5 of the Best Ways to Experience Hilton Head Sailing

Hilton Head Island gives its visitors a whole slew of options to enjoy the water, from picture-perfect beaches to standup paddle boarding. But if you really want to experience the water, then a Hilton Head sailing trip should top your to-do list. Feel the breeze and take in the pristine views as you cruise the Atlantic waters in a yacht or catamaran. Plenty of local businesses offer great packages that will get you off the sand and out on the Calibogue Sound. Check the list below to help make your Hilton Head sailing experience the best!

Hilton Head Sailing

H20 Sports

H20 Sports stays true to its in name the services they offer, and you can rent anything from a paddleboard to sailboat from them. How about an afternoon on a catamaran with a trampoline, or lessons from an instructor that will get you closer to fulfilling your secret dream of being a boat captain? You’ll find that H20 Sports offers all that and more. Reserve a boat today!

Pau Hana and Flying Circus

Not only do these two boats sound like fun, they back it up! This miniature fleet features the larger "Pau Hana” sailboat, perfect for you and a large group of friends to enjoy, and the speedy "Flying Circus,” smaller in size, but just what you’re looking for if you prefer a more intimate sailing experience. According to
, United States Coast Guard licensed captains man both boats, so you can sail worry-free. The boats are managed locally by Advanced Sail, Inc. Visit Hilton Head Island Sailing's website and book an outing on either catamaran. You won’t want to return to shore.

Commander Zodiac

Need a smaller boat, and maybe a lesson? Hand things over toCommander Zodiac. You’ll find they offer affordable rental prices and lessons, handy if it’s your first time sailing. Plan your trip wisely though; as stated on Commander Zodiac’s website, sailing is only offered from June to August.


With the features and prices that Cheers boasts, you’ll have a reason to celebrate! As little as $30 will get you a two-hour trip on the "Morgan” sloop, where you’ll be able to observe local wildlife, great amenities and enjoy refreshments. Visit cheerscharters.com, and book a memorable Hilton Head sailing adventure!

Pirates of Hilton Head

You won’t find anyone threatening to take your treasure here – only the best family-friendly sailing experience that Hilton Head has to offer! Ranked by TripAdvisor.com as the number one activity in Hilton Head, your kids will experience the thrill of a fun-filled treasure hunt and a battle against Stinky Pete, all aboard the Black Dagger. Pirates of Hilton Head is a must-see attraction, and a great way to experience sailing with your young ones. Visit piratesofhiltonhead.comfor rates, hours and all other necessary information.

Few activities are as peaceful as a sailing excursion off Hilton Head Island, and as you can see above, there are plenty of options, each one unique. Beachside Getaway would love to help you find a place to stay on the island, and with our rentals, you’ll only be moments away from a great Hilton Head sailing experience!