Top Hilton Head Island Sailing Tours

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.

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.

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

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

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.

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.

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