiful lined mansions and waterfront promenade that is one of the most visited spots in all of Charleston.
St. Michael’s is one of Charleston’s oldest churches, dating back to 1752. Its steeple is a prominent feature on the city’s skyline and is known for surviving numerous hurricanes.
Great private boat experience! Captain Will was great… informative and very knowledgeable. We went with 5 college friends celebrating birthdays. Would definitely recommend to anyone looking for a wonderful charter!
Absolutely the best way to explore Charleston! Captain Will made this one of the best private charters I’ve ever taken. We enjoyed an amazing sunset sail with perfect views of the Battery and the Ravenel Bridge. The Esprit de Joy is beautiful, and I can’t wait to sail again! Highly recommend!
Great experience and wonderful views! Would highly recommend booking a sailing tour if you're visiting Charleston!
It was amazing and so fun. We had calm waters and saw plenty of dolphins. Captain Will was also super nice and fun to chat with.
Will was very knowledgeable and a very skilled captain. Would definitely recommend!!!
I would highly recommend this charter! My five girlfriends and I had a wonderful experience. It is a beautiful boat and enjoyed sailing at sunset. After a lot of walking on land, it was so fun to experience Charleston from the water. Our captain Will was great. Friendly, knowledgeable, pointed out landmarks and other fun Charleston facts during our sail, answered all of our questions about sailing and was overall very personable and accommodating. It was evident he was there to ensure we had a great time. And we also appreciated his offers to take as many pictures as we would like! Important for six ladies that wanted to document the experience. :) Highly recommend this very professional and enjoyable experience!
What an amazing afternoon! Captain Will was relaxed and knowledgeable. He chatted with us about local attractions and historical places in a manner that seemed like visiting with a friend, rather than taking a tour with a guide. Will answered questions about the Esprit de Joy, as well as other boats we saw. And he ordered up dolphins! A dolphin pod delighted us by following our boat and playing for several minutes. We can't wait to go back to Charleston and take another tour with Charleston Harbour Sailing!
We went out on the boat with my family and best friend for my birthday and I absolutely loved it!! The sunset was beautiful, we got to bring our own wine and got amazing pictures!! I also want to say that Will, our captain was awesome and we just had a great experience!! I absolutely recommend!!
Excellent experience! Our captain Will was amazing!
I live here in Charleston, and I love being out on the water. It is so special to experience Charleston and the surrounding areas from the Harbor, and Charleston Harbor Sailing is the best in the business! The boat is impeccable, and Captain Will creates a memorable experience for you to take home and remember this beautiful city! I have been out many times, and on several different boats, but Charleston Harbor Sailing is, without a doubt, the best!
Will was a great Captain! We had a great time and he was very knowledgeable about the area. I would recommend to anyone looking for a sail in the area. Thanks Will for a great time!
Enjoyed our evening on the water with Captan Will. Spent our first evening in town on this sailing trip. Highly recommended!
Great relaxing experience that would recommend for any couple looking for a romantic private getaway
It was a great experience! Meeting the boat and Captain was easy! The Captain was great!! He was personable, informative and GREAT with my 5 year old grandson!
This was the highlight of our old girls trip. Captain Will was so knowledgeable. He made us feel very comfortable. We highly recommend this sailboat experience!
A second time around with Captain Will on the Charleston Harbour was just as awesome as 4 friends all enjoyed the Sunset cruise! The route provided the perfect combo of open water and interesting shoreline. Will is a skilful navigator, knowledgeable about Charleston and a great guy. Sailing into the stunning sunset on this beautiful boat was the icing on the cake.
The sail met each of our expectations and Captain Will exceeded our expectations. He was equal parts professional, experienced,, friendly, and fun. .
We had a wonderful harbor sail with Captain Will. Instructions provided were perfect. Will was the perfect host complete with lots of good local recommendations. I would book again when back in the area!
2 couples in their 60s enjoyed a great sunset sail on a beautiful night. Captain Will was fantastic. We brought our own drinks. Had no difficulty finding it. FYI, the parking at the Marriott is now $15.
Fantastic tour! It exceeded our expectations in all regards. We’ve visited Charleston many times, but this was our first sail. Now, we won’t plan a vacation here without this tour. Sailing and the boat were lovely. We took the afternoon sail, and the boat had an awning/cover to shade those who preferred to be. Will was a great captain, knowledgable and a pleasure to spend the time with.
We had sooo much fun! The boat was perfect and loved getting to see Charleston from the water! Captain was awesome and truly can’t wait to come aboard again!
Amazing experience! Will was super relaxed, but very safe and aware of what was happening at all times. He was very accommodating and professional. This tour was agreed to be the top highlight!
Had a great time sailing with my friends. The captain Will was super friendly and took us around the harbor on a gorgeous Charleston day on the water. The waters were calm and the trip was smooth. Will definitely recommend them!
Every aspect of the experience, from beginning to end, was simply perfect! My wife and I took the sunset cruise to celebrate our 35th Anniversary. Captain Will was waiting for us at the gate when we arrived, helped us board, gave a quick tour and safety briefing and then we were off on a fantastic sail. The boat was in great shape, easy to move around on and had all the essentials with plenty of comfortable seating. Captain Will was an interesting, thoughtful, gracious and entertaining host and guide and shared his local knowledge to help us with the remainder of our visit. This was an outstanding experience for us as visitors to Charleston and, I expect, it would be for locals as well!
I had booked the trip for my sisters bachelorette party. Captain Will was fantastic, the weather was fantastic and we even got to see a few dolphins as an added bonus. We had a very fun evening during our sunset excursion!
Captain Will was a fantastic tour guide! So kind and had great recommendations for our trip. Absolute gem!
Fantastic sail with Captain Will! Very relaxing sail on a beautiful vessel. We had a great time!
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.
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!
Cold but great day out on the boat. Captain Will was super friendly and knowledgeable. Def recommend this tour.
Perfect afternoon sailing around Charleston with the family. Captain Will did a great job. Such an amazing activity for our weekend getaway.
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.
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
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!
10/10 recommend! So relaxing and captain Will was amazing! We even got to see dolphins along the way.
We had a great experience with Captain Will. Very relaxing and the perfect evening activity for our girls trip.
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.
We had an amazing time! I would do it again in a heart beat. Especially seeing the sunset on the water.
Friendly captain. Beautiful views of the battery and historic forts. Good tunes. Relaxed vibes. Made for a great boat ride with my twin sister!
Beautiful evening sail! Very relaxing and laid back experience! Great way to see the harbor! Fun trip.
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.
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!
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!
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.
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.
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!
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.
Reserved this as part of our honeymoon. Well worth it! The view was incredible and we both really enjoyed it. Definitely 10/10
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!
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.
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