We're here to help
    Book online or call (650) 414-7338
    Ask AIAI
    Ask AIAI
    1. Local experiences/
    2. Things to do in Provincetown…/
    3. Water Activities/
    4. Sailing/
    5. Sail Boston Harbor on the Cutter Bloodhound
    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

    Concierge Support

    • Help Center
    [email protected](650) 414-7338

    Safe & Secure Payments

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

    Sail Boston Harbor on the Cutter Bloodhound

    Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

    From$72/ personincl. taxes and fees

    Duration

    1.5 - 2 hours

    Highlights

    Step aboard the Cutter Bloodhound, a gaff-rigged cutter designed in 1874, and cruise Boston Harbor during the Sail Boston 2026 Festival. Bring your own food and drinks and take in the feel of classic sailing under canvas.

    • Sail aboard a 1874-designed royal racing yacht
    • Experience a gaff-rigged cutter with William Fife II design heritage
    • Bring your own food and drinks for the sail
    • Choose a 90-minute day sail or a two-hour sunset sail
    • Meet in Charlestown, Boston, Massachusetts

    Things to know

    Boarding requires a ramp and a few steps, and restroom access uses four steep ladder-like steps. The operator may cancel for heavy rain, thick fog, high winds, thunder, or lightning.

    Cancellation Policy

    Cancel at least 48 hours before your sail for a full refund. Once inside 48 hours, tickets are refunded only if they cancel the sail because of weather. If you do not show up because of the weather and the boat sails, your ticket is not refundable.

    FAQs

    Yes. Your sail is bring your own food and drinks, and you can bring whatever food and drinks you wish.

    To board the vessel, you’ll navigate a ramp and a few steps. The restroom level is reached by four somewhat steep, ladder-like steps. There is a restroom with a regular household commode.

    If you’re somewhat ambulatory, the crew can assist you while boarding. They can also lock a rascal or personal chair to the dock and/or bring it on board if two crew members can lift it.

    Meeting details

    Charlestown Boston, MA US

    Experience provided by Hindu Charters LLC - Schooner Hindu
    Experience provided by Hindu Charters LLC - Schooner Hindu

    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 (650) 414-7338

    Report an issue

    Reference #WTWD8E

    Sail Boston 2026 Adult Daysail

    $72.56

    0

    Sail Boston 2026 Child Daysail

    $64.98

    0

    Sail Boston 2026 Senior Daysail

    $64.98

    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

    Nearby activities

    Thumbnail
    Sailing

    2-Hour Sunset Sail in Key West

    $136.64/ person
    Thumbnail
    SailingUp to 42

    Private Sailing Charter In Key West

    $2,782.91
    Thumbnail
    Private Whale Watching ToursUp to 6

    Private Whale Watching Charter in Provincetown

    $715.50
    Thumbnail
    Whale WatchingUp to 6

    Provincetown Whale Watch at Stellwagen Bank

    From$185/ person
    Thumbnail
    SailingUp to six guest…

    6-Hour Provincetown Private Sailing Charter

    $1,712.61
    Thumbnail
    SailingUp to 6

    2-Hour Private Sailing Charter in Provincetown

    $912.86