Encompassing 34 blocks, downtown Boston features the city’s top attractions, including historic Faneuil Hall. Visit its shops and a small military museum featuring weapons and uniforms from the American Revolution. Also pop in to the white-columned, second- and third-floor Great Hall, the site of symposiums by founding father Samuel Adams. Outside, view the gilded grasshopper weathervane, atop the building, that has survived earthquakes, fires and snowstorms to remain one of the building’s only original 1742 features.
Nearby in McKinley Square, admire the 1837 Greek-revival rotunda at Marriott Vacation Club Pulse at Custom House, Boston with its grand cupola and artifacts that include seafaring navigational tools. At 2 p.m., for a small fee and weather permitting, take the elevator up the clock tower to the 26th-floor observation deck for a 360-degree view of Boston that encompasses the harbour and Long Wharf, which resembles a ship.
Head to the Granary Burying Ground where you’ll find 17th-century tombstones and, just outside, one of the country’s oldest independent libraries, which contains almost 500,000 books (including a memoir bound in the writer’s own skin). Embark on a free, hour-long tour of the 19th-century, Neo-Palladian-style Boston Athenæum to view its private libraries, spiral staircases and reading rooms once frequented by Nathaniel Hawthorne, Louisa May Alcott and Ralph Waldo Emerson.
Walk five minutes south and slip behind a hidden door in a hair salon to Yvonne’s, a supper club situated in a cellar built in 1832. In its handsome library bar with gilded fireplace, you’ll find funky portraits, including Bill Murray in military uniform. Feast on stone-fired pita topped with Turkish beef sausage, mozzarella and basil marrow butter, as well as onion and parsley salad.
Getting there: WestJet flies to Boston four times a day from Toronto and Halifax.
Read more from our Boston Neighbourhood Guide
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.