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    1. Local experiences
    2. /Things to do in Mount Pleasant…
    3. /Water Activities
    4. /Sailing
    5. /Overnight Sailing Charter to Kiawah Island
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    Overnight Sailing Charter to Kiawah Island

    Sail offshore from Charleston and anchor overnight near Kiawah Island

    5.0 stars• 312 reviews
    From$1,763incl. taxes and fees

    Duration

    24 hours

    Ideal For

    Up to 6 people

    Includes

    50-ft yacht, 2 captains, galley

    Highlights

    Set sail offshore from Charleston aboard a 50-foot yacht and view barrier islands from the water. Share an overnight sailing adventure with your crew near Kiawah Island.

    • Explore offshore waters and barrier island views
    • Work together with your crew during the sail
    • Stock the galley with your own food and beverages
    • Pack layers, sun protection, medications, and an overnight bag
    • Request seasickness bands if needed

    Itinerary

    • 9am departure
    • Day Sail Offshore to Kiawah Island, anchor out overnight
    • Depart Yacht at Bohicket Marina at 9 am or decide to sail back to Charleston

    What's Included

    • 50-foot sailing yacht
    • Two licensed master captains
    • Spacious cockpit
    • Galley refrigeration for provisions
    • Two staterooms sleeping up to four overnight

    Important details

    • Arrive 10 minutes before departure
    • Children must be accompanied by a parent or guardian
    • Complete a waiver before arrival
    • Offshore sailing is suggested for athletic, fit participants
    • Departure depends on forecast wind conditions

    Cancellation Policy

    Receive a full refund with at least 24 hours' notice. No refunds within 24 hours of departure, and no-shows are charged the full price. Receive a full refund if the operator cancels due to weather or other unforeseen circumstances.

    FAQs

    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!

    Meeting details

    St. John's Yacht Harbor, 2408 Maybank Hwy, Johns Island, SC 29455

    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 1-877-GREET-WELL

    Report an issue

    Reference #Y76BAK

    One Day Sail

    $1,763

    Captained Charter • All Ages • Up to 6 Passengers

    0

    Two Day Sail

    $3,475

    Captained Charter • All Ages • Up to 6 Passengers

    0

    Four Day sail

    $51

    Captained Charter • All Ages • Up to 6 Passengers

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

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      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    312 reviews•Google Maps
    259
    2
    0
    1
    2

    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 3
    5/5

    We had an incredible sunset cruise with Captains Jen and Janet. It was our favorite thing on our girls weekend to Charleston. I’ve done a decent amount of boat tours when vacationing, as I love to get out on the water, and this one was excellent. The boat was beautiful and Captains Jen and Janet were knowledgeable and friendly. It was such a relaxing and enjoyable ride. Couldn’t recommend more! Next time in Charleston, I would hands down do this again!

    Photo of Kenly Fischer

    Kenly Fischer

    July 6, 2026

    Review 1 of 1
    5/5

    We had an incredible sunset cruise with Captains Jen and Janet. It was our favorite thing on our girls weekend to Charleston. I’ve done a decent amount of boat tours when vacationing, as I love to get out on the water, and this one was excellent. The boat was beautiful and Captains Jen and Janet were knowledgeable and friendly. It was such a relaxing and enjoyable ride. Couldn’t recommend more! Next time in Charleston, I would hands down do this again!

    Photo of Kenly Fischer

    Kenly Fischer

    July 6, 2026

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