Here’s the situation: You have one day to see Boston, and this is your first visit. You want to experience the city’s iconic, postcard-worthy places, but here, in the Cradle of Liberty, there are many things to see and do! We’ve got the highlights and the must-hits, so follow our lead and get to know Boston in one quick trip.
We’re going to tour the town on foot—it’s the best, not to mention the fastest, way to get around our streets that still resemble Colonial-era lanes—and also by T, Boston’s historic subway system and the country’s earliest.
Batters up at our first stop: Fenway Park. Get here for the earliest tour and get up close and personal with the Green Monster, Pesky’s Pole, and other rarely seen nooks of America’s oldest ballpark. Then, walk up to Kenmore Square and take the T’s Green Line straight into Copley Square.
At Copley Square, look around and note the pretty amazing architecture and venerable historic landmarks that flank you, including the central branch of the Boston Public Library, and, facing it, behemoth Trinity Church. This H.H. Richardson masterpiece, complete with murals and stained glass windows by American artist John LaFarge, is one of the nation’s most significant buildings. Nearby, the whole scene is reflected in the glass windowpanes of Boston’s tallest building, the Hancock Tower.
From there, walk down South Charles Street and into Beacon Hill, Boston’s most highly recognized neighborhood for its Federal-style brick row houses and quaint charm. Grab lunch at The Paramount—we love the turkey Reuben, and breakfast is available all day. Then be sure to check out historic Acorn Street, a narrow, sloped alley laid with cobblestones, which leads up to Louisburg Square, home to privileged Bostonians like U.S. Secretary of State John Kerry.
Next stop: Boston Common, America’s oldest public park, founded in 1634. Enter at Joy and Beacon streets and enjoy a bit of country in the city, plus great views of the gold-domed Massachusetts State House.
The Common also serves as the starting point of The Freedom Trail, which links 16 authentic, historically significant sites of pre-Revolutionary America. Since we’ve only got one day, here are the highlights: Paul Revere’s gravesite at Granary Burying Ground; the historic publishing house of Longfellow, Hawthorne, Emerson, Dickens and Alcott, Old Corner Book Store; and the Old State House, which celebrates its 300th birthday this year. Around the corner, entry to Faneuil Hall is free, so visit the National Historical Park Visitor Center there, learn about the Stamp Act, and pick up a souvenir.
Step off The Freedom Trail for a pit-stop at Faneuil Hall Marketplace, which boasts great shops, pushcart vendors, street theater and historic restaurant Durgin-Park—but wait to whet your appetite, we’re headed to the North End!
Back on The Freedom Trail, follow that now-familiar red line across the Rose Kennedy Greenway and down Hanover Street. You are in the highly ethnic ’hood known for its many authentic Italian and Italian-American family-run restaurants. But before being tempted by red sauce and hand-rolled pasta, note that the North End is also Boston’s original stomping ground. Take a detour to Freedom Trail sites the Paul Revere House and Old North Church with its famous lanterns.
Finally! It is time for dinner. There are too many delicious options to mention, but we recommend calamari-inspired dishes at teeny mom-and-pop spot The Daily Catch, braised chicken at elegant Prezza, or, if you’ve got kids, pizza at Regina.
After dinner, sip on a digestivo at Caffe Vittoria and hit the sack early. You earned it!