Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Monterey…
    3. /Water Activities
    4. /Boat Rentals
    5. /2-Hour Sailboat Rental in Monterey
    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

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Gallery image
    Gallery image 2
    Gallery image 3

    2-Hour Sailboat Rental in Monterey

    Sail a spacious Hunter monohull with room to lounge

    4.9 stars• 246 reviews

    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

    Important details

    • 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.

    Product ID: 9HYKAB

    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

    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

    Rental

    $572.40

    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
    246 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

    We loved the sunset cruise we recently took with Captain Vince. The weather was perfect, the scenery amazing and we were taken care of with blankets (if needed), drinks and snacks. This was a birthday gift to my husband, and he had a great time. We also thoroughly enjoyed the music selection on board. We will be back.

    Photo of Melody (Melodyeco)

    Melody (Melodyeco)

    August 4, 2026

    Review 1 of 1
    5/5

    We loved the sunset cruise we recently took with Captain Vince. The weather was perfect, the scenery amazing and we were taken care of with blankets (if needed), drinks and snacks. This was a birthday gift to my husband, and he had a great time. We also thoroughly enjoyed the music selection on board. We will be back.

    Photo of Melody (Melodyeco)

    Melody (Melodyeco)

    August 4, 2026

    Great for groups

    Sail a 24' Sloop Rental at Old Fisherman's Wharf
    Boat RentalsUp to 5

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

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

    Rent a classic 24-foot wooden sloop from Old Fisherman’s Wharf
    4.9 • 246 reviews
    $313/ boat
    Sail Monterey Bay on a 30' Hunter Sailboat Rental
    Boat Rentals

    Sail Monterey Bay on a 30' Hunter Sailboat Rental

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

    Rent the 30' Hunter Willow and sail Monterey Bay your way
    4.9 • 246 reviews
    $360/ boat
    Monterey 34' Sailboat Rental
    Boat Rentals

    Monterey 34' Sailboat Rental

    Sail a spacious 34-foot Hunter with room to relax with family and friends

    Sail a spacious 34-foot Hunter with room to relax with family and friends
    4.9 • 246 reviews
    $466/ boat

    Nearby activities

    Daytime Catamaran Sailing Cruise
    Sailing

    Daytime Catamaran Sailing Cruise

    Relax on a 35-minute Monterey Bay sail with included drink and snacks

    Relax on a 35-minute Monterey Bay sail with included drink and snacks
    4.9 • 246 reviews
    $63/ person
    Sail a Private Sunset Cruise in Monterey
    Sailing

    Sail a Private Sunset Cruise in Monterey

    Private keelboat sailing for up to 6 from Old Fisherman’s Wharf

    Private keelboat sailing for up to 6 from Old Fisherman’s Wharf
    4.9 • 246 reviews
    $996
    Sunset Catamaran Sailing Cruise in Monterey
    Sailing

    Sunset Catamaran Sailing Cruise in Monterey

    Sail Monterey Bay at sunset with a drink and snacks included

    Sail Monterey Bay at sunset with a drink and snacks included
    4.9 • 246 reviews
    $94/ person
    2-Hour Sailing Lesson in Monterey
    Sailing

    2-Hour Sailing Lesson in Monterey

    Learn sailing basics in a 2-hour class from Old Fisherman’s Wharf

    Learn sailing basics in a 2-hour class from Old Fisherman’s Wharf
    4.9 • 246 reviews
    $169/ person
    Monterey Bay Whale Watching Cruise
    Whale Watching

    Monterey Bay Whale Watching Cruise

    Cruise Monterey Bay with narrated wildlife viewing from a heated vessel

    Cruise Monterey Bay with narrated wildlife viewing from a heated vessel
    4.7 • 3.3K reviews
    $80/ person
    4-Hour Morning Whale Watching Cruise
    Whale Watching

    4-Hour Morning Whale Watching Cruise

    Spot whales and dolphins on a 4-hour morning cruise with marine biologists onboard

    Spot whales and dolphins on a 4-hour morning cruise with marine biologists onboard
    4.8 • 2.2K reviews
    $88/ person