Water activity

Boston: Downtown Harbor Sailing Cruise

Activity provider:Classic Harbor Line Boston
Water activity

Boston: Downtown Harbor Sailing Cruise

Activity provider:Classic Harbor Line Boston

From US$ 57.75 per person

Discover the beauty of Boston Harbor on a sailng tour aboard the schooner Adirondack III and experience its rich history and wildlife. An experienced crew will take care of your needs as you cruise past the Inner Harbor Islands and more.

About this activity

Free cancellation
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Covid-19 precautions
Special health and safety measures are in place. Check your activity voucher once you book for full details.
Duration 1.5 - 2 hours
Check availability to see starting times.


  • Cruise Boston Harbor on board an 80-foot schooner
  • Feel the wind in your hair as you sail past the Inner Harbor Islands
  • Learn the sea legends of Boston and surrounds
  • See landmark attractions such as the New England Aquarium and Moakley Federal Courthouse
Full description

Experience Boston like never before onboard the 80-foot pilot schooner Adirondack III. Enjoy a round-trip of smooth sailing, with some invigorating speed to boot. Within minutes of leaving dock, you’ll forget the distractions of life on land as you experience the joy of a sailing adventure. Cruise past landmark attractions, such as the Boston Fish Pier, Moakley Federal Courthouse at Fan Pier, and Castle Island. Drift past the Inner Harbor Islands and see the historic Charleston Navy Yard. Look out for the green oasis of Waterfront Park and the home to hundreds of marine critters, including sharks and sea turtles, at New England Aquarium. Your knowledgeable captain and crew will be on hand to answer questions about the sights and history of Boston Harbor and its surrounds, from interesting facts to old-time legends. Wines and local micro beers are available to purchase onboard, while complimentary soda and water will keep you hydrated along the way.

  • 1.5 or 2-hour sailing cruise (depending on option selected)
  • Captain and crew
  • Complimentary soda and water
  • Food
  • Tips

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Meeting point

Meeting point may vary depending on the option booked.

Important information

What to bring

  • Passport or ID card

Not allowed

  • Pets
  • Unaccompanied minors

Know before you go

  • Only animals that perform a manual task to assist a person are permitted aboard
  • Emotional support animals and pets are not permitted
  • All children under the age of 17 must be accompanied by an adult
  • Please inform the local supplier in advance if assistance is needed to board
  • Adult beverages are available to purchase onboard. Credit Cards are the only form of payment accepted on your cruise. Please plan accordingly. Soda & Water is $2.00, beer is $6.00, wine is $7.00/glass, and mixed drinks are $9.00
  • Complimentary water is available from the water cooler. Please bring your own water bottle (this is in an effort to reduce the use of plastics aboard the boat)
  • Feel free to bring your own picnic
Customer reviews

Overall rating

4.8 /5

based on 124 reviews

Review summary

  • Transportation
  • Value for money
  • Service
  • Organization

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This was such an unexpected treasure of a discovery in Boston! Besides having unseasonably beautiful weather for an October day, the sailing itself was terrific. Sails raised, light breeze once we motored out of the harbor and very peaceful. The crew was friendly and did not over narrate - they let us enjoy the day and answered any questions if asked. Seating is comfortable and lots of room. You can move around, there is a bathroom on board if needed. Bring a little picnic, order a cocktail, sit back and relax. Great value for the price. HIGHLY RECOMMEND!!!

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May 30, 2023

Overall a pleasant experience. It would be even better if the staff are more interactive with the passengers and provide commentary on things like how sail boats work, history of that boat, history of boston harbor, what buildings are on the skyline. I think that’s a great opportunity to further improve customer experience.

May 30, 2023

It was good. The day was absolutely beautiful. The boat and water spectacular. The service was good. Staff members nice and courteous. We thought there would be more sailing than the zig zag thru the harbor. We figured it would be a sailing trip not sit on the boat while we go thru the harbor. We also thought the captain or crew would point out different sites to see or things to landmarks to look for. That did not happen. The Captain seemed slightly preoccupied with his own guest on the boat. If you are looking for more description of the Boston sites you may be disappointed. The Boston Skyline is beautiful and it was pleasant to see it from the water. Overall we thought it was better than larger tourist boats.

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May 30, 2023

Product ID: 45343