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    Best results for Sailing

    Showing 73-96 of 403 results
    2-Hour Sunset Sailing Cruise in Wrightsville Beach
    Sailing

    2-Hour Sunset Sailing Cruise in Wrightsville Beach

    Sail at sunset off Wrightsville Beach and Masonboro Islands

    Sail at sunset off Wrightsville Beach and Masonboro Islands
    5.0 • 279 reviews
    $122/ person
    2-Hour Performance Sailing in Wrightsville Beach
    Sailing

    2-Hour Performance Sailing in Wrightsville Beach

    Race-boat sailing with a certified captain near Wrightsville Beach

    Race-boat sailing with a certified captain near Wrightsville Beach
    $95/ person
    Learn Sailing After-Work at Soundside
    Sailing

    Learn Sailing After-Work at Soundside

    Learn basic sailing in two after-work classes at Soundside

    Learn basic sailing in two after-work classes at Soundside
    $313/ person
    2-Hour Intro Sailing Lesson in St. Augustine
    Sailing

    2-Hour Intro Sailing Lesson in St. Augustine

    Learn sailing basics in a small group of 2–4 people

    Learn sailing basics in a small group of 2–4 people
    5.0 • 736 reviews
    $168/ person
    2-Hour Sailing Lesson in St. Augustine
    Sailing

    2-Hour Sailing Lesson in St. Augustine

    Build sailing confidence with a beginner-friendly 2-hour coaching sail

    Build sailing confidence with a beginner-friendly 2-hour coaching sail
    5.0 • 736 reviews
    $224/ person
    Join a Sunday Sailing Lesson in St. Augustine
    Sailing

    Join a Sunday Sailing Lesson in St. Augustine

    Train as crew on Sunday sails with a USCG captain or ASA sailing instructor

    Train as crew on Sunday sails with a USCG captain or ASA sailing instructor
    5.0 • 736 reviews
    $309/ person
    Basic Keelboat Sailing Course in St. Augustine
    Sailing

    Basic Keelboat Sailing Course in St. Augustine

    Learn to skipper a keelboat in a two-day ASA 102 course

    Learn to skipper a keelboat in a two-day ASA 102 course
    5.0 • 736 reviews
    $843/ person
    Sunset Sailing Cruise in Key West With Live Music
    Sailing

    Sunset Sailing Cruise in Key West With Live Music

    Sip and sail into the Key West sunset with live music and an open well bar

    Sip and sail into the Key West sunset with live music and an open well bar
    4.8 • 22K reviews
    $102/ person
    Private 3-Hour Catamaran Sailing Tour in Key Largo
    Sailing

    Private 3-Hour Catamaran Sailing Tour in Key Largo

    Sail Key Largo on a private 40-foot catamaran for up to 6 guests

    Sail Key Largo on a private 40-foot catamaran for up to 6 guests
    5.0 • 40 reviews
    $546
    Private Sunset Sailing Charter in Key Largo
    Sailing

    Private Sunset Sailing Charter in Key Largo

    Sail Key Largo at sunset on a private 40-foot catamaran for up to 6 guests

    Sail Key Largo at sunset on a private 40-foot catamaran for up to 6 guests
    5.0 • 40 reviews
    $655
    2-Hour Sandbar Sailing Charter
    Sailing

    2-Hour Sandbar Sailing Charter

    Sail a captained Hobie Cat to a local sandbar with complimentary beverages

    Sail a captained Hobie Cat to a local sandbar with complimentary beverages
    4.9 • 271 reviews
    $283
    Team Racing Sailing Series on Long Island Sound
    Sailing

    Team Racing Sailing Series on Long Island Sound

    Build team racing skills and strategy on Long Island Sound

    Build team racing skills and strategy on Long Island Sound
    4.5 • 62 reviews
    $53& up
    Private 5-Hour Power Island Sailing Cruise
    Sailing

    Private 5-Hour Power Island Sailing Cruise

    Cruise to Power Island on a 5-hour private sail for up to 6 people

    Cruise to Power Island on a 5-hour private sail for up to 6 people
    5.0 • 77 reviews
    $741
    Private 2-Hour Sunset Sailing Cruise on West Bay
    Sailing

    Private 2-Hour Sunset Sailing Cruise on West Bay

    Private 2-hour sunset sail on Grand Traverse West Bay for up to 6 people

    Private 2-hour sunset sail on Grand Traverse West Bay for up to 6 people
    5.0 • 77 reviews
    $345
    Private Sunset Sailing Charter on Grand Traverse Bay
    Sailing

    Private Sunset Sailing Charter on Grand Traverse Bay

    Sail Grand Traverse Bay at sunset on a private 2-hour charter for up to 6 guests

    Sail Grand Traverse Bay at sunset on a private 2-hour charter for up to 6 guests
    4.9 • 8 reviews
    $359
    Sailing Lesson at Wolverine Park Marina
    Sailing

    Sailing Lesson at Wolverine Park Marina

    Learn sailing basics with hands-on coaching tailored to your goals

    Learn sailing basics with hands-on coaching tailored to your goals
    5.0 • 146 reviews
    $191/ person
    Private Sailing Charter in Traverse City
    Sailing

    Private Sailing Charter in Traverse City

    Charter the Wind Dancer schooner for your group of up to 18

    Charter the Wind Dancer schooner for your group of up to 18
    4.9 • 328 reviews
    $2,800
    Private Sailing Yacht Charter in San Diego
    Yacht Charters

    Private Sailing Yacht Charter in San Diego

    Charter a private sailboat in San Diego with captain and crew, for up to 14 guests

    Charter a private sailboat in San Diego with captain and crew, for up to 14 guests
    5.0 • 811 reviews
    $1,113& up
    Afternoon Sailing & Snorkeling Tour in Kailua-Kona
    Snorkeling

    Afternoon Sailing & Snorkeling Tour in Kailua-Kona

    Sail the Kona Coast and snorkel Kealakekua Bay’s marine sanctuary

    Sail the Kona Coast and snorkel Kealakekua Bay’s marine sanctuary
    4.8 • 2.7K reviews
    $143/ person
    Private Sailing Charter in New York City
    Yacht Charters

    Private Sailing Charter in New York City

    Sail the NYC skyline on a private yacht with your own captain

    Sail the NYC skyline on a private yacht with your own captain
    4.9 • 79 reviews
    $783& up
    Private Sailing Charter for 2 in New York City
    Yacht Charters

    Private Sailing Charter for 2 in New York City

    Sail NYC Harbor on a private yacht for two, with Statue of Liberty views

    Sail NYC Harbor on a private yacht for two, with Statue of Liberty views
    4.9 • 79 reviews
    $671& up
    Private Sailing Yacht Charter in NYC
    Yacht Charters

    Private Sailing Yacht Charter in NYC

    Sail NYC on a private yacht with skyline views and Statue of Liberty close-ups

    Sail NYC on a private yacht with skyline views and Statue of Liberty close-ups
    4.9 • 79 reviews
    $783& up
    Private Sailing Yacht Charter in San Diego
    Yacht Charters

    Private Sailing Yacht Charter in San Diego

    Charter a private sailing yacht in San Diego with your own captain and crew

    Charter a private sailing yacht in San Diego with your own captain and crew
    5.0 • 811 reviews
    $1,590& up
    Private Sunset Sailing Charter in Maalaea Bay
    Yacht Charters

    Private Sunset Sailing Charter in Maalaea Bay

    Sail a private sunset catamaran with appetizers and room for up to 6

    Sail a private sunset catamaran with appetizers and room for up to 6
    5.0 • 153 reviews
    $2,729
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