Here are the Hilton Head sailing cruises I’d actually spend an evening on, catamarans and classic monohulls both. Most work Calibogue Sound past the candy-striped Harbour Town lighthouse, where flat water keeps first-timers comfortable. Sunset slots go first, so claim those early.
Embark on a thrilling pirate adventure aboard the legendary Black Dagger! Set sail on Hilton Head Island and experience the swashbuckling fun you've always dreamed of.
Most Popular★ 5.0“The staff was outstanding and made the adventure come to life. The kids were so excited and busy the entire time. Definitely recommend!”
★★★★★★★★★★
668 reviews1 hour 30 minutes (approx.)From $47.99by Pirates of Hilton Head
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Experience the thrill of sailing on a 12-meter yacht in the Americas Cup race! Join us for an unforgettable afternoon sail from Hilton Head. Book now!
★ 4.5“Peter was an excellent captain who encouraged those passengers familiar with sailing to assist in many ways. Seating and movement around boat challenging for anyone with any physical issues but captain tries to accommodate as much as possible. Very beautiful sail and afternoon!”
★★★★★★★★★★
504 reviews1 hour 30 minutes (approx.)From $55.00by Vagabond Cruise
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Glimpse into the enchanting world of dolphins at dusk on the Hilton Head Island Sunset Dolphin Cruise...
★ 4.6“Within minutes we were taken to a shrimp boat that was cleaning fish and there were probably a thousand birds and countless dolphins enjoying the waste. Then we were taken to another area close by and lots of dolphins were swimming around and there was…”
★★★★★★★★★★
412 reviews1.5 hoursFrom $50by Vagabond Cruise Hilton Head
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Awe-inspiring sunset views and the chance to witness the graceful movements of Atlantic bottlenose dolphins make the Hilton Head Sunset Dolphin Watching Cruise a must-try experience.
★ 4.5“Fantastic cruise!! It was a highlight of our trip and helped us appreciate the beauty and natural wonders of the area. The captain and crew were great. Highly recommend and glad we went at sunset.”
★★★★★★★★★★
393 reviews1 hour 30 minutes (approx.)From $50.00by Vagabond Cruise
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Experience the thrill of soaring above the stunning Hilton Head Island with our exhilarating parasailing adventure. Get ready to take flight and create unforgettable memories!
★ 5.0“We had a great time from first getting there with parking lot young lady directing to space to amazing time in air so peaceful and Crew (Jackson and Captain) keeping us safe and providing fun!”
★★★★★★★★★★
352 reviews1 hour 30 minutes (approx.)From $115.17by Island Head
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Experience the magic of the sunset on a private Hilton Head cruise. Sip champagne, watch dolphins play, and create unforgettable memories. Book your 2-hour escape today!
★ 5.0“Great sunset cruise as entire family enjoyed the cruise around the area, with lots of dolphin pods along the way. Captain Neil was great with the kids as well.”
★★★★★★★★★★
260 reviews2 hours (approx.)From $323.10by Hilton Head Boat Charters
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Cruise into the captivating world of Hilton Head Island's Sunset Dinner Cruise for an evening filled with charm, elegance, and...
★ 4.5“Wonderful staff, the cruise was on time. Great photo opportunities.”
★★★★★★★★★★
211 reviews2 hoursFrom $109by Vagabond Cruise Hilton Head
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Embark on the 'Hilton Head Island: Pirate Cruise' aboard the Black Dagger, where a mysterious treasure map leads to unexpected discoveries—what lies at the journey's end?
★ 4.9“My grandchildren loved the trip. The staff were great and kept all the children engaged. Very nice from beginning to end.”
★★★★★★★★★★
174 reviews1.5 hoursFrom $41by Pirates of Hilton Head
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Experience the breathtaking beauty of Hilton Head's sunset on a luxurious dinner cruise. Indulge in a delectable meal while witnessing nature's stunning masterpiece.
★ 4.5“Beautiful sunset and excellent service. Was a little disappointed in the food. Salad and desert was great but our chicken and pork were kinda dry.”
★★★★★★★★★★
172 reviews2 hours (approx.)From $109.00by Vagabond Cruise
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On Hilton Head Island, the America's Cup Sailing Yacht Cruise offers a blend of luxury and adventure that will leave you craving more.
★ 4.8“The young crew was friendly and knowledgeable. We totally enjoyed our experience. Certainly will recommend this excursion to our friends who vacation here in Hilton Head.”
★★★★★★★★★★
152 reviewsFrom $53by Vagabond Cruise Hilton Head
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Intrigued by the allure of soaring above Hilton Head Island's coastline?
★ 4.7“The 5 of us had a wonderful time parasailing! The 2 gentlemen were very nice and so helpful. They talked to us about safety and made sure we were safe. We definitely recommend.”
★★★★★★★★★★
83 reviews1.5 hoursFrom $102by Island Head (Hilton Head Harbor)
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Experience a unique dining experience on our Sunset Hibachi Dinner Cruise. Enjoy delicious food cooked right in front of you while cruising along the beautiful sunset views. Don't miss out!
★ 4.0“The instructions as to where to go to reach the boat were non-existent. When we did find the boat it was over crowded with not enough seating for everyone! The food was plentiful and tasty!”
★★★★★★★★★★
79 reviews2 hours (approx.)From $127.86by Island Head at Broad Creek
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Marvel at the captivating coastal wonders of Hilton Head Island as you embark on a sunset dolphin tour that promises an unforgettable experience.
★ 5.0“Personable tour guide Kim and Captain Mary were lovely hosts! We saw lots of dolphins (including an adorable baby!), a double rainbow, and the sunset from the boat. Everyone had a good time!”
★★★★★★★★★★
77 reviews1 hour 30 minutes (approx.)From $49.99by Lowcountry Watersports
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Experience an unforgettable sunset on a private boat cruise in Hilton Head! Relax, unwind, and soak in the breathtaking views. Book now and create memories that will last a lifetime.
★ 5.0“Great location and house for a golf trip with the fellas! There’s a breakfast spot and mini mart walking distance. The beach is close by and everything else is a short uber ride. Would recommend this location!”
★★★★★★★★★★
63 reviews2 hours (approx.)From $596.49by Island Head
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Immerse yourself in the magic of Hilton Head Island's Dolphin Tour at Sunset & Fireworks Show, where nature's beauty meets explosive excitement.
★ 4.5“Boat was overcrowded and a low boat so whenever the captain sped up, we were doused with water. On a day tour where you’re speeding about you expect to get wet, but not on a sunset cruise to see dolphins and fireworks. Also no notice…”
★★★★★★★★★★
43 reviews2 hoursFrom $69by Lowcountry Watersports
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