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    5. /Gloucester Schooner Festival Private Sailing Charter
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    Gloucester Schooner Festival Private Sailing Charter

    Sail in company with visiting schooners during Gloucester Schooner Festival Weekend

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

    Duration

    2 hrs

    Ideal For

    Up to 6 people

    Includes

    Private charter, sailing

    Highlights

    Sail aboard Isabella during Gloucester Schooner Festival Weekend and travel alongside visiting schooners. Bring your camera for views of the festival fleet on the water.

    • Explore Gloucester waters in company with visiting schooners
    • Capture photos of the festival fleet under sail
    • Bring food and beverages for your party
    • Pack sunscreen and sunglasses for time on the water
    • Wear sneakers, sandals, or boat shoes
    • Bring a sweatshirt or windbreaker for cooler conditions on the water

    Important details

    • Arrive with ample time to find parking and reach the boat before your reservation time
    • Leave illegal drugs, including cannabis and cannabis products, ashore
    • Bring only trained service animals as defined by the Americans with Disabilities Act; pets are not permitted
    • Expect the captain to make the sailing decision close to departure; severe or unsafe weather may cancel the sail

    Cancellation Policy

    Cancel up to 14 days before sail time without penalty. Within 14 days, your deposit is non-refundable and the reservation can't be rescheduled. If the operator modifies or cancels the reservation, you can reschedule or receive a full refund.

    FAQs

    Yes. Every passenger, including infants and toddlers, needs a ticket. The boat cannot exceed its United States Coast Guard passenger capacity.

    Yes. The restroom is below decks and reached by a steady boat ladder. If you have limited mobility, use the Maritime Gloucester restrooms before departure.

    Consider taking Dramamine 30 minutes before sailing.

    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 #PU79JV

    Isabella Festival Private Charter

    $477

    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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