sailboat in charleston sc

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Book a Tour Aboard "Prevailing Winds"! Sailing daily from the Charleston Maritime Center, located in historic downtown Charleston. Book Now Our Tours

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Sunset Harbor Sail Book Now Learn More

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Sailing Tours of Charleston Harbor Stunning views of historic downtown Charleston from the water! Book Now About Us

Welcome aboard Charleston Sailing Adventures!

Sailing tours offered daily from the Charleston Maritime Center in historic downtown Charleston, South Carolina.

What Our Clients Are Saying

See our sailing adventures in action.

Four of us did a sunset sail and it was the perfect ending to an awesome day. It's great to be out in our beautiful harbor with such a knowledgeable and skilled guide. Brian made us feel right at home on his boat and was quick to point out any points of interest including the local wildlife. Would do it again it again without hesitation!

Discover Charleston Harbor's Beauty On Board Esprit De Joy

Experience the beauty of Charleston Harbor from the vast ocean on an unforgettable journey on board Esprit de Joy. Sit back, relax, and immerse yourself in the breathtaking views during this once-in-a-lifetime escapade. Don't miss out on this truly remarkable experience! Book your adventure today.

Sunset Sail

About the boat

Private charters.

Embark on an exclusive adventure with our private sailing charters, perfect for up to six guests seeking an intimate and personalized experience. Delight in the historical and picturesque beauty of Charleston Harbor as you set sail from the renowned Ashley Marina, guided by our experienced licensed captain.

Our private sailing charters are offered every day, seven days a week. Whether you are celebrating a birthday, milestone event, team retreat or date night, aboard the luxurious Esprit de Joy .

Book now and create cherished memories with your guests during this unforgettable local private charter!

Concierge Experience

With Charleston’s ever growing social scene, there is no better option than to arrive in style - by sailboat.

If you have a specific event in mind like cruising by Party at the Point or Riverfront Park to listen to live music, anchoring for Charleston Race Week or docking on Shem Creek for a patio party - allow our team to prepare a custom experience for you. Call or contact us to inquire and we will make it happen!

Charleston Harbor Sailing Videos

Mary Beth P.

• Parking & Directions
• Meet Esprit de Joy

Hello, Sailor! Don’t miss out on the latest Charleston Harbor Sailing news & offers

843-256-6225

[email protected]

The Harborage at Ashley Marina 33 Lockwood Dr Charleston, SC 29401, USA

WE ARE OPEN YEAR ROUND - BOOK OUR CHARTERS TODAY!

Luxury Sailing Charters in Charleston, SC

Choose your experience.

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Morning Sailing / Dolphin Tours

• User All Ages
• Hour Glass Starting at 2 Hours
• Users Up to 6 Passengers
• Glass Soft Drinks/Water Provided and you are welcome to BYOB

Enjoy a morning sail, best for viewing dolphins, the calm water and light winds are very peaceful and makes dolphin sightings easier!  A great time for catered or BYOB brunch with mimosas and bloody marys!  Catering  options are available through Caviar and Bananas.

Afternoon Sailing

A great way to experience sailing and to see the city and explore more of the harbor. Stronger winds usually pick up after noon and give us more speed helping the boat go a little faster and is a bit more exiting! Crewed with a Captain and first mate our charters are always a private first class experience!

Sunset Sail

The most popular and first to sell out are the sunset charters. The sun sets over the harbor creating amazing sunsets you wont soon forget.  Get dressed up or come casual, have it catered with charcuterie or a full dinner spread, the options are endless with Charleston’s premiere sailing experience!

Kismet Party Boat Tours and Swimming

• Users Up to 23 Passengers

The boat you want if you have more than 6 passengers.  The party boat Kismet is Charleston’s premier private yacht for large family groups, bachelorette, birthday and corporate parties for up to 23 passengers.  We offer swimming trips including water hammocks for lounging in the water at anchor.  Bachelorette’s favorite boat for summer fun!  Trips up to 4 hours.

Southern Charm Private Boat Tours and Beach Excursions

Private motorboat rides on the Southern Charm, our beautiful Scout 235.  Cruise the harbor and stop at secluded beaches for sunbathing, swimming, shelling/fossil hunting and get up close to dolphins.  3 to 4 hour day trips and 2 hour sunset cocktail cruises available daily.  Add on beach accessories including towels, beach chairs, cabana, available for the ultimate experience.  Are you a Fan of the Netflix Outer Banks series? We can personalize your tour to see all the filming locations on the harbor.

Why Charleston Sailing Charters LLC ?

When you sail with us, you’ll immediately see what makes us different. From checking in, to setting sail, then returning safe and sound, we strive to provide an incredible experience for every single person who climbs aboard. Our professional, certified, and fun crew go the extra mile to ensure we provide 5-star service on every sail or cruise!

Our award winning fleet of yachts are of the finest quality and kept to the highest standards. Fate and Mystique are the largest sailboats available for Charter in all of Charleston at 43ft and 50ft, only allowing 6 passengers is not a function of size but regulations set by the coast guard. The motor yacht Kismet is in a class of its own, while most competitors have pontoon boats, Kismet is a true picnic boat motor yacht with class and style capable of carrying 23 passengers and allowing swimming. Our Scout Runabout, Southern Charm is the perfect vessel to explore isolated island beaches or just cruising in style.

Whether you are looking for an action-packed sailing race adventure , craving a relaxing afternoon cruise soaking in the warm Charleston sun lounging on the bow, shark tooth hunting on a barrier island , partying with your bachelorette party on Kismet or making some new memories while marveling at the gorgeous sunset . Whatever you are into, we can accommodate with plenty of southern charm to go around.

Charleston Sailing Charters is Charleston’s #1 overall activity and is in the top-performing 10% of all businesses worldwide on TripAdvisor , with over 10,000 satisfied guests per year. Forbes Travel Guide has also listed Charleston Sailing Charters as one of the top 5 romantic things to do in Charleston ! Book early to guarantee your place on one of our beautiful yachts, we can’t wait for you to join us for an unforgettable experience.

Sailing Yacht Fate

Fate is Charleston’s Flagship private sailboat, at 50ft long she has 2 large staterooms with queen beds, and two full bathrooms plus full galley. We can accommodate up to 6 guests plus crew of two. Fate is equipped with all the creature comforts and amenities that you would have on any first class yacht.

Sailing Yacht Mystique

Mystique is Fates sistership and nearly identical to Fate in every way. A beautiful and spacious 43ft sailboat with two bedrooms, two heads, full kitchen and large cockpit with ample seating for 6 guests and 2 crew. Comfortable for year round sailing in South Carolina and we’re always ready to get out on the water!

Luxury Party Yacht Kismet

Have more then 6 passengers and having a hard time finding a boat that will accept your group? Our yacht Kismet can hold up to 23 passengers in your private party. Luxury tours start with a minimum of 2 hours, rates vary by group size. Perfect for wedding parties, corporate events, family outings and the most popular Bachelor / Bachelorette party boat in Charleston, SC!

Runabout Southern Charm

Southern Charm is the perfect vessel for exploring nearby island beaches, shelling, shark tooth hunting or add a beach cabana and chairs and relax on a secluded beach all to yourself. A beautiful Scout 235 Sportfish equipped with an amazing JL audio sound system and small bathroom. Add on’s include beach chairs, towels, extra coolers, cabanas etc

Cater Your Experience

All of our charters are BYOB and food, we do offer complementary bottled water, soft drinks and sell wine by the bottle. Catering options are also available to make life easy on you, offerings from simple charcuterie to full salmon and filet dinners can be provided through our favorite company Caviar & Bananas.

• Exclusive VIP Offering

VIP Full Day Sail with Beach Excursion

Now offering an exclusive full day Sail with lunch on a secluded beach!  Sail for an hour or two then transfer to the beach for lunch in a private cabana with beach chairs and fully catered gourmet seafood spread.

• Sailboat , Motorboat

Join The Fun!

Charleston Sailboat Charters

Join our boat tours in charleston, sc.

There’s no better way to experience Charleston than to view it from the harbor. Established in 2015, Charleston Sailboat Charters was created by Captain Jay Keeney with one goal in mind… to introduce sailing to anyone with the desire to learn and get out on the water. Whether you’re local or visiting, let’s go sailing!

As we navigate the Charleston Harbor together, tacking and gybing along the way. We’ll view various landmarks including: the Historic District South of Broad, Fort Sumter, the Battery and French Quarter, the USS Yorktown, Waterfront Park, Castle Pinckney and the iconic Ravenel Bridge. Book your Charleston boat tours online today!

• Hour Glass 2.5 Hours
• User Ages 6+

Charleston Harbor Sailing Tours

Our Private and Public sailboat tours are a great way to spend a relaxing day on the water in Charleston SC. With the Private tour you will have the boat to yourself and with the Public tour you will share the boat with other guests. Maximum 6 guests with either option.

Dolphin Tours

Relax and enjoy a boat tour around Charleston Harbor while watching dolphins from a close, but safe and respectful distance.

Go on a Charleston Sunset Cruise

Enjoy happy hour or wind down your day with a Charleston sunset cruise. There’s nothing quite like “chasing shimmer.”

History, Wildlife, and Ecotourism

We’ll raise up the sails and learn about historic landmarks, our local ecology and our resident wildlife.

Private Dining Experiences on our Harbor Tours

We partner with local and award-winning private chef, Lauren Furey , who can create a personalized dining experience that she serves right on the boat! We have local catering partners as well.

Bachelorette & Bachelor Parties

Celebrate the Bride or Groom with your closest friends as you set sail on a Charleston adventure!

Come Enjoy our Boat Tours in Charleston, S.C.

We loved our boat ride, we saw dolphins and a gorgeous sunset. Highly recommend this as a great on-the-water experience for anyone visiting the Charleston- thanks again! We'll be back :)

What a fun way to see Charleston!! The Captain was a cool guy and knew a good bit about the area. Drinks and an amazing sunset on a cool boat! What more could you want? Would definitely recommend anyone and everyone do this when visiting Charleston.

Captain Bob gave us the ride of our weekend - could not have been more friendly, knowledgable, and accommodating. We've done a several similar rides but this was by far the best experience. HIGHLY recommend to both tourists and locals wanting a fun day at sea.

I took my kids out on Captain Jay’s boat who showed us around in the harbor. We saw dolphins, and the kids got to steer the boat too. I highly recommend this tour with Captain Jay or Captain Bob!

SAIL & BOAT THE CHARLESTON HARBOR

Have unforgettable moments aboard sv shenanigan, most popular 3-hour charter.

• Most Popular!
• Hour Glass 3 hours
• Clock 6 p.m.

SUNSET SAIL

Our 3 hour sunset sail from the cockpit of Shenanigan, a stunning 50-foot classic yacht! Relax and look over the City of Charleston skyline from the water for a different perspective and a sunset you will never forget!

MOST POPULAR 6-HOUR CHARTER

• Hour Glass Most Popular - 6 Hour Sail
• Clock 9 a.m.

ISLAND CHARTER

We offer sailing trips to barrier and sea islands in the Charleston Harbor and along the coast. Ask about longer day sailing trips to Kiawah Island, Seabrook, Beaufort, Georgetown, Cumberland Island, and more!

ABOARD SV SHENANIGAN

Morning sail.

Start your day enjoying all the sights Charleston has to offer from the water! Set sail, relax on deck, and cruise by the Charleston Waterfront. Spend quality time with friends and family for a great day out on the water!

• Clock 1 p.m.

AFTERNOON SAIL

Enjoy your afternoon and all the sights Charleston has to offer from the water! Set sail, relax on deck, and cruise by the Charleston Waterfront. Spend quality time with friends and family for a great day out on the water!

• Hour Glass 6 hours

CUSTOM DAY SAIL

For a more personalized day on the water, sail out to a barrier island, drop the hook, and take a swim!

WHAT WE OFFER

Try something out of the ordinary to reset, relax, and change the way you do your time off!

See Historic Charleston from the water as the sun slowly sets over the city. Our private crewed sails show you the historic sights of the Charleston Harbor such as the Charleston Battery, Rainbow Row, Fort Sumter, the Sullivan’s Island Lighthouse, or you can even sail right under the Ravenel Bridge! Our customized chartered sails cater to your requests as best the tides and winds allow as they vary from day to day. Spend time on the water on our most popular sail with friends and family for a memory of a lifetime!

SV SHENANIGAN

Our stunning 50-foot classic yacht has plenty of deck and cabin space plus a full galley and fridge to stock for your trip.

DOS CAPITANAS

Our two awesome female captains are very knowledgeable about their vessel and sailing.

Sail the beautiful Charleston Harbor and see historic Charleston landmarks from the water.

⚓ HEAR FROM OUR HAPPY SAILORS! ⚓

AMAZING EXPERIENCE !!! I loved every second of the sailing adventure from start to finish. Had so much fun bonding with friends on the boat while the very professional crew sailed us around and made sure we had a fun and relaxing time. Jen and Janet did a great job at making sure we got to see all the beauty of Charleston and helped us watch one of the best sunsets I’ve seen.

To say that our experience was perfect is an understatement! Front the awesome views to the dolphins swimming right beside us, it was a trip I will definitely be taking again! Captains Jen and Janet were amazing...professional and laid back, they made us all feel at home and totally relaxed. A must-do in Charleston!

History, dolphins, the harbor of Charleston.... and a little wine. We really couldn’t have had a more perfect trip! The ladies Captaining the Shenanigan were very knowledgeable and made us feel safe the whole time. We plan on going again soon!

So much fun! It was amazing! Can’t wait to go again! We saw dolphins and the most amazing views! They like to knew everything about the harbor!

Private Sailing Tours and Eco Tours in Charleston, SC

Come on board for a first class Charleston Harbor Cruise where we will sail upon the historic and beautiful waters of the Charleston harbor.

Live the Dream, One Sunset at a Time

Daily 2.5 Hour Sails on Charleston Harbor and Beyond. Charleston’s #1 Private Sailing Charter Catamaran “OM” for up to 6 passengers. Please call us for larger groups (up to 12 passengers).

Happy Passengers

Five star reviews, a one-of-a-kind luxury experience.

There is not another Charleston sailing charter that matches the size, beauty, comfort and speed that OM has to offer. OM is a fast and beautiful 2005 Leopard 43′ Catamaran Sailboat.

23′ Beam (width)

12+ knots Max Speed

4 queen size berths, 43′ in length, 23′ beam (width), 8 knots cruising speed.

FIT FOR ALL

Now your entire group can enjoy the water together on one boat!  We will anchor in the harbor so you can swim and party like rock stars and then do a relaxing sail!  You will have an unforgettable experience! Bring your own food and drink and there is no booking fee!

2.5 hour day sails at $600 and 2.5 hour sunset sails at $675 and 5 hour sails at $1200 and only $75 for each additional person over 6 people.

2.5 Hour Day Sail

• No cost to make a reservation
• Cancel up to 72 hours in advance
• Catering Available
• Be hands on, or laid back
• Each Additional Hour $175

2.5 Hour Sunset Sail

5 hour full & sunset sail.

• Let’s go explore!

Trip Advisor Reviews

Schedule your charleston sailing adventure, 843-973-0761, [email protected], contact us:, words on the water, the travels of om.

Flying into July 4th

This July 4th fireworks show was amazing as always. Charleston, SC does an incredible job, the fireworks are shot from a barge in front of the historic "Yorktown" Carrier. The harbor is full of every type of boat ready to catch a glimpse of the insane light show....

Completing the Circle…. One More Time

Summer has passed and the winter is upon us all, no matter what the Latitude. This year has been filled with so many beautiful sunset charters and adventures its impossible to mention them all. Grateful to all of those that came out for a sail on board the beautiful...

Charleston Sunset Charters & Cruises

By far the most popular Charleston Sailing Charter is the Sunset Charter Cruise.  As if Charleston did not have enough to offer, the sunsets from the water are breathtaking.  This town is filled with such beauty the only way to take it all in is from the deck of a...

And Time Rolls On

The islands have a way of just taking away your concept of time, until that time runs out.  Then its back to the rat race of America.  Like all things it happens in the now, like right now.  The last month of my island adventure was full of that, adventure and...

Southern Out-Islands

The Southern Out-Islands Mayaguana was where we left off in our last conversation. The island is some 26 miles long and 9 miles high and has a population of 250. The population is basically in three small settlements.  Your not going to get away with doing much wrong...

No Mans Land–Samana Cay

  The Samana Cays lies in the far southern Bahamas and is a little known or visited place. In all of the cruising guides, charts and folk lore, its a place that only serious cruisers go that are completely self sufficient. The "Cut" or entrance to the anchorage...