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    1. Local experiences
    2. /Things to do in Harwich…
    3. /Water Activities
    4. /Sailing
    5. /14' Catamaran Rental on Pleasant Bay
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    14' Catamaran Rental on Pleasant Bay

    Take the helm of a forgiving catamaran for easy bay sailing

    4.8 stars• 134 reviews

    Duration

    1-4 Hours

    Ideal For

    Up to 4 people

    Highlights

    Take the helm of an easy-to-rig catamaran designed for a relaxed sail. Its forgiving design suits newly initiated sailors and families alike.

    • Sail a 14-foot catamaran with a main sail only
    • Enjoy a forgiving design suited to newcomers
    • Explore several square miles of Big Pleasant Bay
    • Pack clothing and shoes you do not mind getting wet

    What's Included

    • Small dry bag for valuables

    Important details

    • Arrive 20 minutes before your scheduled departure; late arrivals receive no refunds or credits
    • Bring a valid photo ID
    • Renters must be ages 18+ and qualified to operate the vessel
    • An additional instructor charge applies if you lack adequate experience or qualifications; otherwise the reservation ends without a refund
    • Stay in Big Pleasant Bay and within the operator's line of sight at all times
    • Bring a waterproof watch if you do not bring a phone, and return the boat on time
    • Expect sailing to proceed in overcast conditions, light fog, or intermittent sprinkles

    Cancellation Policy

    Cancel at least 7 days before departure for a full refund. Cancellations within 7 days but more than 48 hours before departure are charged 50%. Cancellations within 48 hours and no-shows are charged the full price. Receive a full refund if the operator cancels due to inclement weather or unforeseen circumstances.

    Product ID: VX2DWC

    FAQs

    You may be able to stop at one of the islands in Big Pleasant Bay if tides and your rental duration allow.

    Meeting details

    Wequassett Resort & Golf Club, 2173 Route 28, Harwich, MA 02645

    Experience provided by Down Cape Charters & Boat Rentals

    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

    1 Hour Rental

    $142.96

    0

    2 Hour Rental

    $180.02

    0

    3 Hour Rental

    $217.09

    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

    What people are saying

    Review 1 of 4
    5/5

    Sailing on Maria, Down Cape’s gorgeous sailboat was the highlight of our summer ! From the first phone call to book a sail, to meeting the Captain at the boat, enjoying the sights of Pleasant Bay and feeling safe and comfortable aboard the boat, the experience could not have been better. We are 12 local women who know Cape Cod well, and this activity was the most magical experience for all of us !

    Photo of Beverly Biondi

    Beverly Biondi

    August 19, 2026

    Review 1 of 1
    5/5

    Sailing on Maria, Down Cape’s gorgeous sailboat was the highlight of our summer ! From the first phone call to book a sail, to meeting the Captain at the boat, enjoying the sights of Pleasant Bay and feeling safe and comfortable aboard the boat, the experience could not have been better. We are 12 local women who know Cape Cod well, and this activity was the most magical experience for all of us !

    Photo of Beverly Biondi

    Beverly Biondi

    August 19, 2026

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