Boston, Massachusetts 72-Hour Vacation

Charles River Skyline in Boston, Massachusetts

The Big Dig is but a memory, and the Red Sox have finally won the World Series. The Waterfront and Fort Point Channel are revitalized thanks to initiatives like the Rose Kennedy Greenway and the Institute of Contemporary Art; meanwhile, older neighborhoods like East Boston and the North End continue to thrive with an influx of new shops, restaurants, and galleries. Even Hollywood is getting in on the act, filming hits like "The Departed" and "Mystic River" here. (Ricky Gervais and Christian Bale have been spotted shooting movies here, too.) From the Freedom Trail and the Old North Church to the galleries of the Ladder District and boites of the South End, Boston pleases history buffs, hipsters, and Hollywooders alike. And contrary to popular belief, crusty Bostonians really are friendly—so long as you're not wearing a Yankees cap!

Lodging options here are diverse. If you're seeking something staid, install yourself at the regal The Ritz-Carlton Boston Common or the equally stately Four Seasons Hotel Boston. For edgy, nothing beats the buzzed-about The Liberty Hotel Boston, which was formerly the Charles Street Jail. (In-house bars Alibi and Clink pay homage to its history.) Trendy and sleek, it's not a bad place to be trapped. Onyx Hotel and Nine Zero are reliable boutique bets, and the newly opened Mandarin Oriental, Boston is among the poshest hotels in town.

Before you go, consider getting a CityPass to save up to 50% off the price of regular admissions to some of the city's finest attractions.

DAY 1
Boston is a walking city like few others in the U.S. Even vehicular diehards in the Massachusetts capital (and the most densely populated city in New England) can get used to the pedestrian lifestyle here—the window-shopping, the people-watching and the absorption of living history amid the centuries-old brownstones and English-style squares that mark the city’s oldest neighborhoods. (Plus, as locals will admit, drivers here aren't the kindest.) By the same token, even the most tourism-averse visitors would be remiss not to supplement their wanderings (which make for deliciously personal discoveries in any city) with the singular jaunt that is the Freedom Trail. You don’t have to commit to one of those guided tours led by some Ph.D. candidate in American History and dressed in a powdered wig under his tricorn, either. Just hit the Greater Boston Convention and Visitor Bureau’s Visitor Information Center to gather maps and educational materials, and customize your own version—now that’s freedom! And if you’re curious to know the origin of the city’s primary nickname, during Colonial times beans slow-cooked in molasses was a common dish. But remember: the moniker "Beantown" makes natives bristle, so keep it to yourself.

Beacon Hill Street

Of course, since the VIC is located right on the Boston Common, it’s a smart place to start. Once used by both British and American troops for conducting military exercises (and shortly thereafter by grazing cattle), it’s now a leafy, rolling expanse dotted with tennis courts, baseball diamonds, ponds and—and come summer—lots of sun-starved office workers on break. Keep your eye on the gold dome of the State House, indeed a beacon signaling your arrival on cobblestoned, gas lamp-lined Beacon Hill. Its self-taught architect, Charles Bullfinch, also built or influenced many of the area’s grandest homes—in which the famed Boston Brahmins all lived. Of course, their khaki-clad ancestors are still milling about, meeting and antiquing along the neighborhood’s main drag, Charles Street, a couple of blocks away; reward yourself for making the quick detour with some gourmet goodies from Savenor’s Market (patriarch Jack Savenor was Julia Child’s butcher) to tide you over until lunch.

Paul Revere Statue

Back on the Freedom Trail, your educationally rich options include the Granary Burying Ground, containing the graves of John Hancock and Samuel Adams, among other revolutionary luminaries. Faneuil Hall, where those very Sons of Liberty once met to foment rebellion, has been transformed into a chain-clogged mini-mall that undoubtedly has them turning over in their graves. Sandwiched between the two, there’s The Old State House—also known as the grisly site of The Boston Massacre. Continuing into the North End, you’ll lap up the lore of Paul Revere: One of the nation’s first residential neighborhoods boasts both his home and the Old North Church, of "one if by land, two if by sea" fame.

Bunker Hill Monument

Of course, the North End is also celebrated as Boston’s own tight-knit Little Italy. Granted, with the Big Dig over and the long-awaited Rose Kennedy Greenway open to the public, gentrification has begun in earnest (or is that cynicism?) around here; but for now, salumerie, panetterie and trattorie still abound along the crooked streets. So mangia while the eating’s good, be it a classic pie at creaky old Pizzeria Regina or succulent, spicy seafood and a plastic cup of wine at the teensyThe Daily Catch. If you feel like splurging, Mare turns out organic Italian seafood dishes that, like the chic décor, are at once progressive and posh. Or you can eat your way across the neighborhood with longtime resident Michele Topor’s three-hour North End Market Tours; you'll visit small produce stands, coffee roasters, old-fashioned sweets shops and pasta purveyors. She’ll help you to understand everything from how to buy olive oil to why a buono cappuccino requires the expertise of a real barista. Either way, save room for a couple of ricotta-filled cannoli from Maria’s Pastry Shop. That sugar high should help you as you cross the Charlestown Bridge—which runs parallel to the soaring white Leonard B. Zakim Bridge—over the harbor and into Charlestown, where Old Ironsides is docked, the Bunker Hill Monument stands in its slender granite splendor and the Freedom Trail ends. Treat yourself quick drink at neighborhood hotspot Koullshi, a sultry lounge beneath popular Tangierino, a Moroccan restaurant festooned with gaudy artwork and gaudier belly dancers.

Then saunter back into town at your leisure in anticipation of the sumptuous feast you’ve most certainly earned. Languish in luxury at the refurbished L'Espalier, where Frank McClelland artfully merges French and New England cuisine, or splurge on omakase at Uni, the sexy little sashimi bar adjoining Ken Oringer’s acclaimed French destination Clio.

Continue to Day 2