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    1. Local experiences
    2. /Things to do in Gloucester…
    3. /Water Activities
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    5. /Gloucester Private Sailing Charter
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    Gloucester Private Sailing Charter

    Private schooner sailing with captain and crew included

    5.0 stars• 105 reviews
    From$477incl. taxes and fees

    Duration

    2 hrs–all day

    Ideal For

    Up to 6 people

    Includes

    Exclusive vessel, captain, crew

    Highlights

    Set sail aboard the Schooner Isabella for a private outing shaped around your plans. Explore local waters on a comfortable schooner built for small-group charters.

    • Customize your sail for a sunset, date night, family outing, or day trip
    • Explore nearby coastal villages or the Essex River aboard a shallow-draft schooner
    • Bring your own drinks and food for the sail
    • Use the onboard marine restroom, accessed by a boat ladder below deck

    What's Included

    • Exclusive use of the vessel
    • Captain and crew services

    Important details

    • Arrive before boarding; the vessel leaves at sail time and cannot return for late arrivals
    • No illegal drugs, including cannabis or cannabis products, are allowed onboard
    • Trained service animals are welcome; pets and other animals are not allowed
    • Wheelchair access is not available; boarding requires a sloped gangway, floating docks, and a short staircase
    • Sailing usually continues in light rain and moderate weather; the captain decides whether conditions are safe near departure
    • No cooking, reheating, or food refrigeration is available onboard

    Cancellation Policy

    Cancel up to 14 days before sail time without penalty. Later cancellations are nonrefundable and cannot be rescheduled. If the operator modifies or cancels your reservation, you can reschedule or receive a full refund.

    FAQs

    Bring a sweatshirt or windbreaker for cooler conditions on the water. Wear sneakers, sandals, or boat shoes instead of dress shoes or high heels, and consider bringing sunglasses, sunscreen, and a camera.

    Use the small Maritime Gloucester lot, limited metered parking on Harbor Loop, or metered lots on Rogers Street less than a two-minute walk from the vessel. Allow extra time during summer festivals, concerts, and events.

    For this sailing charter, consider taking Dramamine about 30 minutes before sailing if you are prone to motion sickness.

    Meeting details

    Maritime Gloucester, 23 Harbor Loop, Gloucester, MA

    Experience provided by Maritime Heritage Charters

    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 #SY357Z

    1-6 Passenger 2-Hour Charter - Isabella

    $477

    0

    1-6 Passenger 3-Hour Charter - Isabella

    $636

    0

    1-6 Passenger 5-Hour Charter - Isabella

    $795

    0

    1-6 Passenger 7-Hour Charter - Isabella

    $1,007

    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 5
    5/5

    I thought I was going on a tour of Boston harbor during the Sail Boston event in the Schooner Ardell. Little did I know the hand built schooner I was on would be part of the parade of sail. With Master Shipbuilder and Captain Harold A. Burnham at the helm with his hand picked crew I had the most amazing time of my life, it was a once in a lifetime experience which I will never forget. Captain Harold and his crew was very attentive to every single person on the ship and showed his skill sailing around Boston Harbor during the parade.

    Photo of Richard Schofield

    Richard Schofield

    July 26, 2026

    Review 1 of 1
    5/5

    I thought I was going on a tour of Boston harbor during the Sail Boston event in the Schooner Ardell. Little did I know the hand built schooner I was on would be part of the parade of sail. With Master Shipbuilder and Captain Harold A. Burnham at the helm with his hand picked crew I had the most amazing time of my life, it was a once in a lifetime experience which I will never forget. Captain Harold and his crew was very attentive to every single person on the ship and showed his skill sailing around Boston Harbor during the parade.

    Photo of Richard Schofield

    Richard Schofield

    July 26, 2026

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