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Experience Hilton Head’s stunning sunset aboard the iconic Stars & Stripes sailboat, with options to help sail or relax—perfect for a scenic, memorable evening.
Watching a sunset over Hilton Head Island from the deck of a real Americas Cup 12 Meter yacht sounds like a dream, but it’s a reality you can enjoy with the Americas Cup Sunset Sail. Operated by Vagabond Cruise Hilton Head, this 1.5-hour cruise offers a unique chance to see the Lowcountry’s beauty from the water aboard the legendary Stars & Stripes. Whether you prefer to roll up your sleeves and help hoist the sails or simply sit back, relax, and soak in the view, this experience balances adventure and serenity perfectly.
What makes this tour especially appealing? For starters, sailing on the actual Stars & Stripes, the famous America’s Cup contender, transforms a simple boat ride into a piece of yachting history. Second, the sunset vistas are hard to beat; the sky blazes with color as Daufuskie Island and salt marshes create a stunning backdrop. That said, a possible drawback could be the limited mobility around the boat, so those with mobility concerns should note the steps onto the vessel and small walkways.
This cruise is ideal for couples looking for a romantic evening, families seeking a scenic outing, or anyone eager for a peaceful escape from the hustle — all while enjoying a bit of nautical history. It’s a versatile experience that captures Hilton Head’s natural charm and maritime spirit.


The meeting point is a short walk from the Harbour Town Lighthouse, at the office located just below it. Arriving 45 minutes early is wise, especially since parking can be tight during the afternoon. Once aboard, you’ll find the Stars & Stripes docked and ready, with boarding beginning about 30 minutes before departure. The boat itself features cushions on the deck for seating and small walkways, which creates an intimate, close-to-the-water feel.
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As the cruise starts, the crew will welcome you aboard, and you’ll have the option to jump into the sailing action or relax and let the breeze carry you. For those helping out, expect to learn the ropes and participate in sailing maneuvers — an exciting touch that appeals to adventure lovers. If you prefer a more laid-back experience, you can lounge on the cushions and enjoy the scenery.
The sunset is the star of the show. As the sun dips lower, the sky transforms into a canvas of fiery oranges, pinks, and purples. The views of Daufuskie Island and the salt marshes are particularly striking during this time. Many reviews mention how stunning this moment is — one guest noted that seeing the sunset topped with dolphins in the water made for a “wonderful experience.”
Beverages are available for purchase onboard, including beer, wine, and non-alcoholic drinks. Having a glass of wine while watching the sunset is a simple pleasure many guests cherish. The boat has a small restroom, which is useful during the cruise, and the crew is typically praised for their friendliness and knowledge.
Guests have pointed out that the seating on cushions offers a cozy, close-to-the-water perspective that enhances the scenic experience. However, the walkways are narrow, and there are steps to board, so travelers with mobility issues should inform the operator in advance. While most guests stay dry, a light spray is possible if the wind kicks up or sea spray blows in — packing a light waterproof layer might be wise.
More Great Tours NearbyWhile ticket prices are not explicitly listed here, the reviews emphasize the value of this experience. You’re not just paying for a boat ride; you’re getting a chance to sail on a legendary vessel, witness a spectacular sunset, and enjoy an informative crew. The option to participate or relax adds flexibility, making it suitable for different preferences and energy levels.
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From the rave reviews, it’s clear that the crew’s friendly, knowledgeable manner enhances the trip. Guests mention seeing dolphins in addition to the sunset, adding an extra layer of magic. One reviewer praised the crew for their enthusiasm and fun attitude, making the cruise not just scenic but also engaging.

This sunset sail is perfect for romantic couples, wanting a memorable evening. It’s equally suited for families, especially those who enjoy being on the water and wildlife spotting. The experience is particularly appealing to those who appreciate authentic sailing — whether helping out or simply enjoying the ride. However, travelers with mobility concerns should consider the boat’s layout and steps before booking.
This is also a great choice for history buffs or yachting enthusiasts, given the boat’s iconic status in America’s Cup history. For anyone who simply loves a peaceful, scenic cruise with excellent crew service and stunning views, this outing offers a balanced mix of relaxation and adventure.


The Hilton Head Americas Cup Sunset Sail offers an experience that feels both authentic and special. Sailing on the legendary Stars & Stripes brings a dash of yachting history into your evening, while the sunset views provide an impressive backdrop for memories. It’s a flexible trip — you can join the crew or just relax, which makes it suitable for different types of travelers.
Most reviewers rave about the knowledgeable guides and the stunning scenery, with dolphins often making guest appearances. The availability of drinks and the cozy deck cushions add to the relaxed, enjoyable atmosphere. It’s a beautiful, scenic way to wind down after a day exploring Hilton Head or Daufuskie Island, especially if you’re a fan of outdoor adventures or boat rides.
In short, this cruise is a solid choice for anyone wanting a taste of genuine sailing, a spectacular sunset, and a bit of maritime history. It’s especially great if you’re traveling with family, a partner, or friends looking for a memorable and scenic evening on the water.

Is there a minimum age requirement for this cruise?
All ages require a ticket, so it’s open to families and children. However, the boat isn’t suitable for those with mobility issues.
How long does the cruise last?
The cruise is approximately 1.5 hours long, making it a short but sweet outing.
Can I participate in sailing?
Yes, you can choose to join the crew and help sail the boat or simply relax and enjoy the views from the cushions.
What should I bring?
Comfortable non-slip shoes, sunglasses, a hat, sunscreen, and a light jacket are recommended. Bringing a waterproof layer is also advised in case of spray.
Are drinks included?
No, beverages like beer, wine, and non-alcoholic drinks are available for purchase onboard.
Is parking easy to find?
Parking is limited, especially in the afternoon, so arriving early is best. The meeting point is just below the Harbour Town Lighthouse.
The Hilton Head: Americas Cup Sunset Sail offers a genuinely scenic, engaging, and relaxed way to experience Hilton Head’s natural beauty. Whether you’re a sailing enthusiast or simply want to enjoy a peaceful sunset, this cruise combines history, wildlife, and stunning views into one memorable package.
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