Book this day on the water. You will not regret it! Captain Phil is an absolute gem -- part sailor, part historian, part comedian and 100% the kind of person who makes you feel like you've known him for years. His knowledge of Charleston's history is extraordinary, and the way he tells it? Pure magic. We laughed, we learned and we never wanted it to end. His wife also joined us and was a wonderful addition to the crew -- together they made the whole experience feel like a day out with great friends rather than a tour. Charming, memorable, and one of the best things we did in Charleston. Five stars isn't enough! read more

A sail on Double Fun is a must for Charleston visitors and residents too! Great for a special occasion. I love seeing Charleston from the harbor. There are so many sights to see and so much wildlife. The crew did a fantastic job and the whole boat enjoyed the evening! read more

Charleston Sailing Adventures - Boating Near Me - Charleston, South Carolina

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So much fun! We did the 1.5 private charter for 4 of us and it was so fun! We laid out on the nets and our captain was so sweet she was awesome, they provide you with a speaker to play music and it's such a pretty view! very easy experience definitkey will be using them again read more

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I booked this sail when my parents came to visit and we had the best time! It was a very welcoming and relaxing environment. Being able to BYOB and snacks was so fun! We will definitely be coming back read more

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Ray was a great captain, he and Cole his mate was knowledgeable and answered all of our questions. They both were very friendly and welcoming. The ride was amazing and the views spectacular. read more

I had my second sailing outing on the catamaran with Captain Colin this week. I returned because my first adventure last fall was so wonderful. It's the best way to experience the harbor in my opinion. The captain is knowledgeable and the scenery is stunning. A great value as well. read more

To start, Brian is a wonderful guy to work with. He really does return your call as promised. He allowed me to make a same day booking on a FRIDAY! And then when my friend and I were a little tardy, he patiently called and waited for us and didn't shame us for being late. The experience of sailing was great, the views were to die for and we even saw some dolphins! While waiting for the sunset to happen they went in a few circles around the dolphins and it was truly amazing! The setting was absolutely perfect and it's BYOB and snacks! I cannot wait to go again! read more

Jenny with Charleston Sailing Adventures was absolutely wonderful! She knew a lot about the area, as she is a local, and we had a blast! We were able to bring some of our own drinks on board and she even had a cooler with ice to store them! We were able to play our own music while we sailed around the harbor. It's the perfect thing to do with a small intimate group. We booked this for my bachelorette, and had a wonderful and relaxing time! I can't wait to come back and book again! read more

Charleston Sailing Adventures - Boating Near Me - Charleston, South Carolina

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Great time; great crew. If you're looking for a smaller, more personal sunset cruise this is the one. Like others have said, not touristy and not a lot of people on the boat. We brought a bottle of wine and made friends. Thanks for a great time! read more

Charleston Sailing Adventures - Boating Near Me - Charleston, South Carolina

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We had a beautiful day on the water! I was surprising my boyfriend for his birthday, so I booked a private tour for 4 of us. The online booking was super easy and the directions and safety regulations for COVID were included in the confirmation, which was reassuring. The meeting place is down the dock next to the aquarium and it was pretty easy to find. They're currently doing construction in their normal parking lot so we had to park in the aquarium garage, but it was a short walk over. Their sign is right next to the water taxi, so it's hard to miss. I looked around at a lot of different boat tours and this one was the most reasonably priced for the private tour/ duration. We went with the extended tour, which was 2.5 hours. The weather was absolutely perfect with a slight breeze and a tiny bit of rain to cool us off. Jesse was an amazing guide and was very conversational and pleasant. She obviously knew what she was doing and made us feel very safe on the water. The trip was BYOB so we brought our own coolers and soaked up the sun. Our guests had never toured the harbor before so we were able to play guide and tell them about the different landmarks. They have a small bathroom on board as well if you have a lot of beverages like we were :). We couldn't have asked for a more perfect day out on the water! read more

I picked them because they offered a small sailing cruise, we're reasonably prices and allowed us to byob. They mentioned that they had a minimum number required to sail, and we understood that. My reason for a 2 star review is that they waited until 2 hours prior to call and cancel on me. I asked for a recommendation and every other place I called were fully booked. They could have given us a little more time to find an alternative or given us a heads up in the morning versus waiting until the last minute. Was very disappointed. read more

I booked this cruise as an anniversary gift for my boyfriend and we had such a great time. The captian takes a route depending on the wind, where dolphins may be and where the best spot to see the sunset will be. Seeing Charleston from the water is really special and I look forward to going again! BYOB is a huge plus too!! read more

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Brian and crew were awesome. Just got off the sunset tour and it was perfect. If you want a solid crew, intimate experience, and a bottle of wine(BYO) this is for you. Lastly: if you had a good experience- tip these guys. We saw dolphins, a perfect sunset, and they worked hard. If you can afford a smaller crew tour, you can afford to tip. One of my favorite things we did on our weekend away from day to day. Thanks team read more

Charleston Sailing Adventures - Boating Near Me - Charleston, South Carolina

We had a few girls out of 11 that were nervous about the weather. Ray and Christian were the best in managing our expectations. We went out and all the girls said this was a great day. Ray is super knowledgeable and Christian was personable. Would recommend this anytime! read more

We took a sunset cruise with Charleston Sailing Adventure and it was fantastic. We looked at some other sunset cruise options, which were cheaper, however I wanted to experience sailing. The small group of us (about 15) were the full catamaran, so by the end we were all friends. The captain pointed out the points of interest along the way. He even pointed out a sea turtle, a pod of dolphins and other wildlife. The sunset was breathtaking. I highly recommend this tour and Charleston Sailing Adventure. read more

Charleston Sailing Adventures - Sunset - Boating Near Me - Charleston, South Carolina

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I did the sunset cruise on 8/22/2024 with Captain Ray and Cole. It's the best way to catch the sunrise...on a catamaran on Charleston Harbor...relaxing and peaceful. The crew was outstanding....friendly and knowledgeable. They went out of their way to make sure we had a spectacular time. I highly recommend Charleston Sailing Adventures. Their prices are very reasonable...especially for Charleston. I will definitely make this sunset cruise with Charleston Sailing Adventures a regular experience when I am in Charleston. See ya next time! Cheers! read more

Our private boat cruise with Brian & Jenny was incredible! Money well spent! Every single person in our party kept commenting how great of an experience it was. Not only was the boat beautiful but Brian & Jenny were super helpful and knowledgeable on Charleston history. We will definitely be planning another boat ride with them again! read more

Charleston Sailing Adventures - Private boat charter - Boating Near Me - Charleston, South Carolina

Great way to round out our couples trip. Would definitely recommend for a relaxing evening on the water. Captain Ray was outstanding! read more

Charleston Sailing Adventures - Boating Near Me - Charleston, South Carolina

We had a great sailing experience in Charleston and would do it again. Very relaxing and informative.

My husband and I took the sunset sailboat cruise on 7/20/23 during our 1st anniversary trip to Charleston. Weather was in the high 80s but the wind cooled it down to very mild. The hosts were friendly, I felt safe, and were ready to help take photos. This is our first time on a sailboat and we sat above the nets (which was a perfect sunset watching location and less bumpy). Definitely wear tennis shoes, sunglasses, and sunscreen. The views were gorgeous, the night was a great addition to the memories we had in Charleston. It was well worth the money and will always be remembered! read more

Charleston Sailing Adventures - Sunset cruise - Boating Near Me - Charleston, South Carolina

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This trip was so much fun. It was a rainy night but Brian waited a few minutes to see if the storm would clear and luckily it did! We saw so many dolphins and even a little sun! Everyone on the crew was delightful and interacted with us all night. It was a perfect way to end our Charleston trip. read more

Charleston Sailing Adventures - Boating Near Me - Charleston, South Carolina

Ray was an amazing host and captain, couldn't have asked for a better experience. He was very accommodating throughout the planning and payments up to the day of. highly recommend for anyone wanting to experience Charleston from the water read more

Charleston Sailing Adventures is a must-do on your Charleston itinerary. Captain Jenny, the boat, and overall experience was so much fun. We did the private daytime cruise where you can BYOB, play your own music- everyone in our party enjoyed it and it was the highlight of our trip. 10/10 would recommend! read more

Such a great sunset tour. Captain Ray and First Mate Cole were very hospitable and funny. The boat was clean and very comfortable. If you are looking for a sunset tour, you can't go wrong with this team! read more

Disclaimer: this review is based solely on customer service. Brian is hands down one of the best people I have ever worked with in terms of customer service. After some friends recommended this company to me for a private sailing experience for a bachelorette party, I called MANY times asking questions, checking availability, etc. Brian was extremely professional, gave many options to fit my group's needs, and really made me feel he was offering times and boat sizes that were most appropriate for my group- not what would create the most profit. In light of COVID, we've had to cancel said bachelorette party and I've been working with Airbnb and other companies to recoup our deposits. Brian called ME and gave me the options for a future credit, or cancelling at no charge since we were still two weeks out. I WILL get to Charleston at some point, and will absolutely be sure to use these guys for a boat ride. The professionalism/hospitality from our phone interactions was five stars, so I can only imagine the actual experience would be the same. Bravo to Charleston Sailing Adventures for setting the customer service gold standard! read more

Bryan was very helpful in planning our sailing excursion around our limited flight times. We had scheduled a quick weekend anniversary celebration in Charleston and he was very accommodating. Jenny our Captain was confident, experienced, and very knowledgeable about the area. I would 100% recommend the company and team. Can't wait to return! read more

We had a great time on Charleston Sailing Adventures! My group of 12 people (bachelorette party) went on the Double Fun sailing catamaran boat. The crew was very nice and they were great to work with when planning ahead of time. I loved that we could bring your own food and drink. I would highly recommend! read more

We've sailed in other places but Charleston Sailing Adventures was our favorite. Captain Jenny was friendly, experienced and helped us enjoy a relaxing sail to celebrate our 10 year anniversary. Highly recommend! read more

We had the most wonderful sunset sail with Charleston Sailing Adventures. The crew was amazing and attentive. They even helped us take photos! I would highly highly recommend. One of the best things we have done in Charleston! read more

This was such a great time! The captain was very friendly! I went with a group of 5, and we all had a blast. Highly recommend.

We went on the sunset booze cruise for my friends bachelorette and it was the highlight of our trip! We had such a great time and Captain Ray and Laura were amazing. They were so friendly and made sure we got the best views and even helped us find some dolphins! I highly recommend this tour. read more

We thoroughly enjoyed our sailing adventure with Phil. If I could give our experience 10 stars I would. Phil is a friendly and easy going individual. He did a great job engaging with everyone on the boat including the kids. We learned a lot about Charleston's history and the sea life. We had the best weather and it was very relaxing. read more

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Such a perfect day! We chartered the 27' catamaran for our family of 5. Our captain, Phil, is an experienced sailor and local historian which made our sail even more interesting. If you want to see an even more beautiful view of Charleston, do it sailing!!! read more

Even without much wind to fill the catamaran sails, we had a fun and relaxing time with Captain Phil! We saw dolphins, the stunning architecture of Charleston's waterfront and other historical landmarks while being entertained by Phil-he is a singer- songwriter and has stored an amazing amount of information about Charleston- culture, heritage and history. Highly recommended experience! read more

Went out for 3 hours for my birthday, and it was one of the best birthdays I've ever had! The crew was amazing and very friendly. I would definitely recommend them for anyone looking to spend a day on a sailboat, and plan on using them again for future events. read more

Had a wonderful time with Charleston Sailing Adventures on double fun! The crew was extremely nice and accommodating. With it being a girls bachelorette trip, they even helped make sure we got the perfect pictures. Highly recommend! read more

I am not a booze cruise kind of gal. I don't like being packed on a boat, like a sardine, with a bunch of drunk people. If you agree and are looking for a quieter and more intimate outing, check out Charleston Sailing Adventures. Brian is the captain and crew of the boat "Prevailing Winds", a 27' Stiletto Catamaran. We booked the very relaxing sunset cruise and it could not have been better. There were 5 of us on the tour that evening which is the perfect-sized crowd. While we did not see any dolphins, we saw lots of other interesting sailboats. On Wednesday evenings, there are sailboat races to entertain while on the cruise. TIPS: Cruises are BYOB, which works for me. Also, no bathroom on board so make sure you take care of business beforehand. Lastly, venture out on to the trampoline. Lay down to feel like you are flying on the water...so relaxing. Thanks Brian for an awesome night. I have been telling everyone how wonderful the evening was. read more

Charleston Sailing Adventures - Make sure you venture out onto the trampoline. I thought it was very comfortable and loved peering down into the water. - Boating Near Me - Charleston, South Carolina

The sunset tour was such a great experience and Brian was an awesome captain! He made out experience enjoyable from the time we initially met on the dock until we returned to the dock after the ride. Brian was completely in control, I felt safe under his care, even while out front on the trampoline. The views were absolutely amazing and gave such a relaxing cruise. We even got to see several Dolphins while we were out on the harbor. My boyfriend and I had the pleasure of riding with two other amazing couples, though we all met there they made the ride even better. I highly recommend Brian and Charleston sailing adventures. The quant privacy the smaller boat provides only adds to an already wonderful excursion! read more

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We tried Prevailing Winds after purchasing a coupon on Go Charleston Deals. We originally had gone and were only the water ten minutes before a massive storm decided to roll in... We came back to the dock and the super awesome guide said we could call back and reschedule any time. On our second outing, we made it all the way out! It was not very windy out, so sailing around quickly was not happening. We used the motor a lot. Understandable, but still disappointing. We did not go out as far as I had hoped. We kind of just moved around a little bit. The tour guide was great, though. He answered a lot of our questions about Charleston, where things were, etc. There were two other people on our boat (teenage girls) who sat on the trampoline part of the boat taking selfies and sunbathing the whole time. (It was a tad annoying- I would go with a group of friends (it accommodates up to 6) so you don't have to worry about things like that) There was a cooler on board we were able to put our beverages in. It was a BYOB trip, so we enjoyed wine and snacks while out on the water. I think this trip would be great if we went during a time when it was a bit windier, but I did enjoy the views of the city/bridge and seeing dolphins! read more

This sail charter was exactly what we were looking for. Jennifer, our captain, welcomed our private party aboard, along with our fur baby. We enjoyed touring the harbor, and she was very knowledgeable about the area. All in all we highly recommend this tour company and would book this again! read more