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    5. Sail From Historic Charleston to Kiawah Island, South Carolina
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    Sail From Historic Charleston to Kiawah Island, South Carolina

    Sail offshore with licensed captains to Charleston's barrier islands on a full-day adventure

    From$1,712

    Duration

    24 hours

    Ideal For

    Up to 6 people

    Includes

    Sailing yacht, Licensed captains

    Highlights

    Set off from Charleston for an offshore sailing adventure to barrier islands south of the city. Sail with two USCG licensed captains; provision the galley with your favorite food and beverages, with seasick bands available on request.

    • Set Sail For Offshore Waters From Charleston
    • See Barrier Islands From The Ocean
    • Provision The Galley With Your Favorites
    • Relax In A Spacious Cockpit With Views
    • Rely On Two USCG Licensed Master Captains
    • Request Seasick Bands If Needed

    What's Included

    • One 50 ft luxury sailing yacht
    • Two USCG Licensed 100 ton Master Captains with Sailing Auxillary
    • Spacious Cockpit for seeing the sights
    • Fully stocked galley to keep your provisions cold
    • Two Staterooms to sleep 4 guests overnight

    Things to know

    Children must be accompanied by a parent or guardian. Trips are weather dependent and may be adjusted based on wind analysis. Athletic and fit persons are suggested for offshore sailing trips.

    FAQs

    What is the best thing about an offshore sailing adventure?
    The sense of teamwork and accomplishment of working together to sail to another island south in latitude and enjoy the quality time spent with your crew for a truly unique experience for memories of a lifetime!

    Cancellation policy

    Full refund up to 24 hours before departure. Full refund if the operator cancels due to weather or other unforeseen circumstances. No refund within 24 hours; no-shows are charged in full.

    Meeting location

    Saint Johns Yacht Harbor

    Experience provided by Sundog Sailing Charleston
    Experience provided by Sundog Sailing Charleston

    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 #Y76BAK

    One Day Sail

    $1,712

    Captained Charter • All Ages • Up to 6 Passengers

    0

    Two Day Sail

    $3,424

    Captained Charter • All Ages • Up to 6 Passengers

    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

    4.9 stars• 216 reviews

    Review summary

    4.9
    Excellent
    216 reviews•Google Maps

    Captains Janet and Jen have created something special here with their woman-owned sailing operation. The reviews paint a picture of two professionals who genuinely love what they do and know how to share that passion with guests. They prioritize safety while keeping the atmosphere relaxed and fun, making everyone from first-time sailors to bachelorette parties feel completely at ease on the water. What stands out most is the personal touch. The captains take time to explain interesting details about Charleston's waters and marine life, they're approachable and friendly, and guests consistently mention feeling welcomed rather than just shuttled around. The boat itself gets high marks for being well-maintained and comfortable. Several families mention bringing kids who had a blast, while others rave about romantic sunset cruises with drinks. The experience seems equally suited to celebrations, family outings, or anyone checking sailing off their bucket list for the first time.

    What people are saying

    Review 1 of 5
    5/5

    A wonderful adventure. Never been sailing before and what a treat this was. Amazing sunset cruise seeing Charleston. Janet & Jen were so friendly and we felt right at home. Thank you for this experience. I can check it off my bucket list! This is a must!!

    Photo of andrea seiler

    andrea seiler

    August 26, 2025

    Review 1 of 1
    5/5

    A wonderful adventure. Never been sailing before and what a treat this was. Amazing sunset cruise seeing Charleston. Janet & Jen were so friendly and we felt right at home. Thank you for this experience. I can check it off my bucket list! This is a must!!

    Photo of andrea seiler

    andrea seiler

    August 26, 2025

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