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    5. /Sail Monterey Bay on a 30' Hunter Sailboat Rental
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    Sail Monterey Bay on a 30' Hunter Sailboat Rental

    Rent the 30' Hunter Willow and sail Monterey Bay your way

    4.9 stars• 229 reviews
    From$360/ boatincl. taxes and fees

    Duration

    2 Hours

    Includes

    Hunter 30T sailboat rental

    Highlights

    Take the helm of Willow, a 1991 Hunter 30T, and spend your time on the bay at your own pace. Depart from 78 Old Fisherman's Wharf with wheel steering, a furling jib, and an inboard diesel engine onboard.

    • Rent a 1991 Hunter 30T sailboat for your own outing
    • Steer with wheel steering for easier handling
    • Use the furling jib to adjust sails on the go
    • Motor as needed with the small inboard diesel engine
    • Complete a first-time renter checkout for an extra $50
    • Send a sailing resume for approval before your departure date

    What's Included

    • Willow (1991 Hunter 30T) rental
    • Wheel steering
    • Furling jib
    • Small inboard diesel engine
    • Brand new sails

    Things to know

    If this is your first rental with Sail Monterey, you must submit a sailing resume showing relevant experience and certifications. If your resume is not received or approved by departure day, your reservation may be postponed or canceled.

    Cancellation Policy

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

    FAQs

    Yes. Before you rent Willow, submit a sailing resume that shows your relevant experience and certifications. If your resume is not received or approved by departure day, your reservation may be postponed or canceled.

    Yes. If this is your first time renting, you must complete a rental checkout, which costs an additional $50.

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

    Meeting details

    78 Old Fisherman's Wharf

    Experience provided by Sail Monterey
    Experience provided by Sail Monterey

    More about Old Fisherman's Wharf

    Old Fisherman's Wharf sits at the heart of Monterey's working waterfront, a salt-sprayed stretch of weathered pilings, seafood shacks, and bobbing fishing boats that has welcomed mariners since the 1840s. Setting sail aboard the Willow Hunter 30T from this historic harbor means slipping past the same docks where Monterey's sardine fleets once unloaded their catch, with sea lions barking from the rocks below and the scent of clam chowder drifting from the wharf's restaurants. The contrast is immediate and unforgettable: within minutes of leaving Old Fisherman's Wharf behind, you trade the bustle of the boardwalk for the open swell of Monterey Bay.

    The journey out from Old Fisherman's Wharf reveals the bay from a perspective most visitors never see. As the sails of the Willow Hunter 30T fill with the steady afternoon breeze, the wharf shrinks into a colorful ribbon of red rooftops and white-trimmed storefronts, framed by the green hills of the Monterey Peninsula. Keep watch for harbor seals lounging on buoys, sea otters cracking shells in the kelp beds, and pods of dolphins that often shadow boats just beyond the breakwater. On clear days, the views stretch from Pacific Grove to the curve of the bay toward Santa Cruz, with Old Fisherman's Wharf serving as your familiar landmark on the return leg.

    This sail is perfect for couples celebrating something special, small groups of friends looking for an alternative to the crowded wharf restaurants, and travelers who want to experience Monterey's maritime soul rather than just snap photos of it. Families with older kids who love marine wildlife will find plenty to point at, and seasoned sailors will appreciate the Willow Hunter 30T's classic lines and responsive handling. Whether you book a sunset cruise or a midday outing, returning to Old Fisherman's Wharf with the wind still in your hair is the kind of memory that turns a Monterey trip into a story worth retelling.

    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 #M5S5M3

    Rental

    $360.40

    Rentals are 2 hours minimum

    0

    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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