Tours/Charleston/Private Sailing Charter with Captain, BYOB

Private Sailing Charter with Captain, BYOB

5.0(94)Charleston1 hour
VIATOR5.0(38)TRIPADVISOR5.0(56)
Private Sailing Charter with Captain, BYOB
Private Sailing Charter with Captain, BYOB
Private Sailing Charter with Captain, BYOB
Private Sailing Charter with Captain, BYOB
Private Sailing Charter with Captain, BYOB
Private Sailing Charter with Captain, BYOB
Private Sailing Charter with Captain, BYOB
Private Sailing Charter with Captain, BYOB
Private Sailing Charter with Captain, BYOB
Private Sailing Charter with Captain, BYOB
Private Sailing Charter with Captain, BYOB
Private Sailing Charter with Captain, BYOB

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.

Pass by

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.

Pass by

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
94 reviews
5
94
4
0
3
0
2
0
1
0

Important Information

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

Reviews(94)

I
I2523IYericam
September 9, 2026
Perfect Sailing Tour!

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

M
Melea_N
September 9, 2026
Beautiful 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.

E
erinlP9078WH
September 4, 2026
Relax and Enjoy the Experience

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

M
Melanie_P
September 1, 2026
Great 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!

1
122mega
August 29, 2026
And 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!

R
Ryann_C
August 16, 2026
We 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!!

D
DeniseLucas
August 5, 2026
Private family sailing experience

Excellent experience! Our captain Will was amazing!

Operator response

We’re so glad your family had a wonderful time on the Charleston Harbor with Captain Will. It means a lot that you chose to spend part of your trip with us, and we hope to welcome you back aboard again soon!

K
kathrynmA3155VZ
July 29, 2026
A great, relaxing and rejuvenating way to spend time in Charleston Harbor!

I live here in Charleston, and I love being out on the water. It is so special to experience Charleston and the surrounding areas from the Harbor, and Charleston Harbor Sailing is the best in the business! The boat is impeccable, and Captain Will creates a memorable experience for you to take home and remember this beautiful city! I have been out many times, and on several different boats, but Charleston Harbor Sailing is, without a doubt, the best!

Operator response

Thank you so much for sharing this! It means the world to hear that even as a local, you enjoyed experiencing the Charleston Harbor from a different perspective. We hope to sail with you again soon!

C
Cote_W
July 20, 2026
Will was a great Captain!...

Will was a great Captain! We had a great time and he was very knowledgeable about the area. I would recommend to anyone looking for a sail in the area. Thanks Will for a great time!

Operator response

Thank you for the 5 star review! We’re thrilled you enjoyed your time on the Charleston Harbor, and we hope to have you back aboard for another sail in the future!

T
Travis_B
July 20, 2026
Loved it

Enjoyed our evening on the water with Captan Will. Spent our first evening in town on this sailing trip. Highly recommended!

Operator response

Thank you for sailing with us! We’re honored you chose to spend your first evening in Charleston on the water with us. We hope it was the perfect start to your trip and would love to welcome you back anytime!

You might also like...

5.0(94)
Book now