Hello and welcome to Boston! Despite what you may have heard from movies starring Matt Damon, Boston isn’t all cold weather, tough guys, and people pronouncing words weirdly.
Boston is one of the most interesting cities in the USA. It’s stuffed full of fascinating history, cutting edge science, and wonderful architecture. One of the capitals of innovation in the country, the Boston area is home to almost 60 universities and colleges, and takes great pride in being the de facto intellectual capital. And like the rest of the world, we are sports nuts – Boston’s teams can lay claim to the most professional titles in the country!
But it’s not just brains and brawn here, Boston knows how to have fun too. It’s one of the most socially liberal cities in the United States, the food and drink scene is world class, and our landmarks are a bit quirky.
It’s also incredibly walkable, so grab your shoes and let’s hit the road for a 48 hour tour of what we locals get up to in The Hub.
Day 1: 09:00 – 14:00
If you must hit Faneuil Hall and Quincy Market, make your visit brief, and head to the Boston Public Market further down Congress Street for a true taste of local produce in a market setting. While at Quincy Market you’ll find a glorified, expensive, and overcrowded mall food court, the Public Market is Boston’s answer to Seattle’s Pike Place Market; a haven of local foods and vendors sourced from an average of 30.56 miles from the market, and the easiest way to sample some of the best of Boston’s independent companies, like Taza Chocolate, Union Square Donuts, and Red’s Best fishmongers.
But don’t get too full.
Continue on to the North End, but counterintuitively, you’re not here for Italian. Wander past all the Italian spots that line Hanover Street to Tenoch for the best torta — a Mexican sandwich of telera bread, Oaxaca cheese, marinated meats, and crunchy veggies — you’ll find in New England. Spotter Lia says to pair your new sandwich obsession with a stroll around Boston’s waterfront, and take in some views of Boston Harbor.
Now you’re suitably full, begin to walk off some of that meal with some sightseeing. On Saturdays, the Marriott Hotel which owns the Custom House Tower allows people to go up to the top of the building for a tiny fee, and you can see views of the brick red North End from above few Bostonians have even discovered. A family of Peregrine Falcons frequently nests at the top, Spotter Lia says, so you can people — and bird — watch at the same time! Call ahead to check open times.
Day 1: 14:00 – 19:00
No trip to Boston would be quite complete without visiting the city’s younger, hipper neighbour, Cambridge. You can see it from afar at the magnificent Charles River dock, where Bostonians love to sit and relax on warm evenings. There are other ways to reach Cambridge than swimming though. Whether you choose to take the T — Boston’s subway system — a car, or walk across one of the several bridges spanning the Charles, there is plenty of stuff to do once you get there.
Begin in Central Square, and check out the ever-changing art gallery that is Graffiti Alley. The rainbow-canopied alleyway is covered on both sides with spray paint and al fresco artwork, and wonderful light as it filters through the multicoloured glass above. The layers of paint on the walls are constantly being added to, so the experience is different every day.
You’ve travelled across a river, which is a long way! If you feel like rewarding yourself with a small sweet snack while you’re in the area, Toscanini’s is Spotter Lloyd’s favourite local ice cream place. The micro sundaes are the perfect quality treat for an afternoon (or morning, we won’t judge) pick me up, and for your wallet.
Head deeper into Cambridge to get to Harvard Square, where you can follow the legions of tourists around the prestigious college grounds and book store, or do as Spotter Zac does, and head to Black Ink to pick up some curious gifts and knick knacks you didn’t know you needed until you had them in your hands. Zac also suggests heading further into Cambridge to get to Mount Auburn Cemetery, where stunning gravestones are just part of the appeal. The cemetery is a National Historic Landmark, and reaching the summit of Mount Auburn makes for a stunning fall walk, with amazing skyline views of downtown Boston visible in the distance.
Day 1: 19:00 – ???
Time for dinner. Work your way back into Cambridge to finish the night at Alden and Harlow, a veggie-heavy favourite of Spotter Abigail. But get there early to snag one of the (not-so) secret burgers! Just across the square, Park makes for an excellent backup, and the cocktails are so good you’ll forget it wasn’t your first choice. And if you’re still raring to go after dinner, make your way back down the Red Line to Kendall Square, to sample some of the best beers the area has to offer at Cambridge Brewing Company. Sample until you sleep.
Day 2: 09:00 – 14:00
Boston is one of the United States’ most historical cities, and we have some world class museums which are worth spending some time in, even on just a short visit to the city. But begin your day with a refuel at Mike and Patty’s, a tiny grab-and-go breakfast sandwich spot where eggs, cheese, and bread are turned into an art form. Boston’s smallest neighbourhood, Bay Village is a fascinating stroll to help digest those splendid sammies.
From there, make your way westward, toward the Prudential Center — if you’re not sure of the directions, just look upward! — where you can shop, or pop outside to check out the stunning Christian Science Center Reflecting Pool, an enormous rectangular plaza with a stunning shallow pool at the center, and a giant fountain which shoots out of the ground — a summer favourite for kids looking to cool off. Spotter Kristian says remember to bring your camera. You’ll want it!
Almost equally impressive are the wedding cakes in the window of Oakleaf Cakes, a bakery and cafe just across the street from the bottom of the plaza. The cafe’s spicy hot chocolate with a homemade marshmallow is one of the city’s redeeming features in winter. A ten minute walk away is the Museum of Fine Arts, an outstanding institute of both contemporary and ancient art.
If you fancy a slightly more unique experience, just around the corner is the Isabella Stewart Gardner Museum, the hidden gem of Boston’s Emerald Necklace. The museum is worth a visit for the insanely well curated courtyard garden built right into the Fenway soil, at the center of the Venetian-style building that Ms Isabella Stewart Gardner used to call home, and decorated with hundreds of decadent works of art from around the globe. Admission is even free for those wearing Red Sox gear, or named Isabella!
Day 2: 14:00 – 16:00
Speaking of Red Sox, no trip to Boston would be complete without checking out the giant green sporting monument that is Fenway Park. A short journey across the Fens will lead you right to the stadium, and into the heart of one of Boston’s most rapidly changing neighbourhoods. No longer just a runoff zone for fans and student housing, some of the city’s best restauranteurs are opening eateries here, including Sweet Cheeks Q, the best barbecue in the city, a fast-casual greek spot called Saloniki, and Mei Mei, an innovative, casual Chinese-American sit down spot that sources all the ingredients for its fantastic dishes as locally as possible. You’ve definitely earned a spot of lunch, and some stunning options on offer.
Day 2: 16:00 – 20:00
Finish your tour of Boston’s historical elements by catching an Uber or jumping on the Green Line to the Arlington stop, and head to Beacon Hill. The easiest way to get there just happens to be through the Public Garden, Boston Common’s prettier neighbour. There are photo ops abound in the country’s first public botanical garden, and after a stroll through, you’ll be perfectly set to spend some time exploring Boston’s prettiest neighbourhood, Beacon Hill.
Once your legs are tired of ascending the hill in search of the perfect picturesque doorway to Instagram — hint, you’ll probably find it on Acorn Street — make your way back down to Charles Street. By day, The Paramount Cafe is one of the city’s most bustling brunch institutions, boasting a line to the service counter that can take almost an hour to finish, and a bizarre, but effective, method of seating people only once they’ve received their grub. However, at night, it transforms into a lovely neighbourhood restaurant, serving a broad menu of high quality, crowd pleasing dishes for reasonable prices. And best of all, the wait time is non-existent compared to brunchtime.
Day 2: 20:00 – ???
Head into the rapidly gentrifying Downtown Crossing, where you’ll find one of the best bars in the city. It’s hidden behind a blow dry bar, but Yvonne’s is a glitzy, glamorous speakeasy with an inventive craft drink menu, creative modern artwork adorning the walls, and classy bar snacks like stone fired pitas.
Whether you spend the rest of your last few hours swigging drinks under the chandeliers or fancy an adventure, you’re in the heart of downtown, and the night awaits.