
Private Sailing Charter with Captain, BYOB
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 91 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Sailing Charter with Captain, BYOB worth booking?
Private Sailing Charter with Captain, BYOB is a 2.5-hour experience in Charleston, United States, from $500 per person. It scores 68 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 91 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 68 / 100
- Rating
- 5/5 (91)
- Duration
- 2.5 hours
- From
- $500 per person
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
What you get
About this experience
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.
What's included
Included
- Bottled water
- All Fees and Taxes
Not included
- Gratuity
What you'll see and do
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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Fort Sumter National Monument
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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Arthur Ravenel Jr. Bridge
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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Battery & White Point Gardens
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 Church
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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Where it starts and ends
Meeting point
Charleston
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.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
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.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Charleston Harbor Sailing
Know before you go
- Suitable for all physical fitness levels
- The total duration includes travel time.
Photos






What travelers are saying
Outty’s summary of the themes that recur across 89 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
4 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Good for families
2 mentionsReviewers traveling with kids report it landed well with their group.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
89 verified traveler reviews for Private Sailing Charter with Captain, BYOB. Ratings and reviews provided by Viator and Tripadvisor.
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!!
via Viator
Private family sailing experience
Excellent experience! Our captain Will was amazing!
Response from the operator: 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!
via Tripadvisor
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!
Response from the operator: 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!
via Tripadvisor
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!
Response from the operator: 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!
via Viator
Loved it
Enjoyed our evening on the water with Captan Will. Spent our first evening in town on this sailing trip. Highly recommended!
Response from the operator: 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!
via Viator
Good to know
- Duration
- 2.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $500 to $550
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 32
- Verdict
- Solid Choice
Why this scores 68
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Sailing Charter with Captain, BYOB: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Charleston.
How much does Private Sailing Charter with Captain, BYOB cost?
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Prices start at $500 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Charleston usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Sailing Charter with Captain, BYOB take?
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Plan for about 2.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Charleston is not rushed.
Is Private Sailing Charter with Captain, BYOB worth it?
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It holds an Outty Ranking of 68 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 91 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Charleston, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Sailing Charter with Captain, BYOB?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Private Sailing Charter with Captain, BYOB suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 2.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Sailing Charter with Captain, BYOB?
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Around 32 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Charleston can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Charleston and add a light layer if any part of the 2.5-hour experience runs outdoors or after sunset.
Where does Private Sailing Charter with Captain, BYOB start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Charleston within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Charleston?
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Charleston's best experiences are small: house museum tours with an architectural historian, Gullah heritage walks, harbour sails at sunset and Lowcountry food crawls through the market district. Plantation day trips vary enormously in how honestly they handle the history, and our ranking factors that in directly. On Outty we rank every Charleston experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Historic Charleston Guided Sightseeing Walking Tour, Charleston historical walking tour with a Professor of History at The Citadel, Charleston Eco Boat Cruise with stop at Morris Island Lighthouse. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Charleston?
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March to May and September to November, the two mild shoulder windows. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Charleston?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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