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

    Best results for Sailing

    Showing 313-336 of 497 results
    Private New York City Lights Sailing Charter
    New York, NY

    Private New York City Lights Sailing Charter

    Sail past Manhattan’s night skyline on a private 1.5-hour charter

    Sail past Manhattan’s night skyline on a private 1.5-hour charter
    4.8 • 60 reviews
    $663& up
    Private 4-Hour Sailing Charter in Fort Myers Beach
    Fort Myers Beach, FL

    Private 4-Hour Sailing Charter in Fort Myers Beach

    Sail a private catamaran to Lovers Key with time to swim and shell

    Sail a private catamaran to Lovers Key with time to swim and shell
    5.0 • 567 reviews
    $1,631
    Sunset Sail in Southwest Florida
    Fort Myers Beach, FL

    Sunset Sail in Southwest Florida

    Sail into golden-hour views on a 2-hour sunset cruise

    Sail into golden-hour views on a 2-hour sunset cruise
    5.0 • 567 reviews
    $68/ person
    Private 2-Hour Sailing Cruise on Lake Champlain
    Burlington, VT

    Private 2-Hour Sailing Cruise on Lake Champlain

    Sail Lake Champlain on a private classic sloop with captain and crew

    Sail Lake Champlain on a private classic sloop with captain and crew
    5.0 • 957 reviews
    $452& up
    Cruise New York Harbor on a 3-Hour Private Sail
    New York, NY

    Cruise New York Harbor on a 3-Hour Private Sail

    Private 3-hour sail past the Statue of Liberty from Jersey City

    Private 3-hour sail past the Statue of Liberty from Jersey City
    5.0 • 505 reviews
    $954& up
    Sunset Sailing Cruise in South Lake Tahoe
    South Lake Tahoe, CA

    Sunset Sailing Cruise in South Lake Tahoe

    2-hour sunset sail with complimentary beer, wine, and non-alcoholic drinks

    2-hour sunset sail with complimentary beer, wine, and non-alcoholic drinks
    5.0 • 465 reviews
    $148/ person
    Take a Morning Mimosa Sailing Cruise in Lake Tahoe
    South Lake Tahoe, CA

    Take a Morning Mimosa Sailing Cruise in Lake Tahoe

    2-hour morning sail on Lake Tahoe with mimosas and non-alcoholic drinks

    2-hour morning sail on Lake Tahoe with mimosas and non-alcoholic drinks
    5.0 • 465 reviews
    $148/ person
    Private Daytime Sailing Charter in New York City
    NEW YORK, NY

    Private Daytime Sailing Charter in New York City

    Sail NYC on a private charter with a U.S. Coast Guard licensed captain

    Sail NYC on a private charter with a U.S. Coast Guard licensed captain
    5.0 • 42 reviews
    $631& up
    Guided Daytime Sailing Cruise on Lake Champlain
    Burlington, VT

    Guided Daytime Sailing Cruise on Lake Champlain

    Sail Lake Champlain on a classic sloop with a small group

    Sail Lake Champlain on a classic sloop with a small group
    5.0 • 957 reviews
    $77/ person
    Charleston 2.5-Hour Sunset Cruise
    Charleston, SC

    Charleston 2.5-Hour Sunset Cruise

    Bring your own drinks on a 2.5-hour Charleston sunset sail for up to 6 guests

    Bring your own drinks on a 2.5-hour Charleston sunset sail for up to 6 guests
    5.0 • 290 reviews
    $635
    2-Hour Private Sailing Charter in Newport
    Newport, RI

    2-Hour Private Sailing Charter in Newport

    Sail Narragansett Bay on a private 36-foot sloop with your captain

    Sail Narragansett Bay on a private 36-foot sloop with your captain
    5.0 • 193 reviews
    $419
    2-Hour Chesapeake Bay Day Sail in St. Michaels
    St. Michaels, MD

    2-Hour Chesapeake Bay Day Sail in St. Michaels

    Sail the Chesapeake on a 1935 ketch with the option to join the crew

    Sail the Chesapeake on a 1935 ketch with the option to join the crew
    5.0 • 1.3K reviews
    $131/ person
    Private 3.5-Hour Sailing Cruise in Newport
    Newport, RI

    Private 3.5-Hour Sailing Cruise in Newport

    Sail Narragansett Bay on a private 3.5-hour cruise aboard the 36' sloop Hurrah

    Sail Narragansett Bay on a private 3.5-hour cruise aboard the 36' sloop Hurrah
    5.0 • 193 reviews
    $843
    2-Hour Private Sailing Cruise in Folly Beach
    Folly Beach, SC

    2-Hour Private Sailing Cruise in Folly Beach

    Sail the Folly River on a private 2-hour cruise for up to 6 guests

    Sail the Folly River on a private 2-hour cruise for up to 6 guests
    5.0 • 209 reviews
    $477
    Sunset Shared Sailing Cruise in New Orleans
    New Orleans, LA

    Sunset Shared Sailing Cruise in New Orleans

    Sip included drinks on a 2-hour sunset sail with a small 21+ group

    Sip included drinks on a 2-hour sunset sail with a small 21+ group
    5.0 • 281 reviews
    $99/ person
    Spot Dolphins on a 2-Hour Sail in Hilton Head
    Hilton Head, SC

    Spot Dolphins on a 2-Hour Sail in Hilton Head

    Private 2-hour sail to learn the salt marsh and watch for dolphins

    Private 2-hour sail to learn the salt marsh and watch for dolphins
    4.9 • 116 reviews
    $457
    Sail, Swim & Sunset Fireworks Charter in Destin
    Destin, FL

    Sail, Swim & Sunset Fireworks Charter in Destin

    Private 3.5-hour catamaran sail with snorkeling, sunset, and summer fireworks

    Private 3.5-hour catamaran sail with snorkeling, sunset, and summer fireworks
    5.0 • 219 reviews
    $791
    Waikiki Friday Night Fireworks Sail
    Honolulu, HI

    Waikiki Friday Night Fireworks Sail

    Sail off Waikiki for Friday night fireworks with complimentary drinks

    Sail off Waikiki for Friday night fireworks with complimentary drinks
    $69/ 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
    Navy Pier Fireworks Cruise in Chicago
    Chicago, IL

    Navy Pier Fireworks Cruise in Chicago

    Sail Lake Michigan for Navy Pier fireworks views on a private charter

    Sail Lake Michigan for Navy Pier fireworks views on a private charter
    $1,007& up
    2.5-Hour Private Catamaran Charter in Dana Point
    Dana Point, CA

    2.5-Hour Private Catamaran Charter in Dana Point

    Sail privately aboard Manute'a with underwater viewing pods

    Sail privately aboard Manute'a with underwater viewing pods
    4.9 • 2.7K reviews
    $3,493
    Dana Point Sunset Champagne Sail
    Dana Point, CA

    Dana Point Sunset Champagne Sail

    Sail a 1926 schooner along the Orange County coast at sunset

    Sail a 1926 schooner along the Orange County coast at sunset
    4.8 • 7.8K reviews
    $101/ person
    Key West Full-Day Private Sailing Charter
    Key West, FL

    Key West Full-Day Private Sailing Charter

    Sail, snorkel, and explore Key West waters on your private catamaran

    Sail, snorkel, and explore Key West waters on your private catamaran
    4.8 • 71 reviews
    $2,452& up
    Key West Full-Day Sail & Snorkel Charter
    Key West, FL

    Key West Full-Day Sail & Snorkel Charter

    Customize a private day on the water with snorkeling and onboard lunch

    Customize a private day on the water with snorkeling and onboard lunch
    4.8 • 19 reviews
    $1,060
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