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    Best results for Sailing

    Showing 385-403 of 403 results
    Sail Lake Tahoe on a Live Music Sunset Cruise
    Sailing

    Sail Lake Tahoe on a Live Music Sunset Cruise

    Cruise Lake Tahoe at sunset with live local music

    Cruise Lake Tahoe at sunset with live local music
    $170/ person
    Watch Friday Night Fireworks on a Waikiki Sail
    Sailing

    Watch Friday Night Fireworks on a Waikiki Sail

    Friday fireworks sail with front-row views from the water

    Friday fireworks sail with front-row views from the water
    5.0 • 100 reviews
    $117/ person
    Sail Boothbay Harbor on a 1.5-Hour Guided Cruise
    Sailing

    Sail Boothbay Harbor on a 1.5-Hour Guided Cruise

    Sail Boothbay Harbor aboard the Friendship Sloop Bay Lady on a 1.5-hour trip

    Sail Boothbay Harbor aboard the Friendship Sloop Bay Lady on a 1.5-hour trip
    3.5 • 49 reviews
    $45/ person
    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
    4.7 • 1.5K reviews
    $80/ person
    Sail Boston Harbor on a 1.5-Hour Day Cruise
    Sailing

    Sail Boston Harbor on a 1.5-Hour Day Cruise

    Sail Boston Harbor on a 1.5-hour schooner cruise from Rowes Wharf

    Sail Boston Harbor on a 1.5-hour schooner cruise from Rowes Wharf
    4.7 • 1.5K reviews
    $72/ person
    Sail Provincetown on the Schooner Hindu
    Sailing

    Sail Provincetown on the Schooner Hindu

    Sail Cape Cod Bay on the historic Schooner Hindu

    Sail Cape Cod Bay on the historic Schooner Hindu
    $64/ person
    2-Hour Sunset Sail in Provincetown
    Sailing

    2-Hour Sunset Sail in Provincetown

    Sail Provincetown at sunset on the historic Schooner Hindu

    Sail Provincetown at sunset on the historic Schooner Hindu
    $94/ person
    Sail Boston Harbor on the Historic Schooner Hindu
    Sailing

    Sail Boston Harbor on the Historic Schooner Hindu

    Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

    Sail Boston during Sail Boston 2026 on the restored Schooner Hindu
    $73/ person
    2-Hour Provincetown Wine Tasting Sail
    Sailing

    2-Hour Provincetown Wine Tasting Sail

    Taste Truro Vineyards pours on a 2-hour schooner sail in Provincetown

    Taste Truro Vineyards pours on a 2-hour schooner sail in Provincetown
    $110/ person
    Private 1.5-Hour Sunset Sail in Honolulu
    Sailing

    Private 1.5-Hour Sunset Sail in Honolulu

    1.5-hour private sunset sail with wine, beer, and non-alcoholic drinks

    1.5-hour private sunset sail with wine, beer, and non-alcoholic drinks
    4.9 • 807 reviews
    $4,601
    1-Hour Fireworks Sail in Honolulu
    Sailing

    1-Hour Fireworks Sail in Honolulu

    Watch Honolulu’s Friday-night fireworks from a private sail

    Watch Honolulu’s Friday-night fireworks from a private sail
    4.9 • 807 reviews
    $3,745
    Waikiki 1-Hour Friday Night Fireworks Cruise
    Sailing

    Waikiki 1-Hour Friday Night Fireworks Cruise

    Sail out for close-up views of Honolulu’s Friday night fireworks

    Sail out for close-up views of Honolulu’s Friday night fireworks
    4.8 • 2.2K reviews
    $95/ person
    Cruise West Grand Traverse Bay on a Kids Sailboat
    Sailing

    Cruise West Grand Traverse Bay on a Kids Sailboat

    Sail the Nauti-Cat on a 1.5-hour kids cruise in Traverse City

    Sail the Nauti-Cat on a 1.5-hour kids cruise in Traverse City
    4.8 • 1.2K reviews
    $39/ person
    Sail Kennebunkport Coastline With Wine Tasting
    Sailing

    Sail Kennebunkport Coastline With Wine Tasting

    Sip wine on a 90-minute Kennebunkport sail with a sommelier-led tasting

    Sip wine on a 90-minute Kennebunkport sail with a sommelier-led tasting
    4.9 • 254 reviews
    $178/ person
    2-Day ASA 114 Cruising Catamaran Class In Coronado
    Sailing

    2-Day ASA 114 Cruising Catamaran Class In Coronado

    Build catamaran handling skills in a 2-day ASA 114 course

    Build catamaran handling skills in a 2-day ASA 114 course
    $995/ person
    Private Oyster Sloop Charter on CHRISTEEN
    Sailing

    Private Oyster Sloop Charter on CHRISTEEN

    Charter the 60-foot Oyster Sloop CHRISTEEN for a private cruise

    Charter the 60-foot Oyster Sloop CHRISTEEN for a private cruise
    4.5 • 62 reviews
    $1,146
    Brunch Cruise in Traverse City
    Sailing

    Brunch Cruise in Traverse City

    Sail the bay on a 2-hour brunch cruise with your first drink included

    Sail the bay on a 2-hour brunch cruise with your first drink included
    4.8 • 1.7K reviews
    $88/ person
    Cruise Traverse City on a 2-Hour Live Music Sail
    Sailing

    Cruise Traverse City on a 2-Hour Live Music Sail

    Dance to live music on a 2-hour evening sail on Grand Traverse Bay

    Dance to live music on a 2-hour evening sail on Grand Traverse Bay
    4.8 • 1.7K reviews
    $86/ person
    Private Sailboat Cruise Around Oyster Bay
    Sailing

    Private Sailboat Cruise Around Oyster Bay

    Charter the Ida May for a private sail with up to 44 guests

    Charter the Ida May for a private sail with up to 44 guests
    4.5 • 62 reviews
    $1,484& up
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