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    1. Local experiences
    2. /Things to do in Harwich…
    3. /Water Activities
    4. /Sailing
    5. /Private 2-Hour Sailing Charter in Harwich
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    Private 2-Hour Sailing Charter in Harwich

    Set sail privately with your group on Pleasant Bay

    4.8 stars• 134 reviews

    Duration

    2 hrs

    Ideal For

    Up to 6 people

    Includes

    Licensed captain, bottled water

    Highlights

    Explore Pleasant Bay aboard a private day sail reserved for your group. Bring simple refreshments and enjoy time on the water together.

    • Sail with only your party aboard
    • Bring simple snacks and beverages to enjoy on the boat
    • Relax in an open-air setting on the water
    • Share a daytime sailing experience with your group

    What's Included

    • Licensed captain
    • Complimentary bottled water

    Important details

    • Arrive 20 minutes before your scheduled departure time
    • Maximum 12 passengers, regardless of age or size
    • Bring beer only in cans and wine in reasonable amounts if you are 21 or older; no hard alcohol
    • Dress for changeable weather; sails may operate in overcast conditions, light fog, or intermittent sprinkles
    • Expect the captain to make the final decision on weather-related cancellations

    Cancellation Policy

    Full refund with at least 7 days' notice. Cancellations 48 hours to 7 days before departure are charged 50%. No-shows and cancellations within 48 hours are charged full price. Full refund if the operator cancels due to inclement weather or other unforeseen circumstances.

    Product ID: U9E3JU

    FAQs

    You do not need to update your reservation. Your final rate for the Private Day Sail is adjusted to the number of people who arrive on the day of your charter.

    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

    2 Hour Charter

    $1,349.99

    Covers 1 - 6 People

    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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