15 Charleston Sailing Tours for the Logbook

1.Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

★★★★★★★★★★4.5 · 620 reviews · 1 hour 30 minutes (approx.) · from $45Our pick

Spend 90 minutes aboard the 84-foot Schooner Pride, a real sailing ship that uses wind power when conditions allow. The crew raises the sails, answers questions, and may let you help with the lines. Look for dolphins, Fort Sumter, the USS Yorktown, the Battery, and the Ravenel Bridge. Snacks are welcome, but drinks must be purchased on board.

“It was so fun! They really give you the experience you signed up for. We saw dolphins and they provided drinks and a few snacks as well.”

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2.Private Luxury Yacht Charters, BYOB & Dolphins

★★★★★★★★★★5.0 · 395 reviews · 2 hours 30 minutes (approx.) · from $499 whole boat, up to 6Top rated

Set sail from Ashley River Marina on a private 2.5-hour yacht charter for up to six people. Your captain and first mate handle the sailing while you enjoy Charleston Harbor, Fort Sumter, the Ravenel Bridge, dolphins, and sunset views. Bring drinks and snacks, or request catering.

“Brian and Austin were amazing captains and gave us an incredible and memorable experience to culminate our trip to SC. The sunset sailboat trip was as informative as it was relaxing and the vibe was very chill. They took amazing family photos for us as well. The sunset was the best we’ve ever seen. Would recommend 1000%.”

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3.Schooner Sailing Harbor Tour & Dolphin Watch

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

Join the captain and crew of the three-masted Schooner Pride for a 1.5-hour sail from Aquarium Wharf. You can help raise sails reaching 84 feet, drift past Fort Sumter and Castle Pinckney, and watch for dolphins. This is mainly a quiet harbor sail, not a narrated sightseeing tour, with drinks available to buy onboard.

“We really enjoyed sailing on the schooner, the captain and his crew were wonderful and were willing to answer any questions we had. We had a fantastic afternoon sailing in the harbor and would highly recommend that tour.”

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

★★★★★★★★★★5.0 · 84 reviews · 2 hours (approx.) · from $575 whole boat, up to 6

You’ll spend about two hours aboard Mystique with a private crew of up to six, sailing past the Charleston Battery, Ravenel Bridge, Yorktown, and sometimes Fort Sumter. Captains Will, Rob, Scott, and Dustin have led trips, with crew members adding local history, sailing know-how, drinks, shade, and a chance to spot dolphins.

“A highlight of our trip to Charleston was riding with the crew on this magnificent boat. Spotless boat, with beautiful sails and ropes, tables to hang out outside and inside, great sound system and an amazing experience. It was a little too easy in fact to book and go on this tour - but amazing nonetheless!”

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5.Charleston Harbor Sunset Cruise with Music & Onboard Bar

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

Spend two hours on the 55-foot Palmetto Breeze catamaran, cruising Charleston Harbor with music, sunset views, cushioned seating, and a cashless bar. The friendly crew, including captains such as Michael and Justin on select sails, keeps things relaxed and social. Expect Fort Sumter, the Ravenel Bridge, USS Yorktown, and possible dolphins.

“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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6.Private Sailing Charter with Captain, BYOB

★★★★★★★★★★5.0 · 64 reviews · 2 hours 30 minutes (approx.) · from $500 whole boat, up to 6

Book a private 2.5-hour Charleston Harbor sail for up to six people, with Captain Will at the helm. Bring your own drinks and snacks, then cruise past the Battery, Castle Pinckney, Fort Sumter, Ravenel Bridge, USS Yorktown, and St. Michael’s steeple. Sunset departures offer the best light for photos.

“The weather was perfect! The boat captain was pleasant and knowledgeable. He really made our time memorable.”

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7.Private Luxury Sunset Sail on the 50ft Sailing Yacht Fate BYOB

★★★★★★★★★★5.0 · 55 reviews · 2 to 4 hours (approx.) · from $760 whole boat, up to 6

Book the 50-foot sailing yacht Fate for a private Charleston Harbor sunset cruise for up to six people. Captain Scott and other local skippers may point out the Battery, Ravenel Bridge, USS Yorktown, and Fort Sumter while you enjoy complimentary soft drinks, bring your own alcohol and snacks, and choose your own music.

“Captain Scott and first mate Sam did an awesome job of making our experience memorable! My saw a beautiful sunset, dolphins, and learned about Charleston along the way. The boat is beautiful and Sam they went above and beyond to give us a once in a lifetime experience! Highly recommend to anyone!”

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8.Private BYOB Afternoon Harbor Sail On 50ft Sailing Yacht Fate

★★★★★★★★★★5.0 · 42 reviews · 2 to 4 hours (approx.) · from $599 whole boat, up to 6

Book the 50-foot sailing yacht Fate for a private Charleston Harbor cruise for up to six people. Captain Scott, Captain Will, Captain Adam, and first mate Sam are among the crew members who may guide your sail past the Battery, Ravenel Bridge, USS Yorktown, and possibly Fort Sumter. Bring your own alcohol, enjoy complimentary soft drinks, and choose from several departure times.

“We celebrated my sister’s 50th birthday with Captain Scott and first mate Sam on Fate. It was the best part of our visit to Charleston. A definite must do.”

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9.Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

★★★★★★★★★★5.0 · 42 reviews · 2 to 4 hours (approx.) · from $599 whole boat, up to 6

Set sail from Lockwood Drive aboard the 43-foot Mystique for a private Charleston sunset cruise. Bring your own wine and food, then watch for dolphins while Captain Scott, Will, Sam, Maddie, or another crew member points out the Battery, Ravenel Bridge, Yorktown, and possibly Fort Sumter. Soft drinks and bottled water are included.

“This was amazing! The boat was beautiful and the captain and crew, Dustin and Sam, were the best. They literally knew everything about the area and narrated the whole trip. We will do this again, highly recommend!”

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10.Private Morning Sail/ Dolphin Tour on 50ft Fate, BYOB or Catering

★★★★★★★★★★5.0 · 40 reviews · 2 to 4 hours (approx.) · from $599 whole boat, up to 6

Set sail from 17 Lockwood Drive aboard the 50-foot Fate for a private two to four hour Charleston Harbor trip. You can bring a picnic and drinks or arrange catering. Captain Scott and first mate Josh may be available, with views of the Battery, Ravenel Bridge, USS Yorktown, USS Laffey, and sometimes Fort Sumter.

“The boat was gorgeous and the scenery was spectacular but my friend Aubrey and I were most impressed by the ship’s captain Scott and his first mate Josh. Their ability to sail perfectly was noted by Aubrey as he sails regularly in NC where we are from. Thank you for such a memorable experience. We will be back and will request Scott and Josh.”

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11.Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

★★★★★★★★★★5.0 · 32 reviews · 2 to 4 hours (approx.) · from $575 whole boat, up to 6

Take a private afternoon sail on the 43-foot Mystique with your own group of up to six. Captain Scott, Sam, Rob, Sophia, Adam, Darby, Dustin, and other crew members may guide the trip, pointing out Charleston’s Battery, Ravenel Bridge, Yorktown, and Fort Sumter. Dolphins are possible, but never guaranteed.

“Rob and Sophia were great! Very informative and helpful. Sophia was very attentive and catered to our every whim. Book your trip now”

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12.Private Daytime or Sunset BYOB Sailing Charter

★★★★★★★★★★4.8 · 18 reviews · 2h 30m · from $500 whole boat, up to 6

You and up to five companions cruise Charleston Harbor aboard Esprit de Joy, a 35-foot private sailboat with a USCG-licensed captain. Choose an afternoon or sunset departure, bring your own drinks and snacks, and pass the Battery, Castle Pinckney, Ravenel Bridge, Fort Sumter, and USS Yorktown. Captain Will often adds local history and points out wildlife along the way.

“Our Captain Will was so kind & knowledgeable! Great way to spend the afternoon”

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13.Charleston Harbor Daytime Sightseeing Cruise with Music

★★★★★★★★★★5.0 · 7 reviews · 2 hours · from $59

Cruise Charleston Harbor aboard the 55-foot Palmetto Breeze, an open-air catamaran with partial shade, restrooms, music, and a debit or credit bar. You’ll pass Fort Sumter, the Ravenel Bridge, USS Yorktown, and working boats. The crew answers questions, but there is no formal narration. Dolphins are possible, not promised.

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14.Charleston Harbor Mimosa Brunch Cruise with Brunch Bites

★★★★★★★★★★4.8 · 6 reviews · 2 hours · from $65

Spend two relaxed Sunday hours aboard the Palmetto Breeze, a 55-foot open-air catamaran leaving from Shem Creek. Your ticket includes self-serve brunch bites, while mimosas, wine, beer, seltzers, and soft drinks are available to buy. Enjoy cushioned seating, music, harbor views, and possible dolphin sightings.

“Super chill and relaxing. Great crew and music. Brunch bites were great and loved the mimosas!! Would definitely do this again. Great start to my Sunday.”

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15.Wednesday Happy Hour Sunset Sail | Charleston Harbor

★★★★★★★★★★5.0 · 2 reviews · 2 hours · from $79

Settle into the open-air Palmetto Breeze, a spacious 55-foot catamaran, for a two-hour sunset cruise from Shem Creek. Your ticket includes select beer, wine, seltzers, and non-alcoholic drinks as you pass Fort Sumter, Yorktown, the Ravenel Bridge, and Charleston’s skyline. Expect smooth sailing, partial shade, restrooms, and a lively but easygoing crowd.

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