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Island Head Sailing

Luxury Sailing Charters in Hilton Head Island, South Carolina

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Discover Hilton Head Island with our Public Cruises

Sail Into the Best Part of Your Day

Step aboard our custom-built 36-foot sailing catamaran for a one-of-a-kind Hilton Head Sailing Charter experience. Whether you’re chasing the morning breeze or watching the sky melt into sunset, our 24-passenger vessel is the perfect setting for unforgettable memories — complete with a restroom onboard for your comfort.

Choose from our signature public Hilton Head Island cruises:

• Brunch Under Sail – A relaxed morning sail with breakfast treats, mimosas, wine, and beer.
• Golden Hour Sail – A stunning two-hour Hilton Head sunset cruise with appetizers and our featured Rosé.
• Day Sail – Let the sails do the talking. No food, no fuss — just the pure joy of sailing.

Your front-row seat to Hilton Head’s beauty is waiting — let’s set sail.

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Bonjour Private Cruise

From $799 - $7,990

Step aboard Bonjour, Hilton Head’s newest and most luxurious charter boat, built for unforgettable experiences on the water. This brand-new vessel is perfect for family gatherings, bachelor & bachelorette parties, company outings, private charters, dolphin cruises, and sunset tours.

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  • All Ages
  • 1-10 Hours
  • Up to 35 Passengers
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Perfect for your Private Events!

Our 36-foot custom-built sailing catamaran is built for breezy fun, smooth cruising, and unforgettable moments. It seats up to 24 guests and includes a restroom onboard for added comfort.

Planning something special? Our catamaran is also available for private charters, ideal for family reunions, birthday parties, bachelor/bachelorette celebrations, corporate events, or just a great time with great people.

Celebrate any occasion or just enjoy a custom sailing experience for your group. Ideal for:

• Family Reunions
• Birthday Parties
• Bachelor/Bachelorette Groups
• Corporate Outings
• Just Because Moments

All Hilton Head sailing charters include a licensed captain and first mate, onboard beverage service (optional), and a whole lot of good vibes.

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Discover More Things to Do in Hilton Head Island

Join Island Head Sailing for a Fun and Memorable Adventure in Hilton Head Island

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a man standing next to a body of water
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a group of people in a boat on a body of water
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Rated ★★★★★ on Google and Tripadvisor

Island Head Sailing
"Wonderful excursion!"

Professional crew! Beautiful boat and clean, felt very safe and great music! Captain Steve and Nate were great! Would do it again!

– CarrieTee2002 • Tripadvisor
Island Head Sailing
"Recommend 100%"

Daryl, Donny and Jose made the entire experience for us! They were professional but also so down to earth and fun! We got to see the sunset, watch dolphins and eat delicious food all while being entertained.

– Coastal Comforts Cleaning • Google Reviews
Island Head Sailing
"Great memories"

Steve and Nate were terrific!!! What a day! What an experience!! I would absolutely recommend to anyone wanting a great time on the Island to use Island Head!!!

– Gregory M • Tripadvisor
Island Head Sailing
"Wonderful sunset cruise with Captain Steve!"

We took it on our last day and saw a gorgeous sunset. Highly recommend. We ate at the nearby Sunset Grill afterwards, which is right at the marina and also excellent.

– Sara Melzer • Google Reviews
Island Head Sailing
"Highly recommend"

We had such a great time ! Our Captain was so informative and so nice! I would definitely do this again! Such beautiful views of the area.

– Heather O • Tripadvisor
Island Head Sailing
"We had such an awesome time!"

The crew members were fun yet they took their job seriously. I felt safe and secure. 10/10 experience and I would absolutely recommend

– The Finance Queen Inc. • Google Reviews