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    1. Local experiences/
    2. Chapel Hill, NC/
    3. Water Activities/
    4. Sailing/
    5. Two-Hour Afternoon Sail
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    Two-Hour Afternoon Sail

    Ride afternoon breezes across the inlet with a brief ocean sail when conditions allow

    From$93/ person

    Highlights

    Set out for an easygoing afternoon sail aboard an 18-ton sailboat. Cross Masonboro Inlet and, when seas allow, enjoy a brief ocean run.

    • Experience steady afternoon winds for a smooth ride
    • Cross Masonboro Inlet on a classic sailboat
    • Enjoy a brief ocean sail when conditions allow
    • Bring your favorite drinks and snacks
    • Sip complimentary bottled water and ginger ale
    • Choose public or private charter options

    What's Included

    • Bottled water
    • Ginger ale

    Things to know

    Arrive at the departure docks at least 15 minutes before your cruise. Children under 6 are not recommended. Adults 21+ may bring beer and wine onboard. All passengers must sign a liability release before departure.

    Cancellation policy

    Full refund with at least 5 days' notice. Full refund if the operator cancels due to weather or unforeseen circumstances. No-shows are charged the full price.

    Experience provided by Shamrock Sailing
    Experience provided by Shamrock Sailing

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Reference #S2XJHG

    Child

    $93.81

    Under 12 years old

    0

    Private Charter

    $467.15

    Base price includes 2 people

    0

    Guest

    $107.88

    0

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

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    Discover what we've curated for you

    Duration

    2 Hours

    Includes

    Bottled water, Ginger ale

    5.0 stars• 278 reviews

    Review summary

    5.0
    Excellent
    278 reviews•Google Maps

    Captain Jim creates sailing experiences that clearly leave a lasting impression on his guests. Couples celebrating anniversaries, first-time sailors, even self-proclaimed "not a people person" types find themselves completely at ease with him. His infectious enthusiasm for being on the water combines with genuine expertise that goes way beyond surface-level tour guide facts. He shares detailed insights about local history, ecosystems, and wildlife in a conversational way that keeps guests engaged throughout the trip. Many visitors specifically mention his ability to explain complex topics with real depth and passion. The sailing itself delivers those magical moments people hope for: dolphins swimming alongside the boat, stunning sunsets over the water, and the unique sensation of cutting through waves under sail. Captain Jim's flexible and accommodating, working around weather issues to reschedule when needed. He often lets interested guests take the helm, which turns a lovely outing into something truly memorable. The Shamrock is well-maintained and comfortable, whether you're cruising the Intracoastal Waterway or heading out to open water off Wrightsville Beach. Return visitors are common, with some guests coming back multiple times and considering Jim a friend by their third trip.

    What people are saying

    Review 1 of 5
    5/5

    We were gifted a trip for our wedding and we we had so much fun with Captain Jim. So respectful and professional the whole time you are with him. He has so much experience with sailing and was constantly giving us information about the surrounding areas and wildlife. We had a constant conversation with him throughout the whole trip. The sunset was amazing and the whole trip was relaxing and peaceful I would 1000 percent recommend booking with him it was worth it!

    Photo of Brannon “Brannon Kennedy” Kennedy

    Brannon “Brannon Kennedy” Kennedy

    September 22, 2025

    Review 1 of 1
    5/5

    We were gifted a trip for our wedding and we we had so much fun with Captain Jim. So respectful and professional the whole time you are with him. He has so much experience with sailing and was constantly giving us information about the surrounding areas and wildlife. We had a constant conversation with him throughout the whole trip. The sunset was amazing and the whole trip was relaxing and peaceful I would 1000 percent recommend booking with him it was worth it!

    Photo of Brannon “Brannon Kennedy” Kennedy

    Brannon “Brannon Kennedy” Kennedy

    September 22, 2025

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