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Boston private guides and walking tours


We're excited to add Boston, our newest city, to the Context pantheon. Here, with a number of alumni docents from our programs in Rome, Paris, and elsewhere, we're ready to help you dig deeply into the history and artistic patrimony of this American treasure.


  • thematic walks
  • historian-led
  • slow travel approach

Check out the John Singer Sargent Seminar, a tour focused on this seminal American painter.

the North End, Portrait of a City

History of Boston
North End Walk
A three-hour walking tour of Boston's North End with a Context historian, in which we explore the history of the city from colonial to contemporary eras.

Featured Walks in Boston

History Walks (1 of 3)

North End Boston, Portrait of a City

Boston featured walking tour - North End Boston, Portrait of a City

Since its founding in 1630, Boston has embodied many of the historical themes that have shaped America including commerce, political revolution, social innovation, and waves of imm

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Art Walks (1 of 2)

Museum of Fine Arts

Boston featured walking tour - Museum of Fine Arts

Boston's Museum of Fine Arts is one of the country's oldest and most important art museums. With a collection that spans millennia and the globe, the MFA provides an endless opport

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History Walks (1 of 3)

Brahmins of Boston

Boston featured walking tour - Brahmins of Boston

At the dawn of the 19th century, descendants of the original Puritan settlers of Boston began to adopt a more enlightened, cosmopolitan, and progressive set of social and political

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Architecture Walks

Big Dig

Boston featured walking tour - Big Dig

In the 1990s work began on what at the time was—and still is—one of the most ambitious urban engineering projects in history: the burying of Boston's highway system to free its his

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