Hilton Head Island isn’t just a beach lover’s paradise — it’s also one of the best places in the Southeast to hoist the sails and ride the breeze. Whether you’re a seasoned sailor or simply want to relax and enjoy the view, these five top-rated sailing tours offer something for everyone. From high-speed catamarans and historic racing yachts to serene dolphin-spotting excursions, Hilton Head’s sailing scene blends adventure, comfort and unbeatable coastal scenery. No experience? No problem. These local charters make it easy to enjoy the thrill of sailing without ever having to trim a jib.

Sail Hilton Head’s Historic Racing Yacht: Stars & Stripes America’s Cup Tour

This one’s a legend. The Stars & Stripes is an America’s Cup 12-meter racing yacht once helmed by Dennis Conner (aka Mr. America’s Cup). It now cruises the waters of Calibogue Sound, offering guests a chance to sail aboard a piece of sailing history. Operated by Vagabond Cruise out of Harbour Town, the 65-foot yacht features original racing winches and grinders and a towering mast that still turns heads. You can grab a line and help raise the sails or just relax as the crew handles the hard work. Public sails are $50 per person for daytime and $70 at sunset. Private charters are available for up to 28 guests at $1,400.

Fastest Sailboat Tour on Hilton Head: SUMO Trimaran Sailing Experience

If speed is your thing, this is your boat. SUMO is a 38-foot trimaran operated by H2O Sports and known as the fastest sailboat on the island. With three hulls and wide trampoline decks for lounging, it’s built for both thrills and comfort. Inside there’s a full cabin with seating, a kitchen area and a bathroom. You can stretch out and soak up the sun or keep an eye out for dolphins, sea turtles or even the occasional manatee. SUMO sails out of Harbour Town Yacht Basin and accommodates up to six passengers. A private day sail (1.5 hours) runs $325. A sunset cruise (2 hours) is $425. Drinks and snacks are welcome, and the views are always on the house.

Private Dolphin & Wildlife Sail in Broad Creek on the Spartina Catamaran

For a quieter, closer-to-nature experience, Spartina is a perfect pick. This 27-foot Stiletto catamaran, run by Salt Marsh Sailing, is wide, stable and built for comfort with roomy bench cushions and bean-bag chairs. The shallow draft means you’re sailing just a few feet above the water, which makes dolphin sightings feel extra personal. Trips are private for up to six guests and offer a peaceful cruise through the creeks and marshes of Broad Creek, with plenty of wildlife and local insights from your captain. Departing from Shelter Cove Harbour & Marina, the two-hour dolphin day sail is $359, the sunset version is $399 and the Tuesday night sunset fireworks sail runs $479.

Hilton Head Sunset Cruises & Brunch Sails on Rosé Catamaran

Head Sailing’s newest addition is a 36-foot sailing catamaran named Rosé, and it’s all about good vibes and great views. With a spacious deck and soft seating, this boat is built for social cruising. Think sunset sails with appetizers, morning mimosas on the water or just a laid-back sail with a drink in hand. It holds up to 24 passengers and departs from Broad Creek Marina. Choose from several signature options: Brunch under sail ($89), day sail ($69), golden-hour sail with appetizers and rosé ($99) or the Tuesday night fireworks sail ($89).

Private Monohull Sailing Charter from Skull Creek: Knot the Office

If you’re looking for the feel of classic sailing with just your group, this Catalina monohull might be your best bet. Knot the Office is a private sailing charter out of Skull Creek Marina, operated by Anchors Away Sailing Charters. The boat was recently upgraded with plush cushions and new flooring, making it extra comfortable. It holds up to six people and offers a true sailing experience: engine off, sails up and a steady heel of around 30 degrees as you cruise through Port Royal Sound. Trips are completely private, and you can help sail or sit back and enjoy the ride. Dolphins, seabirds and the occasional stingray or manatee might show up along the way. Morning trips are $375, afternoon charters are $395, and sunset sails cost $445.