The best things to do in Boston

By Eloise Barker

Photography by Sean Pavone Photo / Getty Images

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Updated January 2019

Boston is a city of neighbourhoods and exploring them on foot is easy-breezy. So, go for marathons and tea parties, chowder and Red Sox. Boston’s spirit is more than a feeling, it’s a way of life.

Walk the Freedom Trail

Boston is full of monuments to the American revolution – and the Freedom Trail takes in many of them. This easy 2.5-mile-long walking route is one of the city’s must-do activities, stopping at Paul Revere’s house and Old Ironsides, Boston’s famous navy frigate. The trail is easy to pick up and deviate from at your leisure; so if you see a photogenic alleyway that you simply have to explore, you can always slip down it to investigate, and re-join the path later. The Freedom Trail finishes up at the Bunker Hill Monument, a granite obelisk surrounded by parkland in Charlestown.

Get into Harvard University

Boston is right next to Harvard University, which is across the Charles River in the city of Cambridge. Rightly famous as one of the most prestigious universities in the world, Harvard makes a great day out, since you can see both the campus and several interesting science and art museums during your visit. There are walking tours run by students which you can join to enjoy the campuses and hallowed halls; and count up how many Nobel prizes and Olympic medals the former alumni share between them.

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Hunker down with a hot dog in the stands on game day at Fenway Park, where Bostonians take baseball very seriously.

Explore Boston Common and Beacon Hill

The United States’ first ever public park is also one of its most beautiful. Boston Common has instantly recognisable features – swan-shaped pedalos wheel across the frog pond and statues stand in the dappled shade. If you stray out of the park, you’ll find Beacon Hill, one of the most photogenic areas of the city. The narrow, cobbled streets are lit by glowing gas lamps and the wealthy homeowners put up with photographers crouching under their wrought iron fire escapes all year around.

Head to Fenway Park

Bostonians take baseball very seriously. Hunker down with a hotdog in the stands on game day at Fenway Park, and see if you don’t catch the baseball bug. The Boston Red Sox have played in ‘America’s most beloved ball park’ since 1912. If you can’t get a ticket to a game, you can always book a tour, where the tour guide will explain exactly why fans call the stadium the ‘green monster’ (hint: it’s a large green wall on the side of the stadium, that stops right-handed hitters ‘knocking it out of the park’).

Stop in Faneuil Hall

Tourists flock to the communal tables of Faneuil Hall for street food in a historic setting. Built in 1742, the building and its accompanying square is a bit of a Boston hub, much like Covent Garden in London, or Pike Place Market in Seattle. Tourists and locals drop in for a snack or stay for an afternoon browsing the shops. People meet to shop, dine, and be stopped in their tracks by the antics of charismatic street performers. Grab a crawfish bun – or check out the Magnolia Bakery – the famous New York chain opened a Boston outpost here in 2018.

  • Boston sailboats on the Charles River, at The Esplanade in Massachusetts. © LUNAMARINA.

    Sailing city

    Keen sailors flock to Boston’s waterways. Working the winches not for you? Head to the lagoon on Boston Common instead for a steadier voyage on a swan boat.£594 pp

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Enjoy Boston’s culinary scene

Boston is known for its seafood – whether you’re hankering for a warm chowder or ice-cold oysters from a seafront bar, you’ll have your pick of fish dishes here. If you prefer your lunch ‘by the slice’, then head to Boston’s Little Italy quarter, where you’ll find traditional Italian-American food served in local eateries. Choose a family-run restaurant and you may well be treated to a whole pantomime of family life whilst you’re eating. Try Pizzeria Regina, which is often voted top of the pizza pie places in town. If you’d prefer Asian food, head to Chinatown in Boston’s South End and sample Dim Sum from the trolley at China Pearl.

  • Razor clams; Boston Massachusetts USA. © Design Pics Inc / Alamy Stock Photo.

    Open for dinner

    Boston’s seafood is stunning. And you don’t just have to have your clams in a chowder. Razor clams resemble squid in taste, but their distinctive shape makes for a showstopper plate.

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  • Cheers Pub and Restaurant, Beacon Street © Melvyn Longhurst / Alamy Stock Photo.

    Make like Frasier

    And visit Cheers – the actual setting for the American sitcom, which ran for eleven seasons. New York doesn’t even have a real Central Perk. In the Cheers bar you can order a touristy t-shirt, a drink or a full sit-down meal.

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  • Brattle Book Shop, Boston. © Letterbox Digital / Alamy Stock Photo.

    Well read

    Pick up a copy of The Bostonians by Henry James, or Infinite Jest by David Foster Wallace – both have scenes set in Boston. Clocking in at over half a million words, Infinite Jest will take up more suitcase space.

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Prepare for the Boston nightlife

Top of the Hub, on the 52nd floor of the Prudential Tower, is a great place to start a night out, as you can watch the sun go down from the panoramic windows. Otherwise, join the crowds in the bar from Cheers, where you can order your first Samuel Adams of the night. Then you can stumble in and out of Irish bars all across the city. Gimmicky speakeasies crop up in every capital, whether the city ever banned booze or not; but in Boston, backbar comes close to the real thing. Try a gin gimlet in this hidden space off Union Square.

  • Institute of Contemporary Art (ICA) by Diller Scofidio + Renfro architects © age fotostock / Alamy Stock Photo.

    Clean lines

    Sit on the decking of the ICA and enjoy the façade of the first art museum to be built in Boston for 100 years. £594 pp

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Take advantage of tax-free shopping

The tax-free shopping on low and mid-price clothing in Boston makes it more than a little bit tempting to hit Downtown Crossing and get lost in Macy’s. Bargain hunters head to Filene’s Basement, a Boston institution with plummeting prices. Elsewhere, in the vast warehouses of Seaport, you’ll find fashion-forward boutiques and the great gallery shop at the Institute of Contemporary Art. In upmarket Copley Place Mall, seek out Neiman Marcus for all your designer needs in one department store, whilst Back Bay has plenty of boutiques. Unsurprisingly, considering the nearby universities, you can also find plenty of bookstores in town. Head to Brattle Book Shop, where the owner wheels out the shelves into the street every day.

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Museum of Fine Arts

With close to half a million items in its collections, The Museum of Fine Arts in Boston has something for everyone – it’s got plenty of beautiful works on canvas – from Impressionist landscapes to pieces by Georgia O’Keeffe, Frida Kahlo and Botticelli. Then there’s the impressive Neoclassical building, the fashion exhibitions, the Egyptian artefacts and the Japanese garden, too. Don’t miss Man at His Bath by Gustave Caillebotte – the gallery sold eight paintings – including a Monet and a Gauguin, just to get their hands on it. The Museum of Fine Arts is open seven days a week and carries an admissions charge.

Boston Harbour

You’ll find some of Boston’s best attractions clustered on the waterfront in Boston Harbour. The tall masts of the USS Constitution are easily spotted as you walk along the edge of the water, as is the jutting architecture of the Institute of Contemporary Art. Walk down Fort Point Channel and you’ll find the floating Boston Tea Party Museum, where the famous ‘no taxation without representation’ demonstration saw chests of tea dumped in the harbour water to protest the British. Celebrate Boston’s maritime history, get some bracing sea air, and, if it’s a nice day, enjoy strolling with an ice cream between the sights.

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Where to stay:

Omni Parker House

Omni Parker House is an historic hotel on the Freedom Trail, which opened in 1855. Order the Boston Cream Pie while you’re here – a custardy, chocolatey cake for which the hotel bar is famous.

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The Godfrey

The Godfrey – this luxury boutique hotel sets its rooms within striking architecture in Downtown Boston, five minutes from Boston Common. The hotel’s Peruvian-Japanese restaurant serves sushi and cocktails.

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Studio Allston

Find bright, good-value rooms in a trendy setting in the Allston neighbourhood, near Harvard University. You’ll make friends playing ping pong in the lobby.

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