2. The South End
In the 1980s, this neighborhood was considered dangerous and remote. In other words, cheap, which is why people on the front lines (i.e., artists and gay men) started moving in. As these things inexorably go, the area quickly gentrified, becoming too expensive for the early adopters. It's not hard to see why young, upscale families and finance industry fauxhemians are drawn here today: street after tree-lined street of red-brick bow-front townhouses dating to the 1800s, along with some of Boston's best restaurants, design stores and boutiques. The food and retail shops are scattered along Tremont, Shawmut and Washington streets. The latter is where you'll find perhaps the city's best cafe, the tiny bakery Flour, at the corner of Washington and Rutland streets, which, in addition to creating a transporting chocolate macaroon, also serves pies, cakes, tarts and sandwiches and ever-popular sticky buns. If you hanker for something more substantial, stop by B&G Oysters, which does shellfish right (i.e., not merely submerged in chowder).
It's also worth walking around SoWa (for South of Washington) — Harrison Avenue, between East Newton and Union Park streets — where some of the city's better contemporary art galleries are located. Each spring, during SoWa Art Walk weekend, artists open their workshops to the public.