North End, Boston, MA

Boston’s own Little Italy, the North End is actually the oldest inhabited section of the city and boasts a charming maze of narrow, winding cobblestone streets and a unique European flair.

The neighborhood may be small, but it’s still home to countless authentic Italian restaurants, cafés, and gelaterias, as well as historic locations along Boston’s Freedom Trail, including the Old North Church and the Paul Revere House.

Although the North End maintains a large population of Italian immigrants, recent gentrification and convenient access to the city’s Financial District has attracted a growing number of young professionals.

By day, the North End bustles with tourists as they visit landmarks and stop in at the famous pastry shops for cannolis.

By night, couples in the mood for a late-night dinner and a few carafes of wine head to the sleek Italian restaurants on Hanover Street, known more for their contemporary wine-bar vibes than the red-checkered tablecloth venues of years past.