Boston Itinerary: USS Constitution to the Prudential

Gregg Squeglia, Knockabout Travel

19 June 2019

This Boston walking tour will have you traveling through time as we start with one of Boston’s best historical attractions. Then enjoy a ferry ride across Boston Harbor to the waterfront where you will enjoy some classic architecture, New England’s largest IMAX cinema, and the best view in Boston from the city’s second tallest building. 

  1. Start your day with a cup of coffee and a breakfast sandwich at Sorelle Bakery and Café. It’s located in Charlestown, just over the North Washington Street Bridge and on the walking route to your first attraction.
  2. USS Constitution: Visit with the US Navy’s oldest commissioned warship. Tours are free to all and conducted by active duty Sailors in conjunction with the National Park Service. (Read the full blog article of the USS Constitution HERE). After your tour, head to the MBTA Ferry dock, co-located with the Charlestown Naval Shipyard for a quick ride to your next destination.
  3. Take in a 3D IMAX film at the New England Aquarium. Although you may be able to do this in many large cities, these films are almost always excellent and educational. If you are traveling with children, it’s a great stop.
  4. Lunch at Quincy Market: Choose from the huge food court that features a wide variety of international cuisine including Asian, Middle-Eastern, Mediterranean, and of course a number of traditional American dishes. Afterward, stroll on over to Faneuil Hall to check out some of Boston’s best street performers.
Boston Walking Tour Prudential Tower

The Prudential Tower in Boston’s Back Bay neighborhood.

Photograph CC-BY 2.0

  1. Boston Public Garden: Walk through Boston Common to America’s first public botanical garden. Enjoy the green space and flowerbeds, take a swan boat ride, or just have a seat on a park bench with a pretzel or hot dog from one of the street vendors.
  2. Copley Square: Hang out at one of Boston’s most popular outdoor gathering places. Plenty of vendors line the perimeter of the square, selling everything from fresh fruit to souvenirs. If you are a fan of classic architecture, then this neighborhood will not let you down. The Boston Public Library is considered a masterpiece of 18th-century architecture. You do not need to be looking for books to enjoy the library. The building itself is the attraction. In addition, Trinity Church is located adjacent to Copley Square and has been named by the American Institute of Architects as one of the most important buildings in America. Whether you are religious or not, you will have a healthy appreciation for the detail that went into its construction and the sacred atmosphere it creates. Drop-in tours, either guided or self-guided are available Tuesday-Sunday.
  3. Prudential Center: Includes a large, upscale shopping mall and restaurants. Across the road is the Christian Science Center which has a large plaza with a reflection pool and beautiful architecture to enjoy, as well as the Mapparium. (Note: The Prudential Tower’s Skywalk Observatory is now permanently closed and in the process of being reimagined).

“Chinese food in Texas is the best Chinese food in the United States except Boston.”

-John Updike, Author

It’s true. You cannot beat the Chinese food in this town, so be sure to have lunch in Chinatown as you walk this itinerary, or come back for dinner after hanging at the hotel room for a bit. I highly recommend Q Restaurant if you’d like one more recommendation.

Use this map to assist with navigating. Walking is the recommended method of travel.

The USS Constitution is the US Navy’s oldest comissioned ship

Knockabout Boston Audio Tour

Take a self-paced walk through Boston’s most historic neighborhoods. Includes all audio files streamed directly to your smartphone. No apps, no accounts, no passwords to remember.

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