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

    Best results for Sailing

    Showing 145-168 of 317 results
    Private Key West Sunset Sailing Charter
    Key West, FL

    Private Key West Sunset Sailing Charter

    Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included

    Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included
    4.9 • 5.7K reviews
    $3,426
    Sandbar, Snorkel & Sunset Sail in Key West
    Key West, FL

    Sandbar, Snorkel & Sunset Sail in Key West

    Sail to a Key West sandbar with snorkeling, snacks, and sunset views

    Sail to a Key West sandbar with snorkeling, snacks, and sunset views
    4.9 • 5.7K reviews
    $148/ person
    Proposal & Anniversary Sailing Cruise in Fort Walton Beach
    Fort Walton Beach, FL

    Proposal & Anniversary Sailing Cruise in Fort Walton Beach

    Sail with a licensed captain for a proposal or anniversary cruise

    Sail with a licensed captain for a proposal or anniversary cruise
    5.0 • 58 reviews
    $482
    Morning Schooner Cruise in Bar Harbor
    Bar Harbor, ME

    Morning Schooner Cruise in Bar Harbor

    Sail Frenchman Bay for sea views of Acadia National Park

    Sail Frenchman Bay for sea views of Acadia National Park
    4.2 • 2.5K reviews
    $48/ person
    Sunset Sailing Cruise With Live Music in Bar Harbor
    Bar Harbor, ME

    Sunset Sailing Cruise With Live Music in Bar Harbor

    Sail at sunset with live folk music on the Margaret Todd

    Sail at sunset with live folk music on the Margaret Todd
    4.2 • 2.5K reviews
    $61/ person
    Basic Coastal Cruising Sailing Class in Sandusky
    Sandusky, OH

    Basic Coastal Cruising Sailing Class in Sandusky

    Learn basic coastal cruising skills in a 2-day sailing class

    Learn basic coastal cruising skills in a 2-day sailing class
    5.0 • 34 reviews
    $631/ person
    ASA 111 Sailing Skills Review Class in Sandusky
    Sandusky, OH

    ASA 111 Sailing Skills Review Class in Sandusky

    Review and refresh your ASA 111 sailing skills in a 3-hour class

    Review and refresh your ASA 111 sailing skills in a 3-hour class
    5.0 • 34 reviews
    $207/ person
    Private Sailing Charter on Calibogue Sound, Hilton Head
    Hilton Head Island, SC

    Private Sailing Charter on Calibogue Sound, Hilton Head

    Private captained sail on Calibogue Sound with room for your snacks and drinks

    Private captained sail on Calibogue Sound with room for your snacks and drinks
    4.7 • 972 reviews
    $345
    Afternoon Cocktail Sail Along Waikiki Coastline
    Honolulu, HI

    Afternoon Cocktail Sail Along Waikiki Coastline

    Cruise Waikiki toward Diamond Head with drinks and snacks included

    Cruise Waikiki toward Diamond Head with drinks and snacks included
    4.8 • 652 reviews
    $86/ person
    Sail Ko Olina on a 1.5-Hour Sunset Catamaran Cruise
    Honolulu, HI

    Sail Ko Olina on a 1.5-Hour Sunset Catamaran Cruise

    Sail Ko Olina at sunset with live Hawaiian music and an open bar

    Sail Ko Olina at sunset with live Hawaiian music and an open bar
    4.8 • 652 reviews
    $160/ person
    Ko Olina Sunset Sail & Luau Experience
    Honolulu, HI

    Ko Olina Sunset Sail & Luau Experience

    Sail Ko Olina at sunset, then head ashore for a Kaula Luau

    Sail Ko Olina at sunset, then head ashore for a Kaula Luau
    4.8 • 652 reviews
    $342/ person
    Private Sunset Catamaran Sail In Cocoa Beach
    Cocoa Beach, FL

    Private Sunset Catamaran Sail In Cocoa Beach

    Sail a private catamaran at sunset with room to lounge

    Sail a private catamaran at sunset with room to lounge
    5.0 • 3.6K reviews
    $339
    Sail San Francisco Bay & Alcatraz Night Tour
    San Francisco, CA

    Sail San Francisco Bay & Alcatraz Night Tour

    Combine an afternoon bay sail with an Alcatraz Island night visit

    Combine an afternoon bay sail with an Alcatraz Island night visit
    4.7 • 620 reviews
    $139/ person
    Sail to Sand Island on a 7-Hour Pensacola Beach Cruise
    Pensacola Beach, FL

    Sail to Sand Island on a 7-Hour Pensacola Beach Cruise

    Spend 7 hours sailing, swimming, and grilling on a private trip for up to 6

    Spend 7 hours sailing, swimming, and grilling on a private trip for up to 6
    5.0 • 1.9K reviews
    $773
    Private 1.5-Hour Sailing Cruise on the Delaware River
    Philadelphia, PA

    Private 1.5-Hour Sailing Cruise on the Delaware River

    Private Delaware River day sail for up to six guests

    Private Delaware River day sail for up to six guests
    $424/ boat
    Sail the Delaware River on a 3-Hour History Tour
    Philadelphia, PA

    Sail the Delaware River on a 3-Hour History Tour

    Sail the Delaware River and hear Philadelphia waterfront history from your guide

    Sail the Delaware River and hear Philadelphia waterfront history from your guide
    $254/ person
    Golden Hour Cocktail Sail in New York City
    New York, NY

    Golden Hour Cocktail Sail in New York City

    Sail past the Statue of Liberty with a welcome cocktail at golden hour

    Sail past the Statue of Liberty with a welcome cocktail at golden hour
    4.5 • 699 reviews
    $104
    City Lights Sailing Cruise in New York City
    New York, NY

    City Lights Sailing Cruise in New York City

    Sail past NYC’s lit-up skyline on the Clipper City at night

    Sail past NYC’s lit-up skyline on the Clipper City at night
    4.5 • 699 reviews
    $90/ person
    2-Hour Private Sailing Charter in Provincetown
    Provincetown, MA

    2-Hour Private Sailing Charter in Provincetown

    Sail Provincetown Harbor on a private, captained 2-hour charter for up to six guests

    Sail Provincetown Harbor on a private, captained 2-hour charter for up to six guests
    $913
    2-Hour Private Sunset Sailing Cruise in Narragansett Bay
    Barrington, RI

    2-Hour Private Sunset Sailing Cruise in Narragansett Bay

    Private sunset sail for up to 4 on Narragansett Bay

    Private sunset sail for up to 4 on Narragansett Bay
    4.9 • 66 reviews
    $159
    Happy Hour Sailing Cruise in Traverse City
    Traverse City, MI

    Happy Hour Sailing Cruise in Traverse City

    Sail West Grand Traverse Bay on a 2-hour happy hour cruise

    Sail West Grand Traverse Bay on a 2-hour happy hour cruise
    4.8 • 1.2K reviews
    $71/ person
    Champagne Sunset Cruise in Traverse City
    Traverse City, MI

    Champagne Sunset Cruise in Traverse City

    Sail West Grand Traverse Bay at sunset with a champagne toast

    Sail West Grand Traverse Bay at sunset with a champagne toast
    4.8 • 1.2K reviews
    $77/ person
    Cruise West Grand Traverse Bay at Noon in Traverse City
    Traverse City, MI

    Cruise West Grand Traverse Bay at Noon in Traverse City

    Relax on a 2-hour noon catamaran cruise on West Grand Traverse Bay

    Relax on a 2-hour noon catamaran cruise on West Grand Traverse Bay
    4.8 • 1.2K reviews
    $58/ person
    Sail a Private Charter on Oahu's North Shore
    Haleiwa, HI

    Sail a Private Charter on Oahu's North Shore

    Private sailing charter on Oahu’s North Shore for up to 6 people

    Private sailing charter on Oahu’s North Shore for up to 6 people
    5.0 • 56 reviews
    $918& up
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