Hilton Head Island: Americas Cup Afternoon Sail

If you’re looking to combine a taste of sailing adventure with breathtaking scenery on Hilton Head Island, the Americas Cup Afternoon Sail on the Stars & Stripes yacht might just be your ideal choice. This experience offers a blend of history, hands-on participation, and natural beauty, making it perfect for travelers who crave authentic maritime fun.

What really sets this tour apart? First, you get to sail on a genuine Americas Cup racing yacht—not a replica or touristy boat, but the real Stars & Stripes. Second, the chance for everyone to help crew the boat, whether trimming sails or steering, adds an interactive element that many sailing trips lack. Third, the frequent dolphin sightings and impressive coastal scenery enhance the sense of being part of something special.

However, one thing to keep in mind is the duration—just 1.5 hours—which is perfect for a quick escape but might leave some wishing for a longer adventure. That said, this tour is ideal for those of all ages, from young kids to seniors, especially if you want a memorable, active water experience without the long commitment.

This sail suits travelers interested in history, hands-on fun, and nature watching who are okay with a shorter trip. It’s especially great for families, couples, or anyone wanting a genuine slice of yachting life on Hilton Head.

Good To Know

• Authentic Experience: Sail on the Stars & Stripes, a true America’s Cup yacht.
• Interactive Elements: Help with sailing tasks, making it engaging for all ages.
• Wildlife & Views: Spot dolphins and enjoy sweeping Lowcountry landscapes.
• Expert Crew: Knowledgeable guides enhance the experience with interesting facts.
• Value for Money: At $48 per person, it offers a memorable, hands-on water adventure.
• Short & Sweet: 1.5 hours is perfect for a quick getaway, but might leave some wanting more.

You can check if your dates are available here:

A Detailed Look at the Americas Cup Afternoon Sail

Starting Out at Harbour Town

Your trip begins at the iconic Harbour Town Yacht Basin, a picturesque spot famous for its lighthouse and maritime charm. Arriving 45 minutes early is advisable, especially given parking is limited during the afternoon; arriving early helps avoid stress and ensures a smooth check-in process.

Once checked in at the local partner’s office, located just below the lighthouse, you’ll receive a friendly introduction to the Stars & Stripes yacht and its legacy. The crew, who are not only skilled sailors but also eager storytellers, will brief you on the boat’s history and what to expect during the trip.

Boarding the Stars & Stripes

Boarding begins approximately 30 minutes before departure. The yacht features cushions on deck for seating, making it comfortable to lounge and enjoy views during the cruise. You might want to bring a hat, sunscreen, and perhaps a light jacket depending on the weather.

The Stars & Stripes vessel is a 12-meter America’s Cup racing yacht, a vessel with serious design and racing pedigree. Being on such a boat feels like a step into yachting history, especially as the crew shares stories about its past victories and significance. The crew members are approachable and experienced, ready to answer your questions and share their passion for sailing.

The Sailing Itself

Once out on the water, the atmosphere shifts to one of vibrant activity. The crew hoists the sails, and you’ll feel the rush of wind filling the rigging. It’s a real sailing experience, not just sitting back and relaxing—unless you prefer that, in which case you can simply soak up the sunshine and coastal views.

You will have opportunities to help trim the sails or take the wheel, depending on your interest and ability. This hands-on element has been a highlight for many, with reviews mentioning the crew’s willingness to involve guests. One reviewer shared how their nephew was able to crew and steer, making the experience memorable for the whole family.

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Wildlife & Scenic Highlights

As the yacht glides through the waters, keep your eyes open for dolphins, which often play in the boat’s wake. Reviewers frequently mention dolphin sightings, with one noting, “we caught some wind and the dolphins were fabulous.” The crew also points out local landmarks like Harbour Town Lighthouse and discusses the natural beauty of the Lowcountry, adding layers of interest to the cruise.

The views are spectacular, providing a different perspective of Hilton Head’s coastline—both lush and rugged, with a chance to spot wildlife and coastal homes along the shore.

The Crew & Their Knowledge

Our sources praise the crew, with many reviews mentioning how knowledgeable and friendly they are. Captain Peter, in particular, stands out as someone with over 50 years of local sailing experience. Guests appreciated how he shared stories, took photos for them, and even let passengers take the helm.

This personal touch creates an inviting atmosphere where you feel like a valued crew member rather than just a passenger. The crew’s safety-minded approach also gives peace of mind, especially when weather conditions unexpectedly shift, as noted in one review where the crew kept everyone safe during a sudden weather change.

Returning & Final Thoughts

After about 1.5 hours on the water, the yacht gently makes its way back to Harbour Town, offering one last chance to take photos and soak in the scenery. Many guests mention leaving with lasting memories of a genuine sailing experience—not just a typical boat ride.

Pricing & Value

At $48 per person, this experience offers solid value—especially considering you’re sailing on a real America’s Cup vessel and actively participating. For the price, guests get a short but immersive outing that combines history, nature, and hands-on fun.

It’s a smart choice for those who want a taste of yachting, wildlife watching, and coastal scenery without a lengthy commitment or high cost. Given the reviews, many find it worth every penny, citing the knowledgeable guides, the engaging crew, and the stunning setting as key factors.

Practical Tips

• Arrive early to find parking and check-in comfortably.
• Bring cash for the $9 Sea Pines Resort entry fee if you’re staying outside the resort.
• Dress appropriately—sun protection is essential.
• Consider bringing additional cash for souvenirs or extra photos taken by the crew.
• Since seating is cushions on deck, bring a hat or sun protection for comfort.
• No food or drinks are included, so plan accordingly if you want a snack or beverage onboard.

Who Should Book This Tour?

This sail is ideal for families, couples, and anyone curious about sailing or interested in seeing Hilton Head from the water. It’s particularly suitable for guests who appreciate interactive experiences and enjoy wildlife viewing.

It’s also perfect for history buffs intrigued by the Stars & Stripes story, as the crew shares fascinating details throughout the trip. Since the trip is only 1.5 hours long, it’s a great option for those with tight schedules or looking for a quick but meaningful adventure.

FAQ

• How long is the cruise?

The cruise lasts approximately 1.5 hours, making it a perfect short escape.

• What is included in the price?

The cruise, sailing instruction, and crew assistance are included.

• Are there age restrictions?

The experience is fun for all ages from 3 to 99, but it’s not suitable for people with mobility impairments.

• Do I need to bring anything?

Bring cash (for the resort fee and optional extras), sunscreen, a hat, and comfortable clothes.

• Can I help crew the yacht?

Yes, you can actively participate by trimming sails or steering, depending on your interest.

• Is there a chance to see dolphins?

Yes, dolphins are often spotted playing in the yacht’s wake.

• Are drinks or food provided?

No, food and drinks are not included. You might want to bring water or a snack.

• Where do I meet the tour?

At the Harbour Town Yacht Basin, 45 minutes before departure, at the local partner’s office below the lighthouse.

• Is parking easy?

Parking is limited during the afternoon, so arrive early for a smoother experience.

• What happens in bad weather?

The tour has a flexible cancellation policy (up to 24 hours in advance), and safety is always prioritized.

The Americas Cup Afternoon Sail on Hilton Head offers a wonderfully authentic taste of yachting, blending history, nature, and adventure all in one compact trip. You don’t need to be an experienced sailor to enjoy it—just bring your curiosity and a love for beautiful scenery.
The knowledgeable crew, the chance to help sail the Stars & Stripes, and the potential for dolphin sightings make this experience a standout for water lovers and history enthusiasts alike.

While it’s a shorter trip, many guests find it deeply rewarding and worth the price tag. Whether you’re celebrating a special occasion or simply want to enjoy a unique perspective of Hilton Head from the water, this sail is a solid choice that promises fun, learning, and plenty of photo ops.

In sum, this tour is best suited for those seeking an active, educational, and scenic outing—perfect for families, couples, or solo travelers eager for a taste of classic yachting on Hilton Head.

You can check if your dates are available here: