Boston Travel Planning by Neighborhood

Our local expert shares her tips to help you plan your vacation to Beantown and discover its many wonderful historic neighborhoods.


Boston, as any schoolchild can tell you, is where the Boston Tea Party occurred and the seeds of the American Revolution were planted, but not everyone knows the country’s first subway system was built here, as was the nation’s first free library. Boston is thick with historical sites, from the Paul Revere House to the Old North Church, but it is not a city stuck in the past, though it does honor its history. A happy juxtaposition of old and new live happily together, as do the permanent residents and the thousands of students who flock here to attend the numerous colleges and universities in the area. [Read our Boston College Visit Guide.]

In addition to the historical, there are plenty of things to see in Boston, from successful sports organizations—the Red Sox, Bruins and Patriots—to the world class art found at the Museum of Fine Arts and the Institute of Contemporary Art (to name just two museums) to all of its rich history, Boston never fails to offer more than can be done in just one visit. Here’s a Boston guide to help you make the most of any trip.

Getting Oriented and Getting Around

The main Boston neighborhoods—Beacon Hill, Back Bay, Downtown, the Seaport District, Fenway, the North End and the South End—are very accessible to each other. Each has a distinct character, but there is no real demarcation line between any of them. In the middle of all these neighborhoods are Boston Common and the Public Garden, two of the city’s best public spaces, separated only by Charles Street.

The streets downtown, rather than following any logical order, instead follow the old routes of days long past. The one-way streets, dead-ends and random turns make sense only if you’re on foot. For drivers, they are just a hassle. Take public transportation whenever you can to save yourself a bunch of frustration. A little farther afield, but still accessible by the subway, are the Fenway, Charlestown, Brookline, Jamaica Plain and Dorchester neighborhoods. Across the Charles River are Cambridge and Harvard Square, also easily accessed by subway. [More on these sites on page 3.]

Boston Transportation

When visiting Boston, by far the best way to get around town, other than your own two feet, is “The T,” short for the Massachusetts Bay Transportation Authority (MBTA). The T is America’s oldest subway line and the fourth largest in the country. It goes almost everywhere you’ll want to go. There are four main subway lines that go downtown and out to various neighborhoods. When people talk about the T, they usually are referring to the train service, but the MBTA also runs buses, boats and commuter trains. Riding the T can be a little confusing for newcomers. If you remember that “inbound” trains head toward the Park Street Station (the heart of the city) and “outbound” trains head away from Park Street, you should be OK. [Read more about T service in our 5 Free Boston Attractions article.]

When to Visit

Boston attractions occur throughout the year and every season has its charms—spring brings the Boston Marathon and the Red Sox; summer holds the Boston Pops and the Fourth of July celebrations; fall has legendary New England foliage; and winter offers many celebrations, from holiday shows to ice skating to the country’s original First Night on New Year’s Eve. All just a few reasons to visit Boston.  

For additional Boston travel-planning information, read these related articles:
Best Boston Restaurants—Classic and New
Top 10 Boston Pubs: Cheers!
Boston’s Best New and Newly Renovated Hotels
Best Boston Museums and Institutions
Following Boston’s Freedom Trail

5 Free Boston Attractions
College Visit Guide: Boston

Boston’s Neighborhoods

Beacon Hill

With its old-world Brahmin feel and cobblestone streets, Beacon Hill is quintessential Boston and where many tourists start their Boston vacations. The gold-domed Massachusetts State House presides over the neighborhood, which is adjacent to the Boston Common, the country’s oldest public park.

Gorgeous 19th century homes and tiny winding streets beckon explorers and photographers. Charles Street is a haven of trendy boutiques and small bistros. If you are planning on following the Freedom Trail, 16 historical sites linked by a red painted or bricked line that runs 2.5 miles through the city, visit the Freedom Trail Foundation office on Boston Common to get a map. [Read tips for Following Boston’s Freedom Trail.]

Downtown Crossing

On the other side of Boston Common, you’ll find Downtown Crossing, where the hub of the MBTA sits (Park Street) with lots of big box shopping, plus the Old City Hall, Old South Meeting House, the Old State House and the Boston Massacre Site. Government Center is just up Tremont Street and home to the tourist hotbed Faneuil Hall and Quincy Market (also known as Faneuil Hall Marketplace). In the other direction, the Theater District is home to Boston’s large live arts scene. [Read about Boston’s Best New, Renovated Hotels.]

Back Bay

Graceful brownstones on wide boulevards, the tranquil Public Garden and bustling Copley Square frame this vibrant neighborhood, which ranges from residential to commercial in a matter of blocks. Trinity Church and the Boston Public Library bookend Copley Square, a half-acre park, while the towering John Hancock Building (Boston’s tallest skyscraper) sits on one side. High-end shops and expensive restaurants draw in the fashionable and well-heeled to Newbury Street. [Read our Best Boston Restaurants article.]

South End

The South End is packed with popular restaurants and funky shops, and is famous for the largest neighborhood of Victorian homes in the country. It’s had its ups and downs: Once a 19th century hotbed of the very wealthy who built beautiful brownstones, it fell out of favor and into disrepair. Gentrified in recent years, it’s now the center of Boston’s gay and lesbian community.

Seaport District

The waterfront area is exploding with growth and new development. Don’t miss visiting the stunning Institute of Contemporary Art, the remodeled Children’s Museum, and the emerging Harborwalk, which follows the harbor. [Read more about Best Boston Museums and Institutions.]

Fenway/Kenmore Square

Any Boston trip would be remiss without a visit to the Fenway area, of course, home to famous Fenway Park and the Boston Red Sox. A fun mix of bars and restaurants cater to fans. Around the corner, Kenmore Square is seeing a lot of development and some upscale establishments are springing up. Many of Boston’s finest cultural institutions line the nearby “Avenue of the Arts,” Huntington Avenue. The Museum of Fine Arts and the Isabella Stewart Gardner Museum are sure to attract your interest.

North End

This is Boston’s oldest neighborhood and home to innumerable Italian restaurants, shops and bakeries. Once an enclave of Italian immigrants in the 19th century, many third and fourth generations now claim the North End as home, though it’s a lot more diverse than in years past. Boston’s Chinatown is in this neighborhood too (and is where you get the cheap Chinatown buses to and from New York). The Paul Revere House, the Old North Church and the Copp’s Hill Burial Ground (on the Freedom Trail) also are found here.


Charlestown is actually older than Boston by one year. A group of 10 puritan families settled Charlestown in 1629 and it remained its own community until 1874, when it was annexed to Boston. The Battle of Bunker Hill occurred here in 1775, which you can learn about at the Bunker Hill Monument. The town was pretty much destroyed then and rebuilt after the American Revolution. The Charlestown Navy Yard, no longer in operation, is a national historic monument and home to the USS Constitution. Tours of the ship and the nearby museum offer a fascinating look into its past.

Cambridge, Massachusetts

The city of Cambridge, just to the north of Boston, was once a rural farming community founded by Puritans in the 1630s. Today it is a diverse, world-renowned center for intellectual pursuits, being home to both Harvard University—the oldest university in the United States—and the Massachusetts Institute of Technology (MIT). Spend a day taking in its various museums and historical site, or if you time it right, catch a lecture, panel, book reading or live music event. 

To get there by public transportation, take the Alewife-bound red line subway from Park Street in Boston. It will take you to MIT, Central Square and Harvard Square.

Harvard Square

At the heart of Cambridge you’ll find bustling Harvard Square. One nickname for Cambridge you might have heard is “Boston’s Left Bank.” Another is “The People’s Republic of Cambridge.” This is due to its liberal leanings and independent character from Boston. Harvard Square is a destination by itself, offering endless people-watching and entertainment, all for free. Check out the Coop bookstore and other independent shops; various pubs, coffeehouses and ethnic restaurants; or the Brattle Theatre, which shows top classic, foreign and indie films.

Harvard University

Any visit to the square is not complete without wandering around Harvard University. Though you can walk through Harvard Yard any time, I recommend going on a free tour if you can. The student guides are full of information about the history and architecture of the campus and can tell you all about the libraries, museums—the Arthur M. Sackler Museum, Fogg Museum and Busch-Reisinger Museum—and famous alum. (The museums are all undergoing a major renovation project that began in 2008 and is expected to last five years. Highlights from each collection are on display at the Sackler.)

Look for the statue of John Harvard, called the “statue of three lies,” which makes for a good story. The statue, sculpted in 1884, is just an idea of what the artist thought he looked like, as there are no known images of Harvard. Also, the school was founded in 1636, not 1638 as it states and, finally, Harvard was not the founder, he was a benefactor. 1350 Massachusetts Ave., tel. 617-495-1573. Tours are offered when school is in session. Call for times.

Destinations: Boston

Themes: Art and Museums, Historical Vacations, Urban Endeavors

Activities: Arts and Entertainment, Museums, Sightseeing

User Comments

Great Article I really enjoyed it-- however, your link to "Best Boston Restaurants" goes to the Hotels Page.

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