Top Charleston Sailing Tours

Travel back in time to discover one of America’s most historic cities—Charleston, South Carolina—on this guided walking tour. Visit points of interest including Charleston City Hall; the Dock Street Theatre, America’s first theatre; the Old Exchange Building, South Carolina's most historic building; White Point Garden, in the heart of Charleston’s historic district with a spectacular view of Fort Sumter, and many more.

Experience more than 300 years of history on this guided carriage tour of Charleston. See the many mansions, churches, and gardens as your horse-drawn carriage tour covers more than 2.5 miles and 30 blocks of historic Charleston. Belgian and Percheron draft horses will you lead you through the streets while you learn about this “Holy City” and its role in the Civil War.

Get out on the waters of Charleston Harbor during this cruise aboard an 84-foot-tall (25-meter) classic tall ship. As the crew hoists the sails of the schooner, you'll glide past some of the city's historical sights and watch for dolphins in the water. Drinks are available for purchase on board. Select a departure time when booking.

Get all the thrills of a Charleston ghost tour without any walking on this haunted horse and carriage ride. A horse and carriage takes you down twisting side streets and cobbled alleyways with ease as your guide shares spooky stories from Charleston’s past. Make your way past the Mills House, the Circular Congregational Graveyard, and and Provost Dungeon in the heart of the Holy City.

Watch the sun set above Charleston, South Carolina with a 2-hour sunset harbor cruise aboard a 45-foot motorized catamaran. Find a comfortable seat on deck, spot the landmarks of downtown Charleston and the waterfront, and watch for the dolphins and sea birds that thrive along the South Carolina shoreline. Enjoy a relaxing break from the city while spending a romantic evening on the water.

Cruise through Lowcountry tidal creeks and marshes en route to the uninhabited Morris Island on this boat cruise from the Charleston area. A private boat company launches from Bowens Island for the scenic ride through an estuary rich in biodiversity before a soft landing on Morris Island. Spend free time to taking photos of the historic Morris Island Lighthouse, combing for seashells, and looking out for birds, sea turtles, and dolphins before your return.

More than a welcome sight for sore eyes, the tidal marshes around Charleston are a hotbed for Lowcountry biodiversity. Keep your eyes peeled for sightings of wildlife such as Loggerhead turtles, bottlenose dolphins, and more as you paddle down Folly Creek en route to the tidal creeks that wrap around the Hammock Islands. This leisurely paced kayaking tour is capped at 12 participants for a more personalized experience.

See Charleston from the water, and enjoy a luxurious way to admire the sights, with this private sailing charter. This flexible experience is tailored to your preferences: pick your own departure time, bring aboard a picnic and drinks (or upgrade for gourmet catering), and request a photographer if you want to capture the moment. As you go, circle the Charleston Harbor, see landmarks like Fort Sumter, and enjoy a relaxing ambiance.

Ride a horse-drawn carriage through the heart of historic Charleston on a guided tour through the heart of the city. Soak up the old fashioned charm of cobblestone streets lined with antebellum houses, lush gardens, and landmark churches as you listen to stories about Charleston history, architecture, and culture.

Uncover Charleston’s darkest secrets on an evening ghost tour. Stroll through the atmospheric heart of the old city while a guide regales you with tales of the dark deeds, restless spirits, and supernatural phenomena that make Charleston one of the most haunted cities in America. Get exclusive after-hour access to the famous Unitarian Church Graveyard, where an overgrown southern garden surrounds historic plots. If you choose, you can book a shorter tour with just access to the Unitarian Church Graveyard.

See Charleston from the water during a dinner cruise that includes a barbecue buffet and live entertainment. Watch the sky change color as the sun sets, and take in sweeping views of Charleston. Choose from classic dishes such as pulled pork, smoked chicken, mac and cheese, and coleslaw, and have the option to purchase drinks from the bar.

Explore Charleston by water taxi with this convenient harbor cruise. Utilize quick and scenic water-based transportation to reach several popular landmarks including Patriots Point Naval and Maritime Museum and the Aquarium. Check out attractions like Joe Riley Waterfront Park and the Charleston Harbor Marina at your leisure. Keep an eye out for dolphins during the cruise.

Travel back in time to discover one of America’s most historic cities—Charleston, South Carolina—on this guided sightseeing tour. Visit a plethora landmarks including Rainbow Row, the longest cluster of Georgian row houses in the United States; the Old Exchange Building, South Carolina's most historic building; White Point Garden, in the heart of Charleston’s historic district, with a spectacular view of Fort Sumter and many more. Upgrade option available to include a tour of the famous Joseph Manigault House, one of Charleston's most exquisite antebellum structures or the Charleston Museum.

Travel back in time to discover one of America’s most historic cities—Charleston, South Carolina—on this guided small-group walking tour. Explore some of the city’s most enchanting alleys and hidden passages. Visit the Old Exchange and Provost Dungeon, a colonial building with a 300-year history; Rainbow Row, the longest cluster of Georgian row houses in the United States; plus historic Philadelphia Alley, and many more.

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, known for her beauty under sail, exquisite appointments below deck and the best customer service in the industry. Charters depart from Downtown Charleston just minutes from most hotels. Standard sails are 2 hours, sailing to Ft Sumter or the Ravenel bridge depending on wind conditions. We can narrate and give a full history tour or we can just put on some great music and let you enjoy yourselves and take in the beautiful sights of the Charleston Harbor. Its up to you We provide complimentary bottled water and soft drinks but you're welcome to BYOB or make it easy and have it catered through Caviar Bananas and enjoy charcuterie, wine, champagne, beer or brunch on board during your trip, delivered directly to the boat. #1 activity on TripAdvisor since 2010

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor since 2012, our sailing yachts are the highest quality and operated by two professional crew to give you the best experience possible. Standard 2 hour charters are private, only you and the guests in your party will be on board. Additional hours can be added for $275/hour. We depart from the safe Harbor City Marina downtown Charleston and sail out towards fort Sumter or the Arthur Ravenel Jr bridge, past the battery and the historic forts on the Charleston Harbor. We always point out the bottlenose dolphins that we see and try to get as close as we can for your viewing pleasure. Great for children and adults alike, we have plenty of shade, two bathrooms and soft drinks refreshments are included. We strive to provide the best customer service giving our guests the finest sailing experience available in Charleston.

Take in the beauty of the Charleston coastline and even spot dolphins along the way with this exclusive sailboat charter directly from the downtown Harbor City Marina. Enjoy the luxury of an entire boat to yourself as you skirt the coast past highlights like the Arthur Ravenel Jr Bridge, the battery, and historic forts on the Charleston Harbor. Keep your eyes peeled for bottlenose dolphins and stay cool with drinks and shade on board.

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, known for her beauty under sail, exquisite appointments below deck and the best customer service in the industry. Charters depart from Downtown Charleston just minutes from most hotels. Standard sails are 2 hours, sailing to Ft Sumter or the Ravenel bridge depending on wind conditions. We can narrate and give a full history tour or we can just put on some great music and let you enjoy yourselves and take in the beautiful sights of the Charleston Harbor. Its up to you We provide complimentary bottled water and soft drinks but you're welcome to BYOB or make it easy and have it catered through Caviar Bananas and enjoy charcuterie, wine, champagne, beer or dinner on board during your trip, delivered directly to the boat.

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and operated by two professional crew to give you the best experience possible. Standard 2 hour charters are private, only you and the guests in your party will be on board. Additional hours can be added for $275/hour. We depart from the safe Harbor City Marina downtown Charleston and sail out towards fort Sumter or the Arthur Ravenel Jr bridge, past the battery and the historic forts on the Charleston Harbor. We always point out the bottlenose dolphins that we see and try to get as close as we can for your viewing pleasure. Great for children and adults alike, we have plenty of shade, two bathrooms and soft drinks refreshments are included. We strive to provide the best customer service giving our guests the finest sailing experience available in Charleston.

Embark on an exclusive 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 sunset. 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. While you are more than welcome to bring your own selection of beverages & snacks, we go the extra mile by providing a thoughtfully stocked onboard cooler brimming with chilled bottled water & ice. We also have plastic champagne flutes and souvenir cups that you can take home as cherished mementos. Our dedicated captain and crew are here to ensure every moment on board is nothing short of extraordinary.

Sail the Charleston Harbor, see dolphins, historic forts, or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, known for her beauty under sail, exquisite appointments below deck and the best customer service in the industry. Charters depart from Downtown Charleston just minutes from most hotels. Standard sails are 2 hours, sailing to Ft Sumter or the Ravenel bridge depending on wind conditions. We can narrate and give a full history tour or we can just put on some great music and let you enjoy yourselves and take in the beautiful sights of the Charleston Harbor. Its up to you We provide complimentary bottled water and soft drinks but you're welcome to BYOB or make it easy and have it catered through Caviar Bananas and enjoy charcuterie, wine, champagne, beer or dinner on board during your trip, delivered directly to the boat. #1 activity on TripAdvisor since 2010