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    5. /Sail a 24' Sloop Rental at Old Fisherman's Wharf
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    Sail a 24' Sloop Rental at Old Fisherman's Wharf

    Rent a classic 24-foot wooden sloop from Old Fisherman’s Wharf

    4.9 stars• 229 reviews
    From$312/ boatincl. taxes and fees

    Duration

    2 hours minimum

    Ideal For

    Up to 5 people

    Includes

    24ft sailboat rental

    Highlights

    Take the helm of Jeannette, a 24-foot all-wood Carol 24 sloop with simple controls and a comfortable cockpit for small groups and family outings. Depart from Old Fisherman’s Wharf and enjoy a hands-on sailing rental.

    • Rent a 1989 Carol 24 designed by Chuck Paine
    • Steer a full-keel wooden sloop with simple controls
    • Relax in a medium-sized cockpit for small groups
    • Choose a 2-hour minimum rental or an all-day upgrade
    • Depart from 78 Old Fisherman’s Wharf

    Things to know

    If this is your first rental with Sail Monterey, you must submit a sailing resume for approval before departure day. If it isn’t received or approved, your reservation may be postponed or canceled.

    Split the cost with your group

    This booking is for the whole experience, which fits up to 5 guests.

    From$62per person
    Split with

    Cancellation Policy

    Cancel at least 48 hours before departure for a full refund. No refunds for late or no-show renters. Full refund if the captain cancels due to weather or other unforeseen circumstances.

    FAQs

    Submit a sailing resume showing your relevant experience and certifications for approval before departure day. If it is not received or approved by departure day, your reservation may be postponed or canceled.

    Check in at the office no later than 30 minutes before your departure time.

    No. You cannot drive to the office at the end of the pier.

    Meeting details

    78 Old Fisherman's Wharf

    Experience provided by Sail Monterey
    Experience provided by Sail Monterey

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #6UNEBZ

    Rental

    $312.70

    This boat fits up to 5 guests · 2 hours minimum

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.9
    Excellent
    229 reviews•Google Maps
    218
    7
    1
    0
    3

    Monterey Bay sailing doesn't get much better than this. Paul and his team of captains, including Tiki, Kiwi, Tanya, and Vince, have built something genuinely special here. Families, couples, and first-timers all seem to walk away raving, and the enthusiasm these captains bring is clearly contagious. Wildlife sightings, including whales, sea lions, and otters, add an extra layer of magic to what's already a beautiful setting. For those curious about learning to sail, the intro and ASA certification courses earn particularly high praise. Captain Kiwi has a real gift for teaching, breaking down technical concepts in ways that actually stick, while Tanya brings impressive organization and warmth to the longer courses. Even on breezy or less-than-ideal days, the team communicates proactively and makes the most of conditions. The one hiccup worth noting is a cancellation that happened with short notice, so if your schedule is tight, it's worth confirming closer to your departure time.

    What people are saying

    Review 1 of 5
    5/5

    Great sail and great captain!

    Photo of C Rosare

    C Rosare

    May 5, 2026

    Review 1 of 1
    5/5

    Great sail and great captain!

    Photo of C Rosare

    C Rosare

    May 5, 2026

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