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    1. Local experiences
    2. /All experiences
    3. /Water Activities
    4. /Sailing

    Best results for Sailing in San Diego, CA

    Showing 1-24 of 26 results
    Private Sailboat Cruise & Wine Tasting in San Diego
    San Diego

    Private Sailboat Cruise & Wine Tasting in San Diego

    Sail San Diego Bay, then savor local wine on a private outing

    Sail San Diego Bay, then savor local wine on a private outing
    3.4 • 217 reviews
    $529& up
    2.5-Hour Private Sunset Sail in San Diego
    San Diego

    2.5-Hour Private Sunset Sail in San Diego

    Sail San Diego Bay at sunset on a private 2.5-hour charter

    Sail San Diego Bay at sunset on a private 2.5-hour charter
    5.0 • 307 reviews
    $525& up
    Sail San Diego Bay Catamaran Cruise With Drinks
    San Diego

    Sail San Diego Bay Catamaran Cruise With Drinks

    Sail San Diego Bay on a small-group catamaran with drinks included

    Sail San Diego Bay on a small-group catamaran with drinks included
    4.9 • 235 reviews
    $660
    Private Catamaran Charter on San Diego Bay
    San Diego

    Private Catamaran Charter on San Diego Bay

    Charter a private catamaran for your special occasion on San Diego Bay

    Charter a private catamaran for your special occasion on San Diego Bay
    4.9 • 235 reviews
    $660
    San Diego 2.5-Hour Private Day Sail
    San Diego

    San Diego 2.5-Hour Private Day Sail

    Take the helm on a private sail past San Diego landmarks

    Take the helm on a private sail past San Diego landmarks
    5.0 • 307 reviews
    $525& up
    Morning Sailing Charter in San Diego
    San Diego

    Morning Sailing Charter in San Diego

    Private bay sailing with Point Loma or Coronado routes

    Private bay sailing with Point Loma or Coronado routes
    5.0 • 307 reviews
    $525& up
    San Diego 4-Hour Sail & Swim Charter
    San Diego

    San Diego 4-Hour Sail & Swim Charter

    Cruise San Diego Bay, swim in Glorietta Bay, and explore your preferred route

    Cruise San Diego Bay, swim in Glorietta Bay, and explore your preferred route
    5.0 • 307 reviews
    $795& up
    Sunset Sailing Cruise in San Diego
    San Diego

    Sunset Sailing Cruise in San Diego

    Unwind on an evening sail with drinks and skyline views

    Unwind on an evening sail with drinks and skyline views
    4.9 • 235 reviews
    $131/ person
    San Diego Rady Shell Concert Sailing Experience
    San Diego

    San Diego Rady Shell Concert Sailing Experience

    Sail to a Rady Shell concert and watch from the water

    Sail to a Rady Shell concert and watch from the water
    5.0 • 307 reviews
    $795& up
    Private 3-Hour Sailing Charter in San Diego
    San Diego

    Private 3-Hour Sailing Charter in San Diego

    See San Diego’s historic waterfront on a private daytime sail

    See San Diego’s historic waterfront on a private daytime sail
    4.9 • 877 reviews
    $631& up
    Private 3-Hour Sailing Lesson in San Diego
    San Diego

    Private 3-Hour Sailing Lesson in San Diego

    Learn to sail in a private 3-hour lesson with a US Coast Guard certified captain

    Learn to sail in a private 3-hour lesson with a US Coast Guard certified captain
    4.9 • 877 reviews
    $689
    Private Sailing Charter in San Diego
    San Diego

    Private Sailing Charter in San Diego

    Customize a private sail with your own captain and crew

    Customize a private sail with your own captain and crew
    4.9 • 877 reviews
    $1,198& up
    3-Hour Private Sunset Sailing Cruise in San Diego
    San Diego

    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 • 877 reviews
    $631
    Bottomless Mimosa Sailing Cruise in San Diego
    San Diego

    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 • 877 reviews
    $80/ person
    3-Hour Sailing Charter in San Diego
    San Diego

    3-Hour Sailing Charter in San Diego

    Private coastal views with complimentary drinks and snacks

    Private coastal views with complimentary drinks and snacks
    4.9 • 877 reviews
    $631
    Cruise San Diego on a 3-Hour Bachelorette Sail
    San Diego

    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 • 877 reviews
    $583& up
    Cruise San Diego Coastline on a 3-Hour Sunset Sail
    San Diego

    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 • 877 reviews
    $631& up
    3-Hour Private Sunset Sail in San Diego
    San Diego

    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 • 877 reviews
    $631& up
    Private 6-Hour Sailing Charter in San Diego
    San Diego

    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 • 877 reviews
    $954& up
    3-Hour Midday Sailing Cruise In San Diego
    San Diego

    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 • 877 reviews
    $116/ person
    Sail On A 3-Hour San Diego Sunset Cruise
    San Diego

    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 • 877 reviews
    $126/ person
    2-Hour Morning Sail in San Diego
    San Diego

    2-Hour Morning Sail in San Diego

    Enjoy a relaxed San Diego Bay sail with snacks, drinks and family-friendly fun

    Enjoy a relaxed San Diego Bay sail with snacks, drinks and family-friendly fun
    4.9 • 877 reviews
    $94/ person
    Private Morning Sail in San Diego
    San Diego

    Private Morning Sail in San Diego

    Set sail through historic San Diego with complimentary drinks and snacks

    Set sail through historic San Diego with complimentary drinks and snacks
    4.9 • 877 reviews
    $477& up
    Private Sailing Charter in San Diego
    San Diego

    Private Sailing Charter in San Diego

    Sail San Diego Bay or the open ocean with your own captain and crew

    Sail San Diego Bay or the open ocean with your own captain and crew
    4.9 • 877 reviews
    $1,675& up
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