Sailing options on Hilton Head Island deliver authentic maritime experiences without the tourist traps.
The hands-on 90-minute yacht sail stands out as a top pick, letting you work the sails while learning seamanship basics.
Active travelers will appreciate the 1.5-hour racing yacht cruise, complete with frequent dolphin sightings.
Nature enthusiasts should consider the private catamaran tour – it’s pricier but offers intimate wildlife viewing and expert commentary on local ecosystems.
For special occasions, the 80-foot motor yacht provides floating luxury with premium amenities.
Let’s look at the most worthwhile sailing tours around the island.
Key Points
- The 12-meter yacht sail offers an interactive sailing experience with the opportunity to participate as crew members.
- The Hilton Head Island sailing yacht cruise provides a 1.5-hour experience on a 12-meter racing yacht with the potential to spot dolphins.
- The private dolphin day or sunset catamaran sail is a 2-2.5 hour tour focused on local wildlife and ecosystems, with options to add a fireworks display.
- The Hilton Head yacht charter on an 80-foot motor yacht offers a luxurious and private cruise with a capacity of up to 12 passengers.
- These sailing experiences in Hilton Head Island provide various durations, group sizes, and amenities to cater to different preferences and budgets.
Americas Cup 12-Meter Yacht Afternoon Sail From Hilton Head
Visitors can enjoy a peaceful 90-minute sail aboard a 39-foot (12 meter) yacht that once competed in the prestigious America’s Cup regatta. The cruise offers a quiet exploration of the Lowcountry’s scenic waterways without the noise of a motor.
Passengers can participate as crew members and help handle the sails, adding to the interactive experience.
The meeting point for the activity is at 149 Lighthouse Rd, Hilton Head Island, SC 29928, where guests check in at the Vagabond Cruise reservation office near the Harbour Town Lighthouse. The sail ends back at the same location.
The yacht is USCG approved for up to 30 passengers, but due to COVID-19 restrictions, the capacity is limited to 20. While the cruise isn’t wheelchair accessible, service animals are allowed. A moderate level of physical fitness is required, and all ages need a ticket.
Priced from $52.95 per person, the cruise offers free cancellation up to 24 hours before the experience. Private charters are also available.
Read our full review: Americas Cup 12-Meter Yacht Afternoon Sail From Hilton Head Review
Book now: Check availability
Hilton Head Island: America’s Cup Sailing Yacht Cruise
Hilton Head Island invites you to embark on a captivating journey aboard a 12-meter racing yacht that once competed in the prestigious America’s Cup.
Designed by Dennis Conner, the Stars & Stripes yacht offers a 1.5-hour sailing experience that allows you to participate in the sailing activities or simply relax and enjoy the scenic views of Calibogue Sound.
Led by a live tour guide, the excursion provides an opportunity to learn about sailing from experienced crew members.
Keep an eye out for dolphins as you cruise the waters. Onboard, you can purchase drinks and merchandise to enhance your experience.
With a price starting from $52.95 per person, this activity is a must-try for those seeking an authentic America’s Cup-inspired adventure in Hilton Head Island.
Secure your spot by reserving now and paying later, and take advantage of the free cancellation policy up to 24 hours in advance.
Read our full review: Hilton Head Island: America’s Cup Sailing Yacht Cruise Review
Book now: Check availability
Hilton Head: Private Dolphin Day or Sunset Catamaran Sail
For those seeking a truly private and immersive sailing experience in Hilton Head, the Private Dolphin Day or Sunset Catamaran Sail offers an exceptional opportunity to explore the area’s natural wonders.
Priced at $379.18 for up to 6 participants, this 2-2.5 hour tour allows you to spot dolphins and birds in their natural habitat, learn about the local salt marsh ecosystem and history, and enjoy the breathtaking sunset from the water.
With the option to add a stunning fireworks display, this private catamaran tour provides a fully customizable experience. The knowledgeable guide, complimentary water and cooler, and life jackets ensure a comfortable and informative journey.
Reviewers praise the transportation, value for money, and the captain’s expertise, which enhances the overall experience.
Whether you’re with friends, family, or colleagues, this private sailing adventure in Hilton Head is an unforgettable way to connect with nature and create lasting memories.
Read our full review: Hilton Head: Private Dolphin Day or Sunset Catamaran Sail Review
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Hilton Head Yacht Charter: 80-Foot Top Shelf Motor Yacht
One premier option for a luxurious sailing experience in Hilton Head is the 80-Foot Top Shelf Motor Yacht charter. This private charter accommodates up to 12 passengers and offers an unforgettable journey along the island’s picturesque coastline.
Captained by knowledgeable local guides, the yacht features plush seating, a full wet bar, and ample space for relaxation and entertaining.
Guests can choose from a variety of tour options, including a 2-hour daytime cruise or a 2-hour sunset cruise. The daytime cruise allows visitors to take in the stunning scenery and spot local wildlife, such as dolphins, while the sunset cruise provides a romantic and serene way to end the day.
Both tours are priced at $475 for the entire group, making it a cost-effective option for families or small groups.
With its luxurious amenities and breathtaking views, the 80-Foot Top Shelf Motor Yacht charter is an exceptional way to experience the beauty of Hilton Head Island from the water.
Read our full review: Hilton Head Yacht Charter: 80-Foot Top Shelf Motor Yacht Review
Book now: Check availability
The Sum Up
Hilton Head Island offers a variety of sailing experiences for visitors. The America’s Cup 12-Meter Yacht Afternoon Sail and the Hilton Head Island: America’s Cup Sailing Yacht Cruise provide opportunities to sail on historic racing yachts. The Hilton Head: Private Dolphin Day or Sunset Catamaran Sail and the Hilton Head Yacht Charter: 80-Foot Top Shelf Motor Yacht offer more relaxed options for dolphin watching and sunset cruises. Visitors can choose from these diverse sailing experiences to suit their interests and preferences.