4. Back Bay
The eight-block shopping stretch of Newbury Street in Back Bay conforms to an easily deciphered grid: at Mass Ave., where the strip begins, you find the more downmarket stores (e.g., Urban Outfitters). As you progress eastward, you graduate to increasingly higher-end outposts (Banana Republic, Lucky Jeans) until you find yourself at the street's terminus, at Arlington Street, loitering outside Chanel and Cartier.
Perhaps a better, or at least more scenic, way to gape at Back Bay's wealth is to walk a block or two north of Newbury, and check out the residential sections of Commonwealth Ave. and Marlborough and Beacon streets, which, since the area's development in the mid-1800s, have been among the most desirable — and expensive — places to live in Boston. Here you'll find sumptuous Victorian brownstones with inviting front stoops and small but well-tended gardens. Many of the buildings have been carved into apartments, but a few have remained single-family homes.
If all the strolling and ogling causes your blood sugar to dip, you can refuel at Stephanie's on Newbury, an American bistro with very large, very good and very expensive salads.