Charleston Sailing Charters

Super fun sail with Captain D and Madi, the Seabreeze marina was just down the street from our Airbnb. The Serendipity is beautiful and so stable and perfect for our 2 hour sail around the harbor. It was too cold to swim but the maybe next time..

Two hour sunset sail was fabulous!!! so many dolphins and the crew, Captain D and Madi were so nice! The boat is amazing, so clean and spacious for our group of 8 girls!

We found Serendipity last minute and they had availability for our group of 12 guys for a sunset sail. We departed from downtown near King street so its really close. The sunset sail was nice and we saw some dolphins. The Cabana bar at the marina is also super fun and full of people!

We looked around for a nice boat for our large group but most boats can only take six. We wanted a catamaran and were so glad we found Serendipity, the nicest catamaran and could fit our group of 15 girls with plenty of room to spare. Has a spotless bathroom too! It was early march so we didn't swim but we still had an amazing time! Captain Dustin and First Mate Madi were the best!

Will & Sam were great! We came for a bachelorette trip and the 2 hour sailboat ride made our entire trip! They were so fun and welcoming, and played games with us during our boat ride! Would highly recommend!

Quent and Hailey were the BEST! They made our bachelorette trip so fun and enjoyable! Highly recommend!!

Captain Quent and his Mate Hailey were by far the highlight of our bachelorette party! We were aboard on the Kismet and they provided our group the BEST time! They made sure we always had our beverages and catered to our needs, along with providing an incredible swimming location for our group. I cannot recommend them enough!!

Will & Sam were great! We came for a bachelorette trip and the 2 hour sailboat ride made our entire trip! They were so fun and welcoming, and played games with us during our boat ride! Would highly recommend!

Captain Scott was amazing from start to finish! He helped us with all of our baggage, kept us safe on and off the boat, shared historical facts and pointed out landmarks, and he took plenty of pictures for us. 10/10 Captain Scott and the Southern Charm (& my ladies) made it the ultimate bachelorette weekend!

10/10 Experience - The Best Day on the Water! We had an absolutely unforgettable day with Scott and Hailey on their private boat charter in Charleston! From start to finish, they created the perfect balance of laid-back vibes and high-energy fun, making it ideal whether you’re looking to relax, celebrate, or both. What truly set this charter apart was the next-level hospitality. Hailey met us at the dock with a wagon and handled all of our bags and coolers like a pro - total lifesaver! She went above and beyond to make sure everyone was comfortable, even helping our friend (who recently had surgery) safely on and off the boat and into the water on a floaty so she could still join the fun. That kind of thoughtful, hands-on care really made the day feel extra special. The boat was spotless, spacious, and super comfortable, perfect for soaking in the sun or snapping photos with the stunning Charleston charm in the background. Scott is a skilled captain who made us feel safe the entire ride, and Hailey’s energy and attention to detail made sure everyone had what they needed and more. It’s the perfect experience for families, friend groups, and bachelorette parties. We’re still talking about how much fun we had and we are already planning our next trip! Don’t think twice, book with them and thank me later!

Scott & Hailey were an absolute delight. The boat was clean, well stocked, and the service was exceptional. I did extensive research on charters for a friend’s bachelorette trip and am so glad to have chosen Charleston Sailing Charters. Thank you for a wonderful day on the water!!

Captain Quent and Mate Monique were absolutely amazing! They shared some history about Charleston with us and were super helpful in making our friend’s bachelorette party a success. Super kind and accommodating as well. Thank ya much!

Captain Quent and his Mate Hailey were by far the highlight of our bachelorette party! We were aboard on the Kismet and they provided our group the BEST time! They made sure we always had our beverages and catered to our needs, along with providing an incredible swimming location for our group. I cannot recommend them enough!!

Captain Quent and his Mate Hailey were by far the highlight of our bachelorette party! We were aboard on the Kismet and they provided our group the BEST time! They made sure we always had our beverages and catered to our needs, along with providing an incredible swimming location for our group. I cannot recommend them enough!!

Captain Scott was amazing from start to finish! He helped us with all of our baggage, kept us safe on and off the boat, shared historical facts and pointed out landmarks, and he took plenty of pictures for us. 10/10 Captain Scott and the Southern Charm (& my ladies) made it the ultimate bachelorette weekend!

Captain Quent and Mate Monique were absolutely amazing! They shared some history about Charleston with us and were super helpful in making our friend’s bachelorette party a success. Super kind and accommodating as well. Thank ya much!

We had the best time on the Kismet for our friend’s bachelorette trip! Scott and Hailey were so kind and fun to spend the afternoon with! Would definitely recommend!

Captain Quent and First Mate Hailey took us out for my bachelorette and it was the best afternoon!! They both took great care of us and we had a blast. I’d highly recommend this anyone looking for a fun time!

Scott & Hailey were an absolute delight. The boat was clean, well stocked, and the service was exceptional. I did extensive research on charters for a friend’s bachelorette trip and am so glad to have chosen Charleston Sailing Charters. Thank you for a wonderful day on the water!!

10/10 Experience - The Best Day on the Water! We had an absolutely unforgettable day with Scott and Hailey on their private boat charter in Charleston! From start to finish, they created the perfect balance of laid-back vibes and high-energy fun, making it ideal whether you’re looking to relax, celebrate, or both. What truly set this charter apart was the next-level hospitality. Hailey met us at the dock with a wagon and handled all of our bags and coolers like a pro - total lifesaver! She went above and beyond to make sure everyone was comfortable, even helping our friend (who recently had surgery) safely on and off the boat and into the water on a floaty so she could still join the fun. That kind of thoughtful, hands-on care really made the day feel extra special. The boat was spotless, spacious, and super comfortable, perfect for soaking in the sun or snapping photos with the stunning Charleston charm in the background. Scott is a skilled captain who made us feel safe the entire ride, and Hailey’s energy and attention to detail made sure everyone had what they needed and more. It’s the perfect experience for families, friend groups, and bachelorette parties. We’re still talking about how much fun we had and we are already planning our next trip! Don’t think twice, book with them and thank me later!

Will & Sam were great! We came for a bachelorette trip and the 2 hour sailboat ride made our entire trip! They were so fun and welcoming, and played games with us during our boat ride! Would highly recommend!

We had the best time on the Kismet for our friend’s bachelorette trip! Scott and Hailey were so kind and fun to spend the afternoon with! Would definitely recommend!

Quent and Hailey were the BEST! They made our bachelorette trip so fun and enjoyable! Highly recommend!!

10/10 Experience - The Best Day on the Water! We had an absolutely unforgettable day with Scott and Hailey on their private boat charter in Charleston! From start to finish, they created the perfect balance of laid-back vibes and high-energy fun, making it ideal whether you’re looking to relax, celebrate, or both. What truly set this charter apart was the next-level hospitality. Hailey met us at the dock with a wagon and handled all of our bags and coolers like a pro - total lifesaver! She went above and beyond to make sure everyone was comfortable, even helping our friend (who recently had surgery) safely on and off the boat and into the water on a floaty so she could still join the fun. That kind of thoughtful, hands-on care really made the day feel extra special. The boat was spotless, spacious, and super comfortable, perfect for soaking in the sun or snapping photos with the stunning Charleston charm in the background. Scott is a skilled captain who made us feel safe the entire ride, and Hailey’s energy and attention to detail made sure everyone had what they needed and more. It’s the perfect experience for families, friend groups, and bachelorette parties. We’re still talking about how much fun we had and we are already planning our next trip! Don’t think twice, book with them and thank me later!

Kudos to Captain Quent and Mate Hailey! The Bachelorette Party of our dear friend was a blast! Thank you for keeping us safe, the hospitality and for the lovely experience! Go Kismet!

Scott & Hailey were an absolute delight. The boat was clean, well stocked, and the service was exceptional. I did extensive research on charters for a friend’s bachelorette trip and am so glad to have chosen Charleston Sailing Charters. Thank you for a wonderful day on the water!!

Quent and Hailey were the BEST! They made our bachelorette trip so fun and enjoyable! Highly recommend!!

Kudos to Captain Quent and Mate Hailey! The Bachelorette Party of our dear friend was a blast! Thank you for keeping us safe, the hospitality and for the lovely experience! Go Kismet!

Kudos to Captain Quent and Mate Hailey! The Bachelorette Party of our dear friend was a blast! Thank you for keeping us safe, the hospitality and for the lovely experience! Go Kismet!

We had the best time on the Kismet for our friend’s bachelorette trip! Scott and Hailey were so kind and fun to spend the afternoon with! Would definitely recommend!

Captain Quent and First Mate Hailey took us out for my bachelorette and it was the best afternoon!! They both took great care of us and we had a blast. I’d highly recommend this anyone looking for a fun time!

Captain Quent and First Mate Hailey took us out for my bachelorette and it was the best afternoon!! They both took great care of us and we had a blast. I’d highly recommend this anyone looking for a fun time!

Captain Scott was amazing from start to finish! He helped us with all of our baggage, kept us safe on and off the boat, shared historical facts and pointed out landmarks, and he took plenty of pictures for us. 10/10 Captain Scott and the Southern Charm (& my ladies) made it the ultimate bachelorette weekend!

Captain Quent and Mate Monique were absolutely amazing! They shared some history about Charleston with us and were super helpful in making our friend’s bachelorette party a success. Super kind and accommodating as well. Thank ya much!

We had a fantastic time on our outing with Scott. The start of our ride was very informative. He knew so much about Charleston's history. The rest was the perfect mix of hunting for shark's teeth on the shore, dolphin watching and cruising. I would absolutely recommend this to a bachelor/bachelorette, family, pals day.