Charleston Sailing Adventures
Charleston Sailing Adventures
Charleston Sailing Adventures
4.9
9:00 AM - 7:00 PM
Monday
9:00 AM - 7:00 PM
Tuesday
9:00 AM - 7:00 PM
Wednesday
9:00 AM - 7:00 PM
Thursday
9:00 AM - 7:00 PM
Friday
9:00 AM - 7:00 PM
Saturday
9:00 AM - 7:00 PM
Sunday
9:00 AM - 7:00 PM
Full view
About
Independently owned and operated, Charleston Sailing Adventures offers intimate, customized experiences in Charleston Harbor. Join us for adventure on the Prevailing Winds, our 27' Stiletto catamaran, and Double Fun, our 40' Crowther Spindrift catamaran. We host a number of trips, both public and private, and each one is BYOB! Feel the wind whip through your hair as you take in the beautiful views. Your USCG-licensed captain will tell you about Charleston’s history and the local marine wildlife as you enjoy the sunset or keep your eyes out for a pod of dolphins. Whether you’re looking for a fun adventure or a romantic cruise, we’ll make sure your sail is one to remember.
Charleston, South Carolina
Awards
Travelers' Choice
2024
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Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
Popular mentions
4.9
455 reviews
Excellent
437
Very good
14
Average
2
Poor
1
Terrible
1
Mary Rutledge C
4 contributions
Jun 2024 • Family
We had family in town visiting us and ended their trip with Charleston Sailing Adventures, captain Phil took us out on the harbor and the entire experience was exceptional! We felt comfortable as he guided us through the harbor pointing out landmarks and showcasing Charlestons history. We couldn’t have had a better time together, truly can’t say enough good things about our time on the water!
Written June 4, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
CHRISTINE h
Houston, Texas3 contributions
Aug 2024 • Couples
Awesome sunset cruise on a fun and comfy catamaran! Capt Ray and his first mate were great…easy going, friendly, knowledgeable, and accommodating! They even helped set the mood for a young man to make a surprise marriage proposal…and she said YES!! The sea breezes and sunset were lovely, and the whole experience was fantastic!!
Written August 30, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Megan W
1 contribution
Mar 2025 • Friends
Quent and Madi were fantastic! We had a group that went on the water with them and couldn't have asked for a better experience. Quent was great and gave really cool tid bits about the city and was very relaxed and easy going. Madi was also really great and helpful and we enjoyed it so much!
Written March 21, 2025
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
TLSanders
Baltimore, MD15 contributions
Jul 2024 • Family
Our family spend the morning of July 4th with Charleston Sailing Adventures and it did not disappoint. A lifelong sailor, our captain was knowledgeable in all things Charleston and provided us with historical details on the harbor, nearby islands, maritime battles, and marine biology programs. We thoroughly enjoyed our day, thanks so much!
Written July 7, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Kim L
Greenville, SC4 contributions
Aug 2024 • Solo
I did the sunset cruise on 8/22/2024 with Captain Ray and Cole. It's the best way to catch the sunrise...on a catamaran on Charleston Harbor...relaxing and peaceful. The crew was outstanding....friendly and knowledgeable. They went out of their way to make sure we had a spectacular time. I highly recommend Charleston Sailing Adventures. Their prices are very reasonable...especially for Charleston. I will definitely make this sunset cruise with Charleston Sailing Adventures a regular experience when I am in Charleston. See ya next time! Cheers!
Written August 25, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
mrmartinabrams
4 contributions
Apr 2022 • Couples
My wife and I booked a private sunset sail with Charleston Sailing Adventures on Easter Sunday. Our captain, Phil, was outstanding! He did a great job pointing out historical landmarks we passed, had funny and interesting stories, and also did a great job of letting us take in the scenery. It was a little windy that day so we were initially curious if the ride would be rough but Phil could not have been better at making sure it was a smooth sail. We even saw 5 dolphins! To cap it off we brought our own wine but forgot cups and Phil had some handy for us. Would highly recommend! But as Phil said never have airtight plans right after your trip is to end just in case anything goes over time. Also make sure to use the bathroom before.
Written April 20, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Amy D
1 contribution
Oct 2021
An awesome sunset cruise. The crew - Colin and Laura - were so friendly, knowledgeable, engaging and fun. The scenery was beautiful, the catamaran was awesome ~ felt very safe. I have lived in SC for over 40 years & own a second home in Mt Pleasant. Had friends in town so we thought this would be a fun thing to do. If you are visiting Charleston (or live there) I highly recommend the sunset cruise ~ so different to see the city from the water. Again, can't say enough about Colin and Laura they made the trip so memorable!
Written October 13, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
CujoRobbinsvilleNJ
Robbinsville NJ7 contributions
Jun 2022 • Friends
Wanted to do a sunset cruise on our girls trip to Charleston. After some research we decided on the sunset sail with Charleston Sailing Adventures and beyond thankful we did. To say amazing is an understatement. The captain and his first mate were so friendly, attentive and focused on giving us the best experience on our sail. From bringing us our drinks, to sitting with us to share some history and sites and then taking the best pictures so we’d have the memories of this fabulous night. Not to mention pointing out the dolphin on the side of the boat when we departed the dock. Even slowed down so we could all get a look!!
You will not regret booking with Charleston Sailing Adventures regardless of which boating experience you choose. But the sunset sail is a bargain and would have paid double for that expensive!!
You will not regret booking with Charleston Sailing Adventures regardless of which boating experience you choose. But the sunset sail is a bargain and would have paid double for that expensive!!
Written June 29, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Elizabeth C
1 contribution
Sep 2023 • Couples
We had an incredible experience sailing with Jenny. Jenny ensured our comfort throughout the ride, and it was a perfect combination of relaxation and fun. We were even fortunate enough to spot dolphins! I highly recommend sailing with Charleston Sailing Adventures and suggest extending your booking time, as you'll definitely wish for more time on the water. This exceeded our expectations.
Written September 5, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Lauren B
16 contributions
Mar 2021
The private sunset charter was incredible! They were friendly and knew exactly what they were doing - they were even able to teach our local group a little something about the islands in the harbor. They took multiple great pictures of our group and were incredibly accommodating. I highly recommend Charleston Sailing Adventures to anyone looking for a unique way to see the beautiful city of Charleston.
Written April 27, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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*Likely to sell out: Based on Viator’s booking data and information from the provider from the past 30 days, it seems likely this experience will sell out through Viator, a Tripadvisor company.