Free Concierge Service
    Text or call (650) 414-7338
    Ask AIAI
    Ask AIAI
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Concierge Support

    • Help Center
    [email protected](650) 414-7338

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Free Concierge Service
    Text or call (650) 414-7338
    Ask AIAI
    Ask AIAI
    1. Local experiences/
    2. All experiences/
    3. sailing

    Best results for Sailing

    Showing 193-216 of 404 results
    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
    5.0 • 813 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
    5.0 • 813 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
    5.0 • 813 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
    5.0 • 813 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
    5.0 • 813 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
    5.0 • 813 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
    5.0 • 813 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
    5.0 • 813 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
    5.0 • 813 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
    5.0 • 813 reviews
    $477& up
    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 • 103 reviews
    $631/ person
    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 • 244 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 • 244 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 • 244 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 • 244 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 • 244 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 • 244 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 • 244 reviews
    $195/ 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 • 244 reviews
    $404/ 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 • 244 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 • 244 reviews
    $150/ 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 • 244 reviews
    $16/ 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 • 244 reviews
    $32/ 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 • 244 reviews
    $195/ person
    1…8910…17