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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.
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 or buy fresh fruit from Haymarket’s street vendors. 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 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.
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 newly restored 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 stir-fry noodles in pan-Asian Chinatown or go upscale at an übertrendy restaurant (Pigalle, Troquet) in the Theater District where restorations in recent years have been, well, dramatic.
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 it 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 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, both recently expanded and beautified. 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.
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 three authentic-looking vessels and interpretive center. 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. On the wharf, sign up for a harbor cruise, whale-watch boat trip, or ferry ride to the beckoning Boston Harbor Islands.
Getting your mitts on Red Sox tickets may be 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 www.brushhilltours.com) 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 buy a pass. The "Go Boston" Pass (866/628–9027 www.smartdestinations.com) 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 www.citypass.com) covers five key sites for $51/$36 (adults/kids $3/$11).
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 Museum of Natural History, loaded with dinosaur bones, gemstones, and 21 million stuffed critters. The Harvard Art Museum is another must. If you’re visiting before Renzo Piano’s newly reimagined facility has opened on the site of the original Fogg building, 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 handsome Sanders Theatre.
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 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.
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.