Do it all in Boston

By Eloise Barker

Photography by Sean Pavone Photo / Getty Images

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July 2017

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.

A bit of an institution

Boston is full of monuments to the American revolution. Imagine the scene when Paul Revere fled the town and rode through the night to pass the message down the line: “the British are coming”. If you’re a Brit abroad, the tale incites… mixed feelings. But to engage with Boston you need to hear its revolutionary stories. The Freedom Trail tells the city’s story on a 2.5-mile-long walking route.

Pass by stout Trinity church flanked by glassy-eyed skyscrapers and Boston library, with its bottle-green lampshades within and tranquil leafy courtyard outside. Stretch out the trail with trips down photogenic alleyways and picnics on Boston Common.

For history in the making, America’s oldest city is right next to Harvard University, where students stoop from lofty lectures to take you on walking tours. Enjoy the campuses and hallowed halls whilst you listen to cheering dropouts-done-good stories designed to make visitors feel better.

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

Book the Boston Old Town Trolley - 2 Day ticket

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

Waterside wanderings

Bostonians live on the water. Start your trip by taking the ferry from the airport to the centre. White sailboats are strung out across the waterways of the Mystic and Charles river as sailing fanatics ply the waves. To go out to sea and return intact, take a whale-watching cruise or simply stand on the bank and enjoy the vying rowing boats from Harvard striking out on the Charles river.

The United States’ first ever public park is also one of the 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.

Stay at: Taj Boston – looking out over Boston Common, the Taj is a grand dame of the Boston hotel scene. Live like old money and enjoy afternoon tea in The French Room.

Book a whale watching cruise

  • 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.

Cha and chowder

Boston is known for its seafood, whether you’re hankering for a warm chowder or ice-cold oysters from a seafront bar. For lunch by the slice, Little Italy serves traditional Italian American food with flair. Take a seat and try to blend in with family life played out in very local eateries. Try Pizzeria Regina, often voted top of the pizza pie places in town. Chinatown brings Asian flavours to Boston’s South End – sample Dim Sum from the trolley at China Pearl.

Tourists flock to the communal tables of Faneuil hall for street food in a historic setting, or you can hunker down with a hot dog in the stands on game day at Fenway Park, where Bostonians take baseball very seriously. In the afternoon, instead of the Tea Party museum, go for a real high tea in Boston Library’s courtyard restaurant.

Stay at: The Godfrey –  this luxury boutique hotel sets its rooms within striking architecture and has had a recent restaurant update on its ground floor.

Book an Autumnal Cape excursion

  • 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.

    Discover the coast
  • 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.

    Spend 48 hours in Boston
  • 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.

    Book flights to Boston

Nights on the town

On a night out, start with sunset as seen from Top of the Hub, on the 52nd floor of the Prudential Tower. Join the crowds in the bar from Cheers, where you can order your first Samuel Adams. Then you can stumble in and out of Irish bars with the best of them 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.

Stay at: Aloft Boston Seaport has the best new places for a night away from the tourist trail. Head to Drink, where there’s no menu, so you better know your Boston Sidecar from your Boston Cooler.

Book a Cape Cod excursion from Boston

  • 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.

Bag a bargain

Cheaper than New York, 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.

Supplying the university town, you can find plenty of bookstores with stacked shelves and peeling piles of paperbacks. Head to Brattle Book Shop, where the owner wheels out the shelves into the street every day. In the vast warehouses of Seaport, you’ll find fashion-forward boutiques, where the Institute of Contemporary Art has a great gallery shop. 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.

Stay at: InterContinental Boston sits on the very spot where the Boston Tea Party took place. It’s striking, modern and right on the waterfront.

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