Great Itineraries in Boston

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 then 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 you might as well tackle it sooner rather than later. Linger wherever you like, leaving ample time for lunch amid magicians and mimes in Faneuil Hall Marketplace. Next, cross into the North End via the Rose Fitzgerald Kennedy Greenway. Though small in size and hemmed in by water on three sides, this neighborhood is crammed full of history. Be sure to tour Old North Church and Paul Revere's former home (Boston's oldest house, it was constructed almost 100 years prior to his arrival); then, after wandering the narrow Italian-tinged streets, fortify yourself with a gelato and keep going across the Charlestown Bridge. You can see the 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 earth was scraped off its peak and used as landfill not far away. What remains—namely gas-lighted streets with shady trees, brick sidewalks, and stately Brahmin brownstones—evokes old Boston. (One of the loveliest is Mt. Vernon, which opens onto leafy Louisburg Square where Louisa May Alcott once lived.) When soaking up the ambience, don't forget to take in some of Beacon Hill's "official" attractions. Major sites from Boston's various theme trails, including the Massachusetts State House, Boston Athenaeum, Granary Burying Ground, and newly-restored African Meeting House are here. Afterward, stroll to the Common and Public Garden. Both promise greenery and great people-watching. If shopping is more your bag, cruise for antiques along Charles Street, the thoroughfare that separates them. In the evening, feast on affordable chow mein in Chinatown or go upscale at an über trendy restaurant in the Theater District where improvements in recent years have been, well, dramatic.

Day 3: Get an Overview

From the Back Bay you can cover a lot of Boston's other attractions in a single day. Start at the top (literally) by seeing 360-degree views from the Prudential Center's Skywalk Observatory. Once you understand the lay of the land, just plot a route based on your interests. Architecture aficionados can hit the ground running at the neoclassical Public Library and Romanesque Trinity Church. Shoppers, conversely, can opt for the stores of Newbury Street and 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 (expanded in early 2012). Carnival-like Fenway Park beckons baseball fans to the other side of the Fens. Depending on your taste—and the availability of tickets—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 the artful way at the Institute of Contemporary Art (ICA) on Fan Pier. The mod museum has a bold cantilevered design that makes the most of its waterside location. It makes the most of its art collection, too, by offering special programs that appeal even to little tykes and hard-to-please teens. Of course, keeping kids engaged may prove difficult given that the Children's Museum is close by. Check out its innovative exhibits; then relive a turning point in American history at the Boston Tea Party Ships & Museum (three authentic-looking vessels and an interpretive center are expected to start welcoming guests in June 2012). From there, continue on to that waterfront favorite, the New England Aquarium. Highlights include the Giant Ocean Tank, hands-on tidal pools, a seal-training tutorial, and a new 25,000-gallon touch tank brimming with sharks and rays. Outside the facility you can sign up for a harbor cruise, whale-watching trip, or ferry ride to the Boston Harbor Islands.

Beyond Boston Proper


Although charming neighborhoods lend Boston a small-town vibe, it's subject to the same problems that plague other urban centers. Violent crime is rare, but residents and tourists alike sometimes fall victim to pickpockets, scam artists, or car thieves. As in any large city, use common sense and stick to well-traveled routes after dark.

Getting your mitts on Red Sox tickets is tricky. Savvy spectators reserve online as soon as tickets become available. Procrastinators may get lucky at the ticket office next to Gate A, which opens at 10 am. If you strike out, a limited number are sold at Gate E two hours before game time. As a last resort, sidle up to that guy holding up tickets just after the opening pitch and haggle—or watch the action at Game On!, a sports bar attached to Fenway Park.

Think you need a car to venture beyond Boston? Think again. Grayline affiliate Brush Hill Tours (800/343-1328 or 781/986-6100 offers coach excursions for Boston-based day-trippers to Lexington, Concord, Salem, and Plymouth. In autumn, foliage-themed tours are available, too.

Diehard sightseers may want to take a pass—a "Go Boston" Pass (866/628–9027 covers more than 70 attractions, tours, and excursions and is sold in one-day to one-week increments from $59.99; CityPass (888/330–5008 covers fivekey sites for $46.

Day 1: Explore Cambridge

From pre-Revolutionary times, Boston was the region's commercial center and Cambridge was the 'burbs: a place more residential than mercantile, with plenty of room to build the nation's first English-style, redbrick university. Not surprisingly, the heart of the community—geographically and otherwise—is still Harvard Square. It would be easy enough to while away a day here browsing the shops, lounging at a café, then wandering over 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" (#105 was occupied by both Washington and Longfellow!). There are fine museums here, too, including the family-friendly Museum of Natural History, replete with dinosaur bones, gemstones, and dazzling displays of taxidermy. The Harvard Art Museum is another must: if the newly reconfigured facility hasn't yet opened on the site of the original Fogg building, you can view a "greatest hits" collection across the street at the Sackler building. End your day in true Cantabrigian style by taking in a concert or lecture at the handsome Sanders Theatre.

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 Mayflower II are well worth the trip. A second option is to veer northwest to see Revolutionary-era sites in Lexington (now a well-to-do bedroom community). 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 Historic 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 Henry David Thoreau wrote one of the founding documents of the environmental movement.

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 beach yourself? In summer, 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.

Alternatively, get a taste of the beach-bum lifestyle with a day in Provincetown. Boston Harbor Cruises runs fast ferries to the colorful artists' hub at the tip of Cape Cod. Once there, race across nearby dunes, get back on the water and watch for whales, or soak up some rays at Race Point, a Cape Cod National Seashore beach. For a bit of culture, head to the East End's growing number of galleries or inspect the architecture along Commercial Street. Properly sunned and relaxed, return to Boston on the evening ferry or plan ahead and book a cottage for the night.