If you’re considering a day out on the water during your trip to Hilton Head Island, the Americas Cup Afternoon Sail offers a unique way to enjoy the area’s natural beauty and maritime charm. This sailing adventure is perfect if you’re after a mix of relaxation, hands-on fun, and impressive scenery. From the moment you step aboard the famous Stars & Stripes yacht, you’ll get a glimpse of what makes Hilton Head’s coast so special.
What we love about this experience is how accessible it is—it’s suitable for almost everyone, with plenty of opportunities to relax or get involved. Plus, the chance to spot dolphins and soak in iconic landmarks like Harbour Town Lighthouse really makes it memorable.
On the flip side, a possible consideration is the limited duration—at just 1.5 hours, some might want a longer trip, especially if they’re eager to sail more extensively.
I knew the sail would be amazing but I did not expect it to be as fun as it was. Peter was a wonderful captain and the crew was a lot of fun. We couldn’t have asked for a better experience and it was truly the best day! I would make a trip to South Carolina just for this. Definitely recommend!
I’ve never been on a sailboat before and it was magical to watch the crew set the sails and give us a delightful 2 hours AND a sunset! This boat actually won the America’s Cup years ago. The crew was very friendly—we especially enjoyed hearing stories about the island—the captain (I regret I didn’t catch his name) has been here since the beginning of Hilton Head’s development! Everyone who wanted to, got to steer the boat with directions from our skipper! I highly recommend this over just going out on a covered boat, if you enjoy the wind moving you through the waters instead of an engine.
We did the sunset cruise and I never wanted to leave. It was the most relaxing gorgeous evening I have ever had. The crew was awesome! We learned about the other islands and a bit of their history which was fascinating! The Captain was so knowledgeable as he has been a captain on the island for 50+ years! He was also the first one to grab our cameras and take awesome pictures! We will definitely do this again!
If you’re someone who enjoys maritime adventures, appreciates scenic views, and likes a mix of relaxation and activity, this tour could be just right. It’s especially appealing if you’re traveling with friends or family who want to participate actively or simply take in the sights.
- Key Points
- What to Expect: Sailing in Hilton Head
- The Sailing Experience: A Balance of Relaxation and Activity
- Wildlife & Coastal Views
- The Practical Details
- Accessibility and Comfort
- What’s Included & What’s Not
- What Do Travelers Say?
- Who Would Enjoy This Tour?
- Final Thoughts
- FAQ
- More Boat Tours & Cruises in Hilton Head Island
- More Tour Reviews in Hilton Head Island
- Our NewestHilton Head Island Activity Reviews
Key Points

- Authentic Sailing Experience: You get to sail on the real Americas Cup Stars & Stripes yacht, not just a replica or sightseeing boat.
- Interactive and Fun: The crew invites you to help with sailing tasks, making everyone feel involved regardless of age.
- Wildlife & Scenery: Expect to see dolphins in their natural habitat and enjoy breathtaking views of Hilton Head’s coastline and landmarks.
- Informative Guides: The crew shares fun facts and local insights, enriching your understanding of the area.
- Great Value: For around $48, this 1.5-hour experience offers a lot of hands-on fun and scenic beauty.
- Limited Afternoon Timing & Short Duration: The cruise is mainly an afternoon activity and might leave you wanting more if you’re eager to explore longer.
What to Expect: Sailing in Hilton Head

The adventure kicks off at the Harbour Town Yacht Basin, where you’ll meet the crew and board the legendary Stars & Stripes yacht. This vessel isn’t just any boat; it’s an actual part of America’s sailing history, known for competing in the America’s Cup. The crew will give a quick intro about the boat’s storied background and some basic sailing instructions. If you’re a sailing novice, don’t worry—it’s straightforward, and the crew is eager to help.
Once the sails are hoisted, you’ll feel the thrill of being part of a real racing yacht. The boat glides smoothly across the water, powered by the wind, with the scenic lowcountry landscape unfolding around you. The views of Hilton Head’s coastline and the iconic Harbour Town Lighthouse are picture-perfect, making for some great photo moments.
Keep your eyes peeled for dolphins that often play in the yacht’s wake. The crew is friendly and eager to point out marine life and share stories about the local environment. As you cruise along, you can choose to relax on deck, soaking up the sun and sea breeze, or get involved by helping to trim the sails or steer the boat. This hands-on approach makes the trip truly memorable, especially for those who enjoy a bit of adventure.
You can also read our reviews of more boat tours in Hilton Head Island
The Sailing Experience: A Balance of Relaxation and Activity
What sets this tour apart is the interactive nature. Tourists of all ages can try their hand at sailing, which adds an element of excitement. Several reviews mention how much fun it was to assist the crew and even take the helm, turning passive sightseeing into active participation.
The crew’s knowledge and friendliness top the list of positive feedback. One reviewer noted that the captain was “so knowledgeable,” sharing fascinating details that made the experience more engaging. Others appreciated the helpful and courteous staff, making everyone feel comfortable and involved.
Our sailing experience was so much fun! Captain Peter and the crew were knowledgeable and skilled. They kept us safe when the weather (unexpectedly) changed in a heartbeat, which only made the experience more exciting. 💯 recommend!!
Lack of wind, no one can control, obviously, but the crew made the best of it! My nephew got to crew and steer and when we finally caught some wind it was fabulous!
Ot was fun n to sail on the Stars and Stripes racing sailboat. The Captain was great!
Wildlife & Coastal Views
Spotting dolphins was a common highlight. Many travelers shared how they loved watching these playful creatures dart through the water, often very close to the yacht. The natural scenery around Hilton Head is equally impressive, with lush landscapes, historic landmarks, and the lighthouse framing your views. It’s a calm, scenic cruise that captures the essence of coastal life.
The Practical Details

The tour lasts about 1.5 hours, which is perfect if you’re looking for a short but memorable activity. It generally departs in the afternoon, so it fits well into most day plans. The price is $48 per person, which many consider a good value, especially given the hands-on sailing and the chance to see dolphins.
The meeting point is at the Harbour Town Yacht Basin, just below the iconic lighthouse. Arriving 45 minutes early is recommended, especially since parking can be limited during the afternoon. You’ll need to bring cash for the resort entry fee if you’re not already within Sea Pines, and note that coolers aren’t allowed onboard.
More Great Tours NearbyAccessibility and Comfort
The seating on the yacht consists of cushions on the deck, which means it’s best to be comfortable with sitting on the open air. The boat isn’t suitable for those with mobility issues, so if that’s a concern, you might want to consider other options.
What’s Included & What’s Not
Your fare covers the cruise, sailing instruction, and crew service. Food and drinks are not included, so plan accordingly if you want to bring snacks or beverages (cash is needed for onboard purchases). Also, keep in mind that the $9 vehicle entry fee to Sea Pines Resort is payable in cash.
What Do Travelers Say?

The reviews are overwhelmingly positive, with a 4.8 out of 5 rating based on 163 reviews. Many highlight how the crew is knowledgeable, friendly, and helpful. Quotes like “The captain was so knowledgeable,” and “They kept us safe when the weather unexpectedly changed,” reflect the professionalism and care taken during these trips.
Several reviewers mention how participatory the cruise was—people loved helping with the sails or steering, making it more than just a typical boat ride. One even said, “The captain took a ton of great pictures,” which adds a personalized touch to the experience.
The scenic views received frequent praise, with travelers describing the sunset cruise as “gorgeous,” and the overall experience as “fabulous,” “fun,” and “worth all the fee.” The short duration is sometimes noted as a minor drawback, but most agree it’s a well-paced, enjoyable experience.
Who Would Enjoy This Tour?

This sail is ideal for those who like active experiences but also want to relax and take in coastal scenery. It’s perfect for families with children, as long as they’re comfortable on open decks, and for couples or groups of friends looking for a fun, memorable outing. It’s also an excellent choice for sailing enthusiasts eager to be on a real race yacht.
If you’re looking for a longer tour or more elaborate dining options, you might want to explore other cruises, but for a short, engaging, and scenic adventure, this is tough to beat.
Final Thoughts
The Hilton Head Island: Americas Cup Afternoon Sail offers a well-rounded, authentic sailing experience that combines history, wildlife, and coastal beauty. The chance to help sail a legendary yacht and spot dolphins makes it stand out. While the short duration might leave some wanting more, the overall value, friendly crew, and stunning scenery make this a captivating activity for most visitors.
It’s especially suited for those wanting a hands-on adventure without committing to a full day on the water. If you’re after a fun, scenic, and engaging experience that showcases Hilton Head’s maritime charm, this tour deserves a spot on your list.
Hilton Head Island: Americas Cup Afternoon Sail
"I knew the sail would be amazing but I did not expect it to be as fun as it was. Peter was a wonderful captain and the crew was a lot of fun. We co..."
FAQ
Is this tour suitable for children?
Yes, this experience is designed to be fun for all ages, from 3 to 99, as long as children are comfortable on the open deck and can participate safely in sailing activities.
How long does the tour last?
It runs for approximately 1.5 hours, mainly in the afternoon, making it perfect for a quick yet memorable outing.
Do I need sailing experience to join?
Not at all. The crew provides sailing instructions, and everyone has the chance to help with tasks like trimming sails or steering.
What should I bring?
Bring cash for the resort vehicle entry fee and any onboard purchases. Wear comfortable, weather-appropriate clothing, and consider sunscreen and sunglasses.
Is parking easy at Harbour Town Yacht Basin?
Parking is limited during the afternoon hours, so arriving early is advisable.
Are food and drinks included?
No, food and drinks are not included. You can bring snacks or beverages if you like, but coolers aren't allowed onboard.
Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.
What if the weather is bad?
The tour is weather-dependent. If cancellation is necessary, you'll be notified and can reschedule or get a refund.
Is there a dress code?
No specific dress code, but casual, comfortable clothing suitable for being on the water is recommended.
How many people typically join the cruise?
While the exact group size varies, reviews suggest it’s a cozy experience, with enough room for everyone to participate comfortably.
If you’re looking for a chance to sail a historic yacht, enjoy scenic views, and get hands-on with local wildlife, this adventure on Hilton Head is a fantastic pick. Just remember to arrive early, bring cash, and be ready for a fun, memorable ride.
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