Water activity

Boston: Afternoon Sailing Trip Around Boston Harbor

Water activity

Boston: Afternoon Sailing Trip Around Boston Harbor

From US$ 59 per person

Journey aboard a tall ship as you sail around the Boston Harbor and islands on a cruise. Take the wheel, help set the sails, or just sit back and enjoy the views of the breathtaking city skyline.

About this activity

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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.
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  • Discover Boston Harbor from the decks of the Liberty Clipper or Liberty Star
  • Relax and enjoy the harbor's lovely scenery
  • Enjoy the stunning city skyline, fresh air, and sunshine
  • Set the sails and take the wheel of this 125 foot schooner
  • Choose between a 1.5-hour or 2-hour sailing experience
Full description

Embark on a scenic sailing trip on board an authentic tall ship in Boston Harbor. Sailing offers a great family-friendly way to see Boston from a new viewpoint. Choose between a 1.5-hour sail on the Liberty Star or a 2-hour sail on the Liberty Clipper. Hop on board and be transported back to the time when the tall ships would come in from the Old World. You can help set the sails, take the wheel, or sit back and enjoy the passing scenery of the Boston Harbor and the surrounding islands with the city skyline as a backdrop. The Liberty Clipper is a 125-foot gaff-rigged schooner designed after early American privateers. There is a cash-only bar on the ship with beer, wine, mixed drinks, sodas, bottled water, and snacks available.

The Liberty Star is another gaff-rigged schooner modeled after 19th-century vessels that were once known for their speed and agility. The vessel offers a similar taste of what it was like to sail the magnificent ships that were once a common sight in every port. 

  • Admission and sailing
  • Food and drinks

Select participants and date



Meeting point

Check in at the Green Ticket booth in front of the New England Aquarium. Please arrive 30 minutes before your scheduled departure time.

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Important information

What to bring

  • Snacks
  • Jacket
  • Packed lunch
  • Weather-appropriate clothing

Not allowed

  • Cooler

Know before you go

  • You must be 21 to purchase alcoholic beverages.
  • This activity takes place rain or shine.
Customer reviews

Overall rating

4.6 /5

based on 102 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Service

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Star rating:

My sister and I loved this sailing trip around the Boston Harbor. The captain is an experienced sailor as well as an actor. He's quite the entertainer! Funny! The rest of the crew is helpful and accommodating. The sail is relaxing, interesting, and an interesting way to enjoy Boston. I would do it all over again just to be out in the bay on such a beautiful ship.

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September 28, 2021

This is a nice relaxing sail in the harbor. Really nice crew and other staff, affordable price, affordable simple drinks. Its a very down to earth relaxed atmosphere. We enjoyed ourselves. Would be great if crew knew a little bit more about the buildings or history of Boston to share with tourists. All in all..worth the cost. :)

September 18, 2021

What a relaxing way to spend a couple hours. The captain and crew of the Liberty Star were friendly, knowledgeable, and fun. The sail was smooth and comfortable with drinks and conversation with fellow travelers. We watched the planes land and take off at the airport and had beautiful views of the Boston skyline. Kelly and Shawn were hardworking and accommodating. Worth every penny.

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August 21, 2021

Product ID: 19749