
Private Sailing Charter with Captain, BYOB
Traveler rating
5.0/5
Based on 95 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 95 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 (95)
- 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, 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 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.
Pass by without stopping
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.
Pass by without stopping
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.
Pass by without stopping
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.
Pass by without stopping
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.
Pass by without stopping
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 94 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
4 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
3 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.
Traveler reviews
94 verified traveler reviews for Private Sailing Charter with Captain, BYOB. Ratings and reviews provided by Viator and Tripadvisor.
Perfect Sailing Tour!
Great experience and wonderful views! Would highly recommend booking a sailing tour if you're visiting Charleston!
via Tripadvisor
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.
via Viator
Relax and Enjoy the Experience
Will was very knowledgeable and a very skilled captain. Would definitely recommend!!!
via Tripadvisor
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!
via Viator
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!
via Tripadvisor
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
- 33
- 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 95 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 33 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 Charleston historical walking tour with a Professor of History at The Citadel, Historic Charleston Guided Sightseeing Walking Tour, Hidden Alleyways and Historic Sites Small-Group Walking Tour. 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.
What is included in Private Sailing Charter with Captain, BYOB?
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Included: Bottled water; and All Fees and Taxes. Not included: Gratuity. Always check the voucher for the final list before you travel.
Where is the meeting point for Private Sailing Charter with Captain, BYOB?
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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. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.
What languages is Private Sailing Charter with Captain, BYOB offered in?
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It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Private Sailing Charter with Captain, BYOB?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
What happens to Private Sailing Charter with Captain, BYOB if the weather is bad?
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This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.
What do travelers say about Private Sailing Charter with Captain, BYOB?
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Across 95 reviews averaging 5.0 out of 5, recurring themes include knowledge and storytelling, photo opportunities, good for families. Reviewers describe the commentary as informative rather than scripted.
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