Free Concierge Service
    Text or call (650) 414-7338
    Ask AIAI
    Ask AIAI
    1. Local experiences/
    2. Things to do in Monterey…/
    3. Water Activities/
    4. Boat Rentals/
    5. Sail Monterey Bay on a 30' Hunter Sailboat Rental
    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
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Sail Monterey Bay on a 30' Hunter Sailboat Rental

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

    4.9 stars• 228 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 (650) 414-7338

    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
    228 reviews

    LEI delivers consistently exceptional charter experiences, with reviewers praising everything from their well-maintained catamarans to their attentive crews. Nicole handles bookings with clear communication and helpful recommendations (including private chef referrals that guests rave about), while captains like Alex, Trevor, Guy, and Ross earn repeated mentions for being professional, personable, and great at making everyone feel comfortable. Multiple guests have returned for their third or fourth charters, which speaks volumes about the quality. The boats themselves impress, with several reviewers noting the Lagoon 42 and Bali 4.6 catamarans look even bigger and more beautiful in person. Crews provide snacks, drinks, and essentials while allowing you to bring your own food and wine for easy celebrations. There was one isolated timing hiccup where a dock mix-up delayed departure by 20 minutes without compensation, but this appears to be an outlier in an otherwise seamless operation. Perfect for bachelorette parties, birthdays, family gatherings, or just a luxurious day on the water with friends.

    Nearby activities

    Thumbnail
    Sailing

    Daytime Catamaran Sailing Cruise

    From$62/ person
    Thumbnail
    Boat RentalsUp to 5

    Sail a 24' Sloop Rental at Old Fisherman's Wharf

    $312.70/ boat
    Thumbnail
    SailingUp to 6

    Sail a Private Sunset Cruise in Monterey

    $996.40
    Thumbnail
    Sailing

    Sunset Catamaran Sailing Cruise in Monterey

    $94.34/ person
    Thumbnail
    SailingUp to 6

    2-Hour Sailing Lesson in Monterey

    From$168/ person
    Thumbnail
    Whale Watching

    Narrated 3Hr Monterey Whale Watching Cruise

    From$79/ person