Book this day on the water. You will not regret it! Captain…read morePhil 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!

A sail on Double Fun is a must for Charleston visitors and residents too! Great for a special…read moreoccasion. 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!

Incredible experience with a private sunset sail. Captain Scott and Madde were knowledgeable and…read morefriendly, and we trusted them almost immediately. Would do it again in a heartbeat.

My wife and I had an amazing trip with Capt Scott and his deckhand Grace. We did a harbor cruise,…read moreand it was a great experience. Scott runs a very tight operation, is very knowledgeable about the area, and is a great person to have a conversation with. Grace was also a very knowledgeable sailor, and very attentive to our every need. I highly recommend a trip with Charleston Sailing Charters. We will definitely be back. Connor T.

We booked kinda last minute for a bachelorette boat sail on Memorial Day Weekend, and Capt Greg got…read moreus in for a two hour sailboat trip! It was the highlight of our trip, and very reasonable prices. Capt Greg was extremely helpful with everything to do with our sailboating trip, in addition to everything to do with Charleston! He gave us so many tips and recommendations so that we could enjoy our trip and have the best experiences. He also provided waters, coolers, ice, a speaker, and had extra sunscreen if needed. Also took pics throughout the boat ride and shared that Google photos album with us the day after! Wouldn't book with any other charter when in Charleston!

We had the most amazing time out with Captain Greg and Alex. We did 2 boats with our group of 7. We…read moregot to see dolphins and swim in the water. We were out on the boats for 3 hours and had such a blast. We will be doing this again next time we're in the area. Would highly recommend this boat charter!! The best experience for a bachelorette trip.

Overall it's a nice experience. They request you lineup a half hour before departure time and let…read moreyou on the boat about 10 minutes before you set sail. The front of the boat is full of these seats that are set on the floor of the ship so if you have a problem getting up from the ground that's not the spot for you. There are some bench style seats in the rear. The one thing I didn't love was they pack the boat so for many attendees it's standing room only for 2 hours. There's no narration by crew they just play some music. There is a bar on the ship but no hard alcohol so no mixed drinks. Also no snacks on the boat, It's a sunset cruise but the first hour you're driving straight into the sun so bring shades. There are two bathrooms on board which are clean and the staff is friendly but without any narration or interaction your kinda just floating along, I was a bit bored and I'm not sure why. I've done sunset cruises at other locations like in newport and loved them, this one you sail around for two hours but not much to see to be honest. I'm not saying don't give it a try I just think I was expecting something else.

What an amazing sunset cruise. An amazing staff with fantastic positive attitudes all around!read more

We had a wonderful time with Captains Jen and Janet. They made a special effort to pick us up at…read morethe marina we were staying in and the sail itself was absolutely perfect. Would definitely go out with them again!

Captain Jen and Captain Janet were amazing! I typically get quite motion sick and they provided me…read morewith motionbands and constantly checked in. More importantly, they were professional, friendly, knowledgeable and gracious. The tour was intimate and the boat was impressive. Loved the option to bring our own food and drinks. They encouraged us to explore the boat and took great photos too Such an enjoyable evening which we will never forget! Can't wait to come back.

standing on the deck area waiting for your time is torture when its hot and sunny! they should have…read moresomewhere with shade to wait especially since it's a family friendly activity. my daughters had a nice time and the staff was so friendly! that's a huge plus. we saw dolphins so that was the best part of the day

Such an awesome experience! The crew were all amazing, very…read morepersonable, and interactive. They also gave us some great recommendations for restaurants that we tried through out our stay down there. The boat itself was beautiful! Was able to see plenty of dolphins, and really enjoy the perfect weather we got blessed with! Beverages are available for purchase on board. Totally worth the every penny and can't wait to come back and try out on of their night time tours!

Captain Matt and Bethany took us out on a beautiful sailboat the week of July 4 in Charleston's…read moreharbor. It was relaxing and adventurous. The captain and crew were very friendly with great conversation and also extremely knowledgeable, accommodating and safe. 5 star day all around!

Sending for record purposes. Our reservation reflected in the itinary under "Things to know, that…read moreare allowed on the boat". Specifically, fishing was identified. This information was presented and verbally communicated to the crew member and the boats captain. A screen capture of this was taken. However, the owner (telephonically) and the crew "Stated, we could not fish from the boat, because they did not have a fishing license. Although, mind you the write up indicated "allowed on the boat fishing was cited) However, on June 15, 2025, or about 10:30 a.m. (est) it was noted this item was deleted from the itinary/website. We were refused a full refund (over 1,000.00 $$) and was offered a 10% refund. Needless to say, this was an insult.

All I can say is WOW! Captain Jerry was amazing! His boat was immaculate and his sailing knowledge…read morewas fantastic. I wanted a nice quiet family day and he did not disappoint! He offered us things to do or see or he gave us an option to anchor and go ashore. I loved all my options and he honestly would have been happy with whatever we wanted to do. He made us feel very welcome and "at home" on his boat. He allowed my son and myself to steer his ship! We saw dolphins and birds and ship wrecks! It was so much fun and I would recommend him to my family and friends!

This past October, I met with 5 friends for a Folly Beach reunion. One of my inspired friends…read moresuggested we charter a sailboat, which we enthusiastically agreed to. After a bit of research, we ended up on Captain Jerry Slayton's boat for a two-hour sail. Captain Jerry (who is USCG licensed and ASA certified) provided a short safety orientation and invited us to roam the craft as we pleased. We had the absolutely best time! The Captain was not only a top-notch sailor, he was also a top-notch guy, personable and fun. His sailboat was beautiful, comfortable, and spotless. What a wonderful way to spend a couple of hours. It rained like crazy while we were out, which made for an even more exciting, interesting, and beautiful experience. The six of us highly recommend a sail with Captain Jerry. You will love it!

This was totally spur of the moment and totally worth it - highly recommended! Captain was…read morepunctual and very knowledgeable about the local lore and history. Excellent single-handed boat handling, I was very impressed!

The most incredible sail. Dolphins were in every cove. They were up close and we saw them in…read moretheir natural habitat. Captain Jack really showed us a great time. He is so knowledgeable about sea life and the area. We thoroughly enjoyed our sail. I would highly recommend this wonderful adventure.