Whether you’re a family looking for an adventure on the water or a couple wanting a romantic sunset dinner, sailing is one of Hilton Head Island’s favorite pastimes on the water. Bring your little pirate aboard the Black Dagger and set sail on the pirate cruise of their dreams!
Step aboard our captain charters for a Hilton Head Island Sailing experience at its finest. If you want exhilaration, hop aboard the 38' SUMO trimaran, the fastest sailboat on Hilton Head. If you are an experienced sailor, you can rent our 22' Catalina Capri and explore the local waters on your own. H20 Sports, located in Harbour Town Marina, offers the best experience you can have on the water for all ages. 27 Feet long by 16 Feet wide, Limited to maximum six (6) passengers for comfort, privacy and intimacy! The breathtaking painted sunsets at dusk, combined with our mild evening weather, make evening sails popular.


Pamper yourself with cushioned seats, full cabin and enclosed head for a sailing experience unlike any other. They are easy to sail for the novice, yet with enough power and speed for even the most experienced sailor! Whether you are looking to sit back and enjoy the ride, go fast with the wind in your face, or just have all-around FUN, H2O Sports will handle everything for you. Whether it's daytime cruising, dolphin watching, sailing lessons, taking in a fabulous sunset or enjoying fireworks, and are FUN for all ages.
Outside group catering is welcome, or we can assist with party platters, boxed lunches and dinners, buffets, hor d'ouevres, etc. From private trips and group trips, to dolphin and fireworks outings, you’ll love to set sail in Hilton Head.YachtingSpend a day on a Hilton Head chartered yacht, soaking up the sun in the company of your friends and family. If you prefer sightseeing, you can keep your eyes peeled for the funny dolphins, the gentle manatee, or the graceful and wise sea turtles that may cross our path. Cruise around the Island and take in the changing scene of the coastline, from impressive waterfront homes to incredible nature preserves.


Our sailing trips can also be exciting and fast moving, as the captain sails into the wind.
You’ll feast on meals catered by some of the area’s favorite restaurants while touring the local waterways and gazing at a beautiful sunset over the Lowcountry. There are also several pleasure cruises available that offer bar services and live music as you cruise the waterways.
Perfect for families, friends, lovers, social group outings, motor coach tours, convention group recreational activities, lunch and dinner parties, weddings, anniversaries, honeymoons, birthday celebrations, reunions, church outings, or just getting together for clean, fresh FUN!



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