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    Vagabond Cruise

    Vagabond Cruise

    4.8 • 7.6K reviews
    Hilton Head Island, SC

    Anchored beneath the iconic Harbour Town lighthouse, Vagabond Cruise has been Hilton Head’s original excursion company since 1968. Step onto a classic yacht, swift ferry, or America’s Cup racer and let veteran captains reveal hidd...

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    Private Afternoon Sightseeing Cruise in Hilton Head

    Enjoy a 2-hour private cruise for up to 10 guests along the Carolina coast

    $422.65
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    Private Yacht Charter in Hilton Head

    Cruise Hilton Head's coastline on a 2-hour private charter for up to six guests

    $422.65
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    Private Sunset Cruise in Hilton Head with Captain

    Enjoy a private 2-hour cruise for up to six with coastal views and complimentary beverages

    $529.65
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    Private Sunset Cruise for Up to 6 in Hilton Head

    Savor Lowcountry views on a private 2-hour sunset cruise with complimentary drinks

    $636.65
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    Private Sandbar Cruise in Hilton Head

    Escape to a secluded sandbar on a 3.5-hour private cruise for up to six guests

    $636.65
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    Hilton Head Private Boat Tour with Dolphins

    Enjoy a private morning charter with a knowledgeable captain, scenic views, and possible dolphin sightings

    $422.65
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    Hilton Head Dolphin Cruise with Donut Bar

    Enjoy a narrated dolphin cruise with a complimentary donut bar

    From$48person
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    Sunset Shrimp Trawling on Hilton Head Island

    Join a working shrimp boat at sunset, learn about local marine life, and maybe take home fresh shrimp

    From$58person
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    Hilton Head Sunset Dinner Cruise with Dining

    Enjoy a plated three-course dinner with panoramic sunset views in a climate-controlled cabin

    From$96person
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    Private Crabbing Charter in Hilton Head

    Learn to bait pots and sort the catch on a fun 2-hour boat trip

    From$1,070person
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    90-Minute Lowcountry Sunset & Dolphin Cruise

    Enjoy a narrated 90-minute cruise with guaranteed dolphin sightings as the sun sets over the Lowcountry.

    From$48person
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    Hilton Head Island Ocean Dolphin Cruise

    Spot Atlantic bottlenose dolphins on Hilton Head’s only narrated ocean cruise.

    From$42person
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    Daufuskie Island Boat Tour from Hilton Head

    Enjoy a narrated cruise and three hours of free time to explore historic Daufuskie Island

    From$42person
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    Hilton Head Sailing on Historic America's Cup Yacht

    Join the crew or relax on a 1.5-hour Hilton Head coastal sail aboard a historic America’s Cup yacht

    From$53person
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    Private 2-Hour Yacht Charter in Hilton Head Island

    Explore coastal gems on an intimate six-guest charter with a dedicated captain and flexible shore time

    From$545
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    Daufuskie Island Ferry with 4.5 Hour Exploration

    Cruise to historic Daufuskie Island and explore for 4.5 hours at your own pace.

    From$1,070person
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    Hilton Head Sunset Sail on Stars & Stripes

    Watch Hilton Head's vibrant sunset while relaxing or helping crew aboard the historic Stars & Stripes

    From$74person
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    Catch & Keep Fresh Shrimp on 2-Hour Cruise

    Learn how shrimp are caught and take home part of the catch on this 2-hour educational cruise.

    From$48person

    Review summary

    4.8
    Excellent
    7.6K reviews•Google Maps

    This cruise operation clearly has its act together when it comes to hospitality and wildlife viewing. The crew stands out as a major highlight across the board, with multiple guests praising Captain Windows and Captain Peter by name for their warmth, knowledge, and genuine passion for what they do. Whether you're on the Dolphins and Donuts morning cruise, a sunset dinner sail, or one of their day trips to Savannah or Daufuskie Island, the staff consistently checks in on passengers and creates a welcoming atmosphere. Dolphin sightings are practically guaranteed, with some groups spotting over 20, and the crew takes time to educate guests about the marine life while ensuring everyone gets good photo opportunities. The food on dinner cruises gets mixed feedback. Most guests are pleasantly surprised by how good the salads and desserts are, but one detailed review noted that all the protein options came out dry and disappointing. The bigger consistent complaint involves comfort, specifically the heat and lack of adequate shading while the boat is docked or during sunny portions of the journey. Missing or insufficient window shades became an issue for multiple passengers. Drink prices also raised some eyebrows. Still, the overall experience seems to win people over, especially families and repeat customers who return year after year for specific routes. Just book early if you're eyeing that afternoon Daufuskie trip, as it fills up fast.

    What people are saying

    Review 1 of 4
    5/5

    Fun time sailing with Peter and crew. Pro tip-- sit in the back near the captain-

    Photo of Steve Elliott

    Steve Elliott

    April 3, 2026

    Review 1 of 1
    5/5

    Fun time sailing with Peter and crew. Pro tip-- sit in the back near the captain-

    Photo of Steve Elliott

    Steve Elliott

    April 3, 2026