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Boston Travel Guide

Weekend Getaway

Tearing Up Tea Town
Old World Appeal, New World Flair
by Ruth Tobias

Boats on the Charles River in Boston, Massachusetts
Charles River Skyline in Boston, Massachusetts

Welcome to the City of Champions. There's no getting around the fact that Boston is a sports-crazy city. The Red Sox have finally won not only one but two World Series championships (although most Bostonians refuse to talk about the end of the 2011 season), the Bruins have the Stanley Cup, the Patriots, well, how about them Celtics? The Seaport District, South End and Fort Point Channel have all been transformed, thanks to initiatives like the Rose Kennedy Greenway, the Institute of Contemporary Art and an influx of popular restaurants; meanwhile, older neighborhoods like East Boston and the North End continue to thrive with an influx of new residents, shops, restaurants and galleries. Even Hollywood has gotten in on the act, filming hits here like "The Departed" "Gone Baby Gone," "The Fighter," "The Town," "Mystic River" and of course, "Good Will Hunting." From the Freedom Trail and the Old North Church to the galleries of the Ladder District and boites of the South End, Boston continues to please history buffs, hipsters, and Hollywooders alike. Believe it or not, crusty Bostonians really are friendly — just as long as you're not wearing a Yankees cap!

Lodging options here range from ultra-modern to historic. If you're seeking something luxurious, check into the regal The Ritz-Carlton Boston Common, the equally stately Four Seasons Hotel Boston or the classic Taj Boston. For edgy, nothing beats the much-buzzed-about The Liberty Hotel Boston, which was formerly the Charles Street Jail. (In-house bars Alibi and Clink pay homage to its storied history.) Trendy and sleek, it'sactually a fun place to be trapped. The Onyx Hotel and Nine Zero are reliable Kimpton pet-friendly boutiques, and one of the latest newcomers, Mandarin Oriental, Boston, is among the poshest hotels in town.


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.) Boston's mayor, Thomas Menino, has instituted the popular bike sharing program known as the Hubway, where you can pay for a rental at one location and drop it off at another. 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 2.5-mile Freedom Trail. You don't have to commit to a guided tour led by a costumed college student. 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!

Beacon Hill Street in Boston
Beacon Hill Street

Since the VIC is located right on 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. In winter, couples and families flock to the Frog Pond for ice skating. 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 Bulfinch, 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 or check out some cool shops like Wish.

The Paul Revere Statue in Boston
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 of shops and restaurants (like Durgin Park) 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. Head over to the North End where you’ll lap up the lore of Paul Revere: one of the nation’s first residential neighborhoods, it boasts both his home and the Old North Church, of "one if by land, two if by sea" fame.

The Bunker Hill Monument in Boston
Bunker Hill Monument

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, but for now, salumerie, panetterie and trattorie still abound along the crooked streets. So mangia while the eating’s good — and great it is, be it a classic pie at the creaky old original Regina Pizzeria or succulent, spicy seafood and a plastic cup of wine at the teensy The 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 fresh ricotta-filled cannoli from Mike’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 in the Navy Yard, the Bunker Hill Monument stands in its slender granite splendor waiting to be climbed and the Freedom Trail ends. Treat yourself to a brew at The Warren Tavern, Boston's oldest tavern, before checking out the sexy lounge known as Tangierino, a Moroccan restaurant festooned with gaudy artwork and gaudier belly dancers.

Then saunter back into town at your leisure and head to the Back Bay in anticipation of the sumptuous feast you’ve most certainly earned. Splurge on omakase at Uni, a sashimi bar.

Continue to Day 2


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* Images courtesy of the Boston Convention and Visitors Bureau

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