Great Boston Itineraries

Boston in 1 Day

Twenty-four hours isn't nearly enough time to absorb the city, but it's certainly worth a try. Start in the Back Bay, where you can stroll the shopping mecca that is Newbury Street before crossing over Boylston into Copley Square. Cross the Boston Marathon finish line, then head into the Boston Public Library, an architectural and literary wonder. Stroll through the Boston Public Garden and Boston Common before turning down Charles Street into historic Beacon Hill, where you can leisurely shop or grab a bite while wandering along the quaint cobblestone sidewalks. Head through Faneuil Hall on the way to the North End, Boston's beloved "Little Italy" neighborhood. Grab a cannoli at Modern Pastry (FYI, Mike's Pastries across the street is known for its hoards of tourists, but the locals go to Modern) and pick up the Freedom Trail in North Square, where you can also check out the Paul Revere House. You're just around the corner from the Old North Church and Copp's Hill Burying Ground, and within steps of a variety of delectable Italian restaurants along Hanover and Salem streets. Cap off your day with a heaping plate of pasta.

Boston in 4 Days

Clearly every traveler moves at a different pace. One might be content to snap a pic of the Bunker Hill Monument and push on; another might insist on climbing the obelisk’s 294 spiraling steps and studying the adjacent museum’s military dioramas. Nevertheless, in four days you should be able to see the city highlights without feeling rushed. With more time, explore nearby communities.

Day 1: Hit the Trail

About 3 million visitors walk the Freedom Trail every year—and there’s a good reason why: taken together, the route’s 16 designated sites offer a crash course in colonial history. That makes the trail a must, so tackle it sooner rather than later. Linger wherever you like, leaving ample time to lunch amid magicians and mimes in Faneuil Hall Marketplace. Next, cross into the North End via the Rose F. Kennedy Greenway. Though hemmed in by water on three sides, this bustling neighborhood is crammed full of history. Don’t miss Old North Church and Paul Revere’s former home (Boston’s oldest house, constructed almost 100 years prior to his arrival); then, after wandering the narrow Italianate streets, fortify yourself with espresso or gelato and cross the Charlestown Bridge. See the currently drydocked USS Constitution and climb the Bunker Hill Monument (a breathtaking site in more ways than one) before catching the MBTA water shuttle back to Downtown.

Day 2: Head for the Hill

Named for the signal light that topped it in the 1800s, Beacon Hill originally stood a bit taller until locals dug earth off its summit and used it as landfill nearby. Now its shady, gas-lighted streets, brick sidewalks, tidy mews, and stately Brahmin brownstones evoke a bygone Boston. (Lovely Mt. Vernon Street opens onto leafy Louisburg Square, where Louisa May Alcott once lived.) When soaking up the ambience, take in some of Beacon Hill’s major sites from Boston’s various theme trails: gold-domed Massachusetts State House, Boston Athenaeum, Granary Burying Ground, and the African Meeting House. Afterward, stroll to the Common and Public Garden. Both promise greenery and great people-watching. If shopping’s your bag, cruise for antiques along Charles Street, the thoroughfare that separates them. In the evening, feast on dumplings or dim sum in pan-Asian Chinatown or go upscale at an ubertrendy restaurant (Ostra, Teatro) in the Theater District where restorations in recent years have been, well, dramatic.

Day 3: Take It All In

From the Back Bay you can cover a lot of Boston’s attractions in a single day. Start at the top (literally) by ogling 360-degree views from the Prudential Center’s Skywalk Observatory. (Or end with a drink at Top of the Hub upstairs.) Once you understand the lay of the land, plot a route based on your interests. Architecture aficionados can hit the ground running at the neoclassical Public Library (the nation's first) and Romanesque Trinity Church. Shoppers can opt for stores along Newbury Street and in Copley Place, a high-end mall anchored by Neiman Marcus. Farther west in the Fens, other choices await. Art connoisseurs might view the collections at the Museum of Fine Arts or Isabella Stewart Gardner Museum. Carnival-like Fenway Park beckons baseball fans to the other side of the Fens. Depending on your taste—and ticket availability—cap the day with a Symphony Hall concert or a Red Sox game.

Day 4: On the Waterfront

A spate of openings and reopenings in recent years has transformed the Seaport District into a magnet for museum hoppers. Begin your day artfully at the Institute of Contemporary Art (ICA) on Fan Pier. The mod museum’s bold cantilevered design (computer printer?) makes the most of its waterside location. It makes the most of its art collection, too, by offering programs and exhibits that appeal to little tykes and hard-to-please teens. Keep tiny tots engaged with a run to the Children’s Museum and its innovative exhibits; then relive a turning point in American history at the Boston Tea Party Ships & Museum’s authentic-looking vessels and interpretive center. From there, continue on to that waterfront favorite, the New England Aquarium, where you can watch the sea lions and penguins frolic. On the wharf, sign up for a harbor cruise, whale-watch boat trip, or ferry ride to the beckoning Boston Harbor Islands.

Beyond Boston Proper

Day 1: Explore Cambridge

From pre-Revolutionary times, Boston was the region’s commercial center and Cambridge was the burbs: a retreat more residential than mercantile, with plenty of room to build the nation’s first English-style, redbrick university. The heart of the community—geographically and practically—is still Harvard Square. It’s easy enough to while away a day here browsing the shops, lounging at a café, then wandering to the riverbank to watch crew teams practice. But Harvard Square is also the starting point for free student-led campus tours, as well as for strolls along Brattle Street’s "Tory Row" (No. 105 was occupied by both Washington and Longfellow!). Fine museums include the family-friendly Harvard Museum of Natural History, loaded with dinosaur bones, gemstones, and 21 million stuffed critters. The newly remodeled Harvard Art Museum is another must. End your day in true Cantabrigian style by taking in a concert or lecture at Harvard's Sanders Theatre or with a show at the American Repertory Theater, helmed by noted artistic director Diane Paulus.

Day 2: Step Back in Time

You only have to travel a short distance to visit historic places you read about in grade school. For a side trip to the 17th century, head 35 miles southeast to Plymouth. The famed rock doesn’t live up to its hype, but Plimoth Plantation (an open-air museum re-creating life among Pilgrims) and the Mayflower II are well worth the trip. A second option is to veer northwest to explore Revolutionary-era sites in handsome, suburban Lexington. Start at the National Heritage Museum for a recap of the events that kicked off the whole shebang; then proceed to Battle Green, where "the shot heard round the world" was fired. After stopping by Minute Man National Historical Park, continue to Concord to tour the homes of literary luminaries like Ralph Waldo Emerson, Louisa May Alcott, and Nathaniel Hawthorne. Conclude your novel excursion with a walk around Walden Pond, where transcendentalist Henry David Thoreau wrote one of the founding documents of the environmental movement, "Walden."

Day 3: A Shore Thing

Anyone eager to taste the salt air or feel the surge of the sea should take a day trip to the North Shore towns of Salem and Gloucester. The former has a Maritime National Historic Site—complete with vintage wharves and warehouses—that proves there is more to the notorious town than just witchcraft.

Prefer to just sun yourself? Year-round nature lovers flock to Crane Beach in Ipswich, about an hour north of Boston. Part of a 1,200-acre wildlife refuge, it includes 4 miles of sand rimmed by scenic dunes. For a quick sand-in-every-crevice experience, take either the MBTA’s Harbor Express ferry south to Nantasket Beach in Hull or the commuter train north to Manchester-by-the-Sea’s Singing Beach, where the sand has such a high silica content that it actually sings (or at least squeaks) when you walk on it.

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