The 4 Best Charleston Sailing Trips

1.Private Luxury Yacht Charters, BYOB & Dolphins

★★★★★★★★★★5.0 · 395 reviews · 2 hours 30 minutes (approx.) Our pick

Sail privately around Charleston Harbor for about 2.5 hours with up to six people. Your captain and first mate handle the boat while you bring drinks and snacks, request catering, watch for dolphins, and see Fort Sumter, downtown Charleston, and the Ravenel Bridge.

“Captain Pat Wood, and his sidekick Mike were just amazing. Constant information and all the while diligently working on sailing. They made it look easy even though there were so many intricacies. We are so grateful for such a perfect day sailing!”

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2.Schooner Sailing Harbor Tour & Dolphin Watch

★★★★★★★★★★4.6 · 255 reviews · from $48Best value

Join Captain Dan, Captain Sara, Captain Andy, and the Schooner Pride crew at Aquarium Wharf for a 90-minute sail around Charleston Harbor. Help raise the 84-foot sails, pass Fort Sumter and Castle Pinckney, and watch for dolphins. This is a relaxed boat ride with friendly crew, not a nonstop narrated tour.

“We got to see dolphins, even though the weather didn’t want to cooperate. The captain was sweet enough to let my daughter steer the boat. It’s something she’ll never forget”

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3.Private Morning Sail, Dolphin and History Tour on Mystique

★★★★★★★★★★5.0 · 84 reviews · 2 hours (approx.)

Book a private two-hour morning sail for up to six people aboard Mystique with Charleston Sailing Charters. Your skipper, such as Will, Rob, Scott, or Dustin, guides you past the Battery, Ravenel Bridge, Yorktown, and sometimes Fort Sumter, with drinks, shade, a restroom, and a chance to spot dolphins.

“Captain Dustin and Captain Adam were amazing! It was so relaxing and they know so much about sailing. We are just beginning our sailing adventures and we’re certified. We really enjoyed our afternoon with them.”

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4.Charleston Harbor Sunset Cruise with Music & Onboard Bar

★★★★★★★★★★4.6 · 66 reviews · 2 hours · from $65

Spend two hours aboard the 55-foot Palmetto Breeze catamaran, cruising Charleston Harbor with music, sunset views, and a cashless bar. Captain Michael, Justin, and crew members such as Jessie and McKayla have helped create the friendly, social mood on recent sailings.

“It was a nice evening for a catamaran cruise! Captain Justin and First Mate McKayla were great! Nice way to see some of the sights of Charleston.”

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