Hilton Head
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 kids firing the water cannons at stinky Pete. There needs to be more shade on the boat and they should let the kids wet each other.”
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668 reviews1 hour 30 minutes (approx.)From $47.99by Pirates of Hilton Head
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!”
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504 reviews1 hour 30 minutes (approx.)From $55.00by Vagabond Cruise
Glimpse into the enchanting world of dolphins at dusk on the Hilton Head Island Sunset Dolphin Cruise...
★ 4.6“This was our second sunset dolphin cruise with Vagabond. Each sailings was different but neither disappointed. We learned something new and met interesting fellow travelers.”
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412 reviews1.5 hoursFrom $50by Vagabond Cruise Hilton Head
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“What an amazing experience!!! Captain and the Crew were amazing and we got to see many dolphins. The highlight was a 2 sunset views and a bald eagle that basically hovered over the boat!”
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393 reviews1 hour 30 minutes (approx.)From $50.00by Vagabond Cruise
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“This was a bucket list and i am so glad i did it with the crew i did!!! Nathan was funny and very calming for first timers like everyone on the boat.”
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352 reviews1 hour 30 minutes (approx.)From $115.17by Island Head
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“Fantastic experience! Capt Neil was wonderful!m, very knowledgeable and made safety a priority!!!!!!”
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260 reviews2 hours (approx.)From $323.10by Hilton Head Boat Charters
Cruise into the captivating world of Hilton Head Island's Sunset Dinner Cruise for an evening filled with charm, elegance, and...
★ 4.5“Everything was amazing from start to finish! Beautiful views, but unfortunately no dolphin sighting. Complements to the chef as the food was delicious!! 10/10 experience”
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211 reviews2 hoursFrom $109by Vagabond Cruise Hilton Head
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“Great time! My 7yo daughter has some sensory issues and loud noises and surprises can be a little stressful. The staff did a wonderful job of recognizing when she was comfortable sitting back next to me and observing and when she felt like being engaged…”
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174 reviews1.5 hoursFrom $41by Pirates of Hilton Head
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“Excellent Service and very good meal. Crew is friendly and attentive. Cruise was a pleasure. Ship very clean.”
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172 reviews2 hours (approx.)From $109.00by Vagabond Cruise
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“Wonderful experience. Captain and crew were very friendly, knowledgeable and helpful. We would definitely recommend them”
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152 reviewsFrom $53by Vagabond Cruise Hilton Head
Intrigued by the allure of soaring above Hilton Head Island's coastline?
★ 4.7“It was so fun! My first time and I would definitely do it again! Our guides were professional and masters!!! Thanks!”
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83 reviews1.5 hoursFrom $102by Island Head (Hilton Head Harbor)
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 chefs put on a great show. The food was excellent and we saw a couple dolphins and the trip was smooth”
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79 reviews2 hours (approx.)From $127.86by Island Head at Broad Creek
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“This was a great experience enjoyed by my family. We saw lots of dolphins actually doing lots of flips”
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77 reviews1 hour 30 minutes (approx.)From $49.99by Lowcountry Watersports
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“Captain Steve was FANTASTIC! We had great views, personalized service. We had to reschedule due to bad weather, but he made it easy!Great evening!”
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63 reviews2 hours (approx.)From $596.49by Island Head
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“Wunderschöne Tour mit sehr netten Guids.”
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43 reviews2 hoursFrom $69by Lowcountry Watersports
Hilton Head runs on its tides; dolphins, salt marsh, and slow boat days are the whole point.