The most fashionable neighborhood of Boston, the Back Bay is also one of the most easily navigated. Grand boulevards in the style of Paris are lined with brownstones and large Victorian-style apartment buildings, linked by short side streets that are ordered alphabetically (Arlington, Berkeley, Clarendon…). Ironically, given how swanky the neighborhood has become, the area used to be one big disease-spreading swamp—it’s no accident that the neighborhood’s main drag, Boylston Street, is named after a doctor.

In the days when Boston used to be a peninsula, the Back Bay was literally a bay in the Charles River, where refuse would wash up with the tides and men and boys—including a young Ben Franklin—would fish from shore. As the city expanded in the 1800s, the earth from Beacon Hill and other high ground was used for landfill to fill up the bay, and a new neighborhood was born, quickly filling with larger and more impressive houses built for the glitterati of the day.

The heart of the Back Bay neighborhood, if not the city, is Copley Square. The large plaza, which is half brick and half grassy lawn, is named after the Victorian-era painter John Singleton Copley, and is often the site of classical music concerts in the spring and summer. A statue of the painter, complete with pantaloons and artist’s palette, stands at the southwest corner of the square.

From Copley, each of the boulevards of the neighborhood has its own character. Boylston Street is the main commercial drag, lined with towering office buildings, along with convenience stores and coffee shops. Newbury Street, by contrast, is the ritziest street in town, where you are more likely to hear Spanish or Italian than a Boston accent. Along the street are branches of national chains from Armani to Zegna, along with a few local clothing boutiques and jewelry designers.

Next in line, Commonwealth Avenue is a boulevard in grand Parisian style, with a large pedestrian mall lined with statues running down the center, and trees festooned with lights in the winter. Quaint Marlboro Street has a purely residential feel, enhanced by the legions of flowering dogwoods that spawn floating petals in the springtime. Lastly, Beacon Street lines the river with more giant brownstones, along with the parkland of the Esplanade.