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Boston Sailing Cruise and Skyline
  • Boston Sailing Cruise and Skyline
  • Sailing the Boston Harbor
  • Boston Harbor Sailing

Boston Harbor Sailing Cruise

From: $95
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Rowes Wharf - Boston, MA

Mid-May through Mid-October:
Daily - 3:30 PM
Click here for schedule

  • Spend you afternoon on the water enjoying the beauty of the Boston skyline on the Boston Harbor Sailing Cruise.
    • Your experienced captain and crew will entertain and captivate you with tales of the "City on the Hill" as you sail the harbor on this two-hour cruise
    • Highlights of the sail include the Boston Seaport District, Inner Harbor Islands, the Charleston Navy Yard, Castle Island and other famous Boston landmarks
    • A perfect way to see the sights along the Boston Harbor!
    Full Description>
  • The best way to spend any afternoon on the East Coast is on the water! Climb aboard the Adirondack III, an impressive, 80-foot pilot schooner. Enjoy complimentary beverages while taking in breathtaking beauty offered only by the Boston Harbor.

    Notable scenery on this cruise may include (and is subject to change):

    • The Boston Fish Pier
    • Moakley Federal Courthouse at Fan Pier
    • Castle Island and the Donald McKay monument
    • Inner Harbor Islands
    • Charleston Navy Yard
    • Waterfront Park
    • Harpoon Brewery
    • The New England Aquarium

    Admire the natural beauty and historical landmarks of the Boston Harbor on this afternoon sailing cruise.

    Key Info>
  • Essential Information

    • Food is not included on board; snacks and picnics are recommended
    • Soda & water,are complimentary. Alcohol can be purchased by anyone over 21 with a valid photo ID 
    • This experience is not suitable for young children
    • Passengers must arrive 30 minutes prior to departure time; boarding is 10 minutes prior
    • Captain and crew gratuity is not included, but is appreciated


    2 Hours

    Maximum Participants

    Up to 41 passengers


    This experience will be enjoyed by the participants only.

    Weather Dependent

    The cruise runs rain or shine. A trip is only canceled in the event of severe or unsafe weather conditions. Cancellations are made on the day of the cruise, by the captain, up to one hour prior to sail time. Always contact the experience provider with any questions regarding weather conditions on the day of your experience. In the event of a canceled cruise, passengers will reschedule directly with the experience provider.

    What To Wear

    Dress is typically casual. The temperature can be cooler out on the water, so dress accordingly. Please wear only soft soled shoes such as sneakers, deck shoes, flip-flops or sandals.

    Booking Information

    For this experience, it is recommended to request bookings at least 14 days in advance.

    Cancellation Policy

    Prior to scheduling/booking a date for this experience, Cloud 9 Living's standard return and exchange policy shall apply. Once you have scheduled a date and received a booking confirmation, no refunds will be given. Rescheduling is not allowed and all bookings are final. Failure to appear on your booked date will result in the loss of the value of your experience.

    Experience ID


    1. Will there be food served on board?
      Food is not served on board, but passengers can bring snacks or a picnic. Complimentary soda and water will be provided and alcoholic beverages are available for purchase.
    2. Is the schooner wheelchair accessible?
      No, unfortunately the schooners are not wheelchair-accessible.
    3. Are there any age restrictions?
      All ages are welcome aboard and must have a reservation prior to boarding. All passengers under the age of 18 must be accompanied by a parent or guardian.
    4. What happens if it starts to rain when we're sailing?
      This experience will sail in the rain. Lightweight, plastic ponchos are available to all passengers in the event of a rainstorm.
    5. Will I get seasick?
      The Adirondack III is a gentle, steady vessel. Most people do not experience seasickness.
    6. Is there a bathroom on the boat?
      Yes, the boat is equipped with a restroom that is accessible at all times.
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