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CharlestonSailing trips & boat tours

Our most recommended Charleston Sailing trips & boat tours

Charleston: Sunset Harbor Cruise

1. Charleston: Sunset Harbor Cruise

Discover Charleston harbor in the evening on a sunset cruise by power catamaran. Watch as the city skyline comes alive with glimmering lights as you admire landmarks like the historic Battery, the Ravenel Bridge, and Fort Sumter. Set off from the Maritime Center and cruise through the surrounding waterways of Charleston Harbor. Keep an eye out for dolphins and shore birds and take in the sights and sounds as the sun sets. Admire the sights of the historic forts, the Battery, the islands, and the lighthouses. See the Arthur Ravenel Jr. Bridge from a different perspective as you cruise beneath it. Enjoy the views of the Charleston skyline as it becomes illuminated for the evening. Relax and choose to purchase some drinks or snacks from the onboard bar as you take in the sights.

Charleston: Historic City Tour and Harbor Cruise

2. Charleston: Historic City Tour and Harbor Cruise

Discover 300 years of Charleston history from land and sea with passionate licensed tour guides. Experience a 90-minute narrated tour of Charleston in a climate-controlled luxury coach and then head to the water for another perspective of the city from Charleston Harbor. Learn fascinating historical facts about Charleston while you cruise the gentle waves of her harbor. Knowledgeable and entertaining tour guides are licensed by the City of Charleston and are eager to share their knowledge with all guests aboard the cruise. Don't forget your camera as you will see all that the Holy City has to offer: Charleston's Historic Homes and Churches, the Old Market, Rainbow Row, Fort Sumter, USS Yorktown, and incredible views from Charleston Harbor.

Charleston: Schooner Sailing Harbor Tour & Dolphin Watch

3. Charleston: Schooner Sailing Harbor Tour & Dolphin Watch

Experience the wonder of sailing on a classic, 84-foot tall ship in the idyllic setting of Charleston Harbor. As you cruise, marvel at the power of the wind filling the sails and the tranquility of the sea. Catch glimpses of historic landmarks, like Fort Sumter, and dolphins gamboling on the waves. Begin your sailing excursion at the Aquarium Wharf. There, meet your captain and crew of the striking, 3-masted ship known as the Schooner Pride. Admire the character and class of this authentic model of the classic coastal trading schooners. Next, prepare to set sail and help the crew as you begin to pull away from the dock. Once the sails are raised, sit back and relax on the benches lining the main deck. Enjoy views of Charleston Harbor stretching out before you. Continue your tour as you cruise past Charleston highlights, such as Fort Sumter, Fort Johnson, and Yorktown Point. Onwards, discover the historic waterfront area of Castle Pinckney. Sail further on waters that Blackbeard once traveled before returning to Aquarium Wharf.

Charleston: Private BYOB Luxury Sailing Cruise

4. Charleston: Private BYOB Luxury Sailing Cruise

Enjoy a 2 1/2 hour private chartered cruise for up to 6 guests on a monohull cruising yacht. Choose between daytime or sunset sailing to see the best view of the Holy City. Whether you are 6 people or 2 people, you will have the entire boat to yourselves. Meet the charter at the marina, sail past the Charleston Battery, and take in the sites of downtown Charleston. Once past the peninsula, you will have clear views of Charleston and its surrounding areas from the heart of the harbor. You can view iconic scenes of Castle Pinckney, the Ravenel Bridge, the USS Yorktown, Fort Sumter and more as we continue our sail through the Harbor. Bring your camera for all the scenes but also keep your eyes on the water as dolphins are often seen swimming around the boat. Feel free to bring your own alcohol, snacks and other beverages on to the boat. Bottled water and soda are offered onboard. An extra refrigerator and glassware are kept onboard for guests to utilize.

Charleston: Haunted History Harbor Cruise

5. Charleston: Haunted History Harbor Cruise

Get to know a different side of Charleston on a harbor cruise focused on the city's haunted past. See eerie locations that can't be reached on foot and listen to ghostly tales and ghoulish stories about pirates, sunken ships, and more along the way. Step aboard a 45-foot powered catamaran, the Palmetto, and set out on your nighttime tour. Marvel at the city skyline from the water and pass by antebellum homes that lie at the heart of some of the most famous ghost stories in the South. Listen as your guide lets you in on some of Charleston's most fascinating ghost lore, from the headmistress who guards the grounds where she once lived, to pirates who still haunt their conquests. Learn about Blackbeard, Charles Vain, and Anne Bonney, the first infamous female pirate. Gain a deeper understanding of Charleston's past as the gem of the fledgling American colonies and leave your tour with new insight into how this shaped the city's legends and lore.

Charleston Harbor Sailing w/Captain: Per-Person, 2.5 hours

6. Charleston Harbor Sailing w/Captain: Per-Person, 2.5 hours

Experience a 2.5 hour breathtaking private or per-person sail in the Charleston Harbor on our luxury 35-foot Jeanneau Sun Odyssey. See the "Holy City" skyline as your licensed captain sails along the Battery, White Point Park, with views of the Ravenel Bridge, the aircraft carrier USS Yorktown, Castle Pinckey, and Fort Sumter. Observe marine wildlife in their natural habitat. Bring your family or friends for an afternoon sail or join us for a panoramic view of a majestic sunset over the Charleston Harbor.

Charleston Harbor Sailing: Private Charter, 2.5 hours

7. Charleston Harbor Sailing: Private Charter, 2.5 hours

Sunsets are sunsets, right? Not in Charleston! A sunset viewed from the Charleston Harbor is pure joy that fills your soul! The sun descending over the Charleston peninsula makes you feel like you’re a part of the sky's transformation too. A perfect Charleston sunset will take your breath away. Join us on board the Esprit de Joy today! We will provide water and ice. Bring your own appetizers and beverage of choice! If you would like to use one of our catering partners, please contact Caviar and Bananas.

Charleston Harbor Sailing: Private Sunset Sail

8. Charleston Harbor Sailing: Private Sunset Sail

Sunsets are sunsets, right? Not in Charleston! A sunset viewed from the Charleston Harbor is pure joy that fills your soul! The sun descending over the Charleston peninsula makes you feel like you’re a part of the sky's transformation too. A perfect Charleston sunset will take your breath away. We will provide water and ice. Bring your own appetizers and beverage of choice! If you would like to use one of our catering partners, please contact Caviar and Bananas The temperature on the water might feel cooler than on land. It may also be a bit breezy, so dress accordingly.

Frequently asked questions about Charleston Sailing trips & boat tours

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Other Sightseeing Options in Charleston

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What people are saying about Charleston

Overall rating

4.8 / 5

based on 208 reviews

Having visited Charleston many times, we had a good basic knowledge of the city’s history and geography. But these two tours were very informative and we learned many new interesting things. Although different in scope, the bus tour and the harbor cruise complemented each other and made for a relaxing and pleasant experience. The bus tour was especially exceptional - the driver narrated the entire trip with both factual and anecdotal information.

Great way to spend a rainy day ! Alan was our bus tour guide and was awesome. Afterwards we toured Charleston Harbor and Stephen was our guide. He was awesome also !

Tour Guides were very knowledgeable and entertaining as well. I highly recommend taking the gray line bus tour and harbor cruise.

the guide , driver and doing a good job for charter and for boat, nice , quiet and lady guide too.

Wonderful! Ask for Steve the tour guide for the boat he is awesome!