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    1. Local experiences
    2. /All experiences
    3. /Water Activities
    4. /Sailing

    Best results for Sailing in Salem, MA

    Showing 25-32 of 32 results
    2-Hour Historic Boston Harbor Sailing Cruise
    Sailing

    2-Hour Historic Boston Harbor Sailing Cruise

    Sail Boston Harbor with stories, skyline views, and complimentary pastries

    Sail Boston Harbor with stories, skyline views, and complimentary pastries
    4.6 • 438 reviews
    $79/ person
    2-Hour Boston Harbor Tall Ships Cruise
    Sailing

    2-Hour Boston Harbor Tall Ships Cruise

    Cruise Boston Harbor for views of the tall ships on a classic schooner

    Cruise Boston Harbor for views of the tall ships on a classic schooner
    4.6 • 438 reviews
    $77/ person
    Boston Harbor Sunset Tall Ships Sail
    Sailing

    Boston Harbor Sunset Tall Ships Sail

    Sail Boston Harbor at sunset for views of the tall ships and skyline lights

    Sail Boston Harbor at sunset for views of the tall ships and skyline lights
    4.6 • 438 reviews
    $90/ person
    Gloucester Private Sailing Charter
    Sailing

    Gloucester Private Sailing Charter

    Private schooner sailing with captain and crew included

    Private schooner sailing with captain and crew included
    5.0 • 107 reviews
    $477& up
    Gloucester Celtic Music Sunset Sail
    Sailing

    Gloucester Celtic Music Sunset Sail

    Sail into the sunset with live Celtic tunes and sea shanties

    Sail into the sunset with live Celtic tunes and sea shanties
    5.0 • 107 reviews
    $69/ person
    Gloucester Schooner Festival Private Sailing Charter
    Sailing

    Gloucester Schooner Festival Private Sailing Charter

    Sail in company with visiting schooners during Gloucester Schooner Festival Weekend

    Sail in company with visiting schooners during Gloucester Schooner Festival Weekend
    5.0 • 107 reviews
    $477
    Boston Harbor Sail With Freshly Shucked Oysters
    Sailing

    Boston Harbor Sail With Freshly Shucked Oysters

    Sail Boston Harbor and enjoy freshly shucked oysters onboard

    Sail Boston Harbor and enjoy freshly shucked oysters onboard
    4.8 • 693 reviews
    $80/ person
    Private Sailing Lesson in Natick
    Sailing

    Private Sailing Lesson in Natick

    Build sailing skills with a private instructor-led session

    Build sailing skills with a private instructor-led session
    4.6 • 45 reviews
    $174/ person
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