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    Island Head- Hilton Head Harbor

    Island Head- Hilton Head Harbor

    4.8 • 817 reviews
    Hilton Head Island, SC

    Island Head invites you to see Hilton Head the way the dolphins do—out on the water. Founded by Michael and Taylor, two visitors who loved the Lowcountry enough to make it home, this locally owned team pairs seasoned captain skill...

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    Book Island Head- Hilton Head Harbor

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    Hilton Head Private Sunset Cruise

    Savor low country sunset colors on a private cruise with a captain

    $549
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    Guided Paddleboard Tour on Skull Creek

    Explore Skull Creek on a guided SUP tour and learn essentials in a relaxed 1-hour session

    $40person
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    Private Water Ski Adventure Day

    Customize your own water sports outing with tubing, wakeboarding, and more for up to six passengers.

    From$399
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    Private Tubing Adventure in the Low Country

    Enjoy thrilling tubing with a dedicated captain and space for up to six passengers.

    From$250
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    Hilton Head Parasailing Adventure

    Soar above Calibogue Sound for panoramic island views and an exhilarating flight experience.

    From$95person

    Review summary

    4.8
    Excellent
    817 reviews•Google Maps

    Looking for a memorable water adventure in Hilton Head? This parasailing operation seems to nail the fundamentals that matter most. The crew consistently earns praise for being professional, friendly, and genuinely skilled at what they do. Multiple reviewers mention feeling nervous beforehand, especially those with height anxieties, but the captains and first mates apparently have a gift for putting people at ease with clear instructions and calming reassurance. The actual experience delivers too, with stunning views and the option for a refreshing "toe dip" in the water that gets special mentions from summer visitors. They also offer sunset cruises with dolphin sightings and private charters for larger groups wanting to add tubing or kneeboarding to the mix. The glowing feedback comes from everyone from first-timers to families with teens, and booking appears straightforward across the board. That said, there's one consistent hiccup worth noting: the photo and video situation feels confusing. One disappointed reviewer never received promised footage despite being told it would be sent, and there seems to be unclear communication about whether you need to purchase a package upfront or if it comes standard. It's a shame because people clearly want those keepsake shots from their adventure. Beyond that minor frustration, the overwhelming consensus is that this outfit runs a safe, fun operation with experienced crew members who genuinely care about creating a great experience, whether you're conquering a fear or just seeking an adrenaline rush.

    What people are saying

    Review 1 of 5
    5/5

    ⭐️⭐️⭐️⭐️⭐️ An Unforgettable Sunset Cruise Experience! As part of our health retreat, I treated my clients to a private sunset cruise—and it was nothing short of magical. Captain John was incredible: welcoming, knowledgeable, and made us feel completely at ease from the moment we stepped aboard. The sea was calm, the sky was painted with vibrant sunset hues, and to top it all off, we were lucky enough to see dolphins playing in the surf! It was the perfect way to unwind, connect, and soak in the beauty of nature together. Every single guest walked away feeling relaxed, inspired, and grateful for the experience. I highly recommend this cruise for anyone looking to add something truly special to their wellness retreat or coastal getaway. A huge thank you to Captain John for making it so memorable—we’ll definitely be back!

    Photo of Charlene Myers-Sponholtz

    Charlene Myers-Sponholtz

    June 7, 2025

    Review 1 of 1
    5/5

    ⭐️⭐️⭐️⭐️⭐️ An Unforgettable Sunset Cruise Experience! As part of our health retreat, I treated my clients to a private sunset cruise—and it was nothing short of magical. Captain John was incredible: welcoming, knowledgeable, and made us feel completely at ease from the moment we stepped aboard. The sea was calm, the sky was painted with vibrant sunset hues, and to top it all off, we were lucky enough to see dolphins playing in the surf! It was the perfect way to unwind, connect, and soak in the beauty of nature together. Every single guest walked away feeling relaxed, inspired, and grateful for the experience. I highly recommend this cruise for anyone looking to add something truly special to their wellness retreat or coastal getaway. A huge thank you to Captain John for making it so memorable—we’ll definitely be back!

    Photo of Charlene Myers-Sponholtz

    Charlene Myers-Sponholtz

    June 7, 2025