Charleston Sailing Charters is consistently ranked Charleston’s #1 overall activity and sits in the top 10% of attractions worldwide on TripAdvisor, welcoming more than 10,000 happy guests each year. Forbes Travel Guide has also named it one of the Top 5 Most Romantic Things to Do in Charleston, backed by an award-winning fleet of five distinct vessels.
Fate and Mystique, at 50 and 43 feet, are the largest sailboats available for charter in Charleston, each with two large staterooms with queen beds, two full bathrooms, and a full galley, limited to six passengers plus crew per U.S. Coast Guard regulations. Kismet stands apart as a true picnic-style motor yacht — elegant, spacious, and legally permitted to carry up to 23 passengers, popular for bachelorette parties, weddings, corporate events, and family outings, with swimming stops and water hammocks along the way. Serendipity, the newest addition, is a stunning performance catamaran certified to carry up to 18 passengers, offering both private trips and a nightly Public Luxury Sunset Sail with champagne toast and curated charcuterie from Seabreeze Cabana Bar. Southern Charm, a Scout 235 Sportfish runabout, is perfect for cruising to secluded barrier island beaches for shelling, shark tooth hunting, and dolphin encounters — including a personalized Netflix “Outer Banks” filming location tour.
Every charter is BYOB and food, with complimentary bottled water and soft drinks, and catering available through Caviar & Bananas, from simple charcuterie to full salmon and filet dinners. Rates run from $125/person for the Public Sunset Sail on Serendipity, $400 for Southern Charm, $400/hour for Kismet, $500/hour for Serendipity private charters, and $525-$625 for private sailing charters on Fate or Mystique, up to $3,000 for a VIP Full Day Sail with a secluded beach lunch.
With 241 reviews at a 5.0 average, Charleston Sailing Charters has built one of the strongest reputations of any charter operator researched this entire session.
For groups in Charleston looking for a luxury sailing charter, a large-group party yacht, a performance catamaran, or a private beach excursion, Charleston Sailing Charters offers a highly reviewed, award-winning fleet of five distinct vessels.
