Ask someone from outside of Boston to visualize their ideal Boston street, and they will very likely come up with something close to Charles Street. Running from the Boston Common to the Charles River along the western edge of Beacon Hill, the street has not been taken over by chain stores the way so many other shopping districts have (like Harvard Square). Many of the sides streets still have their original cobblestones and the with a few exceptions, most of the shopping along this street is the kind of sole proprietorship that making visiting a new place interesting. But fear not, at the Common end you can find a ubiquitous Starbucks.

Charles Street has a number of fine antique stores, a handful of bars that run the gamut from classic pub to chic-chic wine bar, and a number of interesting and innovative restaurants. There are also various boutiques specializing in everything from resort wear to Himalayan art and clothing. It also boasts the Charles Street Inn (a high end B&B) and -- at the Charles River end -- the Liberty Hotel, a former jail that has a number of good, if often loud and crowded drinking and dinning options.

Not the most kid friendly part of Boston (narrow sidewalks, mostly high end shops), Charles Street is probably best for couples and groups of adults. Because of its mix of shops and dinning/drinking, its worth visiting by day or in the evenings. Unlike Faneuil Hall, Charles Street is not solely patronized by tourists, but draws a largely local crowd. And -- again unlike Faneuil Hall -- it does not encompass specific historic sights, although Cheers is around the corner and the Duck Tours do drive down it regularly. 

The nearest T stop is Charles MGH (Red Line) or any of the three green line stops along the Common (Park St/Boylston/Arlington)