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    1. Local experiences
    2. /All experiences
    3. /Sailing

    Best results for Sailing

    Showing 481-496 of 496 results
    Private 3-Hour Sailing Lesson in Key West
    Key West, FL

    Private 3-Hour Sailing Lesson in Key West

    Choose your boat and learn to sail with a private instructor in Key West

    Choose your boat and learn to sail with a private instructor in Key West
    4.9 • 49 reviews
    $143& up
    Sail a Historic Schooner Sunset Cruise in Key West
    Key West, FL

    Sail a Historic Schooner Sunset Cruise in Key West

    Catch the Key West sunset on the historic schooner Malabar X

    Catch the Key West sunset on the historic schooner Malabar X
    4.8 • 377 reviews
    $124/ person
    Private Schooner Sunset Sail in Key West
    Key West, FL

    Private Schooner Sunset Sail in Key West

    Charter a 1939 wooden schooner for a sunset sail from Key West’s Historic Seaport

    Charter a 1939 wooden schooner for a sunset sail from Key West’s Historic Seaport
    4.8 • 377 reviews
    $2,474
    Watch Shelter Cove Fireworks on a Hilton Head Sail
    Hilton Head, SC

    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
    Watch Friday Night Fireworks on a Honolulu Sail
    Honolulu, HI

    Watch Friday Night Fireworks on a Honolulu Sail

    90-minute sail with open bar and Friday night fireworks views

    90-minute sail with open bar and Friday night fireworks views
    4.8 • 1.4K reviews
    $90/ person
    Fireworks Sailing Cruise in Hilton Head Island
    Hilton Head Island, SC

    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
    Hilton Head Island, SC

    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
    Biscayne Bay Wildlife Sailing Tour
    Miami, FL

    Biscayne Bay Wildlife Sailing Tour

    Sail, swim and snorkel among Biscayne Bay’s sandbars and mangroves

    Sail, swim and snorkel among Biscayne Bay’s sandbars and mangroves
    $158/ person
    4-Hour Sailing Charter in Hilton Head Island
    Bluffton, SC

    4-Hour Sailing Charter in Hilton Head Island

    Tailor an afternoon under sail with ocean cruising or time at anchor

    Tailor an afternoon under sail with ocean cruising or time at anchor
    $1,276& up
    Sunset Sail in Hilton Head Island
    Bluffton, SC

    Sunset Sail in Hilton Head Island

    Golden-hour sailing with coastal views and wildlife watching

    Golden-hour sailing with coastal views and wildlife watching
    $493
    Private Sunset Sail in Hilton Head Island
    Bluffton, SC

    Private Sunset Sail in Hilton Head Island

    Sail into sunset views and watch for dolphins

    Sail into sunset views and watch for dolphins
    $557& up
    Hilton Head Island Sunset Sail
    Bluffton, SC

    Hilton Head Island Sunset Sail

    End the day sailing beneath the changing coastal sky

    End the day sailing beneath the changing coastal sky
    $117/ person
    Sunset Sail in Hilton Head Island
    Bluffton, SC

    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
    $138/ person
    Women’s Sailing Clinic in Nantucket
    Nantucket, MA

    Women’s Sailing Clinic in Nantucket

    Build sailing confidence with instruction tailored to your experience

    Build sailing confidence with instruction tailored to your experience
    5.0 • 2 reviews
    $90/ person
    2-Hour Sailing Lesson in Oyster Bay Harbor
    Oyster Bay, NY

    2-Hour Sailing Lesson in Oyster Bay Harbor

    Learn the basics aboard a relaxed harbor sail led by a certified instructor

    Learn the basics aboard a relaxed harbor sail led by a certified instructor
    4.5 • 62 reviews
    $159
    Waikīkī Sunset Catamaran Charter
    Honolulu, HI

    Waikīkī Sunset Catamaran Charter

    Private sailing with Waikīkī views, onboard drinks, and space for your group

    Private sailing with Waikīkī views, onboard drinks, and space for your group
    4.7 • 162 reviews
    $1,728
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