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

    Best results for Sailing

    Showing 193-216 of 497 results
    Sunset Catamaran Sailing Cruise in Monterey
    Monterey, CA

    Sunset Catamaran Sailing Cruise in Monterey

    Sail Monterey Bay at sunset with a drink and snacks included

    Sail Monterey Bay at sunset with a drink and snacks included
    4.9 • 239 reviews
    $94/ person
    2-Hour Sailing Lesson in Monterey
    Monterey, CA

    2-Hour Sailing Lesson in Monterey

    Learn sailing basics in a 2-hour class from Old Fisherman’s Wharf

    Learn sailing basics in a 2-hour class from Old Fisherman’s Wharf
    4.9 • 239 reviews
    $169/ person
    Birthday Sailing Charter in San Diego
    San Diego, CA

    Birthday Sailing Charter in San Diego

    Celebrate your birthday with a private sail on San Diego Bay

    Celebrate your birthday with a private sail on San Diego Bay
    4.9 • 848 reviews
    $631& up
    3-Hour Private Sunset Sailing Cruise in San Diego
    San Diego, CA

    3-Hour Private Sunset Sailing Cruise in San Diego

    Sail the San Diego coast at sunset with complimentary drinks and snacks

    Sail the San Diego coast at sunset with complimentary drinks and snacks
    4.9 • 848 reviews
    $631
    Bottomless Mimosa Sailing Cruise in San Diego
    San Diego, CA

    Bottomless Mimosa Sailing Cruise in San Diego

    Sail San Diego Bay with bottomless mimosas on a 2-hour morning cruise

    Sail San Diego Bay with bottomless mimosas on a 2-hour morning cruise
    4.9 • 848 reviews
    $80/ person
    3-Hour Private Midday Sailing Cruise in San Diego
    San Diego, CA

    3-Hour Private Midday Sailing Cruise in San Diego

    Sail San Diego on a private 3-hour midday cruise with complimentary drinks and snacks

    Sail San Diego on a private 3-hour midday cruise with complimentary drinks and snacks
    4.9 • 848 reviews
    $631
    Cruise San Diego on a 3-Hour Bachelorette Sail
    San Diego, CA

    Cruise San Diego on a 3-Hour Bachelorette Sail

    Book a 3-hour private bachelorette sail in San Diego, with daytime or sunset departures

    Book a 3-hour private bachelorette sail in San Diego, with daytime or sunset departures
    4.9 • 848 reviews
    $583& up
    Cruise San Diego Coastline on a 3-Hour Sunset Sail
    San Diego, CA

    Cruise San Diego Coastline on a 3-Hour Sunset Sail

    Sail San Diego at sunset on a private 3-hour cruise

    Sail San Diego at sunset on a private 3-hour cruise
    4.9 • 848 reviews
    $631& up
    3-Hour Private Sunset Sail in San Diego
    San Diego, CA

    3-Hour Private Sunset Sail in San Diego

    Sail privately in San Diego Bay with drinks and snacks included

    Sail privately in San Diego Bay with drinks and snacks included
    4.9 • 848 reviews
    $631& up
    Private 6-Hour Sailing Charter in San Diego
    San Diego, CA

    Private 6-Hour Sailing Charter in San Diego

    Sail San Diego Bay on a private 6-hour charter for up to 12 guests

    Sail San Diego Bay on a private 6-hour charter for up to 12 guests
    4.9 • 848 reviews
    $954& up
    3-Hour Midday Sailing Cruise In San Diego
    San Diego, CA

    3-Hour Midday Sailing Cruise In San Diego

    Midday sail in San Diego with drinks and snacks included

    Midday sail in San Diego with drinks and snacks included
    4.9 • 848 reviews
    $116/ person
    Sail On A 3-Hour San Diego Sunset Cruise
    San Diego, CA

    Sail On A 3-Hour San Diego Sunset Cruise

    3-hour sunset sail on a 40-foot boat with drinks and snacks included

    3-hour sunset sail on a 40-foot boat with drinks and snacks included
    4.9 • 848 reviews
    $126/ person
    Take a 2-Hour Morning Sailing Tour in San Diego
    San Diego, CA

    Take a 2-Hour Morning Sailing Tour in San Diego

    2-hour morning sail with complimentary drinks and snacks

    2-hour morning sail with complimentary drinks and snacks
    4.9 • 848 reviews
    $94/ person
    2-Hour Private Morning Sailing Cruise in San Diego
    San Diego, CA

    2-Hour Private Morning Sailing Cruise in San Diego

    Private 2-hour morning sail with complimentary drinks and snacks

    Private 2-hour morning sail with complimentary drinks and snacks
    4.9 • 848 reviews
    $477& up
    Captain-Chartered Catalina 420 Sailing Charter in San Diego
    San Diego, CA

    Captain-Chartered Catalina 420 Sailing Charter in San Diego

    Sail a spacious Catalina 420 with your group of up to 12

    Sail a spacious Catalina 420 with your group of up to 12
    4.4 • 246 reviews
    $1,050& up
    Sail a 270' Catalina Charter in San Diego Bay
    San Diego, CA

    Sail a 270' Catalina Charter in San Diego Bay

    Charter a Catalina 270 sailboat on San Diego Bay with 3- or 6-hour options

    Charter a Catalina 270 sailboat on San Diego Bay with 3- or 6-hour options
    4.4 • 246 reviews
    $395& up
    Sail a Catalina 270 Charter in San Diego
    San Diego, CA

    Sail a Catalina 270 Charter in San Diego

    Charter an 8-person Catalina 270 sailboat with 3- or 6-hour options

    Charter an 8-person Catalina 270 sailboat with 3- or 6-hour options
    4.4 • 246 reviews
    $395/ boat
    Sunset Sail in Coronado
    San Diego, CA

    Sunset Sail in Coronado

    Sail at sunset with views of San Diego’s skyline

    Sail at sunset with views of San Diego’s skyline
    4.4 • 246 reviews
    $250& up
    Sail at Sunset in San Diego
    San Diego, CA

    Sail at Sunset in San Diego

    Sail into sunset views of San Diego’s skyline with a USCG-licensed captain

    Sail into sunset views of San Diego’s skyline with a USCG-licensed captain
    4.4 • 246 reviews
    $250/ boat
    2-Hour Sunset Sail in San Diego
    San Diego, CA

    2-Hour Sunset Sail in San Diego

    Sail Harbor Island at sunset with skyline views

    Sail Harbor Island at sunset with skyline views
    4.4 • 246 reviews
    $250& up
    Learn To Sail Lesson In San Diego
    San Diego, CA

    Learn To Sail Lesson In San Diego

    Get hands-on sailing instruction at the Marriott Marquis Marina

    Get hands-on sailing instruction at the Marriott Marquis Marina
    4.4 • 246 reviews
    $195/ person
    2-Hour Learn-to-Sail Lesson in Coronado
    San Diego, CA

    2-Hour Learn-to-Sail Lesson in Coronado

    Learn to sail a Capri 22 with an experienced skipper

    Learn to sail a Capri 22 with an experienced skipper
    4.4 • 246 reviews
    $195/ person
    Learn to Sail Lesson in Coronado
    San Diego, CA

    Learn to Sail Lesson in Coronado

    Learn basic sailing skills in a 2-hour session at Loews Coronado

    Learn basic sailing skills in a 2-hour session at Loews Coronado
    4.4 • 246 reviews
    $150/ person
    Learn to Sail in Mission Bay San Diego
    San Diego, CA

    Learn to Sail in Mission Bay San Diego

    Learn basic sailing skills on Mission Bay with an ASA certified instructor

    Learn basic sailing skills on Mission Bay with an ASA certified instructor
    4.4 • 246 reviews
    $195/ person
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