While visiting Hilton Head Island, we usually spend our time biking, walking the beach, lounging by the pool, and strolling the many shops. But we always like to do some kind of excursion as a family. In the past we have done kayaking, gone out on a “pirate ship”, driven Creek Cat boats, and more. This trip we decided to enjoy a 90-minute sail on the 12-meter Stars & Stripes sailboat.

Booking the Excursion

I booked our excursion via TripAdvisor about a month ahead of time. The link is below if this is something you are interested in. It was $53 (no additional taxes or booking fees). TripAdvisor allows you to cancel up to the day before with no fees and for a full refund. You can also choose to pay right then or reserve and pay the day before. It is available to book every day (unless sold out) from 1pm-4pm. You can also book directly through Vagabond Cruising, and I have included their website below.

Here is what the listing promotes:

“Surround yourself in the Atlantic breeze and ocean spray aboard the Stars & Stripes, the America's Cup winning sailboat, on a small-group tour. Apart from leaving and returning to the harbor, the majestic 12-meter boat operates solely on wind power. Assist the crew as they raise the mainsail and help out with any other tasks you like. Or simply relax and enjoy the ride with a drink in hand (available for purchase). Add some excitement to your Hilton Head vacation. Help the crew with basic sailing tasks, if you like. Ride a sailing boat that was skippered Dennis Connor. Enjoy exceptional views of the Intracoastal Waterway.”

Ages 13+

Max of 20 people (we had a group of 14 guests, plus the captain and two deck hands).

What’s Included:

• 90-minute Sail aboard the America's Cup.

• An opportunity to participate as a crew member. They needed two volunteers to help raise the sails and they each got a free beer for helping out!

• Beautiful low-country views. We also saw a pod of dolphins!

What's not included:

• Does not include entry into the Sea Pines Resort ($9.00 cash) per vehicle fee.

• Does not include beverages, available for purchase throughout the sail. Local beer 2 options $5 2 Other beer 3 options $4. Also offered Truly, wine, soda, or water. We brought our own water bottles onto the boat, and this seemed totally fine (no one said anything to us).

  Itinerary:
  
  Pass By: Harbour Town Lighthouse and Museum, 149 Lighthouse Rd, Hilton Head, SC 29928-7207
  
  Views of the Harbour Town Lighthouse and Marina where the America's Cup Stars & Stripes departs!

  Departure details:

  • 149 Lighthouse Rd, Hilton Head Island, SC 29928, USA Stars & Stripes is located in Harbour Town Yacht Basin just below the lighthouse. Check-in for this sail will be at the Vagabond Cruise reservation office just to the left of the Harbour Town Lighthouse.

  Return details:

  • Returns to original departure point.

    
    

Arrival and Check In

The instructions that come in your email along with your tickets (my reservation was for 4 people and I got a single QR code “ticket”) are as follows:

At the Vagabond Cruise Kiosk during check in they asked for our names and gave me a different “ticket” and I have included a photo of it below. They then gave us directions to the sailboat and told us to be there thirty minutes prior to departure.

These photos show the landmarks of the directions we were given from the women at the ticket booth to get to the sailboat. We walked down to the big sign signaling the pier (Harbor Town Pier) and saw the smaller white sign signaling all boats with an arrow. We then followed the ramp down and the Stars & Stripes was the only sailboat at the dock and was the first boat on the left. It was also very clearly marked with a sign and obviously had its name written on the actual sailboat which made it easy to spot.

The Stars & Stripes

The online listing boasts that you get to spend your cruise aboard the famous Stars & Stripes sailboat that was skippered by Dennis Conner. They did not share which one we were on but here is some general information about the Stars & Stripes:

From Wikipedia: The well-funded Sail America Foundation commissioned four 12-metre yachts to support a campaign led by Dennis Conner, representing the San Diego Yacht Club, to win back the America's Cup in the 1987 competition in Fremantle, Australia.

• Stars & Stripes 83 (US 53) built in 1985 by Geraghty Marine, designed by Chance/Nelson/Pedrick.

• Stars & Stripes 85 (US 54) built in 1985 by Robert E. Derektor Inc., designed by Chance/Nelson/Pedrick. Proved to be faster than Stars & Stripes 83.

• Stars & Stripes 86 (US 56) built in 1986 by Robert E. Derektor Inc., designed by Chance/Nelson/Pedrick. Designed with a different keel and more sail area.

• Stars & Stripes 87 (US 55) built in 1986 by Robert E. Derektor Inc., designed by Chance/Nelson/Pedrick. Designed and built with the experience gained from the first three designs. Stars & Stripes 87 won the trials to select the challenger and went on to defeat the Australian defender Kookaburra III in a four-race sweep to win the Cup back for the USA. During the 2017 Hurricane Irma, Stars & Stripes 87, the third iteration of the Stars & Stripes sustained major damage in Saint Maarten.

Either way, it was still fun to be on a sailboat and it was an empowering and exhilarating experience to know it had once been in these world-renowned races.

Here are some photos of the boat and some of the specific areas of the boat or parts of the boat.

The Sailing

The confirmation email told us to arrive an hour prior to the start time, so that’s when we arrived. Once we checked in at the Vagabond kiosk, they told us to be down at the boat 30 minutes before start time. We went down to take some photos, and one of the crew members approached us and told us to come back at 15 minutes till departure time.

At 15 minutes till departure time, everyone had arrived, and the sweet captain took some photos for us around the dock and by the boat and talked to us about the surrounding islands and shared his knowledge about the area. They let us onboard but told us that we could not set sail until exactly 2:00 so we sat in the blazing hot sun until then. They did have little blue cushions for us to sit on. They had seating at the very front tip of the boat for about 6-8 (6 of us sat here) people to sit cross legged, or you could sit at the back of the boat and let your legs dangle like a normal seat (everyone else sat here except the captain and 2 crew members who stood the whole time).

Once we all got settled and started to back out of our “parking space” one of the crew members (Price) gave a brief safety overview and introduced himself, the Captain (Jack) and the other crew member (Wyatt).

He shared information like:

• The blue cushions were to be thrown over if someone fell in the water, and life jackets were below deck if needed.

• Move slowly and carefully when walking around the sailboat.

• Don’t cross the rope up front (he actually said “no Jack and Rose photos up there-it did not turn out well for them and it will not turn out well for you”). 

• He also shared info about the parts of the boat but very brief and tied to safety like the deck was aluminum and would hurt if you fell on it and if you stood to hold the railing or something sturdy.

• Watch for the jig as it could move from side to side suddenly (it only happened once when we turned around to head back in to dock and they warned us before it happened).

Once we were out in the open water, he asked for two volunteers to help him raise the sails. They stood at the back and used their arms to crank these levers and the sails opened up with such grace and ease that they made it look effortless. The two gentlemen that assisted each got a free beer and then the crew offered beer, wine, sodas, or water to the rest of the guests for a fee. Then it was all about relaxing and enjoying the sail.

While we savored the slow but smooth journey across the sea, the guests enjoyed light conversation amongst each other and with the crew. The Captain let guests take turns steering the sailboat which was great fun for everyone and he was very patient and kind as he explained where to aim to get us to where we needed to go and gave direction when you needed to make adjustments. He also took your phone to take photos for you. Not every guest took part in steering but he did consistently encourage everyone to give it a try.

The crew shared information about the boat, the island, the real-estate we were passing, the other boats in the harbor, and even the other cruises they offer (like the shrimping tour where earlier that day they caught 200 pounds of shrimp but the day before they caught literally two shrimp). They were engaging and easy to talk to. The most exciting thing during our voyage was when we passed a shrimping boat and a pod of dolphins trailed behind it and we got to observe the dolphins for a few minutes!

We reluctantly headed back to the harbor but thoroughly enjoyed our trip. It was easygoing and relaxing and the weather was perfect. It was not particularly exciting (except when we saw the dolphins), but if you are looking for a low key activity to fill your afternoon I highly recommend it. Make sure you take a hat and sunscreen as it gets super hot especially when you are waiting to set sail and when you are coming in to dock.

Have you ever taken a trip on a sailboat? Ever been to Hilton Head Island and done this or a different Excursion that you enjoyed? Tell us about it in the comments!