Top South Carolina Sailing Tours

A sailboat cruise from Hilton Head is a peaceful way to see stunning Lowcountry landscapes without the noise of a moor. Join a captain and crew aboard a 39-foot long (12 meter) sailboat that competed in America’s Cup—head through quiet waters and past gorgeous scenery without the roar of a motor. You can even try your hand on deck and help out with the sails.

Embark on a nautical adventure aboard the Black Dagger pirate ship, which transforms kids into little pirates for a treasure hunt on the waters of Hilton Head. The crew provides kids with pirate costumes and pirate lessons before setting sail in search of treasure. This family-friendly cruise has a choice of several departures in the morning and afternoon, making it easy to fit into your schedule.

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.

Go sailing at sunset in Hilton Head Island with this private dolphin-watching tour. Climb aboard a sailboat and cruise out into Port Royal Sound during this tour. Keep an eye out for wildlife including dolphins, manatees, sting rays, and more. Learn about sailing if you choose or just sit back and enjoy the ride, complete with sunset views.

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

Go sailing in Hilton Head Island with this private dolphin-watching tour. Motor out to Port Royal Sound and then put up the sails for a true sailing adventure. Keep an eye out for a variety of wildlife including birds, dolphins, manatees, and sting rays during this boat tour. Maximize time with a private tour and learn about sailing from your guide.

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.

Explore the waters around Hilton Head, South Carolina aboard your own vessel during this morning excursion. Meet your dedicated captain and sail to Port Royal Sound to begin your tour. Take in the views of Hilton Head, Pickney Island, Paris Island, and many other landmarks while you keep your eyes peeled for playful dolphins that play in the wake of 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.

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.

Sit back and let us take the helm while you enjoy the harbor breeze aboard a Leopard 40 sailing catamaran. Our modern layout provides a panoramic view with large sliding glass doors between the saloon and the rear deck space, with an access door to the front of the boat. These features offer an open concept feel and easy navigation in and around the yacht. Better to see the dolphin and other happenings in the harbor! This innovative design also increases air flow and ventilation throughout the yacht, creating a more pleasant and breezy experience on the water. Catamarans provide a more stable ride on the water, giving ultimate comfort and relaxation while underway. Minimal leaning/heeling over. Owner/operators, captain Todd and wife Kathy, look forward to showing you the harbor and their beautiful boat. Once you request a day, we will contact you to find a mutually agreeable time for our sail- or find us at Ezsailingcharters.com for up to date schedule.

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

Put your feet up, relax, and learn about the unique Salt Marsh Ecosystem with all of its nature & beauty, and enjoy some of our local history on this day sail! We’ll cut the engine and let the wind do all of the work while you keep an eye out for dolphins and birds! You are welcome to bring any other drinks and snacks you would like. Please make sure your beer is in cans and you have a plastic cup to pour your wine into.

Our Sunset and Fireworks sail is a Hilton Head must-do!! Every Tuesday night during the heart of our peak season Shelter Cove puts on a fantastic fireworks show just after the sun goes down. Your evening starts with our relaxing Sunset Sail, then we drop anchor and watch the dazzling display from the boat! Hurry, this one sells fast! You are welcome to bring any other drinks and snacks you would like. Please make sure your beer is in cans and you have a plastic cup to pour your wine into. This Hilton Head sailing adventure is one you do not want to miss!

Finish the day the most relaxing way possible. From the comfort of our stable, peaceful sailboat, you'll enjoy dolphins, birds, and nature as you take in the ecosystem of the low country. You finish your sail as the sun fades away.