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Cheers Sailing Charters

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Hilton Head, SC, USA
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About Cheers Sailing Charters
Join us aboard Cheers for a morning, afternoon or sunset sailing cruise on the pristine waters of Hilton Head Island. Bring the whole family, we carry 24 guests, and two crew! Offering a professional and experienced team, fun and informative cruises,sailing lessons, relaxing sailing, and a long tradition of turning guests into friends. Let’s go sailing!
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Hours Today: 9:00 AM - 9:00 PM
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Cheers Sailing Charters
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Brett P wrote a review Jul 2022
3 contributions2 helpful votes
I took my family on a sunset sail during a family vacation. None of us have been on a sailboat so I thought it would be a great surprise. Capt. Robert and First Mate John were amazing and did not disappoint. Seeing my families' faces while relaxing on the water was priceless. It was such a peaceful ride watching the sunset and dolphins while hearing some of the history of the island. We were also able to watch the island firework show from the boat. This sail made the vacation and is a must do when visiting the island. Thanks again to Capt Robert and F.M. John for an experience we will never forget.
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Date of experience: July 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Tim L wrote a review Jul 2022
Chicago, Illinois2 contributions
Captain Rob and his first mate Randy are top notch. Their boat is awesome too. We had a 2.5 hour sailing adventure. Saw amazing scenery, dolphins, etc. This is something to definitely consider doing while on the island.
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Date of experience: July 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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JAS wrote a review Jun 2022
Louisville, Kentucky1 contribution
Fun and nice crew led to a relaxing sunset sail on our Hilton Head trip this year. 😃 Great views, and even saw some dolphins during our evening cruise. Can bring your own drinks and kick back while enjoying the sunset.☀️
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Date of experience: June 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Gloria H wrote a review May 2022
West Palm Beach4 contributions5 helpful votes
The Captain and Randy were terrific. FIVE Type A FEMALES on a Friday Night Sunset cruise can make for "chaos". These guys, their safety, their knowledge, were all "on point"! Happy Sailing, and we will be back.
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Date of experience: May 2022
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Al wrote a review Mar 2022
Alpine, New Jersey6 contributions5 helpful votes
This was my second time sailing on Cheers, the first time was this past October. Both sails were fantastic. A great time to wind down after a hectic day- very relaxing. The first time, back in October, I was with some friends and we were in a partying mood- nice that Rob had no problem with us bringing beer aboard. Rob has a great sense of humor and it was great having him as captain. Thanks for the great trips, Rob.
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Date of experience: March 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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