Boston, in Massachusetts, is a fantastic city – full of history, incredible architecture, beautiful art and great restaurants. We’ve been to Boston twice and, for us, 5 days was plenty of time to explore the city. What I love about Boston is that it’s a very walkable city but it also has a metro (The MBTA or ‘The T’ as it’s affectionately known) if you’d prefer to travel that way.
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Where to stay in Boston
Boston is a city of neighbourhoods. The most central areas to stay are Beacon Hill, Back Bay, Downtown and the Waterfront.
On our first visit to Boston in 2017, we stayed at The Taj, which is now The Newbury. It’s located in Back Bay just across the road from Boston Common and on the corner of the very popular Newbury street, which is packed full of shops and restaurants.

On our second visit in 2024, we stayed at The Whitney Hotel on Charles Street, which is in the Beacon Hill area. I loved this area as Charles Street is so pretty and has lots of independent shops, restaurants and plenty of places to get a coffee.
Both hotels are ideally located to explore Boston by foot or via ‘The T’. They are also both close to the airport at an under 20 minute drive, depending on traffic.
Top things to do in Boston
We’ve only been to Boston in Winter so some of these activities, like ice-skating in Boston Common Frog Pond, are seasonal. That’s why I’ve also not included some popular activities, like doing a boat tour or visiting the Harbour Islands, because they don’t run in Winter. However, the majority of the top things to do in Boston that I’ve listed below you can do all year round.
Visit the Boston Public Library
You absolutely cannot visit Boston without visiting the magnificent Boston Public Library in Copley Square. Founded in 1848, it was the first large, free municipal library in the United States. Today it has 25 neighbourhood branches, serving around 4 million visitors a year.
The McKim Building’s staircase hall is pretty breathtaking with its yellow Siena marble and pair of lions which lie on marble plinths. Apparently you should rub the lions’ tails for luck. The artwork along the staircase is simply stunning too. It feels like you’re in an art gallery, rather than a library!

At the top of the staircase you will find the beautiful Bates Reading Room. You are allowed to enter and walk around, as long as you are quiet and respectful as people are studying, reading or working.

And don’t forget to go outside to see the courtyard. It’s absolutely gorgeous! And there’s a Courtyard Tea Room if you fancy an afternoon tea.

Here’s a quick mini tour of the Boston Public Library on my YouTube channel. It’s hands down the best public library I’ve been to and if I lived in Boston, I’d be a regular visitor!
Explore Beacon Hill, Boston’s prettiest neighbourhood
Beacon Hill is an historic Boston neighbourhood and the prettiest – in my opinion! The architecture is simply stunning and many of the streets are cobbled, with 19th century gas lamps. During Christmas it is so pretty as many houses go all out with their decorations and even the gas lamps are decorated with red bows and wreaths.

Beacon Hill is also where the Massachusetts State House, with its iconic gold dome, is located. It was designed by Charles Bulfinch and completed in 1798. It serves as the state capitol and the seat of government for the Commonwealth of Massachusetts. There are free tours daily from 10 am to 3:30 pm.

Just down the road from the Massachusetts State House is the Cheers Bar, from the TV sitcom Cheers. Previously the Bull & Finch, this Boston pub became the inspiration for the hit TV show and fans flock to sit at the bar as it’s now a restaurant. I grew up watching this show so I loved seeing it in real life!

Get your art fix at the Isabella Stewart Gardner Museum
The first time we visited Boston we had no idea about the Isabella Stewart Gardner Museum. It was only when we watched ‘This is a Robbery: The World’s Biggest Art Heist’ on Netflix a few years later, that documented the robbery of a number of famous artworks in 1990 (that have still not been recovered) that we realised what we’d missed out on! Thankfully we got to visit the second time round.
The Isabella Stewart Gardner Museum opened in 1903 and was inspired by Isabella’s travels and her love of art. It is like no museum I’ve ever been to. It is SPECTACULAR!

There are no labels on any of the artworks, rather it is designed like a home with art, tapestries and sculptures on display. There are QR codes that you can use to read more about the art in a particular room, there are audio guides, the leaflet highlights certain artwork on each floor and there are also staff who you can ask questions to. There are also a few portraits of Isabella herself (one is pictured below) around the museum.

The museum is extremely popular so it’s highly recommended that you purchase tickets in advance on their website. If you’re with young people aged 17 and under, they get to visit for free. Every first Thursday of the month, after 3 pm, it’s free to visit. And if your name is ‘Isabella’ you get to visit for free on any day at any time!
Eat pasta or have a coffee in Little Italy
If a city has a Chinatown or a Little Italy, we always have to go and check it out – not least because my husband is Italian. Little Italy in Boston is very cool and authentic – in that there are born and bred Italians who live and work there. We found a coffee shop, called Dolce, where all the staff are Italian and there were lots of Italian customers who are clearly local as they all knew each other. My husband felt right at home! In fact, my husband said he thought Boston’s Little Italy was way better than New York’s Little Italy (although we still love NYC’s Little Italy). And the coffee was great!

You can easily spend half a day exploring Little Italy as it’s home to Paul Revere’s House and the Old North Church, which was established in 1723 and is a national historic landmark. It was apparently the first stop on Paul Revere’s ‘midnight ride’ where he gave instructions for two lanterns to be hung in the steeple.

Just a two minute walk from the Old North Church is Copps Hill Burying Ground, which is part of the Freedom Trail. It dates back to 1659 and there are people buried here who participated in the Boston Tea Party. Their graves are marked with special commemorative plaques.

And of course you can’t not eat in Little Italy if you’re visiting. There are lots of restaurants and pizzerias to choose from where you can sit down or you can grab a sandwich or a slice and eat in one of the parks. We had lunch at Ciao Roma, which is a Roman-inspired Italian restaurant. It’s right near Paul Revere’s House and had good food and great service.

Go to a Boston Celtics game
We went to a Boston Celtics game at TD Garden on the afternoon of New Year’s Eve and it was a ‘kids day’ game so there were lots of families attending. Basketball isn’t really my thing and I honestly thought I’d be quite bored but it was SO much fun!

There was a lot of entertainment before and in-between the quarters, such as dancing and mascots shooting hoops and doing tricks. When we went, the Boston Celtics were playing the Toronto Raptors and they annihilated them! I was super impressed with how everything was so efficient and organised – getting in and out the stadium was super quick. There were also loads of places to get food and drink – although it was expensive! We paid $10 for a box of popcorn. If you’re going to book tickets to see a game, I recommend using Ticketmaster.
Walk the Freedom Trail
The Freedom Trail is a 2.5 mile-long walk through Boston, which passes by 16 locations that have historical significance and covers 250 years of history. Some of the locations include the Paul Revere House in North End, the Bunker Hill Monument, Massachusetts State House, Old South Meeting House and The Old State House (pictured below). Print off a map on their website or book a guided tour to explore Boston’s history.

Go inside Paul Revere’s house
Whether you’re doing the whole Freedom Trail or not, I’d still recommend visiting Paul Revere’s House, which is a national historic landmark. The house was built in 1680 and Paul Revere’s family lived there in 1770 (parts of the house has been restored since). It’s located in Little Italy in North End so you can easily visit if you’re in the area. It doesn’t take that long to visit as you only have access to a few rooms of the house. We probably only spent around 20 minutes maximum. It cost (at the time we visited) $6 per adult.
You’re not allowed to take any photos inside the house as some of the furniture is on loan and they don’t have image rights, but you can take photos of the outside as well as the visitor centre. There are a couple of staff inside the house who you can ask questions to and there’s also some information to read on panels.

Have a meal in Chinatown
Boston’s Chinatown overlaps with the Theatre and Leather district. It’s fairly small but very characteristic. The official entrance, The China Trade Gate, was gifted to the city by the Taiwanese government in 1982. I wouldn’t say there’s a lot to do in this area but having a meal here is a must!

The first time we visited Boston we had lunch at Hei La Moon and it made me feel like I was in China as many of the staff barely spoke English and it was packed with Chinese locals. There were carts of food, such as dumplings and chicken feet, being wheeled around, making us feel like we were in a lively market. It was a very interesting experience!
On our second visit to the city, we had lunch at Taiwan Cafe. It’s been around for about 30 years and is one of the top rated restaurants in Chinatown. The restaurant is fairly basic – they don’t serve wine or bottled water, for example, but the food was great and the service was friendly.

Visit Harvard University
As one of the most prestigious universities in the world, you cannot go to Boston and not visit Harvard University! Located in the pretty neighbourhood of Cambridge, a visit to Harvard is a must. The first time we visited it was covered in snow and so picturesque. We just walked around ourselves but you can do a student-guided walking tour if you’d like to learn more about the university and its history.

Cambridge is such a lovely area and you can easily spend a day or half a day here, exploring the university and wandering around the shops. Explore Harvard Square and the side streets and pay a visit to Harvard Bookstore, which is the oldest poetry bookstore in America. Apparently T.S Eliot, EE Cummings and more famous names have passed through these doors.

There are also lots of restaurants and cafes to get coffee or lunch. If you fancy a burger, head to Mr Bartley’s Burger Cottage which is a Cambridge institution. Family run since 1960, it’s served famous guests such as Johnny Cash, Jackie O, and Al Pacino. It’s also been voted one of the best burgers in Boston.
To get to Harvard University, take the Red Line on the MBTA in the direction of Alewife and get off at the Harvard Stop. The university is about a 2 minute walk from the station.
Go ice-skating in Boston Common
During the Winter season, you can go ice-skating at the Boston Common Frog Pond. The ice-rink normally opens from mid-November until March but check their website before your visit. It’s a fun activity for the whole family! Adult skate hire is $15 and $10 for children (at the time of writing this blog post). You can also skate for as long as you like, as long as you don’t leave the gates.

Visit the USS Constitution and Bunker Hill Monument
Although the USS Constitution and Bunker Hill Monument are both included in the Freedom Trail, I’ve added them here in case you decide not to do the whole Freedom Trail but still want to see some of the historical landmarks. I’ve included them together because they are about a 10 minute walk apart, so easy to combine. They are also just about a 20 to 25 minute walk from Little Italy.
Located in Charlestown Navy Yard, the USS Constitution is the oldest commissioned warship that’s still afloat. She was launched in 1797 and earned her nickname, ‘Old Ironsides’, during 1812 when she fought in the war against Britain’s HMS Guerriere. You can go onboard on Wednesdays through to Sundays from 10 am to 4 pm and tours are on a first-come-first-served basis. It’s free to visit but you must bring ID with you.

Just a short 10 minute walk from the USS Constitution is Bunker Hill Monument, which marks the spot where the Battle of Bunker Hill took place on 17 June 1775. It was the first big battle of the Revolutionary War and although the British technically won, it proved that Colonial forces could fight effectively against the British.
Bunker Hill Monument is located in Charlestown, which is an historic waterside neighbourhood with Irish-American roots. Apparently it’s Boston’s oldest neighbourhood and the architecture reflects that with its brick townhouses and colourful clapboard homes. It’s definitely worth a visit.

So those are my top things to do in Boston. I hope it’s helped if you’re planning a visit to this great city!
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