Despite continuously serving for more than 200 years as the political, economic and cultural hub of New England, Boston’s reputation as a staid municipality with rabid sports fans hadn’t changed much over the years. But the dust has settled from the Big Dig and the arrival of international luxury hotels and an economic boom has gradually transformed run-down neighborhoods into centers as hip as their counterparts in more stylish cities. On a brisk fall day, as the river reflects the changing colors of the leaves or an early snow transforms the historic lanes of Beacon Hill into a winter wonderland, it’s hard to resist Boston’s charms.

Cheat Sheet

  • Sleep…at Fifteen Beacon, a classic boutique hotel of the finest order
  • Experience…downtown vibrancy while staying at the Ames
  • Splurge…on a mini getaway in the VIP Lounge of the Emerge Spa on Newbury Street
  • Eat…inventive Italian tapas as South End staple Coppa
  • Drink…what the mixologist creates at the Hawthorne, a posh cocktail bar
  • Savor…a Stumptown coffee with the hipsters at Thinking Cup
  • Visit…the pre-Revolutionary War Paul Revere House in the North End
  • See…the light-filled Renzo Piano wing of the Isabella Stewart Gardener museum
  • Shop…for top designer finds at consignment shop the Closet
  • Know…that as an Indagare member you can contact our Bookings Team for customized recommendations and itineraries

Lay of the Land

“In Boston they ask, how much does he know? In New York, how much is he worth? In Philadelphia, who were his parents?”
~Mark Twain

“You can’t get there from here” is a fairly common in phrase in Boston, due to its system of one-way streets, arcane routes and traffic flows that only the city faithful can puzzle out. But Boston is compact and walkable. Beacon Hill, home to some of the city’s most spectacular historic homes, sits between the Boston Common and the Charles River, and most of its commercial activity happens along Charles Street. Just on the other side of the Common is Downtown Boston and the Financial District, which also borders the North End. To the southwest, adjacent to the Public Garden, is Back Bay, a former swamp filled in during the late 1800s and now populated by expensive Victorian town houses and some of Boston’s best shopping and dining (along Newbury Street).

The South End, which has been transformed from a run-down slum to row after row of pricey brownstones, lies south of Back Bay, just the other side of the Prudential Center and Copley Square. Slightly younger and hipper than the northern neighborhoods, the South End most closely compares in look and feel to New York’s West Village or Brooklyn Heights. Tremont Street remains the main drag for dining, but Washington Street, a little grittier and with more warehouses than historic row homes, is making a bid to be the hipper of the two.

The Big Dig used to separate the North End from the rest of the city, but now that the construction is complete, a leisurely walk along the new greenway takes you from the northeastern part of Beacon Hill right to Boston’s version of Little Italy. Although many of the dining options are on Hanover Street, explore the narrow back alleys to find other charming trattorias and cafés.

Cambridge, while technically a separate city, is treated (and feels) like another Boston neighborhood, particularly Harvard Square, a ten-minute taxi ride north from Back Bay along Massachusetts Avenue.

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Beyond… Boston

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