Superb historical sights, rich Irish heritage, brainbox universities… if this is starting to sound like a holiday checklist for your parents, then think again. Once famed as a haunt for academics, Boston, Massachusetts has now evolved into a major city-break destination, with slick new hotels, mounds of seafood and cheap new flight routes all present.
This is a city that lacks the grit that I’ve come to love in American cities, and the brashness of others. It’s understated, yet at the same time grand. Old (in relative terms), architecturally rich buildings line the streets; students throng the pavements; locals approach you in the coffee shops, restaurants and pubs, desperate to talk to you about baseball, beer and even algorithms. Yes, really. That happened.
It doesn’t need the fast-paced schedule of New York, the pockets of cash like Vegas or the ruin-porn obsession that’s necessary for a trip to Detroit. It doesn’t need much of your time, either. For an American city break that feels refreshingly un-American, here’s how to spend 48 hours in Boston.
Day one: Brookline, Fenway Park, Somerville and central Boston
Boston’s a walkable city, but you’ll need some fuel. Jump on the T train and head west to Brookline, a wealthy neighbourhood where pretty houses are home to born-and-raised Bostonians and students from nearby Boston University. A local favourite hangout is Zaftigs – a quirky and colourful diner with leather booths, a menu scrawled on a blackboard and walls adorned with abstract works by a local artist (paintings of the owner’s hat-wearing pugs line the perimeter of the bright room).
Grab a stool at the bar to chat with the friendly staff, who are on hand for recommendations. Mine was an egg, cheese and apple omelette (don’t knock it) with a cinnamon and raisin bagel, but the signature dish is probably the pastrami and sauerkraut sarnie, a monster of a meal that a few oldies were enjoying next to me.
Save your caffeine fix for coffee shop 4a down the road; it’s run by a husband-and-wife team, who seemed to be mid-argument when I wandered in, which only added to my macchiato’s flavour.
I’m not usually one for tours, especially of empty sports stadiums, but the behind-the-scenes walk through Fenway Park – home of the Red Sox and the oldest baseball stadium in the US – is a must if you want to understand what makes Bostonians tick. Our guide strolled with us around the ball park, talking us through its significance in times past (when families would disown you if you went on to support a team other than the Red Sox) to today (when families would probably do the same).
The tour takes you through the press room, the big Green Monster (the nickname of the lefthand wall with the scoreboard) and the wall of fame – with pictures of bands that have played at the stadium. It sounds odd, but there was something quite beautiful about the empty stadium, with its grass being prepped and original metal chairs waiting for groups of eager sports fans.
When you’re not talking about the Red Sox in Boston, you’re probably chatting about beer. The Boston Brew Tours runs fun afternoons taking in some of the best local breweries in the city – even if you’re not that into beer you’re sure to find the warehouse and brewing process interesting.
My first stop is Night Shift Brewing – a craft beer company with a #BeerIsArt ethos and hashtag – which was started by three mates who used to home brew as a hobby. Today there’s a big warehouse out back, where you can see beer ageing in barrels before being bottled and labeled, and you’ll get to try a few ales and lagers, too. They range from banana-scented wheat beers to one called Smells Like Weed.
Afterwards, head over to Shortpath Distillery. Set up by a few friends who ditched high-flying jobs, it’s an indy gin- and vodka-distilling space with eucalyptus- and lavender-infused concoctions, and a cute bar attached. If you’re there on a Sunday, the owner brings in his vinyl record collection. Feel free to have a rummage and pick your favourite (mine was Bruce) – they’ll happily play it.
The final stop – depending on the tour you take – is Down East Cider. Forget everything you know about cider, because this is the real deal. Proper appley, fruity, natural stuff made with Massachusetts apples. The team’s ciders are also far less dry than you might be used to – mainly because they use beer-brewing as opposed to champagne-making yeast (more common in cider brewing). It’s like glugging fresh apple juice, but better.
There’s platters and platters of sushi at Fuji Restaurant in Somerville (to the north of the city). Try some, but save room for the salt-fried pork belly and Sichuan beans and beef. For something less formal (although Fuji is hardly formal, just a tad smarter) check out the Boston Burger Company and its 30-strong burger menu, including the Hot Mess – a heap of jalapeños, bacon sauces and who knows what else, piled on a bun that ends up hidden underneath.
For a pretty and smart city, Boston does dive bars surprisingly well. A great in-town option is The Tam, a sticky-floored, brightly lit long bar where they spin rock tunes, packed with a young crowd of clever people (I meet some type of bearded algorithm genius, among other similar types). End the night at the Fairmont Copley Plaza’s bar with a signature martini, or three.
Day two: Harvard University, central Boston and Seaport
A tour of a university sounds mega dull, but bear with me. Each tour of historic Harvard in the suburb of Cambridge is led by a student at the uni – guys and girls who excel at pretty much everything in life, if my guide Ben Kelly is anything to go by. He’s the sweetest, most enthusiastic guide you could hope for – really smart (obviously), personable, great at singing and sport (all handy at one of America’s top universities).
He takes us on a really engaging tour through various spots on campus recounting stories of each historic building. We find out that the Widener library was donated by the widow of a man who died on the Titanic, and until the 1970s Harvard had a swim test for graduates – one of the wife’s conditions when donating the library. We also meet plenty of Ben’s fellow students on the way, many of whom show their appreciation for him by running up and giving him a big hug. You’ll want to hug him, too.
Take a wander around the Harvard Uni neighbourhood to soak up some of the student vibes before heading back into town. Depending on your interests there are a few things to tick off – I head to the library, a humongous 19th-century building that homes 23.7 million items, and plenty of students getting the hours in, too. The Isabella Stewart Gardner Museum houses her eccentric art collection, from ancient to 19th-century works, but I’m distracted by cannolis on steroids in the cafes in Little Italy – one of the less manicured, but no less charming, areas of the city.
For a stroll, try the Rose Kennedy Greenway, a mile-and-a-half-long stretch of contemporary parks. It’s part of a plan to ‘pretty up’ the city – Boston is one of the first US cities to move roads underground to utilise green space above, and you’ll find kooky artworks and activities along the way. My favourite stop is the carousel, which is decorated with unconventional animals – the creators went to a local school and asked what native Massachusetts animals the pupils would like to see on the ride. Sit on a squirrel and go for a quick spin (they take song requests too).
Further along is the Dewey Square Park, a green space scattered with deck chairs (in the summer people gather here for meetings) and one huuuuge wall that’s regularly replastered with new murals. Arrive around lunchtime and some of the city’s best food trucks will have gathered here with burgers, tacos and coffees, or head to the Greenway on Thursday evenings for sun-drenched block parties.
Bostonians seem to be split when it comes to Seaport. The waterside area, which looks like a mass of car parks and empty buildings, is seen by some as a nothing town, but for others it’s an emerging district that in ten years or so will be a majorly cool hangout. My time here is largely centred around food – start early evening at Legals, a huge glass-encased restaurant on the water that serves some of the best seafood in the city – think lobster rolls, chowder and bloody marys pimped with prawns.
Come nighttime, it’s a great area for drinks. Down the road in Lucky’s Lounge there’s a live reggae band and local beers on tap. But one of my favourite bars is Drink Boston. It’s a dark, wood-filled space downstairs, all dangly lightbulbs and edgy customers, and instead of ordering your drinks from a menu, you tell the bartender what you like (mine’s tequila and citrus) and they’ll shake something up just for you.Don’t forget the famous burger. They create 15 a night and once they are gone they are gone. You smell it before you taste it: a double patty cocooned in a freshly made bun that touches your nose when you go in for your first bite. There’s slices of squidgy American cheese, a smear of sauce and a pickle lobbed on top for texture and tang. Think a grown-up Big Mac, but better. It’s a burger that’s good-looking, clever and a little bit cool – just like Boston.
Norwegian Air has launched direct flights to Boston from £159 one way, norwegian.com. Harvard University tours from £8pp, trademarktours.com; Fenway Park tours from £12pp, boston.redsox.mlb.com; Boston Brew tours from £40pp, bostonbrewtours.com; visit BostonUSA.com for more info.