Charleston Sailboat Charters

My friends and I had an absolute blast with Jay and Rachel on our sunset charter! Everyone was so fun and knowledgeable about the area and they went above and beyond to take care of us. This was such a fun and unique experience, I highly recommend! I will definitely be doing this again next time I’m in town.

Had the best time on Mental Heeling! Jay and crew are awesome at providing the safety, sailing knowledge, and the vibes. The boat is beautiful, and the crew took care of our every need. Would highly recommend if you’re visiting Charleston or you’re a local looking to get out on the water!

Jay and Bella were incredible and very helpful with anything we needed. This was such a wonderful experience and I would highly recommend it to anyone visiting Charleston. You get a unique view of the city at sunset, learn about sailing, and also can get some incredible photos from Bella. If you’re lucky, you’ll get to see some beautiful wildlife too. A memory that will last a lifetime!

My husband and I recently had the privilege of sailing with Captain Jay and Fritzi and couldn’t recommend them more! On top of the amazing view of the Charleston Harbor at sunset on his comfortable boat, Jay taught us about sailing and the history of the harbor as we sailed. We enjoyed making new friends while seeing Charleston from a different viewpoint. Thanks for a great evening!

We had a wonderful time on the MentalHeeling. Jay and his crew made it a very enjoyable and relaxed experience. Directions to get to the place were very written out and we had no problems at all finding it. I would 10/10 recommend and will be back on our next visit to Charleston.

Our group had the loveliest sunset sail aboard the Mental Heeling. Jay was a great captain and made us feel safe throughout the journey. Jay and Rachel both were incredibly knowledge about the area and provided such great hospitality and care throughout the trip. It was also a great activity to do out on the water while the weather is generally so hot.

Jay and Alex were excellent with us. We had a crew of 6 for the trip and they were flexible, funny, professional, and super easy to get along with! I’ll definitely charter w/them again in the future. 100% A++

We had a great experience with Captain Jay for our first sailing charter. Nice accommodations aboard the vessel. Enjoyed the golden hour of sunset before clouds rolled in. Captain Jay got us back to the dock before any rain. Added bonus: we saw a dolphin in the waves.

A friend of mine from out of town and I got to sail on Mental Heeling and we had the best time!! The captain, Jay, and crew member, Bella made us feel right at home on the boat. Jay offered up his sailing knowledge, answered our many questions, and allowed us to take part in some of the tasks. Bella was also so helpful, fun, and kind.
We enjoyed the sail so much and we can’t wait to go again! We got to meet and sail with some other ladies who were also visiting from out of town and sparked up some great conversation. The crisp fall ocean air made for such a refreshing time and we couldn’t have asked for better weather.
If you’re visiting Charleston and a sail on Mental Heeling isn’t already part of your Charleston weekend itinerary, you should definitely change that! If you’re a Charleston local like me, you should also think about booking your charter, for a chance to see Charleston from a whole new perspective and experience something new if you’ve never been on the water here, before.
Our experience was indeed a ‘heeling’ one.
Thanks Jay and Bella. We’ll be back soon!!
:)

Wonderful experience with Captain Jay! Highly recommend for visitors or locals to book a sail. The boat is meticulously maintained and fun to enjoy with your group.

My wife and I went out on the Mental Heeling the other evening for a sunset cruise with Capt. Jay and his sailing assistant Franzi. To say we had an amazing time would to selling it short. The crew was incredibly welcoming and helpful from the very beginning creating a safe and comfortable setting. Our trip started as we pushed off and on the way out to the harbor Jay gave a nice history lesson and pointed out interesting buildings and places while Franzi pointed out local beach spots. Everything was beautiful and Jay did a great job of sailing and instructing even allowing passengers to help out. From start to finish it was a great experience and I would recommend them to anyone.

Y’all haven’t lived right until you’ve gone on a sailboat tour of the Charleston Harbor with Captain Jay! We had to reschedule because of weather and Captain Jay was really accommodating of our small availability and made sure we got on the water. Would definitely recommend and will be rebooking with Captain Jay when I’m back in Charleston! :)

Booked a sunset cruise with Jay. It was magical! The entire evening was perfect. It was me and 4 other friends. The boat felt like the perfect size for our group. Jay and Jess were so easy to talk to and made us feel right at home. We brought wine and a charcuterie plate to enjoy while we took in the view. And we had a gorgeous sunset! The whole evening was perfect. Would book this tour again in a heartbeat.

We chose a sunset cruise on Mental Heeling, and had an incredible experience! Jay and his crew were top notch. They were the perfect mix of professional, laid back, and fun!! Mental Heeling was a beautiful and extremely well maintained boat. Can’t recommend them enough and plan to book another sail on our next return visit!

Favorite company to sail with in Charleston! Always such a fun time, great crew and beautiful views. Much better and more relaxing than the large boat tours. 10/10 would recommend

What a true delight! Captain Jay and Franzi gave us an incredible evening sailing around the harbor. They were such warm and gracious hosts; great conversation, lots of laughs and plenty of photos! We got hands on and learned a thing or two and will absolutely be booking another charter very soon. Great for any occasion you're celebrating or just a beautiful sunset cruise! Would absolutely recommend booking today!

What an unbelievable experience! I had never been on a sail boat like that and certainly never been on one that was Captained by such an amazing woman like Kathleen! The mate, Lauren was also incredible and had so many cool stories to share. We got lucky the night we were out and the sunset was insane and we learned so much about Charleston at the same time. I've lived here my whole life and couldn't believe all the amazing facts I learned about my home city. Can’t recommend this experience enough, especially with an all female crew like the one we had! 10/10.

My friends and I had an awesome time with Captain Jay aboard Mental Heeling!

He was communicative beforehand - texting me to let me know we were all set for our afternoon sail. It's also the best value trip that I found as we got an extra 30 mins on the water compared to competitors.

Onboard, everything was comfortable and relaxing. Captain Jay was great to talk to and even let my friends get involved with steering the sailboat and helping him maneuver. We are already looking forward to our next trip!

We had the pleasure of sailing with Jay and Adj who made our sunset charter amazing. They were great to chat with and had a ton of knowledge about the city of Charleston and obviously loved sailing. My wife and I had a great time sitting on the front of the ship drinking our wine and then chatting with the captain and crew at the back. I would highly recommend Charleston sailboat charters for a private outing like we had but I am sure a group event is also just as great.

Our Charleston sailing experience with Captain Jay & Kathleen was all that we could of hoped for and more! My husband and I had never been to Charleston before and enjoyed the views from the water. Jay & Kathleen were very accommodating & made sure we were comfortable at all times. We felt like friends by the end of our sail. We would recommend this to anyone looking for a peaceful & enjoyable experience!