Tours/Charleston/Private Sailing Charter with Captain, BYOB
Viator · Private tour

Private Sailing Charter with Captain, BYOB

5.0(80)Charleston1 hour
VIATOR5.0(30)TRIPADVISOR5.0(50)

Description

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering you the opportunity to witness one of the most awe-inspiring sunsets. Or join us for an afternoon sail with your friends and family. Prepare to be captivated by the breathtaking beauty of Charleston and discover firsthand why it is affectionately referred to as "The Holy City." Be sure to note the iconic landmarks such as Castle Pinckney, Ravenel Bridge, USS Yorktown, and the historically significant Fort Sumter. You are welcome to bring your own selection of beverages and snacks. We provide chilled bottled water, and ice upon request. We also provide plastic champagne flutes and souvenir cups that you can take home as a cherished memento. Our dedicated captain is here to ensure every moment on board is nothing short of extraordinary.

Tour Options

Private Sailing Charter

Itinerary

Pass by

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.

Pass by

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.

Pass by

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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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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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.

Highlights

Bottled water
All Fees and Taxes

What's included

Included
Bottled water
All Fees and Taxes
Not included
Gratuity

Traveller Ratings

5.0
80 reviews
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80
4
0
3
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2
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1
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Important Information

  • Suitable for all physical fitness levels
  • The total duration includes travel time.

Reviews(80)

C
Camille_J
June 25, 2026
The sail met each of our...

The sail met each of our expectations and Captain Will exceeded our expectations. He was equal parts professional, experienced,, friendly, and fun. .

C
chelseamH4005JV
June 19, 2026
Perfect Sail

We had a wonderful harbor sail with Captain Will. Instructions provided were perfect. Will was the perfect host complete with lots of good local recommendations. I would book again when back in the area!

N
N1192NCtimr
June 7, 2026
Beautiful night of sailing

2 couples in their 60s enjoyed a great sunset sail on a beautiful night. Captain Will was fantastic. We brought our own drinks. Had no difficulty finding it. FYI, the parking at the Marriott is now $15.

M
M448IHjulies
May 27, 2026
Beautiful way to experience Charleston!

Fantastic tour! It exceeded our expectations in all regards. We’ve visited Charleston many times, but this was our first sail. Now, we won’t plan a vacation here without this tour. Sailing and the boat were lovely. We took the afternoon sail, and the boat had an awning/cover to shade those who preferred to be. Will was a great captain, knowledgable and a pleasure to spend the time with.

A
A3764DVkimd
May 26, 2026
MUST DO IN CHS

We had sooo much fun! The boat was perfect and loved getting to see Charleston from the water! Captain was awesome and truly can’t wait to come aboard again!

A
Amber_S
May 26, 2026
Sailing takes me a way to where I’ve always heard it could be

Amazing experience! Will was super relaxed, but very safe and aware of what was happening at all times. He was very accommodating and professional. This tour was agreed to be the top highlight!

J
joshdQ4273UD
May 18, 2026
Smooth Sailing in the Harbor

Had a great time sailing with my friends. The captain Will was super friendly and took us around the harbor on a gorgeous Charleston day on the water. The waters were calm and the trip was smooth. Will definitely recommend them!

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George_A
May 13, 2026
Perfect Sunset Sail

Every aspect of the experience, from beginning to end, was simply perfect! My wife and I took the sunset cruise to celebrate our 35th Anniversary. Captain Will was waiting for us at the gate when we arrived, helped us board, gave a quick tour and safety briefing and then we were off on a fantastic sail. The boat was in great shape, easy to move around on and had all the essentials with plenty of comfortable seating. Captain Will was an interesting, thoughtful, gracious and entertaining host and guide and shared his local knowledge to help us with the remainder of our visit. This was an outstanding experience for us as visitors to Charleston and, I expect, it would be for locals as well!

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Lindsey_K
May 4, 2026
Beautiful Night on the Water

I had booked the trip for my sisters bachelorette party. Captain Will was fantastic, the weather was fantastic and we even got to see a few dolphins as an added bonus. We had a very fun evening during our sunset excursion!

K
Kathleen_O
May 1, 2026
Captain Will was a...

Captain Will was a fantastic tour guide! So kind and had great recommendations for our trip. Absolute gem!

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