Top South Carolina Sailing Tours

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips behind the historic city skyline. During this 2-hour cruise, take in iconic sights like Fort Sumter, the Ravenel Bridge, and the Charleston Peninsula. Enjoy the ocean breeze on the open deck or relax in the comfortable shaded seating. Keep an eye out for dolphins and seabirds as they accompany your journey, adding a touch of magic to the evening. Enhance the moment with a drink from the onboard bar, featuring local beers, seltzers, and wine (card payments only). Whether you’re a visitor exploring Charleston for the first time or a local seeking a fresh perspective of your city, this sunset sail promises a truly memorable evening on the water.

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 glide past some of the city's historical sights and watch for dolphins in the water. The route varies depending on the sailing conditions. Drinks are available to purchase on board. Select a morning or afternoon departure time when booking.

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, making this the ultimate way to sightsee and keep kids entertained. 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.

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, and set sail for a relaxing and refreshing 2-hour cruise through Charleston’s historic harbor. Sip on mimosas and other beverages from the onboard bar as you glide past iconic sights, including Fort Sumter, the Ravenel Bridge, and the USS Yorktown. With vibrant music, ocean breezes, and Charleston’s scenic beauty all around, this sail is the perfect way to recharge and wrap up your weekend. Whether you’re enjoying an afternoon date, reconnecting with friends, or spending quality time with family, the Palmetto Breeze offers the ideal mix of comfort and fun. Relax on deck, soak in the panoramic views, and let the gentle rhythm of the waves set the tone for an unforgettable Sunday Funday. Reserve your spot now and make your Sunday the highlight of your week!

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha Wednesday Sunset Sail. This midweek escape combines tropical charm with stunning harbor views for an evening you won’t forget. Enjoy complimentary drinks—including beers, seltzers, and wine—while you relax aboard our spacious and comfortable catamaran. (Local Craft Beers, Tipsy Wine Coolers, and CBD Seltzers not included.) Feel the ocean breeze on your face as you sail past Charleston’s iconic sights, all bathed in the warm hues of the setting sun. Whether you're unwinding solo, catching up with friends, or making memories with family, this two-hour sail is the perfect way to recharge and reconnect. Leave your worries on shore and let Aloha Wednesday transport you to paradise. Book your spot today and experience Charleston’s beauty from the water, island-style!

Sit back, relax, and sip your favorite drink while your captain takes you and your private party of up to six people for a sightseeing pleasure cruise in the waters around Charleston, South Carolina. Let your captain set sail for the sunset with you, or enjoy a leisurely afternoon charter.

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 by request. 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.

Experience the picturesque beauty of Charleston Harbor on this private 2-hour sailing cruise. See top Charleston landmarks including The Battery, Ravenel Bridge, and the USS Yorktown from the water, for a fresh perspective that lets you escape the land-based crowds. Bring your own drinks and snacks to enjoy during the cruise, or for a special treat, opt for on-board catering.

Enjoy an intimate sunset sailing experience aboard a cozy vessel with only six guests. Glide through the picturesque waters of Port Royal Sound as the sun dips below the horizon, painting the sky with brilliant colors. Keep an eye out for dolphins and coastal birds while feeling the gentle evening breeze fill the sails. Whether you prefer to take the helm and learn the basics of sailing or simply unwind with a drink, this serene sail is perfect for friends and couples alike, offering a unique way to experience Hilton Head Island's beauty. - 2-hour sunset sail with a maximum of six guests - Watch the sunset over Port Royal Sound - Spot dolphins and coastal wildlife - Hands-on sailing or relax on deck - Ideal for all skill levels and special occasions

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 private 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.

Experience a Charleston sunset the way it was meant to be seen—from the water on a private sailing yacht. On this 2-hour cruise, watch for dolphins and spot landmarks from the water, including The Battery, Ravenel Bridge, and the USS Yorktown. This sailing experience is ideal for couples looking for a romantic evening on the water or families wanting a relaxing break from the city.

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 by request. 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.

Looking for a more personal sailing experience without the cost of a private charter? Our Afternoon Public Sail is the perfect balance. With a maximum of just 6 guests onboard, you’ll enjoy an intimate, relaxed atmosphere. Aboard our newest and largest sailboat. Join us for a 2-hour afternoon sail spotting dolphins, birds, and other local wildlife. Once the sails are raised, feel the power and excitement as the wind fills the sails and the boat heels—this is authentic, hands-on sailing at its best. Our experienced captain encourages guests to be as involved or relaxed as they’d like. Discover why sailing is the best way to enjoy the coast—small group, smooth sailing, and unforgettable views. - Enjoy an intimate sailing experience with only 6 guests on board - Spot dolphins and wildlife while sailing through Port Royal Sound - Participate in sailing activities or relax as you prefer - Perfect for small groups looking for a unique afternoon adventure

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.

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.

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.

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.

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to experience the city’s charm from the water, away from the hustle and bustle. As you cruise along, enjoy panoramic views of Charleston’s most iconic sights, including Fort Sumter, the USS Yorktown, and the Ravenel Bridge. Lounge on the spacious deck, feel the cool breeze, and soak up the Lowcountry sunshine. Spot playful dolphins, watch coastal birds in their natural habitat, and take in the peaceful rhythm of the harbor. Ideal for families, couples, or groups of friends, this 2-hour sail provides a relaxing way to explore Charleston’s history, nature, and beauty. The friendly crew adds to the experience with fascinating insights about the city’s landmarks and marine life. Escape your routine and unwind with a refreshing afternoon on the water. Reserve your spot today for a peaceful sailing adventure you won’t forget!

Looking for an intimate sunset sailing experience without booking an entire private charter? Your 2-Hour Sunset Public Sail offers the perfect balance. With a maximum of just six guests onboard, you’ll enjoy a peaceful, uncrowded atmosphere that feels private and special—without the cost of a private sail. Set sail through the stunning waters of Port Royal Sound as the day winds down. Watch the sky transform with vibrant sunset colors while keeping an eye out for dolphins, coastal birds, and other local wildlife. Once the sails are raised, feel the evening breeze fill the sails as the boat gently heels—true sailing at its most serene and memorable. Your experienced captain welcomes guests to be as hands-on or as relaxed as they choose. Help trim the sails, learn the basics of sailing, or simply sit back with a drink and take in the breathtaking Lowcountry sunset. This sunset sail is perfect for couples, friends, family and anyone looking to experience Hilton Head Island from the water.

Create the sailboat cruise of your dreams with this fully customized private tour on board the Fate in Charleston Harbor. Set off for as little as two hours or for half a day to take in the sights along the waterfront, including Charleston Battery, Fort Sumter, and Ravenel Bridge. Upgrade with catering for food and drinks on board, or bring your own refreshments—you can personalize your charter to suit your tastes.

Looking for a more personal sailing experience without booking an entire private charter? The Afternoon Public Sail is the perfect balance. With a maximum of just six guests onboard, you’ll enjoy an intimate, relaxed atmosphere. It’s a shared experience that still feels special, and it keeps the price lower than a private sail. Join us for a 2-hour afternoon sail spotting dolphins, coastal birds, and other local wildlife. Once the sails are raised, feel the power and excitement as the wind fills the sails and the boat heels—this is authentic, hands-on sailing at its best. The experienced captain encourages guests to be as involved or relaxed as they’d like. Discover why sailing is the best way to enjoy the coast—small group, smooth sailing, and unforgettable views. *Enjoy a 2-hour afternoon sail with a maximum of six guests *Spot dolphins and coastal wildlife while sailing *Hands-on sailing experience or relax on deck *Perfect for all skill levels in a tranquil, intimate setting

Looking for a private luxury yacht for your large group? Kismet can hold up to 15 passengers, cruise the harbor, BYOB, awesome stereo, bathroom, history tours, swim and float on rafts. Kismet does it all! Kismet is a custom-built picnic boat, specifically created for carrying private charter groups comfortably, up to 15 adult passengers. Charleston Harbor can see summer water temperatures as high as 88 degrees which means it's perfect for anchoring and swimming near one of our many beaches, or soaking in the views of the harbor from the safety of a natural cove. We include inflatable floats and patented "Water-hammocks" for everyone on board. Complimentary Coke, Diet Coke, Sprite, and bottled water are provided. We encourage you to BYOB and snacks. Comfortable year round an all conditions, perfect for your entire extended family or special occasion. From history tours to wild parties for your bachelorette party we can do it all and in style. Every charter is private.