Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Gloucester…
    3. /Water Activities
    4. /Sailing
    5. /Gloucester Private Sailing Charter
    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
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

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

    Gloucester Private Sailing Charter

    Private schooner sailing with captain and crew included

    5.0 stars• 107 reviews

    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.

    Product ID: SY357Z

    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

    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

    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

    Great sail! Would recommend

    Photo of Tricia Boot

    Tricia Boot

    August 6, 2026

    Review 1 of 1
    5/5

    Great sail! Would recommend

    Photo of Tricia Boot

    Tricia Boot

    August 6, 2026

    Nearby activities

    Newburyport 4-Hour Whale Watch Cruise
    Whale Watching

    Newburyport 4-Hour Whale Watch Cruise

    Spot whales and dolphins with expert narration on the Atlantic Ocean

    4.8 • 594 reviews
    $74/ person
    4-Hour Striped Bass Fishing Trip in Hampton Beach
    Fishing Charters

    4-Hour Striped Bass Fishing Trip in Hampton Beach

    Spend 4 hours striped bass fishing with extra time on the water

    4.5 • 1K reviews
    $57/ person
    Cruise Boston Harbor on a 90-Minute Tiki Boat
    Boat Tours

    Cruise Boston Harbor on a 90-Minute Tiki Boat

    Ride a tiki boat for skyline views and a full-service bar on Boston Harbor

    4.9 • 986 reviews
    $54/ person
    Salem Maritime Walking Tour & Pirate Museum
    Historical Tours

    Salem Maritime Walking Tour & Pirate Museum

    Explore Salem's seafaring past and authenticated pirate treasure

    4.9 • 1.4K reviews
    $52/ person
    Explore Salem Witch Trials 1-Hour Walking Tour
    Ghost and Haunted

    Explore Salem Witch Trials 1-Hour Walking Tour

    Walk Salem’s Witch Trials sites in 1 hour with a guided group tour

    4.9 • 181 reviews
    $31/ person
    Boston Harbor Sunset Cruise & USS Constitution Cannon Fire
    Boat Tours

    Boston Harbor Sunset Cruise & USS Constitution Cannon Fire

    Sunset skyline views and harbor landmarks aboard a classic-style power yacht

    4.8 • 693 reviews
    $51/ person