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Afternoon Sail from Hilton Head Island

 Hilton Head, SC
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Join the crew of the Stars & Stripes and spend an afternoon sailing Hilton Head's coastal waters. Be on the lookout for the Atlantic Bottlenose Dolphin while enjoying the sun and sights of Hilton Head. Relax and work on your tan or join in and help the crew sail. This is a kid-friendly cruise for the novice or experienced sailor, and a great trip for anyone ages 3 and up! Book yours now!

Activity Highlights
  • Sail aboard a true America’s Cup – 12 Meter sailboat, Stars & Stripes
  • Designed and skippered by the famous Captain Dennis Conner also known as “Mister America’s Cup”
  • Participate as a crew member or sit back and enjoy the sail
  • Choose from public or private sail options
  • See the dolphins at play and learn some fun facts about Hilton Head from the crew
  • Beverages available for purchase including beer & wine

Duration: 1.5 Hrs.

Safety Precautions

  • Face masks required for guides in public areas
  • Social distancing enforced throughout experience
  • Regularly sanitized high-traffic areas
  • Regular temperature checks for staff

What's Included
  • Sailing Tour off Hilton Head Island
  • Safety equipment and life vests
  • Instruction
What to bring
  • Weather appropriate and comfortable clothing
  • Shoes with non-marking soles
  • Sunglasses
  • Sunscreen
  • Hat
  • Aboard Stars & Stripes you will find seating on the deck of the vessel While under full sail, you are welcome to move about the deck. When tacking (changing direction of the sail) you simply take a seat if not participating in the tack.
  • Stars & Stripes can carry 18 passengers on the public and private trips. There is a minimum of 8 guests for public trips to depart.
  • Children under 3 are not permitted on this trip.
  • Coolers of any size are not permitted on boat.
  • No glass of any kind permitted on boat.
  • No high heels allowed on deck.
  • Not handicap accessible.
Additional information
  • As a general rule, Vagabond Cruise does not cancel cruises due to weather until the time of departure. Purchasers of Cruise Tickets should be present and ready to board thirty minutes prior to departure regardless of weather conditions. In the event of severe weather Vagabond Cruise reserves the right to take the following actions: Cancel the cruise, delay departure of cruise for up to forty-five minutes, terminate a cruise early to allow for a safe return to the marina. No refund will be given for cruises terminated early due to severe weather.
  • Stars & Stripes measures 65 feet in length, hosting a 92-foot tall mast. All of the wenches and grinders are original from its competitive sailing past. Modifications have been made to the vessel to conform to commercial standards required by the U.S. Coast Guard.
  • The Stars & Stripes features a full crew and cold libations.
  • Parking is available on-site for a fee.
  • Restrooms are available on board.
  • Service animals are permitted.

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

from $65 $53
11 ratings

Afternoon Sail from Hilton Head Island

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Verified Traveler Reviews

Stars and Stripes

about 21 days ago
This was a fun sail on a famous boat! This is an experience for people who enjoy sailing, you even have the opportunity to participate. The knowledgeable staff instruct passengers so they can take part in sailing the boat. We even saw a few dolphins up close. Highly recommend this trip.
Elizabeth Sweeny


about 6 months ago
Capt. Capt. Chuck and crew was outstanding. Looking forward to future trips.
Carol Milazzo

Sailing Trip

about 7 months ago
Exciting and wonderful time sailing.
David Williamson


about 2 years ago
The dolphins that escorted us out of the dock were a great bonus! The sail was amazing, Captains were entertaining, sunset made the night, and the view of the lighthouse at night was beautiful! I will definitely do it again next time I go.
Tricia Lincoln
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