Hilton Head Island is a superb destination for anyone who loves being on the water. Its calm, protected waters and stunning Lowcountry scenery make it ideal for sailing adventures. We especially enjoy the America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head for its blend of history, tranquility, and hands-on sailing. It offers a chance to glide past iconic sights like the Harbour Town Lighthouse without the noise of a motor—and even try your hand at steering. Whether you’re a seasoned sailor or just want a peaceful cruise, this experience offers a memorable slice of the Lowcountry.
For those seeking a private, relaxing outing that combines wildlife viewing with spectacular sunsets or fireworks, Hilton Head also offers intimate catamaran tours. Meanwhile, a brunch sail aboard a luxury catamaran provides a delightful morning outing you won’t forget. Our list covers these options and more, helping you find just the right sailing experience for your trip.
1. America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head
At number 1, this America’s Cup 12-Meter Yacht Afternoon Sail is a standout for its mix of history and serene scenery. You’ll hop aboard a 39-foot sailboat that once competed in the prestigious America’s Cup, adding a touch of racing legend to your leisurely afternoon. The cruise covers quiet waters along Hilton Head’s coastline, passing landmarks like the Harbour Town Lighthouse and Marina where the Stars & Stripes departs.
What makes this tour truly special is its hands-on nature—you’re encouraged to help with sails and steering, making it more than just a sightseeing ride. The crew is known for being friendly and informative, sharing insights about the Lowcountry environment and the boat’s racing past. The calm waters and lack of engine noise mean you’ll experience this scenic area without disturbance. Plus, you can purchase alcoholic beverages on board to enjoy as you relax. With reviews consistently rating it 4.5 out of 5, guests praise its peaceful vibe and engaging crew.
Bottom Line: If you want a peaceful, interactive sailing experience with a splash of historic racing lore, this cruise is a top choice. It’s especially suited for those who enjoy a laid-back atmosphere and a bit of hands-on fun.
2. Hilton Head: Private Dolphin Day or Sunset Catamaran Sail
Number 2 on our list is a Private Dolphin Day or Sunset Catamaran Sail. Perfect for small groups, this tour offers a more personalized experience—ideal for families, couples, or friends who want a relaxed day on the water. You can choose to go during the day with chances of spotting dolphins, herons, and pelicans, or opt for an evening sunset cruise that transforms the landscape with brilliant colors.
This tour emphasizes education and wildlife viewing. The crew shares insights about the salt marsh ecosystem and local history, enriching your experience beyond just riding along. A major plus is the capacity for customization—since it’s private, you can focus on what interests you most. If you upgrade the sunset trip, you’ll enjoy not just the stunning views but also possibly catch a fireworks show, depending on the schedule. Reviews point out its exclusivity and friendly service, making it worth the price for those wanting a more intimate water adventure.
Bottom Line: This tour is ideal for those wanting privacy, wildlife watching, and a flexible schedule—plus, it’s a great way to see dolphins in their natural habitat.
3. Hilton Head: Brunch Under Sail Catamaran Cruise
Number 3 is the Brunch Under Sail Catamaran Cruise. For a relaxing morning on the water, this 2-hour cruise offers a cozy, intimate experience aboard the luxurious Rosé. You’ll enjoy complimentary mimosas and light brunch bites while drifting through the calm Lowcountry waters. It’s perfect for a laid-back start to your day, whether you’re celebrating, catching up with friends, or simply soaking in the scenery.
The tour emphasizes comfort and personalized service. Unlike larger, crowded boat tours, this experience provides plenty of space for guests to unwind and take in the views. The crew is attentive, ensuring everyone feels at home while you sip your drinks and enjoy the gentle sway of the boat. It’s highly rated—though only by one review so far—the focus on quality and intimacy makes it stand out.
Bottom Line: If you’re looking for a refined, peaceful way to enjoy breakfast and drinks on the water, this cruise delivers a memorable, relaxed experience.
$95 per person
4. Hilton Head Island: Golden Hour Catamaran Cruise
Closing our list at number 4 is the Golden Hour Catamaran Cruise. This two-hour sail into sunset is perfect for capturing stunning photos and unwinding after a day of sightseeing. As the spacious Rosé glides through the calm waters, you’ll enjoy complimentary drinks while admiring panoramic views of the Lowcountry’s natural beauty.
The highlight here is the opportunity to photograph the changing colors of the sky and the peaceful surroundings. It’s a laid-back cruise suited for couples, families, and groups who want a photogenic, tranquil experience. With a rating of 5/5 based on a single review, it’s clear that guests love the relaxed atmosphere and beautiful vistas.
Bottom Line: For those seeking a romantic or scenic evening on the water, this sunset cruise offers a memorable and visually stunning experience.
$86 per person
How to Choose the Right Sailing Experience in Hilton Head
When choosing among these options, consider your budget, schedule, and what kind of experience you seek. The America’s Cup Yacht provides a hands-on, historic sailing adventure—great for history lovers and those wanting a peaceful cruise. If privacy and wildlife are your priorities, the Private Dolphin or Sunset Catamaran is perfect. For a relaxed morning or evening, the Brunch and Golden Hour Sunset Cruise are excellent choices.
Booking early is advisable, especially for the private tours and sunset cruises during peak season. Think about whether you prefer a quiet, scenic ride or a more interactive sailing adventure when making your choice.
In summary, Hilton Head offers a variety of sailing trips that suit different interests and budgets. For a taste of history combined with peace, the America’s Cup sail stands out. If you want a private, wildlife-focused outing, the dolphin and sunset catamaran offers intimacy and personalized service. And for a leisurely morning or evening with drinks and good company, the brunch and sunset cruises shine.
No matter which you choose, booking in advance will ensure you don’t miss out on these memorable Lowcountry experiences. Happy sailing!