This sprawling area is home to the oldest Major League Baseball park. For intimate Red Sox action, visit Bleacher Bar underneath Fenway Park’s centre-field bleachers. Grab a seat by the garage door-sized window for a ground-level view of the game for the cost of a Harpoon IPA or a warm pastrami sandwich. On non-game days, head down the street to Blazing Paddles pub and book time to swing away at the official Fenway Park visitors’ batting cage.
On your way to Boston University’s Mugar Memorial Library, cut through Kenmore Square to see the towering CITGO sign with its distinctive red triangle. At the university’s library, the Howard Gotlieb Archival Research Center displays documents and memorabilia from 20th- and 21st-century musicians, actors, writers and more. Admire a caseful of Emmys (Dan Rather), Oscars (Gene Kelly) and Tony Awards, a film script that Bette Davis used to learn her lines, an Edison wax cylinder phonograph and a room dedicated to alum Martin Luther King Jr.
Later, head south to the Isabella Stuart Gardner Museum, where the American heiress once occupied the top floor of this palatial, four-storey building. Displays include around 6,500 objects like paintings, furniture and sculptures in Gardner’s own idiosyncratic layout. Start exploring in the Venetian courtyard, then check out the Titian room, in which everything from the Persian carpet to the Italian glassware complements Europa, an original Renaissance masterpiece painting.
Getting there: WestJet flies to Boston four times a day from Toronto and Halifax.
Read more from our Boston Neighbourhood Guide
Editor’s Note: It was originally published that Bodega, Boston’s hippest sneaker boutique, is located in Fenway-Kenmore. In fact, it is located in the adjacent neighbourhood of Back Bay. Find it on 6 Clearway Street, hidden behind a secret door in a nameless convenience store. Its wood-panel shelving holds shoes from Converse and rare Adidas to US$645 Yeezy boots. Also find curated streetwear by brands like Raised by Wolves.
What to Do in Downtown Boston
Downtown Boston is filled with historic attractions, many with excellent harbour views. Learn about the American Revolution at Faneuil Hall, visit 17th century tombstones at Granury Burying Ground, browse one of the country's oldest independent bookstores and eat at Yvonne's, a hidden supper club.
What to Do in Boston’s North End
Boston’s oldest residential area is just one square kilometre in size, but it’s filled with Italian restaurants, old-world food markets, wine shops and 18th- and 19th-century churches. Tour Old North Church, eat contemporary Italian at Parla and watch a comedy show by Improv Asylum.