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21st Dec 2019

Boston In Four Days: How To Make The Most Of Your Trip This Winter

Kiara Keane

When you mention Boston, most people immediately think ‘shopping trip’ and while there’s definitely plenty of that on the cards, there’s so much more to be explored.

From the cute streets and cafés of Beacon Hill to the gorgeous nearby New England countryside, you can pack a serious amount into four days in Boston. Here’s our guide to doing it all…

Where to stay: Fairmont Copley Plaza

If you’re really looking to treat yourself this Christmas, I definitely recommend staying at this gorgeous hotel that also comes with an adorable resident dog called Carly Copley.

It’s right in the middle of the historic Back Bay area with its fab shops and also a stone’s throw from sights like the Boston Public Garden and the Freedom Trail. You’re also minutes from the nearest subway station which can get you pretty much anywhere you need to go in no time.

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Day 1

What to do: Skywalk Observatory

What better way to get your bearings of the city than from seeing the whole thing from 50 floors up? Located in the Prudential Center, it’s got some seriously stunning 360-degree views of Boston and the greater Massachusetts area and you can spot all the famous sights like Fenway Park and the Charles River while learning more about the city’s history.

Where to eat: Top of the Hub

While you’re at the Skywalk, make a stop at the Top of the Hub restaurant on the 52nd floor for a lunch that you definitely won’t forget any time soon. Get a table by the window if you can and definitely order the New England lobster roll.

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Where to go: Shopping on Newbury Street

It’s filled with fab shops like Alice and Olivia and Brandy Melville as well as having plenty of designer brands if you’re splashing out.

Afterwards, stop in at the beaut Boston Public Library, take a stroll down the gorgeous Commonwealth Mall (and admire all the houses you wish you could live in) and you’ll end up at one of the prettiest spots in the city, Beacon Hill.

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Where to drink: Cheers

You have to indulge the tourist in you here and visit the Cheers bar on Beacon Street. Now, this is where things get confusing because there are actually two Cheers bars in the city – this one was originally called the Bull and Finch and served as the original inspiration for the TV show.

There’s also a replica Cheers bar in the Faneuil Hall Marketplace which has arguably less history behind it but is almost identical and it’s just as fun (although it doesn’t have the same famous entranceway.)

Day 2

What to do: Freedom Trail Tour

Taking in 16 sights along a 2.5-mile walking tour through the downtown area, it’s a genuinely fun and interesting way to learn all about the city’s history. Starting at Boston Common, it’ll take you to famous landmarks like the Massachusetts State House and the site of the Boston Massacre.

Where to go: More shopping at Faneuil Hall Marketplace and Quincy Market

It’s got all the usual favourites like H&M and Urban Outfitters as well as cute market stalls and restaurants. Quincy Market’s food hall is another spot where you can find some of the city’s best lobster rolls. It’s also one of the most Christmassy parts of the city with its 60-foot tree and will definitely get you in the festive spirit.

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Where to eat: Legal Harborside

Arguably the best seafood restaurant in the city’s Seaport District, it’s got three floors and a year-round rooftop bar with a retractable roof so it’s a lively spot to get your evening started.

Where to drink: MFA First Fridays

Boston’s Museum of Fine Arts holds an event on the first Friday night of every month where you can enjoy the extensive art collection with some delish cocktails and tapas. The stunning courtyard where the drinks are hosted is really something else.

Day 3

What to do: Tour of Fenway Park

Even if, like me, you know next to nothing about baseball, it’s well worth a visit to America’s most loved ballpark which has been in operation since 1912.

It’s off season until February so you might not be able to catch a game depending on when you go, but you’ll learn all about its 100+ year history and see parts of the park you usually wouldn’t.

Where to go: Spend an afternoon exploring Harvard in Cambridge, Massachusetts

I was surprised to find out Harvard is only a 10-minute drive away from downtown Boston, so you can get a taxi there or else it’s a 15-minute to half an hour journey on the subway, depending on what part of the city you’re coming from.

How many Good Will Hunting filming locations can you spot? A lot.

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Where to eat: OAK Long Bar + Kitchen

Located within the Fairmont Copley Plaza, the food here is really phenomenal and it’s also a really popular spot with locals for Friday night drinks.

Side note – this is also a fab spot for brunch and the chocolate hazelnut French toast is seriously out of this world.

Where to drink: Bukowski Tavern

A cool little dive bar that’s got a great beer selection, comfort food and a really fun atmosphere. They really do stick to the basics here so you won’t find any fancy cocktails but that’s part of its charm.

Day 4

What to do: Explore the North End

It’s known as Boston’s Little Italy and is full of winding streets with some of the city’s oldest buildings and great little delis, pastry shops and cafés.

Where to eat: Quattro

With its authentic brick oven shipped all the way over from Naples, the pizza from here is a must and there’s also the famous Regina Pizzeria which has been serving up pizzas since 1926.

And while you’re in the area, you absolutely have to try the cannolis from Mike’s Pastry – it’s a Boston institution.

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Where to go: The Seaport District

One of the more modern areas in the city, it’s got heaps of great cultural attractions like the Institute of Contemporary Art overlooking the harbour, Boston Children’s Museum and the cool pop-up shopping village at The Current.

Where to drink: Scorpion Bar

Also located within the Seaport District, this cool little Mexican cantina and tequila bar has floor to ceiling windows overlooking the area.

It’s a great spot to chill out with a few cocktails, though it does get livelier later in the evenings with DJs til late.

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