Charleston Sailing Adventures

Great day sailing with Brian. Couldn’t have been nicer and my wife and I were only ones on morning trip to island and back. Have been on every type of excursion in Charleston and this was the best!

I agree 100% with Irina H’s review. My husband and I were lucky enough to be the only ones on the boat for a Sunset Cruise, but it still would have been comfortable with four other people. The captain was knowledgeable and friendly, without being intrusive. The price was absolutely right for what we were looking for — more intimate than 50+ people on a large boat, or paying over $ 300 for a private sail. Additionally, being able to bring our own snacks and bubbly on board made it feel special.

Amazing sunset cruise!!! My sister and I absolutely loved it! This was definitely a major highlight of our trip to Charleston. The boat is a beauty, the views are incredible, the captain was friendly and knowledgeable without being intrusive — we even saw a dolphin!
The whole experience was smooth and enjoyable. The weather was a bit on the windy side, which made for scattered clouds and a breathtaking sunset (although we did move through a few patches of rain). There’s nothing like being out on the open water — we’d do it again in a heartbeat!
Booking was quick and easy online (and reasonably priced, at $ 60/​person). The meeting location was well-​marked at the Maritime Center (big Prevailing Winds sign near the exit from the parking lot — even I couldn’t miss it), the captain was prompt and accommodating, and the boat was beautiful and clean.
TIPS:
Great choice if there are only two of you and you don’t want to pay for a private sail, but you also don’t want to be on a huge boat with 20 other people. All of the other sunset cruises I found required that you buy all of the spaces on the boat, so you paid between $ 300 and $ 500 whether there were two of you or six. We lucked out and ended up being the only ones on our sail, but we would have been fine with a small group — the boat holds 6 people at most.
There’s a parking lot at the Maritime Center, and it had plenty to free spaces for our Sunday evening trip
if there are clouds, wear a rain jacket and quick-​drying pants.
It’s BYOB snacks and drinks — there’s a cooler for your use.

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!

Absolutely no complaints abut this tour. Brent is an awesome captain. Showed us a great time. Dolphins, sunset, great new friends, very relaxing and highly recommended!

Had a perfect sunset sail with the captain Jeremy. Probably the best thing we did in Charleston and we did a lot of good things. I recommend it to anyone who likes a small group experience and something unique vs being with a cast of thousands.

We purchased a groupon for a tour. It was an hour and a half tour for 6 for $ 120. We arrived and waited for our captain on an extremely hot day. Our captain arrived and took us to the dock, ran through the few rules and away we went. It was relaxing and very enjoyable. Our daughter saw a few dolphins but the views were great and it was just relaxing. The captain was young but experienced, not super talkative but answered any questions I posed and he was pleasant. Our daughter booked the reservation and we had no issues as previously mentioned. Thoroughly enjoyed a more personalized tour than the large sight seeing vessels all around us. There is a cooler on board they bring ice for, so pack some drinks and food and enjoy.

Our experience with Prevailing Winds sailing excursion was TOP NOTCH! It was a wonderful way to enjoy the view of Charleston from the harbor! We made our booking in Feb and sailed in May while attending the College of Charleston commencement weekend. We had no problems with the booking whatsoever. We had six in our party and it was nothing short of excellent! While on the sail, we got to see some dolphins up-​close and pelicans skimming the water in formation looking for fish. Captain Jeremy was a great host with lots of local knowledge of the local area, as well as an expert sailor! The ride was very comfortable and smooth with no heeling. The catamaran boat was very swift and we covered a lot of «ground» in our ninety minute sunset cruise. He has a cooler with ice aboard, so handy for those who like their wine chilled! We also brought some boat snacks and beer. This is definitely to experience a sailing trip in Charleston Harbor! Great value for the money and a trip to remember!

Very poor customer service and business management skills. We had trouble with them throughout the entire process. We continually left messages on their answering machine trying to book a tour. We finally got one booked. They ended up canceling the tour with only 12 hours notice. The reason that they canceled was because the other passengers canceled. That is not our fault and should not have to miss out because of it.

I went on the sunset sailing in June. And I’m very glad I made the choice of sailing with them in a small group setting rather than a large group. The experience is so much better compared to a large group that I did once long time ago (not in Charleston though). The captain is very knowledgeable and a very nice guy. I got to know more about sailing along with some very interesting history of Charleston. We even saw a dolphin!
I also like the fact that they do allowed passengers to bring own food/​snacks/​drinks instead of having to buy something from them for extra cash. Even though I didn’t bring much, just some granola bars and water, but it is always nice to know I didn’t signed myself up to something I didn’t expect. A fellow passenger bought beer~! Next time, I’d bring some wine, cheese and crackers! Imagine relaxing on a sailing boat, with sea breeze on your face and sipping a glass of wine!
It was a great experience and I would definitely recommend it to everyone or any couple who would want to have a romantic sailing experience without the crowd!