Private Sailing Charter with Captain, BYOB

Recommended by 100% of travelers

Badge of Excellence

Charleston, USA

Popular pick

Booked 5+ times last week!

2 hours 30 minutes (approx.)
Mobile ticket
Offered in: English

Why travelers loved this

5.0

· sambelk ·

Nov 2025

This was a great experience. Will was a great host and while cool in November we were prepared and thoroughly enjoyed ourselves. We caught the 5:20 sunset and saw the waterfront all the way up to the aquarium and the Yorktown. Dolphins entertained and we arrived back at dock right on time. We highly recommend this for your small group

· Megan_S ·

Nov 2025

We had such a lovely time sailing around the harbor with Charleston Harbor Sailing! Captain Will was fantastic — friendly, knowledgeable, and made the entire experience so enjoyable. The boat was beautiful and well-kept, and the views of Charleston from the water were unbeatable. Highly recommend this for both visitors and locals looking for a fun and relaxing way to enjoy the city!

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Overview

Sit back, relax, and sip your favorite drink while your captain takes you and your private party of up to six people for a sightseeing pleasure cruise in the waters around Charleston, South Carolina. Let your captain set sail for the sunset with you, or enjoy a leisurely afternoon charter.

Bring your own booze and snacks to enjoy on the cruise
See Arthur Ravenel Jr. Bridge, Fort Sumter National Monument, and more
Enjoy time on the water without having to sail a boat yourself
Great for birthdays, bachelor(ette)s, and anniversaries

What's Included

Bottled water
All Fees and Taxes

Gratuity

Meeting and Pickup

Meeting point

33 Lockwood Dr, Charleston, SC 29401, USA
Rideshare: Get dropped off at The Harborage at Ashley River Marina, 33 Lockwood Drive, OR Pay $10 and park in the guest lot of The Courtyard by Marriott hotel (35 Lockwood Dr) adjacent to the marina. Walk to the sidewalk, turn right on Lockwood Drive, turn right into the marina, to gray building.

End point

This activity ends back at the meeting point.

Itinerary

Charleston Harbor (Pass By)

Fort Sumter National Monument (Pass By)

Arthur Ravenel Jr. Bridge (Pass By)

Battery & White Point Gardens (Pass By)

St. Michael's Church (Pass By)

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Most travelers can participate

The total duration includes travel time.
This is a private tour/activity. Only your group will participate

Supplied by

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Megan_S

Reviews

5.0

based on 68 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Jim & Michele H.

Jim_H, Mar 2026

Captain Will is awesome! He’s a very experienced sailor - definitely ask him about his history. He makes the entire sail relaxing and focused on our total experience - it was an amazing time on the water - highly recommended!

Cold but great day out on...

Angela_H, Mar 2026

Cold but great day out on the boat. Captain Will was super friendly and knowledgeable. Def recommend this tour.

Perfect afternoon sailing...

Robin_M, Mar 2026

Perfect afternoon sailing around Charleston with the family. Captain Will did a great job. Such an amazing activity for our weekend getaway.

Private Charter with Capt Will.

sambelk, Nov 2025

We had such a lovely time...

Megan_S, Nov 2025

10/10 recommend! So...

Madison_B, Sep 2025

10/10 recommend! So relaxing and captain Will was amazing! We even got to see dolphins along the way.

We had a great experience...

Shelby_B, Aug 2025

We had a great experience with Captain Will. Very relaxing and the perfect evening activity for our girls trip.

We had an amazing time! I...

Cassie_C, Jul 2025

We had an amazing time! I would do it again in a heart beat. Especially seeing the sunset on the water.

Beautiful evening sail!...

Scott_S, Jul 2025

Beautiful evening sail! Very relaxing and laid back experience! Great way to see the harbor! Fun trip.

My group of girlfriends...

Brooke_G, May 2025

My group of girlfriends and I had an amazing time on this trip! Thank you for everything! This is a “must” if you are visiting Charleston!

Great overall experience....

Justin_F, May 2025

Great overall experience. Sunset cruise has best lighting for photos. Want with 5 people in May. Great weather and evening to experience sailing. Would do again.

Took an awesome ride in...

Stefanie_K, May 2025

Took an awesome ride in the bay with our captain, Will. Everything was great and Will was the ultimate host making sure we had everything we needed! Highly recommend this activity.

Memorable family evening!! VERY kid friendly!!

Rachelle_A, Apr 2025

WONDERFUL evening spent with Captain Will on the sunset cruise with my husband and two young children. Will really engaged with my 5 year old daughter and taught her how to drive the boat, which she was thrilled with, and created some really special family memories. We loved the flexibility of bringing wine and snacks onboard. It was overall just the most wonderful, memorable evening on our vacation and we are so thankful we did this!

The Brewers

Todd_B, Mar 2025

Will was our captain and he was a great host! Our family had a great time on the boat and he provided a lot of insight on the history of Charleston. We brought along a picnic dinner and he had plates and cups available for us. We would recommend this tour to anyone who wants to see Charleston from the water in a private sailing experience.

Nice relaxing trip and a...

Mark_D, Mar 2025

Nice relaxing trip and a great sailing day overlooking all areas of Charleston and surrounding areas

5 star experience!

Kelly_C, Nov 2024

Absolutely fantastic sailing experience with Will! Would book this again & again ... 5 star experience!

Highly recommended. Beautiful boat, great views (dolphins!). Pro captain. Worth the $$

Gary_C, Nov 2024

We're a "young" couple in our 50s celebrating our birthdays and we're very happy with this boat charter. Captain Will was a pro, calm and knowledgable. There was good communication regarding the booking leading up to the departure date and there was no issue finding Will at the Harborage location. The boat was beautiful as were the views, and a few dolphins came right up close! Will provided lots of interesting facts about the area when asked - but he also gave us space to enjoy our time as a couple. This experience was so much better than being on some ship with 50 other people clamoring for space. We'd highly recommend this experience to others visiting Charleston.

The weather was perfect! ...

Rick_H, Nov 2024

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

Fantastic

Daisy_B, Oct 2024

We had a wonderful 29th anniversary sail. Will was a great captain. Charleston was a beautiful place for a sail. I highly recommend doing it.

Amazing experience!

Emily_M, Sep 2024

My boyfriend and I booked a sunset cruise to celebrate his birthday and we could not have been happier with our experience. Will was such an incredible Captain! He had wonderful recommendations of places for us to visit while in Charleston, and he shared lots of history about the city and the sites we were sailing by. The weather was perfect and we were able to see a gorgeous sunset and get some really nice pictures. I can’t recommend this enough! This was a highlight of our trip to Charleston and we’ll definitely book another cruise on our next visit!

Stunning Sunset Sailing

Cecile_L, Sep 2024

Wonderful time with Will, our captain. He was very professional and attentive to all our needs. The sailboat is very beautiful and the route we took was perfect. I would totally recommend it!

Incredible experience!

Lisa_B, Aug 2024

Will was an awesome captain! The weather was perfect and the views were incredible!! Everything about the experience was memorable! Captain was early to pick us up, we felt welcome anywhere on the clean boat and he was quite informative about the area and answered any questions we had.

Tranquil, nature filled fun time!

Tonya_C, Jul 2024

We had been taking sailing lessons in Ohio and wanted to sail on our Charleston vacation. Captain Will showed us the best time and was so knowledgeable about sailing and the Charleston area. Fantastic time!