Hilton Head Island isn’t just about golf courses and beaches; it’s also a prime spot for sailing adventures. The island’s calm waters and scenic coastlines make it an ideal place to set sail, whether you’re after a relaxing cruise, a hands-on racing experience, or a private outing with friends. Unlike the busy mainland, Hilton Head’s waterways offer tranquility and a chance to see dolphins, seabirds, and stunning Lowcountry scenery without the roar of engines or crowds. For those looking to combine history, nature, and a bit of adventure, these sailing experiences cover a broad range of what’s possible on the water.
If you’re considering booking a trip, it’s worth noting that each of these tours offers something unique—some are shared group experiences, while others are private charters. Prices vary from around $52 to $349 for groups up to six, giving options for various budgets. Whether you want to help crew a 12-meter yacht or simply relax on a private dolphin cruise, you’ll find the perfect match for your interests and schedule.
1. America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head
At number one on our list, the America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head offers a unique chance to experience sailing on a vessel with real racing pedigree. This 1.5-hour cruise takes you aboard a 39-foot yacht that competed in the America’s Cup, the world’s oldest and most prestigious sailing race. The tour departs from Harbour Town Marina, with views of the Lighthouse at Harbour Town and the Marina as a backdrop.
What makes this experience stand out is the opportunity to get hands-on—help with the sails, feel the wind in your hair, and enjoy a peaceful glide through the Intracoastal Waterway. The boat’s design allows for a quiet, motorless cruise, which enhances the feeling of being part of something special. The crew is friendly and informative, often sharing stories about the yacht’s racing history. For around $53, you get a solid dose of Lowcountry scenery without the crowds, plus the ability to purchase drinks on board.
Top reviews praise the helpful crew, the relaxed atmosphere, and the dolphin sightings. Several mention how this trip offers a perfect way to unwind and connect with the water, making it a good choice for anyone wanting a more authentic sailing feel.
Bottom Line: This tour is best for those interested in racing history or wanting a relaxed, hands-on sailing experience. The price reflects good value for the chance to be on a real America’s Cup yacht, especially given its peaceful nature and scenic views.
2. Hilton Head Island: America’s Cup Sailing Yacht Cruise
Coming in at number two, the Hilton Head Island: America’s Cup Sailing Yacht Cruise offers a slightly longer and more interactive experience on a 12-meter racing yacht designed for speed and agility. This 1.5-hour tour is ideal for those who want to learn how to sail from experienced crew members. The boat, famously raced by Dennis Conner during the 1980 America’s Cup, adds historical significance to the day.
During the trip, you’ll get the chance to help work the sails, steer the boat, and learn about racing techniques. It’s a very engaging experience that combines education with fun. The crew’s friendliness and knowledge shine through, and many reviews highlight their willingness to answer questions and take photos. Keep an eye out for dolphins and enjoy the scenic vistas around Hilton Head Island.
For a similar price as the first tour, this experience provides hands-on sailing rather than just sightseeing, making it suitable for those who want to learn or test their sea legs. Passengers often say that the crew’s attentiveness and the chance to participate make this a memorable outing, even if the trip is on the shorter side.
Bottom Line: Perfect for active travelers, sailing enthusiasts, or anyone curious about racing yachts. It’s slightly more interactive than a typical cruise and offers good value for the engaging experience.
3. Hilton Head: Private Dolphin Day or Sunset Catamaran Sail
Finally, the Hilton Head: Private Dolphin Day or Sunset Catamaran Sail offers a fully private experience, ideal for groups of up to six. Priced at $349 per group, this tour lasts 2 to 2.5 hours and can be tailored to daytime dolphin spotting or a romantic sunset cruise. The private setting allows for a more relaxed, personalized outing—perfect for families, couples, or small groups seeking tranquility and nature.
What sets this tour apart is the focus on wildlife watching and ecosystem education. As you sail, you’re likely to see dolphins at play, as well as seabirds and marsh critters. The crew shares insights about the salt marsh environment and local history, creating an educational but laid-back experience. During the sunset option, you’ll witness stunning colors over the water, making for memorable photos. If you choose the fireworks add-on, your trip concludes with a spectacular display from the water.
Reviewers describe the cruise as “totally chill,” with Captain William and Captain Tim receiving special praise for their friendliness and keen eye for wildlife. It’s most suitable for those who want a peaceful, customizable trip with a focus on nature and scenery.
Bottom Line: Best for small groups, those prioritizing privacy, or anyone wanting a tranquil, wildlife-focused cruise. The higher price reflects the private, customizable nature of the tour.
How to Choose
When deciding between these sailing options, consider your interests, budget, and how much hands-on activity or privacy you prefer. If you’re fascinated by racing history and want a hands-on sailing experience, the America’s Cup Yacht tours are excellent choices. For a more relaxed, educational outing with wildlife viewing, the private dolphin or sunset catamaran sail is ideal. Budget-conscious travelers will appreciate the short, engaging America’s Cup 12-Meter Yacht cruise, while those seeking exclusivity and intimacy should consider the private option.
Booking early is recommended, especially during peak summer months, to secure your preferred date and time. Think about whether you want a group experience with lots of interaction or a private trip focused on nature and relaxation.
In summary, Hilton Head offers a variety of sailing experiences that cater to different interests and styles. From the historic racing yachts to private wildlife cruises, there’s something for all. For a taste of sailing adventure and Lowcountry scenery, any of these options can make your trip memorable. Be sure to compare the details, consider your priorities, and book early to enjoy the best water-based adventures Hilton Head has to offer.