Private Sailing Charter with Captain, BYOB

Highlights

Inclusions

Itinerary

1. The golden hour of sunset is our prime booking time! You'll smoothly cruise past the iconic Charleston Battery, soaking up the timeless charm of downtown Charleston. Hold onto your hats because the fun's just starting! As you sail past the peninsula, you're in for jaw-dropping views of Charleston and learn why we call it “The Holy City,” - all right from the heart of the harbor. You won't want to miss iconic sights like Castle Pinckney, Ravenel Bridge, USS Yorktown, and Fort Sumter. Whether you are commemorating a birthday, a significant milestone, a team retreat, or a romantic date night, our aim is to craft an unforgettable experience for you. We've got you covered with plastic champagne flutes and souvenir cups that you can take home as cherished mementos. Our dedicated captain is here to ensure every moment on board is nothing short of extraordinary.

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2. Fort Sumter holds significant historical importance as the site where the American Civil War began. Located in Charleston Harbor, this National Monument is accessible only by boat and offers a glimpse into the events that shaped the nation’s history. As we trim by, we invite our guests to imagine the echoes of the cannon fire that reverberated across the harbor.

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3. The Arthur Ravenel Jr. Bridge, also known as the Cooper River Bridge, is an engineering marvel that spans the entire Cooper River, connecting downtown Charleston with Mount Pleasant. During our time together, you will definitely have opportunities to take pictures with the bridge as a gorgeous backdrop.

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4. This waterfront seawall is a stunning sight from our sailboat and it will be the first landmark you will see as we embark on our journey. You’ll be able to see the beautiful lined mansions and waterfront promenade that is one of the most visited spots in all of Charleston.

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5. St. Michael’s is one of Charleston’s oldest churches, dating back to 1752. Its steeple is a prominent feature on the city’s skyline and is known for surviving numerous hurricanes.

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Cancellation

Free cancellation up to 24 hours before the experience starts, for a full refund.

Reviews

Ratings come from 94 reviews collected by our booking partner. They are travellers' own words, in the order they were written — never reordered to flatter the experience.

Showing reviews written in English.

• 5Perfect Sailing Tour!

  Great experience and wonderful views! Would highly recommend booking a sailing tour if you're visiting Charleston!

  I2523IYericamSeptember 2026via Tripadvisor

• 5Beautiful and Amazing

  It was amazing and so fun. We had calm waters and saw plenty of dolphins. Captain Will was also super nice and fun to chat with.

  Melea_NSeptember 2026via Viator

• 5Relax and Enjoy the Experience

  Will was very knowledgeable and a very skilled captain. Would definitely recommend!!!

  erinlP9078WHSeptember 2026via Tripadvisor

• 5Great sailing tour! Highly recommend!

  I would highly recommend this charter! My five girlfriends and I had a wonderful experience. It is a beautiful boat and enjoyed sailing at sunset. After a lot of walking on land, it was so fun to experience Charleston from the water. Our captain Will was great. Friendly, knowledgeable, pointed out landmarks and other fun Charleston facts during our sail, answered all of our questions about sailing and was overall very personable and accommodating. It was evident he was there to ensure we had a great time. And we also appreciated his offers to take as many pictures as we would like! Important for six ladies that wanted to document the experience. :) Highly recommend this very professional and enjoyable experience!

  Melanie_PSeptember 2026via Viator

• 5And There Were Dolphins!

  What an amazing afternoon! Captain Will was relaxed and knowledgeable. He chatted with us about local attractions and historical places in a manner that seemed like visiting with a friend, rather than taking a tour with a guide. Will answered questions about the Esprit de Joy, as well as other boats we saw. And he ordered up dolphins! A dolphin pod delighted us by following our boat and playing for several minutes. We can't wait to go back to Charleston and take another tour with Charleston Harbour Sailing!

  122megaAugust 2026via Tripadvisor

• 5We went out on the boat...

  We went out on the boat with my family and best friend for my birthday and I absolutely loved it!! The sunset was beautiful, we got to bring our own wine and got amazing pictures!! I also want to say that Will, our captain was awesome and we just had a great experience!! I absolutely recommend!!

  Ryann_CAugust 2026via Viator

Know before you go

How it compares in Charleston

• Its from-price is 809% above the median of the 319 experiences we list in Charleston.
• Its length is typical for the group.
• By number of reviews it ranks 88 of 319.
• The operator lists free cancellation on it.

About Charleston

Charleston is a South Carolina port city of pastel row houses, cobbled lanes, church steeples, Gullah culture and Lowcountry cooking.

Charleston was settled in 1670 and grew on a peninsula between the Ashley and Cooper rivers, and it is one of the best-preserved colonial-era cities in the United States. Rainbow Row, thirteen pastel Georgian houses on East Bay Street, is the best-known sight. The Battery, a seafront promenade with old cannon and oak-shaded White Point Garden, looks out to Fort Sumter, where the first shots of the Civil War were fired in 1861. The city is nicknamed the Holy City for its many church steeples.

Top-ranked sights in Charleston: Charleston City Market, Rainbow Row, Old Exchange & Provost Dungeon.

See all 319 experiences in Charleston