Sunset Sail Aboard America's Cup in Hilton Head

Hilton Head Island, South Carolina

Sunset Sail Aboard America's Cup in Hilton Head

Hilton Head Island, South Carolina

Duration: 2 hours

Overview

Set sail into a stunning Hilton Head sunset aboard the iconic Stars & Stripes, an America’s Cup yacht once captained by Dennis Connor. Enjoy breathtaking views, a relaxing atmosphere, and the chance to experience sailing on a legendary vessel.

🛥️ Set sail aboard the legendary Stars & Stripes, a real America’s Cup yacht

🌅 Take in breathtaking sunset views over Daufuskie Island and Hilton Head’s saltwater marshes

🍷 Relax with beverages available for purchase, including beer and wine

⛵ Join in the sailing fun or simply enjoy the ride—perfect for all ages, from 3 to 99!

Availability

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Year-Round,
Daily

Full description

This two-hour sunset adventure offers breathtaking views as the sun dips behind Daufuskie Island and the serene saltwater marshes, painting the Lowcountry sky in hues of orange and pink. Whether you're a sailing enthusiast or simply love the idea of gliding over tranquil waters, this is an unforgettable way to cap off your day on Hilton Head Island.

Feel the ocean breeze as you relax on deck, or get hands-on and help the crew with sailing duties—it’s perfect for anyone, whether you're 3 or 93. The boat’s storied history, coupled with the stunning backdrop, makes this experience truly one of a kind. Drinks, including beer and wine, are available for purchase, making it easy to toast to a magical evening on the water.

Practical information

Any restrictions to participate?

Age: All age groups are welcome (recommended for ages 3+).
Physical limitations: Guests must be able to board and disembark the vessel independently. Seating is on deck cushions, requiring some mobility.
Experience level: All levels are welcome.

Who can you accommodate for?

Children: All participants, including children and infants, must have a ticket. This experience is not suitable for children under 3 years old.
Individuals with disabilities: The vessel is not wheelchair accessible and may not be suitable for those with significant mobility issues.
Pets: No pets allowed, except service animals.

What to expect on the day of the experience?

Duration: 2 hours.
What’s included:
- Sailing aboard the iconic America’s Cup – 12 Meter – Stars & Stripes, once skippered by Dennis Connor.
- Breathtaking sunset views over Daufuskie Island, saltwater marshes, and the Intracoastal Waterway.
- Beverages available for purchase, including beer and wine.
- Opportunities to relax, enjoy the scenery, or participate in sailing activities with the crew.
Who will be present: A professional captain and crew will guide the sailing experience, assisting guests and ensuring safety.
Photo/ video: Guests are encouraged to take photos to capture the sunset and scenic views.
Specific rules to follow: Smoking is not allowed on board.

How to prepare?

Weather dependency: The sail runs rain or shine but may be subject to cancellation or rescheduling due to severe weather.
Arrival: Plan to arrive at least 1 hour prior to departure to allow time for parking and check-in, especially during busy periods.
- Boarding: Boarding begins 30 minutes prior to departure directly at the Stars and Stripes vessel on the pier.
Parking:
- Parking is limited in Harbour Town. Recommended lots include two large parking areas on Lighthouse Road and an overflow gravel lot.
- A $9.00 cash-only daily pass is required for entry into the Sea Pines Resort.
- During Memorial Day through Labor Day, free trolley service is available from the Sea Pines Trolley Lot to Harbour Town.
What to wear:
- Comfortable and weather-appropriate attire.
- Closed-toe shoes or sandals for safety and comfort.
- Sunscreen, sunglasses, and a hat for sun protection.
What to bring:
- A mobile or printed boarding pass for entry.
- Cash or card for beverages or gratuities.

Anything else I should know before going on this experience?

Merchandise: America’s Cup – Stars & Stripes merchandise is available for purchase at the reservation office and aboard the sail.

Returns, exchanges and cancellation

Unused Experience Vouchers can be returned within 30 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 48 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 48 hours in advance means losing the value of your experience.