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Boston is known as "America’s Walking City" thanks to its compact size and pedestrian-friendly layout. Centrally located just a few blocks from downtown, the Boston Common is a particularly nice spot for a stroll. The nearly 50-acre park—the oldest in the country—anchors both the Charles River Esplanade and the Freedom Trail.

Freedom Trail

• 2.5 miles of brick-lined streets
• 16 historic sites including Paul Revere's home, the Old North Church (of "one if by land, two if by sea" fame), and the Old South Meeting House, where plans for the Boston Tea Party were hatched
• Local cuisine: Faneuil Hall, which rang with cries of "no taxation without representation" in 1764, is filled today with food vendors hawking homemade clam chowder and other New England staples.
• Costumed performers in 17th- and 18th-century garb play the citizens of Revolutionary Boston at key points along the trail.

Boston Mainstays

• Catch an afternoon Red Sox game at Fenway Park, where baseball legends Ted Williams, Carl Yastrzemski, and Babe Ruth all cleared homeruns over the Green Monster looming over left field.
• Shop on Newbury Street: Running for eight blocks through the Back Bay neighborhood, the city’s most upscale retail corridor is lined with high-end boutiques from Chanel and Cartier, as well as vintage consignment shops and swanky cafes.
• Explore the Museum of Science: More than 700 interactive exhibits include a 20-foot-long Tyrannosaurus rex model and a Foucault pendulum swinging along with the rotation of the Earth.

Off the Beaten Path

• SoWa galleries: Located on the edge of the South End, SoWa (short for South of Washington Street) is filled with renovated warehouses now used as contemporary art galleries. SoWa Artists Guild members open their studios to the public on the first Friday of every month.
• Fogg Art Museum: Dating to 1895, Harvard’s oldest museum showcases impressionist paintings, Bernini sculptures, and Picasso masterpieces.
• B&G Oysters: Watch chefs shuck more than 200 varieties of bivalves at one of Boston’s most revered seafood restaurants. Other crowd-pleasers on the menu include fried Ipswich clams, tempura gray sole, and piping hot lobster bisque.

A Quick Guide to Boston’s Neighborhoods

• Back Bay: High-end shopping and dining along Newbury and Boylston Streets lend a ritzy ambiance to Back Bay, though the neighborhood has its fair share of historic treasures, too. These include the Boston Public Library and Copley Square, where the Boston Marathon ends each year. It’s also worth taking a walk along the Charles River Esplanade, a riverfront path that’s so lush it’s been nicknamed the city’s "emerald necklace."

• Cambridge lies on the banks of the Charles River, about 3 miles west of downtown. Best known as the home of Harvard University and MIT, the city served as an important center of rebel activity during the Revolutionary War. Cambridge Common was a training ground for the Continental Army, and, a few blocks away, the house of poet Henry Wadsworth Longfellow functioned as George Washington’s headquarters during the British army’s siege of Boston.

• Southie: South Boston occupies a vast stretch of land where you’ll find an especially strong sense of community—a holdover from the neighborhood’s days as a predominantly Irish-Catholic enclave. The best way to see Southie is along the waterfront; it features the newly opened Institute of Contemporary Art and Castle Island, a Revolutionary-era fort.

• North End: The North End is one of the most historic neighborhoods in all of Boston, and a key part of the Freedom Trail. Cobblestone streets and historic homes, including the residence of Paul Revere, give the area an old-world feel. It’s also the best place in town to find authentic Italian cuisine. Head to Mike’s Pastry to sample up to 15 different kinds of cannoli.

Where to Stay

• Nine Zero Hotel: History buffs may want to splurge on this boutique property along the Freedom Trail, which offers lobby wine tastings and rooms with views of the Charles River.
• Fairmont Copley Plaza: The city’s most opulent hotel lobby can be found just steps from swanky Newbury Street.
• Liberty Hotel: In the summer, guests can borrow bicycles or take a yoga class for free at this historical hotel, housed in a completely transformed building that was a jail in the 19th century.
• The Charles Hotel just off Harvard Square offers sumptuous rooms decorated in a contemporary New England style.