How to Spend a Weekend in Boston

Of all the major U.S. cities, Boston is one of the most quaint. After all, it was settled in 1630 by English Puritans, and many of its charming red-brick colonial buildings remain. But over the centuries, the city has grown and developed its own identity as one of the country’s cultural capitals with plenty of collegiate charm. Fall is an ideal time to visit as the city is cloaked in colourful foliage, the students are returning from summer vacation, and the cultural calendar is brimming with events. Ahead, a guide to the hotels, restaurants, museums, and things to do during a weekend in Boston.


Boston gardens

Photo by Leading Hotels of the World


Where to stay

Boston’s hotel scene has everything from big-name brands to independent boutique hotels. One of the most luxurious places to stay is the Newbury Boston, Right where posh Newbury Street meets the Public Garden, the hotel has an unparalleled location with rooms and suites overlooking the park. Expect top-notch service and delicious cuisine at the buzzy rooftop restaurant, Contessa, owned by Major Food Group, which runs some of the top restaurants in and around the world.


The Newbury Hotel Boston restaurant view

Photo by Leading Hotels of the World


The Newbury Boston

Photo by Leading Hotels of the World



Another great option is the Four Seasons Hotel One Dalton Street, which occupies a shiny skyscraper in the Back Bay neighbourhood, near the Prudential Center and Copley Square. It has some impressive contemporary art pieces, including a large-scale mosaic by Duke Riley behind the reception desk and three installations of books wrapped in colourful African cloth by British Nigerian artist Yinka Shonibare.


Union Oyster House

Photo by Laura Itzkowitz


Where to eat and drink

Book a table at the Union Oyster House—the oldest continually operating restaurant in the U.S.—for oysters and clam chowder with a side of history. This unpretentious tavern with wood-panelled walls and red-leather booths is on the National Register of Historic Places and was a favourite of John F. Kennedy, the only American president from Boston.



Just steps away are Faneuil Hall and Quincy Market, a food hall established in 1826, the same year as the Union Oyster House. Today, the offerings are much more diverse. Inside you’ll find stalls selling everything from sushi to enchiladas—and classic clam chowder and lobster rolls too.

There are also plenty of excellent restaurants serving international cuisine. Long-standing favourites include Sarma, which Bostonians flock to for Middle Eastern mezze by Cassie Piuma and Ana Sortun, the award-winning chef behind Oleana. Another is Toro, a Spanish tapas restaurant by acclaimed local chef Ken Oringer.


Isabella Steward Gardner Museum courtyard

Photo by Laura Itzkowitz


Swan boats in the Public Gardens

Photo by Laura Itzkowitz


What to do

If it’s your first time in Boston, you may want to prioritize historic sites like the Freedom Trail and the Paul Revere House. Culture vultures will find plenty of museums to love, including the Museum of Fine Arts Boston, which has one of the largest collections of Claude Monet’s works outside of France; the Isabella Stewart Gardner Museum, in a Venetian-inspired palazzo filled with Renaissance masterpieces collected by its eponymous creator, a Gilded Age heiress; and the Institute of Contemporary Art, which was originally founded in 1936 as a sister institution to New York’s MoMA and now occupies a modern building on the waterfront designed by Diller Scofidio + Renfro.


Photo by Laura Itzkowitz


Of course, Boston is also known for baseball and beer. Even if there isn’t a Red Sox game on at Fenway Park—America’s oldest baseball park—there are guided tours available every day. Afterward, head over to Harpoon Brewery for a pretzel and tasting to try classics like the Harpoon IPA and limited edition brews such as Octoberfest.