Portland to Boston from $217

🌍 About Boston

Boston is small and walkable, and its subway — the "T" — is the oldest in the US, opened in 1897. Start in the North End, the dense Italian quarter on Hanover Street, where the real argument is Mike's Pastry versus Modern Pastry for cannoli (both cash-only; locals split bitterly, Modern fills the shell to order). Eat clam chowder, the proper thick New England kind, not the watery imitation. The Freedom Trail's red brick line genuinely connects 16 Revolutionary-War sites if history's your thing. Come late September to mid-October: temperatures sit around 50–62°F and the leaves peak the third week of October. Skip humid, pricey July–August and the long grey winter.