After summer ends and amber leaves begin to gather on the ground, the inner traveler in us begins to rustle. While the months of June through August may have been filled with weekends to a lakeside cottage, somehow, it doesn’t feel like true “travel” unless a whole city lays in wait of discovery.

When travelling during the fall season, picturesque scenery is amongst the top three boxes to tick off before settling on a destination, just under the perfect hotel and above entertainment.

With a big check mark in all three categories, Boston is one of our favourite cities to visit come September. Autumn in Boston is cinematic. Set against the backdrop of the city’s historical architecture—from the illustrious grounds at Harvard to the quaint gas lamps, cobblestone streets and purple tinted window panes in the city’s beautiful Beacon Hill neighbourhood—the season colours the city the perfect shade for exploratory jaunts—camera in hand, of course.

But first: where to set up home base.

Over the last 15 years, Boston has enjoyed a revitalization in its hospitality business. New hotels abound, the choice in accommodations has greatly expanded since the days of having to choose between either a grand old establishment or your average not-my-first-choice chain hotel.

For travelers, like us, who prefer luxury and supreme comfort, as much as so as originality and distinct design, The Boxer Hotel is where you want to unpack your suitcase when visiting Boston.


Located in the North End of the city, just walking distance from the bustling and fragrant streets of Little Italy, The Boxer is a stylish accommodation choice for well-heeled travelers, with a fancy for luxury living, a hunger for good eats (particularly cannoli) and a Zen for Instagram. Photo ops are plentiful at this hipster-approved boutique hotel. From the moment one finds themselves nearing the property, they will already feel the urge to capture the hotel’s unique exterior. It’s not every day, after all, that one gets to call a triangular structure i.e. the Flatiron Building, their home away from home. Upon walking through the doors of The Boxer (past the line of ruby red bikes reserved for guest use…snap!) one is taken with the warm modern design of the space. Black and white photos of pugilists past don the moody coloured walls here, alongside a mix of contemporary and antique-inspired furniture of leather and wood that look as if plucked from a 1920s parlour.

Upstairs, room furnishings skew more towards modern industrial design. Suites are dressed in neutral shades of grey and blue and characterized by crisp minimalism, with cozy accents found in wooly tartan blankets and knit throw pillows. Guests of some rooms may even find a sweet picture of a bulldog out for a bike ride with its owner, whimsically painted on their wall—say Instagram!

Guests will find ample room to stretch out in one of the hotels Junior Suites, which offer stunning views of the cityscape (snap!) and bathrooms outfitted with marble countertops and sleek glass shower stalls, or, should you be travelling in a group (planners of bachelor and bachelorette parties listen up!) reserve a Boxer Bunk room and relive your sleep away camp days. This time though, with a fully-stocked mini bar (including unique items like a chic shaving kit by the craftsmen over at Harry’s, tempting enough to “forget” your razor at home) and a 32” flat screen TV. For a city known for flaunting fashion tastes that read like a spread in a J.Crew catalog, The Boxer Hotel is its own spot of Brooklyn—the Creatures-of-the-Wind-wearing-ABC-Kitchen-going-tastemaker side of it—in the North End of Beantown.


With Little Italy a stone’s throw away, handmade pasta and wood oven pizza should be on the dining agenda, but before venturing out of the hotel, guests can satiate their hunger with a visit to the Finch Restaurant. Serving up hearty American fare with modern delicacy, like their classic New England chowder, we recommend starting the day off with breakfast here. Traditionalist will appreciate the Finch Four (coffee, eggs, bacon or sausage and toast or an English muffin), and when-in-Rome types will want to order the Boxer Benedict (ham is replaced with lobster here) while those rushing off to the airport can happily squeeze in the all-you-can-eat Express Buffet. And should you be planning an excursion over to Boston Common, less than a mile away, take the time to order a , the perfect entrée for a picnic in the park.

Drinks at the Finch are equally delightful. Try the quenching Finch 75 (Tito’s vodka, domaine de canton, pineapple juice, prosecco float) after a day of exhausting your Charlie card between visiting the penguins at the New England Aquarium, studying the fossils at the Harvard Museum of Natural History and taking in an exhibit at the Museum of Fine Arts (“Yours Sincerely, John S. Sargent” is a must see)—after such a day of activity (easily accessed by way of the nearby North station), two drinks may well be in order. Or get a takeout order of cannelloni from Mike’s Pastry’s in Little Italy (don’t let the lineup discourage you, these toothsome desserts are worth the wait), get your in-room Keurig coffee maker going and enjoy the finer things in life from the comfort of your own urban retreat.


For travelers that would rather skip the sightseeing and dive straight into the shopping (and post-shopping Chablis), we recommend situating yourself in the Back Bay area while staying in Boston. Here, amidst the rows of Victorian brownstones—housing boutiques galore—the most ardent of shopaholics whims are satisfied pending a stroll down the eight-block shopping stretch of Newbury Street.

Tucked away on a quiet residential street, just a brief walk away from the west side of the aforementioned retail mecca, is the Inn at St. Botolph. A true home away from home, the inn features spacious apartment style suites for travelers looking to live like a local.

Like its surrounding area, the suites here are fashionable, featuring modern design that feel more boutique hotel than inn. Industrial four-poster beds are a common feature of suites here, complemented by Art Deco-inspired accents in shades of gold and black, imbuing rooms with contemporary grandeur.

Rooms range from 300 square feet studio suites, ideal for couples looking for stylish digs at an affordable rate, to two bedroom deluxe suites that offer 850 square feet of penthouse living in the fashion hub of Boston. Should you be booking a stay with your family, consider the latter option. The suite’s large living room area and second room with trundle bed, offer cozy comforts to enjoy on top of a fully loaded kitchenette. (In other words, the fridge comes with an icemaker, and that means chilled Veuve without leaving your room.) Or, if you’re travelling sans family, and just wanting more room for those shopping bags you plan on accumulating during your visit, we suggest the one bedroom suite. Between its picturesque bay window and the gas fireplace, you’ll have plenty of places to cuddle up by after a tiring day of shopping. Bump it up a grade to the deluxe one bedroom, providing even more square footage for your new rag & bone friends and a stunning panoramic view of the neighbourhood to boot.


Accommodations here come with free Wi-Fi and continental breakfast, little bonuses to make the stay convenient and frugal. Plus, for the traveler who refuses to give up their exercise routine, vacation or not, a small basement fitness centre has your workout essentials.

And, without a front desk to fuss with—guests are given their own passcode to enter the building and their room—a stay at St.Botolph feels more like you’re house sitting for a stylish friend—think architect by way of Stockholm—than checking into an inn.

Around the corner from the Prudential Center and its fast-fashion shops, it’s the designer boutiques on West Newbury Street, just minutes away from St. Botolph Street, that we recommend checking out. Enroute to those, stop off for a quick one at Bukowski’s Tavern for a glimpse of local life to go with your pint of ice cold brew. Then, whether mid-way through your shopping or at its end, make it a point to visit La Volle (261 Newbury Street) for a bite and a drink. A favorite among Bostonians, this French brasserie will have visitors seeing the city through rose coloured glasses by their last morsel of foie gras. Beantown, j’adore!

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