How To Spend A Weekend In Boston, MA

By Aidan Walsh Last edited 14 months ago

Last Updated 31 March 2023

How To Spend A Weekend In Boston, MA

We've got city break weekend recommendations for everywhere from Liverpool to Lisbon to the Isle of Man. Check out our Beyond London section for jaunts outside the Big Smoke.

Things To Do In Boston.m Rainbow over Boston; view from Boston University dorm.
Boston is home to the youth — colleges and universities dominate its population.

Picture yourself with 48 hours to explore Boston, a city brimming with American history, world-famous sports teams, and delicious dishes, including our famous cannoli.

In early 2023, Norse Atlantic Airways announced it'd be operating new, lower-cost routes between London and US cities, including Boston. The East Coast city also makes for an achievable weekend trip if you're over in New York.

Don't know how to maximize your time in Beantown? I'm a Boston University student who knows the city well — so allow me to be your guide.

Getting to Boston

Direct flights to Boston depart regularly from Heathrow and Gatwick (at time of writing, Norse Atlantic Airways hasn't launched its flights yet). Although as I say, it may be that you're visiting as part of a longer East Coast trip. From New York, you can get a cheapish Greyhound bus to Boston in around 4 hours 20 (that's assuming it runs on time, which they often don't). Train might be a more comfortable experience, though; direct NYC-Boston services clock in between 3 hours 45 and 4 hours 30.

Boston need to know

Some information to lessen your culture shock.

Things To Do In Boston: High rises reflected in the water
Boston is one of the oldest cities in the US, as this image does not particularly demonstrate. Image: iStock/DenisTangneyJr
  • The basics: Boston is the largest and most culturally important city in Massachusetts and the wider New England region, with a population of around 4.8 million in its urban area. It's one of the oldest cities in America, founded in 1630 by Puritan settlers from Boston, England (hence the name). The city stands on the Charles River, which separates Boston from Cambridge (a city in its own right, though considered part of Greater Boston). The region is served by Logan International Airport.
  • Accommodation: You're spoiled for choice. Many of the chain hotels — like the Hilton Boston Downtown/Faneuil Hall, Hyatt Regency Boston, to the upscale Revere Hotel Boston Common — are located in Boston's downtown, so it's all just a step outside your hotel lobby. My personal recommendation is Hotel Revolution, a modern-chic stay, good for those on a budget travelling with friends. It's sort of like a glamorous hostel. Or go down the Airbnb route, in neighbouring towns like Brookline and Cambridge, for a more homey stay.
  • Transportation: Boston is small compared to London. We have one train system — our version of the tube — which we call the T. There's no contactless payment, so you must go to any underground station to purchase a paper ticket. You can get a one-way or round-trip ticket, or purchase from a variety of passes by day, week, or month. Just be aware that in Boston you only need to tap once upon entry, not on your way out. (For more, check out London Underground Vs Boston's MBTA.)
  • Walking: Whatever rumours you've heard about Bostonians are true. We are similar to New Yorkers in our militant walking manner and speed — so watch out during commuter hours, or please pick a lane and commit to it.
  • Colleges and Universities: Boston is home to the youth — colleges and universities dominate its population. No. 1 is Boston University; obviously, with other names like Boston College (utterly different from BU), Harvard and MIT (in Cambridge), Northeastern, Suffolk, Emerson. I could go on. So be warned that along with longtime Bostonians, there are 18-24-year-olds everywhere. I think we bring life to the place!

Day 1

Coffee & bagels in Boston

Things To Do In Boston Houmous bagel from Pavement Coffeehouse, eaten on Newbury Street.
New England bagels are a big thing in America, and the best you'll get in Boston is from Pavement Coffeehouse.

Dunkin' Donuts

Start your day off with a cup of coffee; it won't be hard to pick a spot with Boston's 85 Dunkin' Donuts locations. America does indeed run on Dunkin', and Boston more than most cities. The first Dunkin' shop opened in Quincy, Massachusetts (a southern suburb of Boston) in 1948. In the same way London is home to a million Prets, we have Dunkin' Donuts. This TikTok sums up what you’ll see.

Pavement Cafe

New England bagels are a big thing in America, and the best you'll get in Boston is from Pavement Coffeehouse. Paired with your coffee, you can order a customisable bagel with toppings including bacon, tempeh, and even vegan egg. A must-try.

Tatte Cafe & Bakery

Tatte is a more upscale cafe, and worth the line for the delicious and fresh soups, sandwiches, pastries, and coffee. It was first opened in 2007 by Tzurit Or, selling her creations at the Copley Square farmers market in Boston. It is almost always packed on the weekends, but don't fret; there's a Tatte in every neighbourhood of Boston.

Sports in Boston

Best Things to Do in Boston: View from inside Fenway Park, Boston MA, from a park tour.
Fenway Park, the oldest stadium in Major League Baseball.


The Fenway-Kenmore area is home to baseball's iconic Fenway Park, the oldest stadium in Major League Baseball, drawing huge crowds for Red Sox games every season. In the area surrounding the Green Monster you'll find many restaurants and sports bars, which buzz even when no games are being played. It's worth a walk down, and if not in the season, check if there's a concert or a tour of the field.  If it is baseball season, my tip for last-minute tickets is to head to Boston-based Ace Ticket.


TD Garden in the North End is home to the Boston Celtics basketball and Bruins hockey teams. Something will be happening there on any given day. It hosts over 3.5 million people yearly at its concerts, sporting events and ice shows. I go for the Beanpot each February, where Boston University, Boston College, Northeastern, and Harvard face off in a two-game Hockey tournament (pretending we didn't lose this past year). It's the most intense game; socially speaking, it's mandatory attendance. But, no matter the event, it's worth seeing pretty much anything that happens on TD's ice. Get some canned beer, ice cream, and pretzels from the concession stands inside.

Best Things to Do in Boston: View from inside TD Garden, Boston, MA.
TD Garden hosts over 3.5 million people yearly at its concerts, ice shows, and the Boston Celtics and Bruins.

Museums in Boston

(They aren't free entry... sorry.)

The Museum of Fine Arts

By the Back Bay Fens (a tiny park often called The Fens) is The Museum of Fine Arts — the 20th-largest art museum in the world. It's got 8,161 paintings and more than 450,000 works of art. Great for a rainy day and a glimpse of the surrounding area. But maybe the best part? The giant baby heads outside the back of the gallery.

Isabella Stewart Gardner Museum

Only a short walk over is the Isabella Stewart Gardner Museum, which houses European, Asian, and American art including paintings, sculptures, tapestries, and decorative arts. The building is a palace once owned by Isabella Stewart Gardner, a leading American art collector, who created the Museum in 1899.

In 1990, thieves stole 13 items from the collection, which have never been recovered. The curators decided to leave the empty frames in place, in memory of the lost works — a work of art in itself.

Best Things to Do in Boston: View from inside the Isabella Garden Museum, specifically the interior garden area.
The building is a palace once owned by Isabella Stewart Gardner, a leading American art collector who created the Museum in 1899.

Day 2


Best Things to Do in Boston: The intersection in between the Public Garden and the Boston Commons in Boston, MA.
You must visit Boston Common.

Boston Common & Public Gardens

The must-go-to park in Boston is the Boston Common, the oldest city park in the US. It's much like New York's Central Park, but arguably more charming. I especially adore the cute centre pond, and how it bleeds into the Public Garden, known for its perfectly manicured, domed flower bushes. There's plenty of opportunity to buy Boston merch here, and see the skyline come to life as you walk further down its 50 acres of land, bounded by Tremont Street, Park Street, Beacon Street, Charles Street, and Boylston Street.


The Esplanade is a fantastic walking path along the Charles River, which begins near the Museum of Science and the Boston University (BU) Bridge. Along the way, there are plenty of pockets of green, and good city views. If you walk the whole thing, it's about 4.8 km. Along the way you can peel off from its series of eight pedestrian overpasses.  

More activities in Boston

Best Things to Do in Boston: View of the Charles from the Esplanade path in Boston, MA.
The Esplanade.


Shopping is BIG in Boston. You can't escape it when walking around Newbury Street. The area is known for its 19th-century brownstones, which foster tons of retail and eateries, making it one of the most expensive streets in the world. There are plenty of boutiques such as consignment store Revolve and hip fashion store Riccardi, with chains like Zara, Vince, and Lily Pulitzer. In the warmer months, they shut down Newbury on Sundays and you'll find more pop-up shops selling accessories and merchandise.

Best Things to Do in Boston: View of red brick brownstones in Boston, MA.
Newbury street is known for its 19th-century brownstones.

Head to Cambridge on the Red Line T

For an outstanding view of Boston's skyline — and to explore the other side of the Charles — you can take the Red Line T train heading towards Cambridge as it travels along the Longfellow Bridge. On either side, you can see the city's east and west ends for a few minutes before heading underground. It's even better at night with the town all lit up. Then you're in Cambridge — a whole other article of things to do (although if you have time, it's worth visiting for Harvard Square, replete with restaurants, bars, and shops — and its art museums (free on Sundays!).

Best Things to Do in Boston: View of one of Boston's bridges crossing over the Charles.
For a unique and outstanding view of Boston's skyline, cross one of the city's bridges.

Take pictures at Acorn Street

For a more grounded activity, and to find some quiet in Boston's downtown, head to Acorn Street, which is hidden in Beacon Hill's charming brick brownstone buildings. The area is made up of historic structures dating back to the late 1700s and early 1800s, but this cute little street is the most picturesque place, especially during the fall season, with the spooky decorations and pumpkins.

Best Things to Do in Boston: Acorn Street house front decorated for the Autumn season.
Residential street hidden in Beacon Hill's charming brick brownstone buildings, named Acorn Street.

Take a walking tour

Boston is swimming in history. Many walking tours will show you around Boston, but the Freedom Trail walking tour will satisfy your curiosity if you're a history buff. The 2.5-mile-long path can take you to 16 locations, starting in the Boston Common, through the North End to the Bunker Hill Monument in Charlestown.

New England Aquarium

This is the perfect rainy day activity (Boston gets many). The aquarium, located in the aptly-named Seaport, houses a 12-meter-wide cylindrical ocean tank, home to hundreds of Caribbean reef animals, including sea turtles, eels and fishes. When you reach the top, you can watch all the sea life rise to join you for feeding time. Elsewhere on site, you can see seals, sea lions and, when you first walk in, the oh-so-close-to-touch penguins hanging out in their open exhibit.  

Ice skating (winter) in the Boston Common or Time Out Market Fenway

My absolute favourite activity is ice skating. I'm not alone. It's a big Boston thing, even if most of us fall over a lot. In Fenway, Time Out Market turns its grass field into an ice rink (the Rink at 401 Park Drive) with rentable skates and blue plastic whales, intended for kids to sit on and be pushed. However, it seems socially acceptable for grown-ups to play about with the whales too. After falling a few times, you're just a few steps from the Time Out Market for grub or Trillium bar for a drink. Alternatively, check out the rink at the Boston Common. This is more expensive, but worth it for the stunning backdrop of Boston's downtown.

Kayaking on the Charles (summer)

During the warmer months, the Charles River comes alive, and if you don't happen to have access to a luxury sailboat, kayaking is another popular pastime. You can also learn to sail, canoe, or paddleboard down the river, adjacent to the Esplanade walking path. You'll get a different view of historic Back Bay, Beacon Hill, and the overarching bridges.

Best Things to Do in Boston: Sailboats on the Charles River in Boston, MA.
In the summer, go kayaking in the Charles.

Enjoy a rooftop bar

Boston has a beautiful skyline... and one that's best enjoyed with a drink! There are plenty of rooftop bars in Boston, but one of the best is Contessa, a part of the Newbury hotel. This low-ceiling indoor/outdoor bar looks out over the north of Boston and the Boston Common. Close by, the Rooftop @ Revere does the trick, with plenty of lounge space, good cocktails and 360-degree views. Lookout Rooftop and Bar, part of the Envoy Hotel, is located in the Seaport area with stunning views of high-rises and the harbour. This one's my favourite, as it has plastic globes available to rent, so you can enjoy the scenery and stay warm.

Eating in Boston

You're spoiled for choice in Boston, so here comes a rapid fire list of restaurants in the best areas of the city...

Best Things to Do in Boston: Spaghetti from Michael Schlow's Italian Kitchen
in Time Out Market, in Boston, MA.
Enjoy the Time Out Market food hall.


  • Yard House: Sports bar with a vast menu of American food and draft beers. Always lots of action, with TVs playing whatever sports hysteria is on.
  • Sweet Cheeks Q: Superb Southern food served on BBQ trays.
  • Time Out Fenway/Trillium: Pizza, burgers, Udon noodles, BBQ sandwiches, doughnuts, and gelato are just a few of the foods you'll find in this cavernous hall. PLUS its outdoor-indoor Trillium bar is only a few steps away.

Downtown/Boylston Street

  • Yamato 2: Top-notch sushi, with an all-you-can-eat deal.
  • The Bepop: Restaurant with frequent live jazz music, an Irish pub menu, and weekly trivia nights.
  • Prudential Center: A massive mall with shopping, but my favourite Italian restaurant is Eataly. Just like its London sibling in Bishopsgate, the Boston version combines a sit-down restaurant with a fresh food market. Tucked away upstairs is Terra (imagine London's Sky Garden, but smaller), with beautiful greenery above its seating area, known for its herb-infused cocktails, beer and wine.

Back Bay/Newbury Street

  • Greco: Great-tasting Greek food, specialising in gyros with your choice of fillings and sauces.
  • Trident Cafe: Half cafe, half bookstore, the perfect place to stop for a meal after walking along Newbury Street's shopping frenzy. You can pretty much spend half a day there, caught up in the books and trinkets stalls.
  • Crazy Good Kitchen: Known for its multi-stacked burgers, impossible to bite down on, and insanely sweet, candy-decorated milkshakes. It's easy to over-do things!

North End

  • Trattoria Il Panino: The whole area of the North End feels like a Little Italy, but this is the best restaurant I've eaten from. It dishes up traditional Italian food, and is known for homemade pasta served in the saucepan it was cooked in. Intimate seating upstairs and downstairs; you really do get a taste of Italy.
  • Mike's Pastries: The most popular cannoli place in Boston; always has a massive line out the door on the weekends. Try different flavoured cannolis like pumpkin spice, Oreo, chocolate chip, etc. My pro tip is ordering online with GrubHub to beat the wait in line.
  • Regina's Pizzeria: Boston's most famous, oldest pizza place. People love its thin-crust, brick-oven pizzas in a no-frills setting.

All images by Aidan Walsh unless otherwise stated.