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    5. /2-Hour Sailboat Rental in Monterey
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    2-Hour Sailboat Rental in Monterey

    Sail a spacious Hunter monohull with room to lounge

    4.9 stars• 239 reviews
    From$572/ boatincl. taxes and fees

    Duration

    2 hrs

    Includes

    Furling sails, autopilot, stereo

    Highlights

    Explore Monterey aboard Calypso, the fleet’s largest monohull. Set out with family and friends on a sailboat equipped for comfortable time on the water.
    • Relax in generous lounging space
    • Raise and trim sails with a furling main and jib
    • Navigate with onboard autopilot
    • Listen to music on the stereo

    Know before you go

    • ASA 104 certification is required to rent this boat
    • First-time renters require a rental checkout with an instructor
    • First-time renters require a sailing resume showing relevant experience and certifications before departure
    • Return the boat before sunset
    • Charges may apply for equipment lost or damaged during your rental

    Cancellation Policy

    Cancel at least 48 hours before departure for a full refund. Late arrivals and no-shows are not refunded. Receive a full refund if the captain cancels due to weather or other unforeseen circumstances.

    FAQs

    Wear flat, non-marking, closed-toe shoes.

    Bring a valid photo ID; identification may be checked.

    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

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    Reference #9HYKAB

    Rental

    $572.40

    Rentals are 2 hours minimum

    0

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      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.9
    Excellent
    239 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 4
    5/5

    I took ASA 101 and 103 on back to back weekends. Not only did I have a great time and learn a ton, I tapped into an amazing sailing community. I went from no experience to feeling very comfortable with basic maneuvers in light winds, and gained experience and confidence in spicier conditions under the calm guidance of Captains Tanya and Tiki. And now I can tie six kinds of knots! Highly recommended them as a sailing school, and the catamaran cruises are a lovely and relaxing way to see Monterey from the water.

    Photo of Liz MacDonald

    Liz MacDonald

    June 29, 2026

    Review 1 of 1
    5/5

    I took ASA 101 and 103 on back to back weekends. Not only did I have a great time and learn a ton, I tapped into an amazing sailing community. I went from no experience to feeling very comfortable with basic maneuvers in light winds, and gained experience and confidence in spicier conditions under the calm guidance of Captains Tanya and Tiki. And now I can tie six kinds of knots! Highly recommended them as a sailing school, and the catamaran cruises are a lovely and relaxing way to see Monterey from the water.

    Photo of Liz MacDonald

    Liz MacDonald

    June 29, 2026

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