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Beyond Hilton Head Island

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

Badge of Excellence
Hilton Head Island, USA
Popular pick
Booked 10+ times last week!
  • 1 hour 30 minutes (approx.)
  • Mobile ticket
  • Offered in: English

Why travelers loved this

4.6
·
· Mary_A ·
Sep 2026
This experience was fantastic CPT Rick, Sam and Haden were absolutely great. I have such beautiful pictures and memories, it was a pleasure.
· Jack_p ·
Aug 2026
Very enjoyable . Captain Peter was wonderful. His crew very accommodating. Perfect for senior citizens. Very relaxing and friendly.

Overview

A sailboat cruise from Hilton Head is a peaceful way to see stunning Lowcountry landscapes without the noise of a moor. Join a captain and crew aboard a 39-foot long (12 meter) sailboat that competed in America’s Cup—head through quiet waters and past gorgeous scenery without the roar of a motor. You can even try your hand on deck and help out with the sails.
  • Hilton Head sailboat cruise aboard a 39-foot vessel
  • Admire views of the coastline and Intracoastal Waterway
  • Peaceful way to explore Lowcountry scenery
  • Alcoholic beverages available for purchase

What's Included

  • 90-minute Sail aboard the America's Cup - 12 Meter
  • An opportunity to participate as a crew member
  • Beautiful low-country views
  • Sea Pines Resort vehicle entry fee
  • Beverages (soda, water, beer, and wine can be purchased on board)

Meeting and Pickup

Meeting point

  • 149 Lighthouse Rd, Hilton Head Island, SC 29928, USA

    The Vagabond Cruise reservation office is located just behind the Harbour Town Lighthouse. If you have your mobile ticket you are able to go directly to the boat (Stars & Stripes America's Cup) 30-minutes before departure to board which is located on the pier in front of the Lighthouse.

End point

This activity ends back at the meeting point.

Itinerary

Harbour Town Lighthouse and Museum (Pass By)

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Service animals allowed
  • Near public transportation
  • Travelers should have a moderate physical fitness level
  • We don't offer any infant rates for this trip as the tickets are a per person rate. All ages will need a ticket.
  • The seating for this cruise is on cushions on the deck of the boat.
  • Private charters are available for Stars & Stripes. Please contact Vagabond Cruise if you are interested to learn more about this option.
  • This tour/activity will have a maximum of 20 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)
Gallery picture 2 (from a traveler's review)
Gallery picture 3 (from a traveler's review)
Gallery picture 4 (from a traveler's review)
Gallery picture 5 (from a traveler's review)

Featured review

Anita_R
Absolutely lovely experience!
 Last summer, I cruised with my family and we had a blast—so much so that I booked it again this year when I brought some friends to the island. We all thoroughly enjoyed the cruise and the wonderful crew. Both Ian and Claudine were incredibly friendly and helpful throughout the trip. And Captain Peter? He’s an absolute rockstar! He shared fascinating facts about the island, patiently answered all our questions, and made sure everyone got great photos on their phones. He truly went above and beyond to make it special. Thanks for the memories!

Reviews

4.6
based on 568 reviews
Total reviews and rating from Viator & Tripadvisor
Sort by: Most insightful

We had three generations...

Charilyn_M, Sep 2026
We had three generations with us from 20years old to 70 and we all loved it. We would do it again. Well worth it

This experience was...

Mary_A, Sep 2026
This experience was fantastic CPT Rick, Sam and Haden were absolutely great. I have such beautiful pictures and memories, it was a pleasure.

Sailing the Sound

Michael_F, Aug 2026
The feeling of gliding across the water is so relaxing and peaceful that we do this activity every year we visit (6 times so far). Every sailing is a little different but the crew makes each time a unique memory.

Great change of pace!

John_T, Aug 2026
We had a fantastic day on the ocean with the entire crew. We have been coming to Hilario Head for years and this one of the best times on the water we have had. Highly recommend for a different way to experience the water.

Sailing

Jack_p, Aug 2026
Very enjoyable . Captain Peter was wonderful. His crew very accommodating. Perfect for senior citizens. Very relaxing and friendly.

Relaxing ride

Virginia_R, Aug 2026
We enjoyed the experience, got a kick out of the captain. Not a fun of the minimum character limit, I almost didn’t leave a review.

Wonderful, relaxing...

Jennifer_B, Aug 2026
Wonderful, relaxing experience! Captain Pete and his crew made my first experience on a sailboat a delight! Would highly recommend!

Great excursion I would do it again

Maryelizabeth_W, Aug 2026
Great trip, and we were able to help pilot the boat! Captain and crew were friendly and helpful shout out to Maddie and Sam

It was outstanding. The...

Michael_P, Jul 2026
It was outstanding. The crew was very friendly, and the captain was also great. Would highly recommend this to anybody that would like to experience sailing.

Captain Pete was...

David_B, Jul 2026
Captain Pete was knowledgeable, expert, and enjoyable to talk with. Those of us seated at the front of the boat were sitting on uncomfortable cushions/flotation devices on the deck. Passengers at the front were largely ignored by the crew except a couple checks to see if there was interest in a cold beverage. It would have been nice for crew to engage a bit more, giving a bit more history about the boat, and point out points of interest during the sail. It's an affordable outing, reasonably priced. Sailors or boaters will enjoy it. Sitting in the back near the Captain is a more comfortable and enjoyable experience than the front deck.

We had a wonderful time...

Deborah_R, Jul 2026
We had a wonderful time on the water. The staff and captain were very personable and friendly. We were on the yacht with a large family and another couple but didn’t feel crowded at all. It was truly a very enjoyable experience.

Wonderful!

silverhokie, Jul 2026
Staff were very welcoming and friendly. Beautiful sailing trip and saw dolphin close up. Perfect trip.

Sailing is relaxing 😎

Maria_C, Jul 2026
This is a great, relaxing experience. The crew is excellent. Letting my Great Nephew handle the wheel was an unforgettable first sailing day for him!

2nd Time!

KEVIN_G, Jul 2026
This is our second time on this boat. We thoroughly enjoyed it. It is a nice, peaceful cruise with dolphins playing around you and drinks available.

Sea Pines sailboat

Paul_L, Jul 2026
It was a lot of fun! Met some new people and my husband got to steer the boat. Captain and crew were so amazing. Truly made our vacation

America's Cup Stars and Stripes Experience

Sonja_J, Jul 2026
No restroom on the yacht. Overall, friendly staff. Staff gave interesting information regarding some historical accounts of people and events

A Must Do!!

Patricia_A, Jul 2026
We had an amazing time sailing aboard the America's Cup - 12 Meter yacht! The captain and his crew were incredibly friendly, welcoming, and helpful from start to finish, making the entire experience relaxing and enjoyable. One of the highlights was seeing dolphins in the wild, which made the trip even more memorable. We were also offered refreshments, which was a thoughtful touch and added to the overall experience. I especially loved getting the chance to ride the sailboat. We got to take some beautiful photos. This cruise was absolutely worth it, and I would definitely do it again. I highly recommend it to anyone looking for a memorable day on the water!

Great to see a competition boat in action and learn about the waterways

JAMES_M, Jul 2026
Tool my sister visiting for the fourth and she loved it. Perfect length and excellent crew! Great way to spend an hour in the afternoon.

enjoyable experience

roger_w, Jul 2026
friendly captain and hand decks! relaxing experience and learned about sailing saw dolphins and sea birds

Highly recommend this...

Sylvia_F, Jul 2026
Highly recommend this activity. We saw dolphins, sailed away with gentle breeze. Fun crew! It can get hot waiting to board as we started at 3 pm but once we got moving, it was pleasant

Great Family Adventure

MichaelC_L, Jun 2026
Sailing an America’s Cup 12 meter is a rare opportunity. Stars & Stripes was significant to the USA recapturing the America Cup. Captain Pete is s legend and fun host allowing passengers to help raise sails and take the helm or just sit back and enjoy a beautiful sail. The crew of young ladies were welcoming, friendly, attentive and amazing at hoisting and trimming sails. A truly wonderful family experience.

Bucket list experience

Anonymous, Jun 2026
Come very early to get a good seat is yiu are over 80. Folks that have extensive sailing experience might get a chance to stear the boat for a while.

Wonderful sail on The Stars and Stripes!

Brad_B, May 2026
Peter and his first mates were very helpful and knowledgeable about the history of the boat, the area and wildlife. Very accommodating...we had someone in our group w a bad back and they loaded her first and gave her a spot she was comfortable in for the entire hour and a half.

Had fun with FAMILY...

Laura_E, May 2026
Had fun with FAMILY Sailing on the stars and stripes. The crew was kind they helped us take pictures and make sure we were comfortable.

Review

Peggy_S, May 2026
A fun way to see the island from the water. The crew was friendly and knowledgable. Would highly recommend this adventure!

Captain and Crew were...

Chester_B, Apr 2026
Captain and Crew were amazing and Very knowledgeable, a very enjoyable time however the cushions were not very comfortable!

Awesome Sailing Experience

Erin_W, Apr 2026
So much fun! Worth it. Would definitely go again. Drinks are for purchase on the boat. Beer, bubbles, soda, etc

Fair wind and following seas

Sandra_L, Apr 2026
A great sail between Hilton Head and Daufuskie islands. The crew did a great job! It was an exciting sail especially as we did our come about several times. Most guests are seated on cushions on deck during the sail. A few seats for those with mobility impairments. Arrive early and stay nearby if special seating is needed.

Fun sail with a pro tip

Steve_E, Apr 2026
Captain Peter and his mates made for a very enjoyable time. Pro tip-- sit in the back by the captain; more comfy and more stories.

Love Stars & Stripes

Lisa_W, Mar 2026
It was really fun, great experience with Captain Pete and the crew. Great way to see Hilton Head Island from the water. If you never been on large sailboat, this is a must. And we saw dolphins.

From $55.00

per person

up to 24 hours before the experience starts (local time)

Book ahead!
On average, this is booked 25 days in advance.

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