Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    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
    Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /All experiences
    3. /Water Activities
    4. /Sailing

    Best results for Sailing in Hilton Head, SC

    Showing 25-37 of 37 results
    4-Hour Sailing Charter in Hilton Head Island
    Sailing

    4-Hour Sailing Charter in Hilton Head Island

    Tailor a private sail with time to anchor and swim

    Tailor a private sail with time to anchor and swim
    5.0 • 379 reviews
    $1,113
    Sunset Sail in Hilton Head Island
    Sailing

    Sunset Sail in Hilton Head Island

    An evening sail with sunset views, sails, and the chance to spot wildlife

    An evening sail with sunset views, sails, and the chance to spot wildlife
    5.0 • 379 reviews
    $138/ person
    2.5-Hour Sailing Charter on Saint Helena Sound
    Sailing

    2.5-Hour Sailing Charter on Saint Helena Sound

    Private sailing with dolphin sightings on Saint Helena Sound

    Private sailing with dolphin sightings on Saint Helena Sound
    5.0 • 39 reviews
    $371
    Saint Helena Island Sunset Sailing Charter
    Sailing

    Saint Helena Island Sunset Sailing Charter

    Private sunset sailing with room below deck for passing weather

    Private sunset sailing with room below deck for passing weather
    5.0 • 39 reviews
    $398
    Dolphin & Monkey Sailing Cruise on Saint Helena Island
    Sailing

    Dolphin & Monkey Sailing Cruise on Saint Helena Island

    Sail quiet Lowcountry waterways while looking for dolphins and Morgan Island monkeys

    Sail quiet Lowcountry waterways while looking for dolphins and Morgan Island monkeys
    5.0 • 39 reviews
    $371
    3.5-Hour Sailing Lesson in Saint Helena Island
    Sailing

    3.5-Hour Sailing Lesson in Saint Helena Island

    Take the helm with a private, customizable keelboat sailing lesson

    Take the helm with a private, customizable keelboat sailing lesson
    5.0 • 39 reviews
    $477
    Sail on a 2-Hour Private Catamaran Charter in Savannah
    Sailing

    Sail on a 2-Hour Private Catamaran Charter in Savannah

    Private 2-hour catamaran sail with champagne for up to 6

    Private 2-hour catamaran sail with champagne for up to 6
    4.9 • 104 reviews
    $525
    Sail on a 2-Hour Private Charter in Savannah
    Sailing

    Sail on a 2-Hour Private Charter in Savannah

    Sail from Wilmington Island on a private 2-hour charter for up to 6 guests

    Sail from Wilmington Island on a private 2-hour charter for up to 6 guests
    4.9 • 104 reviews
    $423
    Fireworks Sailing Cruise in Hilton Head Island
    Sailing

    Fireworks Sailing Cruise in Hilton Head Island

    Sail for 2 hours and watch fireworks from the water

    Sail for 2 hours and watch fireworks from the water
    4.9 • 51 reviews
    $97/ person
    Sail A Rosé Fireworks Cruise In Hilton Head Island
    Sailing

    Sail A Rosé Fireworks Cruise In Hilton Head Island

    2-hour rosé fireworks sail from Broad Creek Marina

    2-hour rosé fireworks sail from Broad Creek Marina
    4.9 • 51 reviews
    $99/ person
    Brunch Sailing Cruise in Hilton Head Island
    Sailing

    Brunch Sailing Cruise in Hilton Head Island

    Savor brunch and drinks aboard a Lowcountry catamaran

    Savor brunch and drinks aboard a Lowcountry catamaran
    4.9 • 51 reviews
    $105/ person
    Watch Shelter Cove Fireworks on a Hilton Head Sail
    Hilton Head

    Watch Shelter Cove Fireworks on a Hilton Head Sail

    Sail at sunset, then anchor to watch Shelter Cove fireworks

    Sail at sunset, then anchor to watch Shelter Cove fireworks
    4.9 • 116 reviews
    $610
    Learn Basic Keelboat Sailing in Savannah
    Sailing

    Learn Basic Keelboat Sailing in Savannah

    Take a 2-day keelboat sailing course with a small group

    Take a 2-day keelboat sailing course with a small group
    4.9 • 104 reviews
    $631/ person
    12