Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Charleston…
    3. /Water Activities
    4. /Sailing
    5. /Charleston 2.5-Hour Private Sailing Charter
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Product image 7
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Charleston 2.5-Hour Private Sailing Charter

    Sail Charleston Harbor's landmark-lined waterfront aboard a private charter

    5.0 stars• 134 reviews
    From$530incl. taxes and fees

    Duration

    2.5 hrs

    Ideal For

    Up to 6 people

    Includes

    Bottled water, souvenir cups

    Highlights

    Sail aboard Esprit de Joy for a private afternoon on Charleston Harbor. Pass the Charleston Battery and downtown peninsula while taking in harbor landmarks.

    • Explore views of Castle Pinckney, Ravenel Bridge, USS Yorktown, and Fort Sumter
    • Bring your own drinks and snacks to enjoy while underway
    • Pack sunscreen, a hat, sunglasses, and a light jacket for changing conditions
    • Capture the harbor and downtown Charleston from the water

    What's Included

    • Chilled bottled water
    • Onboard cooler
    • Plastic champagne flutes
    • Souvenir cups
    • Cutlery

    Important details

    • Arrive 15 minutes before departure to allow for a timely start
    • Wear footwear with non-marking soles
    • Prepare to spend most of the charter outdoors
    • Do not bring glass bottles aboard
    • Do not park at the marina, where visitor vehicles may be ticketed and towed
    • Paid parking at the adjacent Courtyard by Marriott is $10 per day if you drive

    Cancellation Policy

    If the captain cancels due to hazardous weather, reschedule your charter or receive a refund. No-shows are charged the full price.

    FAQs

    Bring sunscreen, a hat, sunglasses, and your camera. Dress for cooler and breezier conditions on the water, and consider a light jacket on windy or cooler days. Wear footwear with a non-marking sole, and plan to be outside most of the time.

    Bring your own drinks and snacks if you’d like. You’ll also have a cooler with bottled water on board, and ice is available on request. Do not bring glass bottles.

    Use the onboard restroom (head) if needed, but plan to use the marina restroom before you board.

    Meeting details

    Harborage at Ashley Marina, 33 Lockwood Dr., Charleston, SC 29401

    Experience provided by Charleston Harbor Sailing LLC

    Related locations

    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 #7FNNAX

    Private Charter

    $530

    Up to 6 People

    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

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    134 reviews•Google Maps
    129
    0
    0
    0
    0

    Captain Will is the clear star of this operation, and reviewers can't say enough good things about him. Knowledgeable, laid-back, and genuinely fun to be around, he has a way of making every outing feel personal rather than touristy. People keep coming back to the same word: effortless. The boat itself is well-maintained and comes equipped with a bathroom and refrigerator, which is a nice touch for longer outings. The harbor views, dolphin sightings, and that classic Lowcountry scenery have a way of turning a sailing trip into a trip highlight. Guests have used this for anniversaries, birthdays, bachelorette parties, client entertaining, and plain old vacation fun, and it seems to land well across all of them. Even one group that hit less-than-ideal weather reported having a great time, which says something about the overall experience holding up beyond just perfect conditions. With a near-flawless rating across a large number of reviews, this one is about as consistent as it gets. If you want a relaxed, scenic way to see Charleston from the water with a captain who actually makes it enjoyable, this is a very easy recommendation.

    What people are saying

    Review 1 of 5
    5/5

    Thoroughly enjoyed our time sailing with Captain Will. Thankful for a great sunset tour and conversation. Highly recommend, they are a small company and passionate about what they do and it shows.

    Photo of Jessika TANNER

    Jessika TANNER

    June 28, 2026

    Review 1 of 1
    5/5

    Thoroughly enjoyed our time sailing with Captain Will. Thankful for a great sunset tour and conversation. Highly recommend, they are a small company and passionate about what they do and it shows.

    Photo of Jessika TANNER

    Jessika TANNER

    June 28, 2026

    Nearby activities

    Charleston Sunset Charter
    Sailing

    Charleston Sunset Charter

    Sail Charleston Harbor at sunset with your own drinks and snacks

    Sail Charleston Harbor at sunset with your own drinks and snacks
    5.0 • 134 reviews
    $583
    Cruise Charleston Harbor at Sunset
    Boat Tours

    Cruise Charleston Harbor at Sunset

    Take a private sunset cruise in Charleston Harbor with your crew

    Take a private sunset cruise in Charleston Harbor with your crew
    $795& up
    Bachelorette Harbor Cruise in Charleston
    Yacht Charters

    Bachelorette Harbor Cruise in Charleston

    Private party boat with a cabin, restroom, and room to celebrate

    Private party boat with a cabin, restroom, and room to celebrate
    $636& up
    Cruise Charleston Harbor on a Private Bring-Your-Own-Drinks Charter
    Boat Tours

    Cruise Charleston Harbor on a Private Bring-Your-Own-Drinks Charter

    Customize a private Charleston Harbor cruise and bring your own drinks

    Customize a private Charleston Harbor cruise and bring your own drinks
    $636& up
    Daytime Charleston Harbor Sail
    Sailing

    Daytime Charleston Harbor Sail

    Sail Charleston Harbor on a private 2.5-hour charter for up to 6 guests

    Sail Charleston Harbor on a private 2.5-hour charter for up to 6 guests
    5.0 • 290 reviews
    $557
    2.5-Hour Daytime Sail Charter in Charleston Harbor
    Sailing

    2.5-Hour Daytime Sail Charter in Charleston Harbor

    Sail Charleston Harbor on a private 36 ft Beneteau—up to 6 guests

    Sail Charleston Harbor on a private 36 ft Beneteau—up to 6 guests
    5.0 • 290 reviews
    $557