Hotel at a Glance: Staypineapple, A Delightful Hotel, South End Boston

In each guest room at Staypineapple, a large photo lays out the city’s skyline. If the image inspires travelers to get out and explore, they’re in luck: this new boutique hotel is within walking distance of shops and restaurants in Boston’s South End and Back Bay neighborhoods. There’s also a subway station a short walk away, and the hotel loans bicycles for leisurely rides.

• The best views: South End corner king rooms
• In-room tech: WiFi and TVs that let guests stream their own content

Boston’s Back Bay: Victorian Architecture and Historical Landmarks on the Charles River

Boston’s Back Bay used to be just that—a literal bay that extended into the Charles River. In the mid-1800s, developers added landfill and created the grid-style neighborhood that remains today. Victorian brownstones and kempt gardens line the wide avenues of this waterside enclave that lies just west of Beacon Hill. Boston is a highly walkable city with a good public transportation system to boot, so you’ll be able to get to several other neighborhoods as well, including the Boston Common, which is the starting point for the famed Freedom Trail.

Often called the Rodeo Drive of the East, Newbury Street stretches eight blocks east from Massachusetts Avenue to Arlington Street. The quaint tree-lined street is home to dozens of high-end retailers such as Chanel and Cartier, as well as vintage boutiques and consignment shops. Between Newbury and the Charles lies some of the most desirable real estate in Boston; the historic brownstones are worth checking out. The Esplanade, a 3-mile jogging path along the Charles, is especially popular in the summer.