Sights—The Freedom Trail, which passes 16 of the most famous sites from early U.S. history; Boston Public Garden and the swan boats; Newbury Street for its boutiques and art galleries; the Italian North End for old-world ambience; Beacon Hill for its gas lamps and Yankee Federal architecture, Louisburg Square mansions and gold-domed State House; the South End, with its Victorian row houses; Fenway Park.

Museums—The Museum of Fine Arts for impressionists and antiquities; the charming Isabella Stewart Gardner Museum with its stunning three-story garden atrium and important works of art; the John F. Kennedy Library and Museum; the Institute of Contemporary Art; Harvard's Museum of Natural History.

Memorable Meals—Durgin Park for authentic New England cuisine; Sonsie for an elegant meal and people-watching on Newbury Street; No Name Diner for New England's best fish chowder; Sibling Rivalry for mouthwatering contemporary creations.

Late Night—Faneuil Hall or Harvard Square (both are well-lit and populated, with bars and restaurants galore); dancing at Avalon or playing pool at Jillian's on Landsdowne Street; the Black Rose (across from Faneuil Hall) for Irish music; the Middle East (in Cambridge) for alternative rock; Ryles (in Cambridge) for jazz.

Walks—The Charles River Esplanade for a romantic stroll or a vigorous jog; Beacon Hill, with its old brick sidewalks and Federal bow-front architecture; Cambridge's Brattle Street, which runs from Harvard Square past stately Tory-era mansions; the Commonwealth Avenue Mall from the Public Garden to Kenmore Square; the walking paths through the Arnold Arboretum.

Especially for Kids—The New England Aquarium with its huge, two-story-high fish tank; the lowland gorillas at the Franklin Park Zoo; the interactive exhibits of the Children's Museum; the displays, giant-screen Omni Theater and planetarium at the Museum of Science.

Although its main attractions are in a relatively compact area compared with other large cities, Boston is made up of distinct districts. Knowing where the most popular ones lie will help you find your way.

The central city sits on a peninsula, surrounded by the Charles River, Boston Inner Harbor and Fort Point Channel. Downtown is roughly in the middle of the peninsula and encompasses many of the Freedom Trail's historic sites. Adjoining downtown to the west are Beacon Hill (also rich in history) and the green expanse of Boston Common and the Boston Public Garden. Farther west is Back Bay (a prime shopping, entertainment and dining district), and then the Fenway area. Northeast of downtown—on the tip of the peninsula—is the North End, the atmospheric Italian neighborhood. South of downtown are Chinatown and the South End. Across the Charles River from downtown (directly north) is Charlestown, home to the Bunker Hill Monument and the USS Constitution.

Also across the river is Cambridge, another popular area for visitors and home to Harvard and MIT. Boston and Cambridge often are spoken of in one breath, but locals would never fuse the two. If they were sisters, Boston would be the traditional, practical one and Cambridge the hip, liberal academic. But like any sisters, they have more in common than they will ever admit.

When getting an address for a Boston destination, make sure that you ask not only for the street address but also for the neighborhood, any nearby landmarks and the nearest T stop (subway station). The names of the city's many narrow, winding streets are often meaningless to Bostonians. For instance, a cabdriver may not recognize a Dalton Street address for your hotel, but if you mention "It's in Back Bay behind the Pru (the Prudential building)," he or she will find it.

Boston's Big Dig, a gargantuan road, bridge and tunnel project that was a headache for drivers and public-transportation riders through most of the 1990s and the first half of this decade, is essentially finished. Though political squabbles are still being played out in the city's courtrooms and newspapers, the average visitor will find Boston easier to navigate than it was just a year or two ago.

The Boston area was inhabited by several Wampanoag tribes before the arrival of Europeans, who brought with them various diseases and an ambition for land that greatly reduced the Native Americans' numbers. The first permanent colonists, led by Puritan John Winthrop, arrived in 1630 and named their settlement after the city of Boston, England. Winthrop's ambition, as he wrote in his journal, was to build a shining citadel of virtue, a "city on the hill." Boston prospered and soon became the capital of the Massachusetts Bay Colony. By the mid-1700s, it had become an important seaport and trading center. As the colonists grew more successful—and self-reliant—England grew more controlling. Increased taxes on sugar, stamps and, finally, tea set the wheels of the American Revolution in motion.

During the next century, waves of immigrants were drawn to Boston for the manufacturing jobs generated by another revolution—the Industrial Revolution. The Irish who settled on the fringes of the city eventually put as strong a stamp on Boston's character as the patrician residents of Beacon Hill, who bolstered the city's status as a center of learning and culture. Charlestown and South Boston, which is known locally as "Southie," remain Irish enclaves. A large influx of Italian immigrants likewise settled the area known as the North End.

Following World War II, Boston's importance as an industrial hub faded. However, it grew in prominence as a center for education and high technology, in large part because of the presence of the Massachusetts Institute of Technology (MIT) and Harvard University in nearby Cambridge. The city's importance as a seaport has declined, but cruise-ship traffic has increased enormously, and Boston Harbor remains a defining presence.

Boston's Big Dig project used enough concrete to build a sidewalk from Boston to San Francisco and back three times. It stands as the largest, costliest public-works project in U.S. history, exceeding the Panama Canal in time and cost. Contractors moved 7 mi/11 km of highway belowground. Space once occupied by downtown's elevated expressway (the Central Artery) is being reclaimed as parks and urban-development space.

The dramatic bridge from downtown to Charlestown, the Leonard P. Zakim bridge, erected as part of the Big Dig's complex infrastructure, is now the world's widest cable-stayed span. In its inverted Y-shaped towers, Swiss bridge designer Christian Menn intended to echo the shape of the nearby Bunker Hill Monument.

Bostonians are among the country's leading consumers of ice cream—even in the dead of winter. Brigham's, a local chain, even created a flavor named after the Big Dig. The company also markets "Curse Reversed," a popular flavor renamed from "Reverse the Curse" after the Boston Red Sox's World Series victory in 2004.

Beacon Hill used to be one of three prominent peaks collectively called Trimountain. This is the origination of the name Tremont in Boston, such as Tremont Street. In the 1850s, two of the hills were leveled.

Some major Hollywood movies have been filmed in Boston, such as Love Story, Mystic River, Good Will Hunting and Mona Lisa Smile. The city keeps producing stars, too, many of whom have homes in the area, including Chris Cooper, members of the band Aerosmith, Kate Bosworth, Denis Leary, Jay Leno and Geena Davis.

Greater Boston is the site of a lot of the "oldests" in the U.S.—among others, the oldest public park (Boston Common), oldest telephone exchange (between Boston and Lowell), oldest historical society (Massachusetts Historical Society), oldest subway (1897), oldest lighthouse station (Boston Light, 1716), oldest college (Harvard, 1636) and oldest professional sports venue (Fenway Park, 1912).

Boston runs on Dunkin Donuts. There are more than 269 stores within a 15-mi/25-km radius of the city—a better concentration than any other region in the country.