Boston Guide: How to Spend 48 Hours in the City

Boston Guide: How to Spend 48 Hours in the City

Where to eat, stay and play in this top New England destination.


Image courtesy of  The Eliot Hotel.

There’s no sense in hiding it — Boston is one of our favourite North American cities. Its old-world charm, storied architecture and quaint waterfront (not to mention, endless options for kicking back with a pint of Guinness and live Irish music) will forever keep us coming back for more. So this time, we decided to hit up all of our favourite locales, and some wonderfully surprising new ones, to bring you a roundup of some of the best the city has to offer if you’re spending the weekend in Boston. Get ready for a wicked-good 48 hours.


A view of the one-bedroom suite at The Eliot Hotel.

Where to Stay:

The beauty about Boston’s navigable and cobblestone streets is that you literally make your way from the city’s North End neighbourhood (which is not technically north at all, we learned) through the Boston Common park and to Beacon Hill on a short trip by foot. So you can stay anywhere in the city and be footsteps away from a historic stop on the Freedom Trail (a 2.5 mile-long red-brick path lined with 16 notable locations across downtown Boston) or a great pub. For our weekend getaway, we booked a two-night stay at the old-world style Eliot Hotel, located in the city’s Back Bay neighbourhood. This boutique hotel boasts a classic European vibe, beginning with actual gold keys for the guestrooms. Our penthouse one-bedroom suite faced out toward Newbury Street, lined with cute cafés and luxury boutiques in between 19th-century brownstones.

This boutique hotel — one of the oldest in the city — offers 24-hour room service and complimentary Wi-Fi, as well as passes to the Boston Sports Club fitness centre around the corner on Newbury Street. The quaint elevator will have you believe that you are being transported to another era. The hotel is a just a short walk away from the Boston Museum of Fine Arts, Fenway Park and the finish line of the annual Boston Marathon, located at the north entrance of the Boston Public Library (for more on this must-see stop, read on!).

Where to Find:
The Eliot Hotel
370 Commonwealth Avenue
Boston, MA


Sweet Italian treats at Bova’s Bakery. Photo by Jonathan Panetta.

Where to Eat:

There’s no shortage of international dishes served up at the hottest local spots in town. In a weekend, you can dine on Spanish-style tapas, including a plato de queso (cheese and olive platter) and scallops in saffron cream at Tapeo, located in Back Bay, and then a plate of shrimp fettucine at Al Dente in the North End (conveniently, the city’s bustling Little Italy neighbourhood) the next night. Post-pasta-and-wine, and a glass of limoncello to sip on, head down the street to the city’s famous 24-hour family-owned Bova’s Bakery. There will most likely be a lineup trailing outside the door, so be sure to stock up on chocolate chip cannoli and classic black-and-white cookies. And for the love of all things wonderful and delicious, do not leave without trying the crème brûlée. For breakfast, opt for a classic upscale American brunch at Joe’s American Bar and Grill or Irish pub-style fare at The Black Rose in Quincy Market. Or for late-night cocktails and a plate of warm, fresh-baked cookies, head to the Top of the Hub — located on the 52nd floor of the Prudential Tower in Back Bay — for your nightcap with stunning panoramic views of the brightly lit city below.


A scene from Good Will Hunting filmed in the Boston Public Garden. Photo courtesy of Miramax Films.

What to See:

Just roaming the historic streets of downtown Boston will bring you front and centre with pivotal moments of America’s past: follow the red-brick-road on the Freedom Trail to the sight of Paul Revere’s House or the Boston Common, the country’s oldest public park, dating back to 1634. Among the greenery is where you’ll also find the Boston Public Garden, a locale famously immortalized in the 1997 film Good Will Hunting — more specifically, the park bench where the scenes between Robin Williams and Matt Damon were filmed (“The Good Will Hunting Bench” became a memorial site for the late actor when Robin Williams passed away in 2014).


The marble-lined architecture of the Boston Public Library. Photo by Jonathan Panetta.

For a breathtaking and scholarly stop on your day touring, stroll through the Boston Public Library, the first-ever free library in the country. The marble interior and mural-lined walls evoke the grandeur of a European cathedral and the quaint tree-lined courtyard is the perfect spot for nestling up to read — a history lesson and a great selfie, you really can have it all.

And don’t forget to take an afternoon trip to Cambridge — a short subway ride away — where you can filled up on banana and blueberry gluten-free pancakes at The Friendly Toast. Be sure to head there early, as the restaurant is almost always packed with local MIT and Harvard students. Then make your way to The Coop at Harvard Square to stock up on university memorabilia. You’ll need your Harvard-branded sweatshirt and hat for your “I-totally-go-here” school Facebook profile photo. Elle Woods would be proud.

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