Introduction
There are a few prerequisites when considering a trip to Boston. First, don't go in February. This may seem obvious, but it bears repeating, not only because the winters are indeed so miserable, but because the other seasons are so immensely enjoyable. Spring and Fall are gloriously verdant and the summers are breezy and temperate.
Second, plan to visit at least some of the same sites you would if you were chaperoning an 8th-grade civics class. You are, after all, in Boston, the City on the Hill, the Cradle of Liberty, and so on and so forth, thus there's no point or pride in avoiding historic landmarks. Conveniently, many are nestled among the city's most beautiful neighborhoods, areas with cobblestone streets and colonial-era architecture that you would want to wander even if you didn't feel obligated to do so.
And third, don't compare it to New York City, at least not unfavorably. Bostonians spend considerable energy trying to prove their city is not inferior to Manhattan, whether in national influence, cultural offerings or American League baseball franchises. The truth is, Boston is not at all like New York, and that's a good thing. The largest city in New England is compact, clean and easily navigable. With a population of only 600,000, Boston is best appreciated as a small city with a hyper-educated populace, an astonishing number of Dunkin' Donuts, and an artistic and historical importance far surpassing its relative size. Here are some ways to weave the past with the present.
1. An Abbreviated Freedom Trail
The Freedom Trail is a 2.5-mile stretch hosting 16 sites pertaining to the Revolutionary War. You could take a costumed guided tour or, more appealingly, download a map and follow your own itinerary. If you have limited time, concentrate on those sites in and immediately around the North End, which is also Boston's Little Italy. Among them are the home of Paul Revere, where you'll get a good sense of how people lived in 1770s (in a word, closely; the house is really small). You can also drop by the Old North Church, where those two famous lanterns warned Paul Revere the British were coming by sea in 1775, essentially igniting the American Revolution. Nearby are the Old State House museum (among the impressive memorabilia is a vial of tea salvaged from the original Tea Partiers), which is worth a visit, and Faneuil Hall Marketplace, which, unless you enjoy food courts and stores you can find at any mall in America, is not.
2. The South End
In the 1980s, this neighborhood was considered dangerous and remote. In other words, cheap, which is why people on the front lines (i.e., artists and gay men) started moving in. As these things inexorably go, the area quickly gentrified, becoming too expensive for the early adopters. It's not hard to see why young, upscale families and finance industry fauxhemians are drawn here today: street after tree-lined street of red-brick bow-front townhouses dating to the 1800s, along with some of Boston's best restaurants, design stores and boutiques. The food and retail shops are scattered along Tremont, Shawmut and Washington streets. The latter is where you'll find perhaps the city's best cafe, the tiny bakery Flour, at the corner of Washington and Rutland streets, which, in addition to creating a transporting chocolate macaroon, also serves pies, cakes, tarts and sandwiches and ever-popular sticky buns. If you hanker for something more substantial, stop by B&G Oysters, which does shellfish right (i.e., not merely submerged in chowder).
It's also worth walking around SoWa (for South of Washington) — Harrison Avenue, between East Newton and Union Park streets — where some of the city's better contemporary art galleries are located. Each spring, during SoWa Art Walk weekend, artists open their workshops to the public.
3. The ICA
Opened in December 2006, the Institute of Contemporary Art in South Boston is arguably more interesting for its architecture than its art. Designed by Diller Scofidio + Renfro, the museum is all glass and sharp angles, a stark departure from the city's presiding aesthetic. One of the most arresting features is the rear of the museum, a cantilevered glass expanse that hovers vertiginously over Boston Harbor. The lure of the ICA has managed to spark a blossoming of the nearby Fort Point Channel district, a short walk away, which until recently had been a somewhat deserted area most notable for the collective of artists taking advantage of ample studio space. Recently, a smattering of new stores has opened, as have some places to eat and drink, most notably Sportello, a by-all-means-go-out-of-your-way Italian restaurant by local celebrity chef Barbara Lynch.
4. Back Bay
The eight-block shopping stretch of Newbury Street in Back Bay conforms to an easily deciphered grid: at Mass Ave., where the strip begins, you find the more downmarket stores (e.g., Urban Outfitters). As you progress eastward, you graduate to increasingly higher-end outposts (Banana Republic, Lucky Jeans) until you find yourself at the street's terminus, at Arlington Street, loitering outside Chanel and Cartier.
Perhaps a better, or at least more scenic, way to gape at Back Bay's wealth is to walk a block or two north of Newbury, and check out the residential sections of Commonwealth Ave. and Marlborough and Beacon streets, which, since the area's development in the mid-1800s, have been among the most desirable — and expensive — places to live in Boston. Here you'll find sumptuous Victorian brownstones with inviting front stoops and small but well-tended gardens. Many of the buildings have been carved into apartments, but a few have remained single-family homes.
If all the strolling and ogling causes your blood sugar to dip, you can refuel at Stephanie's on Newbury, an American bistro with very large, very good and very expensive salads.
5. Charles River Esplanade
Along the Boston side of the Charles River, which separates the city from Cambridge, is a roughly three-mile leafy path known as the Esplanade. To take in its full charm, begin your walk near the Museum of Science (at Monsignor O'Brien Highway and Storrow Drive), which, not incidentally, is a great place to occupy kids for several hours. As you amble west toward the Boston University Bridge, you'll pass playgrounds and marshes and places to rent sail boats and buy lemonade (you are, remember, visiting in good weather). You'll also be swarmed by flocks of wild geese and packs of joggers. More often than not, the joggers will leave you alone, but beware of the geese — they are easily riled and nasty.
6. The Red Sox Fan
As even the most casual baseball fan knows, the altar that is Fenway Park sits smack in the middle of the city. This sucks for anyone interested in moving around Boston on a game day, but it's a convenient place for everyone else to gawk at and ponder the mythic Red Sox fan. Visitors and other observers can attempt, for example, to understand how so many people who presumably hold down day jobs manage to arrive three to four hours before the opening pitch to get hammered and watch batting practice. If you can't get tickets to a game, or the Sox are on the road, you can still pay to get a tour of the stadium and grab a beer at either the Bleacher Bar, built under the stadium stands, or at the Cask 'n Flagon, which proudly, if unambitiously, flies a banner boasting its ranking as "the second best baseball bar in America."
7. Harvard Yard
The streets of Harvard Square are overrun with Au Bon Pains and Gaps, and nary an independent bookstore remains, but once you walk inside the gates of the country's most storied university, it's easy to tune out all the noise and forget everything but your own bitterness at not getting accepted. Walk it off with a stroll around the campus, pop into Memorial Church for some perspective on the school's history, or visit one of the small, excellent museums, such as the Peabody Museum of archaeology or the Sackler art museum, then be thankful that nothing you saw will be on a test. (Click here for an interactive campus map.)
Back outside the gates, there are any number of options for cheap, mediocre food, but for a reliable and reasonably priced lunch, try Cambridge 1 for thin crust pizza and good salads. If you'd like something more expensive, Harvest is a popular place for students to take visiting parents.
8. Jamaica Pond
Well known to locals but somewhat off the beaten path for visitors is Jamaica Pond which sits at the base of Jamaica Plain (J.P., familiarly), a neighborhood about 5 miles south of Boston that was one of the city's original "streetcar suburbs." The freshwater pond is part of what is known as the city's Emerald Necklace, a series of connecting parks designed in the late 1880s by Frederick Law Olmstead. During the summer, you can rent rowboats and sailboats at the boathouse, or, in any season, take the 1.5-mile walk around the perimeter. When you're done, head into Jamaica Plain to grab a cone at J.P. Licks, a local chain that makes its own ice cream and yogurt.
9. The Boston Public Library
While it may feel overly academic to visit a library on vacation, a trip to the BPL need not feel like a chore. Situated on one side of the impressively imposing Copley Square (which also houses Trinity Church) the library was designed by the New York firm McKim, Mead, and White and opened in 1895 (a Philip Johnson-designed addition was added in 1972). Noteworthy features include several vast murals by prominent artists, including a series by John Singer Sargent, and an Italian Renaissance-inspired interior courtyard with bubbling fountains and arched pathways.
10. Black History Trail
Walking along the narrow, red-brick sidewalks of Beacon Hill, with its gas street lamps and stately Federal-style row houses, it's easy to understand why Brahmins past (Oliver Wendell Holmes, Henry Cabot Lodge) and present (John Kerry) have chosen to live here. But to get an alternative view of the area's history, follow the Black History Trail, which traces the events central to the substantial African American population that lived here in the 19th century. A good starting point is the Museum of African American History on Joy Street; the museum's website offers an interactive map of the trail. Among the 14 sites is the African Meeting House, the oldest black church edifice still standing in the United States and the place where in 1860 Frederick Douglass delivered a seminal anti-slavery speech.