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

    Best results for Sailing

    Showing 457-480 of 497 results
    Sail Kennebunkport Coastline With Wine Tasting
    Kennebunkport, ME

    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 • 274 reviews
    $178/ person
    Learn Keelboat Sailing in Monterey 3-4 Day Course
    Monterey, CA

    Learn Keelboat Sailing in Monterey 3-4 Day Course

    Train to sail a 30-foot keelboat in a 3–4 day course (max 4 students)

    Train to sail a 30-foot keelboat in a 3–4 day course (max 4 students)
    4.9 • 239 reviews
    $1,059/ person
    ASA 103 Coastal Cruising Sailing Course in Monterey
    Monterey, CA

    ASA 103 Coastal Cruising Sailing Course in Monterey

    Learn coastal cruising skills in a 3-day ASA 103 course, capped at 4 students

    Learn coastal cruising skills in a 3-day ASA 103 course, capped at 4 students
    4.9 • 239 reviews
    $1,059/ person
    Coastal Navigation Course in Monterey
    Monterey, CA

    Coastal Navigation Course in Monterey

    Practice coastal navigation skills on the water in Monterey

    Practice coastal navigation skills on the water in Monterey
    4.9 • 239 reviews
    $550/ person
    Learn Basic Keelboat Sailing in Savannah
    Savannah, GA

    Learn Basic Keelboat Sailing in Savannah

    Take a 2-day keelboat sailing course with a small group

    Take a 2-day keelboat sailing course with a small group
    4.9 • 104 reviews
    $631/ person
    ASA 101 Basic Keelboat Sailing Class in San Diego
    San Diego, CA

    ASA 101 Basic Keelboat Sailing Class in San Diego

    Learn the basics of keelboat sailing in a 2-day ASA course on San Diego Bay

    Learn the basics of keelboat sailing in a 2-day ASA course on San Diego Bay
    4.4 • 246 reviews
    $404/ person
    Race in a Themed Sailboat Regatta in San Diego
    San Diego, CA

    Race in a Themed Sailboat Regatta in San Diego

    Join an informal sailboat race and dockside after-party in Mission Bay

    Join an informal sailboat race and dockside after-party in Mission Bay
    4.4 • 246 reviews
    $16/ person
    Earn ASA 103 & 104 Sailing Certifications in San Diego
    San Diego, CA

    Earn ASA 103 & 104 Sailing Certifications in San Diego

    Take an advanced 3-day ASA 103/104 sailing course with optional live-aboard

    Take an advanced 3-day ASA 103/104 sailing course with optional live-aboard
    4.4 • 246 reviews
    $1,600/ person
    2-Day ASA 114 Cruising Catamaran Class In Coronado
    San Diego, CA

    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
    4.4 • 246 reviews
    $995/ person
    2-Hour Sailing Skills Refresher Clinic in San Diego
    San Diego, CA

    2-Hour Sailing Skills Refresher Clinic in San Diego

    Practice sailing skills on Capri 22s with a certified captain (2 hours)

    Practice sailing skills on Capri 22s with a certified captain (2 hours)
    4.4 • 246 reviews
    $32/ person
    Learn Sailing After-Work at Soundside
    Wrightsville Beach, NC

    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
    4.9 • 68 reviews
    $313/ person
    Basic Keelboat Sailing Course in St. Augustine
    St. Augustine, FL

    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 • 762 reviews
    $843/ person
    Learn Coastal Navigation in St. Augustine
    St. Augustine, FL

    Learn Coastal Navigation in St. Augustine

    Practice coastal navigation theory in a four-day ASA course

    Practice coastal navigation theory in a four-day ASA course
    5.0 • 762 reviews
    $1,373/ person
    4-Day ASA Advanced Coastal Cruising Course in St. Augustine
    St. Augustine, FL

    4-Day ASA Advanced Coastal Cruising Course in St. Augustine

    Train to skipper a 30–50 ft sailboat on a 4-day ASA 106 course

    Train to skipper a 30–50 ft sailboat on a 4-day ASA 106 course
    5.0 • 762 reviews
    $2,491/ person
    Women’s Sailing Racing & Practice in St. Augustine
    St. Augustine, FL

    Women’s Sailing Racing & Practice in St. Augustine

    Join a women’s sailing race team and practice on Zephyr

    Join a women’s sailing race team and practice on Zephyr
    5.0 • 762 reviews
    $111/ person
    Private Oyster Sloop Charter on CHRISTEEN
    Oyster Bay, NY

    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
    Sail Grand Traverse Bay Fall Flavors Cruise
    Traverse City, MI

    Sail Grand Traverse Bay Fall Flavors Cruise

    Sail Grand Traverse Bay and enjoy Moomers ice cream on a 2-hour fall cruise

    Sail Grand Traverse Bay and enjoy Moomers ice cream on a 2-hour fall cruise
    4.9 • 582 reviews
    $60/ person
    Diamond Head Sail & Swim From Waikiki
    Honolulu, HI

    Diamond Head Sail & Swim From Waikiki

    Sail past Diamond Head, then anchor off Waikiki for a swim

    Sail past Diamond Head, then anchor off Waikiki for a swim
    $110/ person
    Private Sailboat Cruise Around Oyster Bay
    Oyster Bay, NY

    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
    Private Sailing Charter in Traverse City
    Traverse City, MI

    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 • 337 reviews
    $2,800
    1.5-Hour New York City Lights Sailing Charter
    New York, NY

    1.5-Hour New York City Lights Sailing Charter

    Private moonlight sail past the Manhattan skyline and Statue of Liberty

    Private moonlight sail past the Manhattan skyline and Statue of Liberty
    5.0 • 505 reviews
    $928& up
    Sail a Private Historic Schooner in Key West
    Key West, FL

    Sail a Private Historic Schooner in Key West

    Private 2-hour sail on a 1939 wooden schooner in Key West

    Private 2-hour sail on a 1939 wooden schooner in Key West
    4.8 • 377 reviews
    $1,345
    Sail on a New York City Sunset Cruise
    New York, NY

    Sail on a New York City Sunset Cruise

    Cruise NYC Harbor at sunset on the historic yacht Ventura

    Cruise NYC Harbor at sunset on the historic yacht Ventura
    5.0 • 70 reviews
    $144/ person
    Private 3-Hour Sailing Lesson in Key West
    Key West, FL

    Private 3-Hour Sailing Lesson in Key West

    Choose your boat and learn to sail with a private instructor in Key West

    Choose your boat and learn to sail with a private instructor in Key West
    4.9 • 49 reviews
    $143& up
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