Sailing options on Hilton Head Island let you experience the Lowcountry waters in style.
Two standout choices await: a hands-on sailing adventure aboard a 39-foot America’s Cup yacht, where you’ll help crew the vessel, or a 1.5-hour journey on an authentic racing yacht through Calibogue Sound.
I especially love the catamaran tours – they’re intimate, run 2-2.5 hours, and consistently deliver with dolphin sightings and spectacular sunsets.
All tours feature professional captains who know these waters inside and out, and the included amenities make them an excellent value.
Let’s explore the best sailing tours Hilton Head has to offer.
Key Points
- Enjoy a 90-minute cruise along the Lowcountry coastline and Intracoastal Waterway on a USCG-approved 39-foot yacht with the opportunity to participate as a crew member.
- Experience a 1.5-hour adventure on a former America’s Cup racing yacht and enjoy picturesque views of Calibogue Sound with potential dolphin sightings.
- Set out on a private 2-2.5 hour dolphin day or sunset catamaran sail, featuring a private catamaran, complimentary water and snacks, and hotel pickup/drop-off.
- Witness the expertise of the sailing crew who provide instruction and assistance throughout the cruise, ensuring an engaging and informative experience.
- Benefit from various booking options, including free cancellation up to 24 hours before the tour, limited capacity, and advance booking recommendations to secure your desired sailing experience.
Americas Cup 12-Meter Yacht Afternoon Sail From Hilton Head
On the Americas Cup 12-Meter Yacht Afternoon Sail from Hilton Head, you’ll enjoy a 90-minute cruise along the Lowcountry’s scenic coastline and Intracoastal Waterway.
This USCG-approved 39-foot yacht can accommodate up to 20 passengers, though capacity is typically limited to ensure proper social distancing. During the sail, you’ll have the opportunity to participate as a crew member, with the option to purchase alcoholic beverages.
The departure point is the Vagabond Cruise reservation office near the Harbour Town Lighthouse, and free cancellation is available up to 24 hours before the experience.
While the yacht isn’t wheelchair accessible, service animals are allowed, and a moderate level of physical fitness is required.
Customer reviews highlight the friendly crew, engaging captain, and beautiful scenery, with many guests spotting dolphins along the way.
However, some have reported booking issues and refund challenges, so it’s essential to review the policies carefully before reserving your spot.
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
Experience the thrill of sailing on a former America’s Cup racing yacht during the Hilton Head Island: America’s Cup Sailing Yacht Cruise. This 1.5-hour adventure allows you to participate in raising the sails, steering the yacht, and taking in the picturesque views of Calibogue Sound, with the possibility of spotting dolphins.
The crew, with their extensive sailing experience, will provide instruction and assistance throughout the journey. The yacht can accommodate up to a limited number of participants, so booking in advance is recommended to secure your spot. Priced from $52.95 per person, the cruise offers a memorable experience, as evidenced by the exceptional 4.8/5 rating based on 139 reviews.
Before the departure, arrive 45 minutes early at the local partner’s office below the Harbour Town Lighthouse, and be prepared to present your mobile or printed boarding pass.
Keep in mind that there’s a $9 cash-only vehicle entry fee for non-resort guests, valid for the entire day.
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
Set out on a private dolphin day or sunset catamaran sail in the serene waters surrounding Hilton Head. Priced at $379.18 for up to 6 participants, this 2-2.5 hour excursion offers the chance to spot dolphins and birds in their natural habitat, learn about the local salt marsh ecosystem and history, and enjoy a personalized experience with friends or family.
The tour includes a private catamaran, complimentary water and snacks, a cooler with ice, and life jackets. Hotel pickup and drop-off are also provided, with the meeting point at the first slip of the G dock on the wharf, near the King Neptune statue.
Reviewers praise the knowledgeable and relaxed captain, rating the overall experience 4.6/5 and highlighting the excellent transportation and value for money.
Whether you choose a day or sunset sail, this private catamaran tour promises an unforgettable encounter with Hilton Head’s natural wonders.
Read our full review: Hilton Head: Private Dolphin Day or Sunset Catamaran Sail Review
Book now: Check availability
Recap
You’ll find a variety of sailing experiences on Hilton Head Island, from thrilling America’s Cup yacht cruises to serene dolphin or sunset catamaran sails. Whether you’re seeking an adventure or a leisurely excursion, there’s something to suit your preferences. These activities offer unique perspectives of the island’s stunning natural beauty and are sure to create lasting memories of your time on Hilton Head.