There are many activities on Hilton Head Island that take you out on the water, but none quite like the sailboats, which offer unforgettable memories as the sun sits in the sky or sinks into the horizon. With an array of sights to see while on the water, these serene Lowcountry journeys allow adventurers to see the uniqueness of Hilton Head Island and experience her famous waters firsthand. Whether you’re looking to get out and captain your own sailboat or set sail on a cruise around Hilton Head Island, satisfy your seafaring yearning with one of these sails!
1. America’s Cup Stars & Stripes
If you are looking for a unique sail, hop aboard Vagabond Cruises’ Stars & Stripes, a historical and famous vessel, which has sailed the covers of internationally-known magazines, including Sports Illustrated and Time. Once skippered by the legendary Dennis Conner (also known as “Mr. America’s Cup”), this grand boat is sure to provide an enjoyable experience with their 90-minute day cruise or two-hour sunset cruise in which the tides, winds and captain dictate the journey! You can even rent this sailboat, which can accommodate up to 30 people, for a private cruise and plan a customized celebration for your guests.
Call (843) 363-9026 or click here to go to their website to book a trip. To plan a customized private sail, call their Private Charter Sales & Events Manager at (843) 785-2662
2. Flying Circus & Pau Hana
Glide through the smooth waters of the Lowcountry with a guilt-free conscious—because the Flying Circus and Pau Hana offer environmentally friendly sailing excursions! Hop aboard these fun catamarans and learn to captain your own boat with sailing lessons. Or enjoy an evening sailing the seas on a sunset cruise. Catamarans like Pau Hana, the newest and largest addition, do not heel like other sailboats and are even kid friendly! Make sure to pack your coolers for an enjoyable time as you set sail!
Call (843) 686-2582 to book a trip or click here to go to their website.
3. H2O Sports
Promises of salty hair and sun-kissed faces will be kept when sailing this season. Take advantage of H20 Sports’ fastest sailboat on the Island, Sumo, a 38’ trimaran full of luxury and relaxation. Go out on a 1.5-hour daytime sail or on a two-hour sunset sail. Explore the ocean blues on your own and rent their 22’ Catalina Capri, also known as Flick. Or hop on the Hobie Cat and go searching for turtles and other sea dwellers. Setting sail from Harbour Town, these sailboats will allow you to take in the famous southern tip of the Island and get a glimpse of the other islands in the area!
Call (843) 671-4386 or click here to book a trip on their website.
4. Cheers Charters
Grabbing national attention, check out Cheers Charters for a trip through local waterways. Featured in Southern Living as well as on CNN, this sailing excursion is sure to be story worthy. Cheers offers many different times to hop aboard—from morning to sunset. Their 45’ Morgan Sloop will sail your party through the waterways with ease, starting at Broad Creek Marina. Groups of six or intimate celebrations are welcome. Make sure to raise a glass in the sky and toast to the beauty of South Carolina’s coast!
Call (843) 671-1800 to book a trip or click here to go to their website.