Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Bluffton…
    3. /Water Activities
    4. /Sailing
    5. /Afternoon Sailing Charter in Hilton Head Island
    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
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Afternoon Sailing Charter in Hilton Head Island

    Take the helm or relax on a private afternoon sail

    5.0 stars• 379 reviews

    Duration

    2 hours

    Ideal For

    Up to 12 people

    Includes

    Water, soda, sailing instruction

    Highlights

    Set out for a private afternoon on the water, with the option to take part in sailing or simply relax. Learn about the island and local wildlife as you sail.

    • Take the helm and help handle sails if you wish
    • Learn about sailing, the island, and local wildlife
    • Watch for dolphins near the marina
    • Bring small soft-sided coolers, drinks, or food

    Itinerary

    We will board and conduct a safety brief. Followed by motoring out to our sailing grounds, raising the sails and truly sailing without the motor (wind providing). Enjoy the art of sailing and get involved in hoisting the sails, handling lines, steering the boat or simply kick back and enjoy the ride. At the end of the trip, we will take the sails down and motor back to the marina. The trip in and out of the marina is one of the best times to spot dolphins and get them close to the boat. This activity is perfect for all ages to enjoy!

    What's Included

    • Water
    • Coke
    • Diet Coke
    • Sprite

    Important details

    • Arrive at the marina 15 minutes before departure
    • Children under 16 must be accompanied by a parent or guardian
    • Requires a long walk along the docks, four steps up to the boat, and two large steps down into it
    • Do not bring glass containers or red liquids, including red wine
    • Do not use spray sunscreen on board
    • For groups of more than 6, the boat is rented bareboat and requires your own crew or an optional hired crew

    Cancellation Policy

    Full refund with at least 72 hours' notice. Cancellations within 72 hours may receive a partial refund. Full refund if the operator cancels due to weather or other unforeseen circumstances.

    Product ID: Q8M7GB

    FAQs

    You may bring a small soft-sided cooler, drinks, or food. Dress for current weather conditions. Do not bring glass containers, red liquids such as red wine, or spray sunscreen.

    Access involves a long walk along the docks, four standard-height steps up to the boat, and two large steps down into it.

    Yes. Children under 16 must be accompanied by a parent or guardian.

    Meeting details

    Skull Creek Marina, 1 Waterway Lane, Hilton Head Island, SC 29926

    Experience provided by Anchors Away Sailing Charters

    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

    Private Charter

    $524.70

    Accommodates up to 6 passengers, All ages welcome!

    0

    Bareboat - more then 6 passengers

    $715.50

    Bring your own captain , or hire one of our captains.

    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

    What people are saying

    Review 1 of 4
    5/5

    Pierce baby! LOVE. My experience was amazing! Book them

    Photo of Michelle Miner

    Michelle Miner

    July 15, 2026

    Review 1 of 1
    5/5

    Pierce baby! LOVE. My experience was amazing! Book them

    Photo of Michelle Miner

    Michelle Miner

    July 15, 2026

    Nearby activities

    Afternoon Sailing Charter in Hilton Head Island
    Sailing

    Afternoon Sailing Charter in Hilton Head Island

    A breezy private sail with island insights and room to unwind

    A breezy private sail with island insights and room to unwind
    5.0 • 379 reviews
    $451
    Afternoon Sailing Charter in Hilton Head Island
    Sailing

    Afternoon Sailing Charter in Hilton Head Island

    Shape your afternoon around ocean sailing or time in the water

    Shape your afternoon around ocean sailing or time in the water
    5.0 • 379 reviews
    $1,276& up
    Hilton Head Island Morning Dolphin Sailing Charter
    Sailing

    Hilton Head Island Morning Dolphin Sailing Charter

    A calm morning sail for coastal views and wildlife watching

    A calm morning sail for coastal views and wildlife watching
    5.0 • 379 reviews
    $504& up
    Morning Sailing Charter in Hilton Head Island
    Sailing

    Morning Sailing Charter in Hilton Head Island

    Sail Hilton Head’s morning waters and look for coastal wildlife

    Sail Hilton Head’s morning waters and look for coastal wildlife
    5.0 • 379 reviews
    $419
    Sunset Sailing Charter in Hilton Head Island
    Sailing

    Sunset Sailing Charter in Hilton Head Island

    An evening sail for sunset views and wildlife watching

    An evening sail for sunset views and wildlife watching
    5.0 • 379 reviews
    $493
    Hilton Head Island Afternoon Sailing Cruise
    Sailing

    Hilton Head Island Afternoon Sailing Cruise

    Share a small-group sail and take the helm if you like

    Share a small-group sail and take the helm if you like
    5.0 • 379 reviews
    $101/ person