Distinctively Boston things run through my mind – crowds at Fenway Park, eating a Fenway Frank, cheering with Bruins fans, singing Shipping Up to Boston or anything by Noah Kahan at a bar. Even simple pastimes like holding an iced coffee in below-freezing weather and imagining yourself in the classic film Good Will Hunting every time you pass by MIT remind me of the city.
F. Scott Fitzgerald spoke of seeing New York City for the first time again with every drive Gatsby made over the Queensboro Bridge. That is how it feels to enter Boston once more – to see the city from a flight’s window seat is always to see it anew, in its wild promise of all the history and beauty of American metropolitanism.
This sentiment accompanies me on each flight I take back to Boston. Even on quick trips from New York, only an hour away, there is a sense of relief in seeing a whole city from your plane’s window. Sometimes I even request the left-side window seat solely for the view – and I’m typically an aisle person.
Romanticising Boston is not an easy thing. Winters are cold and summers can be humid. In autumn it can rain for days; spring is sporadic and almost always late. Yet between all four seasons, I have learnt that there are these perfect days that make visiting Boston at any time of year worthwhile.

When the Weather Turns

On a rainy day, museums like the Museum of Fine Arts, Boston Children’s Museum, and the Harvard Museum of Natural History make for the perfect itinerary. Even the Museum of Ice Cream or a tour of the Old State House – the first US State House – can be ideal additions between delicious meals and sporadic winds. While you could choose to stroll down the red-brick Freedom Trail, it’s recommended to do so on a sunny, or at least dry, day.

The Freedom Trail has become one of my favourite aspects of living in Boston. Starting at Boston Common, the larger park next to America’s first public park, the Public Garden, it spans four kilometres, winding between cemeteries where founding fathers lie, and ends at the USS Constitution, a famous naval ship now serving as a museum.
Beyond the vast historical points along the trail – which is by no means a nature hike – I have come to find a good mantra in the city: if you stumble out of a bar and land on the Freedom Trail, you’ve found a good one. Favourites like the 21st Amendment and JJ Foley’s, highly rated for its Guinness annually, are Boston classics visited by locals and tourists alike.
The Green Dragon and Bell in Hand have the special flair of Founding Fathers’ portraits lining their interiors, ensuring you never tire of looking round the room. In how many bars in your city can you say you’ve had a drink with George Washington or Thomas Jefferson?

A Revolutionary Spirit

In 1776, Boston was at the forefront of the thirteen colonies seceding from the British Empire. With the help of European nations equally opposed to Great Britain, and with the support of countless brave souls, America took its first breath on free soil. It has been breathing ever since, through wars and turmoil, and throughout it all has grown to absorb a certain mixed culture that is incomparable to other places in the United States.
A tourist might be quick to say Boston is simply a smaller New York City. They would be wrong. And never say that aloud – unless you want a Patriots fan holding an iced Dunkin’ coffee to yell specific Boston insults at you in Southie.

A Season on Newbury Street

Boston was a daunting city to move to at first. In the midst of a blizzard in January, I began to explore the city and fortunately found comfort quickly through my favourite pastimes: shopping and menu tasting. Under holiday-lit trees in Back Bay on Newbury Street, I found my shopping habits a relief in a new city. Even better, the cafés and boutiques I grew to love in winter only became lovelier as spring arrived. Restaurants began opening their outdoor seating, and as summer rolled in, streets would close to traffic at weekends, turning into strolling paradises.

Milk and Money, Covet, Credo Beauty, even classics like Reformation, Alice and Olivia, and a walk through Ralph Lauren are ideal spots to catch up on trends and discover unique additions to a wardrobe. Ivy fashion is at the heart of Boston design – think hydrangeas by the coast and Ina Garten’s cooking. This aesthetic is carried through Boston shopping and only enhances the experience.

Designer shops start at the top of Newbury, and as you make your way down, they become more mainstream. Stopping for a sandwich at DeLuca’s Market, tacos at Lolita Back Bay, or a lobster roll at The Banks will sustain you before exploring another Boston neighbourhood. To dine among the food critics, Contessa’s rooftop restaurant on Newbury Street offers a curated selection of Italian-American brunch, lunch, and dinner.

Close by you’ll find the Boston Public Library, a museum of Boston academia in itself that exudes the higher education atmosphere of the nearby prestigious universities. To further indulge in grand architectural libraries, the Boston Athenaeum is a hidden gem. Located near the Common, and for a small donation, you can tour the grand 1807 library and museum.

Beacon Hill and Beyond

Working upwards from the Common, Acorn Street welcomes you to the beautiful and picturesque Beacon Hill neighbourhood. If you ever aspired to reach a Martha Stewart level of hostess and style perfection, Beacon Hill is where you begin. Speciality food shops start here and continue until you reach the North End, while speciality designer shops and homeware line the streets. Hidden gems await up every side street, and especially during autumnal leaf-changing, the area is a perfect example of Federalist and colonial architecture.

Boston is not a European city, by any means. However, I would go so far as to say it is the most European of American big cities. Without Washington DC’s grand promenades or New York’s skyscrapers, Boston has retained its revolutionary charm in old brick buildings and neighbourhood distinction difficult to find in other metropolitan areas.

The North End

The winding streets of the North End could make you feel as if you were lost in any southern Italian village – and the classic Neapolitan pizza at Bricco or seafood at Mare Oyster Bar and Neptune Oyster will exemplify that Mediterranean breeze you thought just wafted past you. To bring you back to American soil, Neptune’s lobster roll and Mamma Maria’s house-made pastas will do the trick.

Not to compete with any monumental European cathedrals, but Boston holds its own with historic churches. Mass Irish and Italian immigration brought with it good food and a knack for building churches. Within the streets of the North End, you can spot the Old North Church, the oldest church building in Boston, built in 1723. In the Theatre District Downtown, there is Park Street Church, another wonder near the five-star Omni Parker House Hotel. For any book lovers, the Brattle Book Shop is just round the corner and well worth a visit.

A City of Neighbourhoods

Italian food in the North End, day drinking in Southie, a high-end dinner in historic Downtown followed by drinks and jazz in the South End – Boston has it all. Dining at either Michelin-starred restaurant No. 9 or O Ya, followed by music at Beehive, ensures a perfect evening.
Back Bay for shopping, Brookline for off-the-grid foodies, Cambridge for festivals and academia, Somerville for residential charm and hidden bars – the city never ends. Whether above or below the Charles River, Boston is walkable, transport options are abundant (you can even take the ferry to the lavish Encore casino), and exploring never grows tiresome, no matter the weather.

Activities such as touring Fenway Park and Harvard University, walking through the Christian Science Plaza, and watching re-enactments of the Boston Tea Party will keep even a local busy. After strolling beneath the oaks and maple trees shading the quads of Harvard, reserve a table at one of the numerous Michelin-starred restaurants in the area. Pagu in Central Square, Giulia in Porter Square, and Pammy’s, just a few blocks away from campus, are extraordinary restaurants, all in the Cambridge area.

Evening Escapes

After a great meal in Boston, when the evening chill comes in, my favourite thing to do is find a new cocktail bar in which to seek shelter for an hour or two before braving any outdoor storm. One of my first discoveries was local favourite speakeasy the Wig Shop. Like many others, I believed I was walking into a barber’s or perhaps a costume shop, but the red hanging curtains and delicious cocktails before me told another story. Extra Dirty Cocktail Club is a close second with their cocktail-tasting menu style of service, while OFFSUIT, Sushi @ Temple Records, and D16 are all excellent cocktail bars themselves.

Beyond delicious cocktail tasting, after a pasta dinner you would find me at the bar underneath Modern Pastry. And yes, you can bring your cannoli to eat alongside a martini downstairs. There is a longstanding rivalry between Mike’s Pastry and Modern Pastry – try both after getting a slice at Regina’s Pizzeria round the corner – but it is my personal opinion that Modern is simply delightful.

The New Seaport

Before returning to your hotel in the central hub of Boston – whether it be the Four Seasons in Beacon Hill, Raffles in Back Bay, The Langham in the Financial District, or the Newbury Boston – cross the Fort Point Channel to Seaport.
While Seaport may not be the newest of Boston’s neighbourhoods, it is by no means lagging behind the others. Skyscrapers block the winds, and at times it feels like a city within itself, surrounded by glass and modernity. Hotels like the Envoy by the Autograph Collection are excellent examples of what contemporary Boston represents. Nearby Greek restaurant Committee and glamorous Grace by Nia, which always features live music, are reasons in themselves to visit this side of the city.

New England Awaits

Beyond the wonders of Greater Boston, Nantucket, Martha’s Vineyard, the Green Mountains of Vermont, and Maine’s coastline all lie a short flight or drive away. There is no shortage of day trips or weekend getaways that will open your eyes to the beauty and charm of New England. Luxury Airbnbs, five-star hotels, seafood overlooking the very water where it was caught, and an American Ivy flair throughout it all – it is highly recommended to extend your stay beyond the city.

Boston changed my opinion on what life can look like in an American city. I grew up in a suburban metropolis where downtown was reserved for dinner or a hotel conference. Boston is unique in that it offers a combination of concentrated city life with residential charm, and you can choose your own path. Believe me or not, but visit Boston yourself to prove me wrong – this slice of European charm, with perhaps a few more blizzards, is a perfect trip to take.