"Before I lived in Portland, Maine, I would take the quick trip north from Boston every spare weekend I could. Well regarded as a culinary hot spot that’s soaked in seaside charm, the easily walkable city is the perfect place to spend a long weekend—or more."

Best Hotels: The Docent’s Collection

"If you’ve ever wanted to try living in one of downtown Portland’s best neighborhoods, the Old Port, this is the place to do it. The Docent’s Collection offers a handful of loft-style apartments, complete with kitchens. Jordan Nugent, director of travel and events at Experience Maine, says, “I love The Docent’s Collection because it feels more like apartments, each with its own kitchen and living area, located in the heart of the Old Port. It’s great for larger groups traveling together or longer stays."