sailboat in charleston sc

Charter a Sail on Mental Heeling

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.

• User Ages 6+
• Hour Glass 2.5 Hours

Sailing in the Charleston Harbor

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.

Sail into the Sunset

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!

BOOK IT!   GIFT

Sunset Harbor Sail

End the day with a beautiful sunset sail through charleston harbor.

The Sunset Sail offers extraordinary views of the historic city of Charleston from the water

Join us as we end the day with warm sea breezes that mingle with incredible pastel colored skies on our hour and 45 minute Sunset Sail. Our most premier sail time of the day, the Sunset Sail offers extraordinary views of the historic city of Charleston from the water, with the warm, glowing sun setting peacefully in the distance. We often get up-close views of Atlantic Bottlenose dolphin and other marine wildlife while sailing by many of the incredible sites found in historic Charleston Harbor.

And as always, our trips are BYOB so feel free to bring a bottle of wine or whatever you would like to drink to enjoy during the sail.

• USCG Captain
• Weekend Pricing: $75 for adults

Sunset Harbor Sail Book Now Learn More

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.

• Users Up to 6 Passengers
• Hour Glass Starting at 2 Hours
• User All Ages

Morning Sail / Dolphin Tours

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 Sail

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!

• Users Up to 23 Passengers

Kismet Party Boat Tours and Swimming

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.

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!

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, or making some new memories while marveling at the gorgeous sunset. Whatever you are in to, we can accommodate with plenty of southern charm to go around.

Our award winning fleet consists of 3 stunning boats; sailing yachts Fate and Mystique, and the exclusive motor yacht Kismet! With an emphasis on exceptional customer service, every charter is private led by a professional uniformed crew of 2. Fate and Mystique allow up to six guests while Kismet allows up to twenty-three guests. 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 our latest edition to the fleet and nearly identical to Fate in every way, just a few feet shorter. A beautiful and spacious 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!

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.

Join The Fun!

• Frequently Asked Questions
• Reservation Policy
• Bareboat Charters
• Private Yacht Charters
• Powerboat Charters & Lessons
• Individual Courses
• Liveaboard Programs
• Private Training
• Brokerage and Sales
• Charter Management
• Yacht Management
• Call Us at (843) 277-4236

Sailing School

Yacht Charters

• Captained Charters
• Team Building
• Powerboat Charters

Yacht Services

• Private Management and Service
• Yacht Delivery

Yacht Sales

• Buy or Sell Your Yacht
• The Multihull Company
• Balance Catamarans

Charleston Sailing School specializes in creating unique yachting adventures. From our location downtown at the Charleston City Marina we offer a fleet of sail and power yachts available for Sailing Lessons, Private Yacht Charters, and Bareboat Charters. Since our inception in 2004 we have grown to provide unparalleled service with the best options at every pricepoint. Have you ever dreamed of owning your own yacht? Our team of brokerage professionals can guide you through the search, purchase, and ownership processes.

Stop Dreaming, Start Sailing!

Private Training. Liveaboard Programs. Individual Courses

Learn how to sail with our accredited programs.

© 2024 Charleston Sailing School and Yacht Charters. All Rights Reserved.

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Why Charleston Charter and Yacht?

Our elegant 52' yacht features 2 bedrooms and 2 bathrooms. You will be  immersed  in sound with our state-of-the art stereo system. Matching in quality are our televisions, equipped with satellite cable. While Charleston boasts a warm, tropical climate, central heating and air guarantee your ride will be the perfect temperature for you, What are you waiting for? Our staff, 6 ft. long leather couches, and large

sun pad await.

Where to go?

Our yacht primarily tours Charleston's harbor, taking in the sites and sounds of our historic coast. However, there is much more to the Lowcountry . Your charter is fully customizable and tailor-made to

fit your needs! To find out more, click here .

About Charleston

Established in 1670, Charleston is packed with over 350 years of history. Some of this history, such as Fort Sumter, can only be accessed via Charleston's waterways. The city has a subtropical climate, ensuring warm weather almost year-round. The sunny summers and mild winters are perfect for boating, no matter the season. A plethora of wildlife calls our coasts home. It is not uncommon to have dolphins escort our charters throughout Charleston's waters.

About our master captains

Steve Woodard  has been around boats all of his life, owning his first sail boat at the tender age of 11. In 2008, he founded  Charleston Charter and Yacht, a family business. He proudly brought luxurious, customized, private charters to the Lowcountry for the first time. Steve has owned 13 boats throughout the years and has been a Master Captain 100 tons for 16 years. His skill, expertise, and experience in maneuvering a variety of vessels ensures you are in extremely capable and caring hands.

Paul Zobel was born in Charleston, spending much of his formative years on the waters around the area. He has had a captains license for over forty years, owning and piloting boats from Miami to NY for many of them. He was Captain of the Port for Dewees Island for ten years, piloting their ferry boats. Capt. Charleston Charter and Yacht is incredibly proud to have Cpt. Paul continuing work on the water with us.

Pete DeBoer is a native of Seattle, Washington and grew up in a boating family. Because he is a retired U.S. Coast Guard officer, his experience in operating boats and ships covers the spectrum from 14 to 378 feet. He has served and worked in the Pacific, Caribbean, Mediterranean, Bering Sea, and the Atlantic - from Trinidad to Martha’s Vineyard. Multitalented, Pete is a singer-songwriter that enjoys playing the guitar. His novel, Heave To , loosely parallels his 3 years of drug enforcement operations on a Charleston based cutter in the early 80’s. When Pete is your captain, it's guaranteed you will probably enjoy a sea story or two.

Captain Paul Mitchell , Co-founder/Owner of Charleston Sail – Harbor Yacht Tours LLC

Available Charters

Morning and Afternoon Sailing

Charleston harbor sailing is all about having fun. Glide past historic locations as you soak up the sunshine and fresh air.  Learn more

Sunset Cruise

Experience the beautiful city of Charleston at sunset from the water with our 2.5hr BYOB Sunset Sail.

Power Boat Tours

Choose a power boat to suit your group size...  Learn more

Our Sailboat "Viking"

Charleston Sail is pleased to offer private sailing charters on a well maintained 27ft yacht named "Viking".

Come explore Charleston harbor with us and capture that old seafaring spirit.  The cabin facilities, cockpit seating and life jackets offer your family comfort and safety, whilst on board.  Choose a convenient day or sunset departure and don't forget to bring your own beverages and snacks.  We provide bottled water.

Captains Paul Mitchell or Manning Harvey look forward to being your guide and host afloat.

Boat Location

Ripley Light Yacht club 98 Ripley Pointe Drive Charleston, SC

Visit Us on Trip Advisor

Client Comments

Tremendous Experience! I can't recommend Charleston Sail enough. We did the Sunset cruise and it was the highlight of our trip. Thanks Captain Paul for such a memorable experience. - November, 2020 read more (Trip Advisor)

Great 60th Celebration! Brought my family out on Paul's sail boat to celebrate my mom's 60th. This was the highlight of the entire trip! We actually sailed, which to a family from Colorado is a big deal. Saw dolphins and had just an amazing time. This was a perfect celebration! Thanks Paul:) - October, 2020 read more (Trip Advisor)

• Most Popular!

SUNSET SAIL

Quick Details

• User Ages: All ages
• Hour Glass Duration: 3 hours
• Users Passengers: Up to 6 guests
• Clock Sail Time: 6 p.m.
• Anchor Departure Location: Charleston's St. John's Yacht Harbor

EXPERIENCE A CHARLESTON SUNSET!

See the sights of Historic Charleston from the water. Our private crewed sunset sails show you the historic sights 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 with friends and family for a memory of a lifetime!

Our Classic Sailing Yacht can accommodate 6 Guests.

RELATED SAILS

• Clock 9 a.m.
• Hour Glass 3 hours

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!

• Clock 6 p.m.
• Hour Glass 13 or 14 hours

OVERNIGHT SAIL

Enjoy a sunset sail and drop the hook for an overnight stay aboard the yacht!