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Charleston Sailing Adventures

4.9 (116 reviews)
Closed 9:00 am - 7:00 pm

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Leanne C.

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!

Natalie W.

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!

Bella R.

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!!

Kevin D.

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

Sunset
Katelyn K.

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.

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

Private boat charter
Madeline H.

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!

Sunset cruise

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!

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3 years ago

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

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3 years ago

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.

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Brian H.

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4 years ago

Wonderful 90 minute trip in the harbor. Reasonable price. Jenny is a fantastic captain

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Ask the Community - Charleston Sailing Adventures

Review Highlights - Charleston Sailing Adventures

The sailing was great the captain was excellent and he was very knowledgeable about all the islands and history.

Mentioned in 34 reviews

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Charleston Dinner Cruise

Charleston Dinner Cruise

4.1
(17 reviews)
1.1 mi

We booked a dinner cruise on a Monday night to celebrate our first wedding anniversary. The process…read moreof picking up the tickets at the place was super easy. Unless you're a bigger party, I recommend paying the extra amount for a private window seat for 2 otherwise you'd be seated with strangers. It comes with a 4 course meal, and there's a bar on the boat but that's extra. We were shown to our seats right when we boarded and then Kevin was our waiter, super nice. We departed at 7pm and Kevin let us know our first meal would be arriving around 7:30 so we had time to go up to the observation deck. It was very windy but it was still cool to see us leave port and go out to the Charleston Harbor which was nice. There's a covered area in the back and then it's open at the front and that was definitely windy. The meals were so good, we honestly said the food was probably the best food we had on our whole trip! It started off with a she crab soup which was yummy. Second meal was a salad with sweet salad dressing that was also great. Third meal you got to pick your entree, I did the braised short rib that came with mashed potatoes and green beans. My husband did the grilled salmon with same sides. Both were absolutely delicious. I could've eaten it all but wanted to save room for dessert. I did the chocolate torte and my husband did the cheesecake, again so delicious. We also added the bubbly package which was an extra $35 but since it was a special occasion it was worth it. There was live music the whole time too. A guitarist who played really great songs. Overall, highly recommend!

So here in Charleston SC for wifey's family Reunion, so tonight was the first event a Dinner Cruise…read moreon the Spirit line Dinner-cruise it's a tour around the Charleston harbor for 2 1/2 hours. . We were a party of 22 & for this size group everything went off without a glitch, there were 3 tables set up for us. Our server Barbara was so nice and hospitable and very welcoming and knowledgeable. She explained how this would go. 7:15 we will serve the bread, at 7:30 they will serve the first course a She-crab soup, ohh so good with a kick of cayenne delicious, oh by the way Barbara asked our table "who would like more soup we all said yes except wifey she's watching her salt intake and weight. next 2nd course cranberry almond kale Prosecco vinaigrette excellent, also saw into kitchen how each salad was prepped and dressed. Then we were told after the 2nd course there would be a 15-20 minute break for us to go take in the view and atmosphere of our sailing. Then we all received our entrees. My wife had the Braised Beef Short-ribs served with mashed potatoes and vegetables. The beef was so tender if there was a bone it would have fallen off of it. I couldn't come to Charleston and not try the shrimp and grits which had andouille sausage and country ham. If you don't like spicy do not order this.. fortunately I Love spicy. Delicious is all I can say. Dessert is not included however you can purchase a slice of cheesecake or flourless chocolate torte. Wifey is a dessert person me not so much, the cheesecake was light and very tasty now I'm not a dessert person but that chocolate torte tasty however too chocolatey for my taste buds. Beautiful evening view of the sunset and the Ravenel bridge. This bridge connects Downtown Charleston to mount Pleasant. There is also live music during this dinner cruise and a lot of opportunities for some great pSo if you're ever in Charleston do check out Spirit Line dinner cruise.

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Charleston Dinner Cruise
Charleston Dinner Cruise
Ravenel makes a nice backdrop

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Ravenel makes a nice backdrop
Charleston Outdoor Adventures

Charleston Outdoor Adventures

4.9
(311 reviews)
8.1 mi

Captain Matt was AWESOME- knowledgeable, confident, made us feel safe, it was such a memorable trip…read morefor our family of 4, and worth every penny. Something that could've been mediocre turned into something we'd love to do again and again because of Captain Matt and his expertise, shared knowledge, and relaxed boat. We did get lucky, but he helped us see the dolphins, pointed out birds, slowed down to let us take it in, and he also took care of time management so well too. All the things! We saw dolphins so close to the boat, herons, storks, some people got sand dollars from the island too. I highly recommend this company and Matt based on our phenomenal experience- Yes, you drive down a bumpy rocky road to this business- but it's worth it! Trust me.

What a great business! I rented an on-top single kayak from COA for $35 for four hours. A friend…read moremet me out there with his kayak and we hit the water. For me, the check-in process was very easy. There was some miscommunication with the staff however because when they started going over the instructions I was left out while they addressed what looked to be a bachelor party. I assumed they were tackling the party first then would address me but instead started addressing a group birthday party. I had to track someone down as it was twelve minutes past my launch time and they were only focusing on the groups not me who was solo. They were pretty quick about grabbing me a kayak and told me to take a life vest from the birthday group, handed me a map, and then let me be on my way. I like that people with their own gear are allowed to pull up and launch. This worked out great for my friend who didn't need to rent anything. They're located on Bowen's Island that is in the marsh. It's quiet and relaxed and fortunately for us there weren't many boats in the water when we went. Overall it was a good experience. The staff were friendly, the location convenient and easy to access. (Though the road down is littered in potholes. Be mindful and drive slow or you'll be smacking your oil pan.) Ubers were coming and going all morning and dropped guests off right at the front door. COA also offers fishing off their dock for $3. There is a launch fee if you bring your own kayak or canoe but to be honest I can't remember what it was, though I remember my friend saying it was very affordable (so maybe $5/10?). There is a shark toothing expedition as well that I know is a longer paddle and a bit higher of a fee. Tours are offered if you don't feel confident paddling out in your own. I'll definitely be going back!

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Charleston Outdoor Adventures
Morris island
Morris island
Charleston Outdoor Adventures

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Charleston Sailing Adventures - boating - Updated June 2026

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