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The Boston Advantage

Three sailboats with pink and white sails race across choppy water in the foreground, with a city skyline in the background.

A World Class City, Right Next Door

Boston is more than a nearby city—it’s an extension of Milton Academy’s classrooms, a hub for cultural exploration, and a source of weekend fun. Our proximity to Boston makes the Milton experience richer, fuller, and uniquely connected to the world. Students and faculty can visit world class museums, universities, libraries, and performance spaces, as well as connect with the scholars, scientists, artists, writers, and change makers who shape the city and the world.
Milton students can easily access Boston on nearby public transportation, the Massachusetts Bay Transit Authority system (MBTA, or “T”)—and with Student Charlie Cards (available through the Office of Student Life), rides are only half-price. Students can take the T in groups on weekends to visit landmarks like Fenway Park, Faneuil Hall, Harvard Square, and local museums.

Two people in scuba diving gear standing in front of a large aquarium with colorful underwater scenery visible in the background.

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Boston as A Classroom

Boston’s intellectual and cultural landscape offers experiences that expand students’ minds well beyond the classroom:

Why Boston Matters at Milton Academy

At Milton, proximity to Boston isn’t just convenient–it’s transformational.
It connects students to ideas, institutions, opportunities, and the wider world.

Boston as a Playground

Boston also gives Milton students the chance to enjoy the best of city life with friends and faculty:

Learning Independence - Enjoying Boston
Responsibly

Being in close proximity to a major metropolitan city is also a great opportunity to teach students how to explore responsibly, while enjoying the city’s incredible resources. At Milton, we take this responsibility seriously.

Faculty, deans, and house parents organize and support these activities with clear expectations and modeling how to visit Boston with confidence. All Milton students have access to Charlie Cards with discounted student fares for the city’s subway (the T) and buses. As students mature, carefully outlined guidelines and permissions allow them greater independence, always within the framework of safety and trust. Boarding students who take the T into the city have set return times (and occasional curfew extensions approved by house parents) so they enjoy both the freedom and structure to experience the city safely.