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Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in BostonLuxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in BostonLuxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in BostonLuxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston

Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston

"The most beautiful sailboat in Boston Harbor". Peningo is a Family Owned & Operated Charter Boat based out of Boston Harbor. A perfect setting for executive entertainment, celebrating a special day with friends or unwinding for an afternoon or sunset cruise on Boston Harbor and the Harbor Islands! Get ready to have a blast and explore Boston from a brand new perspective on our amazing 50’ world cruiser. If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.

Starting from

  • Hourly
    12 hrs max
  • $500/hr
    2 hrs min


Captain Provided in Price
Professional Captain provided and included in the price.
6 guests
Cruising Monohull

Check Availability




Hi! My name is Jake Dougherty, me and my sister Genevieve are the owners & operators of s.v Peningo, a beautiful 50' sailboat which operates in Boston Harbor. We have a combined 30 years of sailing experience between us and were sailing instructors at Courageous Sailing in Charlestown for many years. We are both passionate sailors who ensure a relaxing, fun and safe trip sailing on Boston Harbor and the surrounding islands and we can't wait to have you onboard!

Features & Details

Dubois Pendennis
Custom World Class Racer/Cruiser
  • Bar
  • Bluetooth
  • Galley Stove & Oven
  • Life jackets/required safety gear
  • BBQ
  • Wi-Fi
  • Depth gauge
  • Snorkel
  • GPS
  • Licensing Required
  • Furling Headsail
  • Fuel type: Diesel
  • Dodger
  • Chart Plotter
  • Center Cockpit
  • Autopilot
  • Wheel steering
  • Inboard Engine
  • Enclosure
  • Cruising Speed
  • Head
  • Music System
  • Other
  • Sailboat
  • Charter
  • Generator
  • Toilet
  • Cabin
  • Radio

Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map

Cancellation Policy

Full refund up to 21 days prior.

Additional Terms & Information

Operator of this vessel must hold a current merchant mariner credential and have experience operating similar vessels, along with at least 2 years of experience navigating in Boston Harbor.  Any renter seeking to operate the vessel themselves or provide another captain will be required to provide proof of these qualifications.  A selection of qualified captains renters can choose from will be provided. Everything necessary to the operations of this vessel are included onboard for every charter including lifejackets, fire extinguishers, fuel, etc. Other accessories included are coolers, Bluetooth speakers, ice and food pickup. *Please note Get My Boat handles all payments and requires full payment to confirm reservations.  Please see Get My Boat terms and conditions regarding their service fees.  The cancellation and weather policy below is specific to our boat. *Reservations are for the exact time listed for the booking and noted in the contract - sent after confirmation of the reservation via payment.  Cruises are not extended due to late arrival. Unless the boat is not able to start a cruise on time, the cruise will end at the specified time regardless of when the boat leaves the dock. Cancellation Policy: Cancellations made 21 days or more prior to the scheduled cruise will receive a full refund of payments made to the boat. Any cancellation less than 21 days prior to the cruise date will not receive any refund unless the captain determines the cancellation is necessary due to unfavorable or unsafe conditions (see weather policy), or there is an unavoidable circumstance (i.e. medical emergency, death in the family etc...) In any event where the captain chooses to cancel, a full refund of fees paid to the boat will be provided. Weather Policy: For situations of unfavorable weather such as steady rain or unsafe weather such as thunderstorms, dangerous winds  etc... we allow for rescheduling up to one year from the date of the reservation.  If a mutually agreeable reschedule date can not be established, a refund of the fees paid to the boat less a 5% administrative fee will be provided.  If the renter chooses to cancel due to normal summer weather conditions (i.e. chance of showers, cloudiness, cool temperatures) that are not considered unsafe no refund will be provided.