*This blog features a press trip in collaboration with United Airlines, TravelUp and the Boston Tourism Board

Dreaming of a USA trip next year? Have I got the best destination for you – here’s my top 22 things to do in Boston, Massachusetts! I had dreamed of seeing the fall foliage in this beautiful city for years, but never did I think I would be ticking Boston USA off the bucket list this year. Now with direct flights from London Heathrow to Boston, it couldn’t be easier to connect with this part of the United States. Whether you’re after a long weekend, or a longer trip, have I got the perfect itinerary for you.

I was invited on a press trip to Boston in November by United Airlines, TravelUp and the Boston Tourism Board. What followed was 5 amazing days of exploring the city and all it had to offer. Now I’ve created this ultimate guide to Boston including the absolute highlights and everything you need to know before you go. [AD]

Like what you read? Check out: My ultimate guide to planning your New York city breaks

Boston Harbor Hotel, things to do in Boston, Massachussets

22 best things to do in Boston

Watch the sunrise from your suite at the Boston Harbour Hotel

Looking for a place to stay in Boston? Look no further than the Boston Harbour Hotel for the ultimate in home-away-from-home comfort and understated luxury. Stay in a suite overlooking Boston Harbour for spectacular views across the water to the airport. You’ll be able to watch as the flights come into land and take off and start their ascent to the skies.

Trust me when I say you’ll want to wake early – as comfy as those beds are – be sure to catch a sunrise from your room. It’s a stunning view of Boston and one that will remain engrained on my memory for years to come. What a magical way to start the morning, sipping your coffee as you watch the sky change from orange to pink to blue as the world outside stirs back to life. Don’t forget to swing by the breakfast buffet for a delicious start to the day and fill up on pancakes, eggs, French toast and bagels. Finally, check out the iconic 60ft archway overlooking the harbour where the American flag flies – a perfect photo opportunity!

Sunrise from the Boston Harbor Hotel

Stroll along the Freedom Trail

The Freedom Trail is considered one of the top things to do in Boston and I wholeheartedly agree! You simply cannot visit the city and not complete at least part of the trail. I highly recommend you take a tour which is available from the Visitors Centre on Boston Common. The guides are super knowledgeable and really paint a picture of the city when it was first built. I remember studying this point in history while at university so it was a really interesting tour to remind me of what I had previously learned and to take that one step further. I really felt like starting the trip with this tour gave me a great welcome to the city, its culture and heritage.

There are so many quirky little stories about characters from Boston’s history and I loved that we got to see so much within just 2.5miles of easy strolling through the city. It’s a great way to get your bearings for “Beantown” and to navigate around 16 major historic sites around the city.

Explore pretty Boston Common

The oldest city park in the entire United States, Boston Common may already be familiar to you from movies such a Good Will Hunting and Ted. It’s the perfect place to spot the fall foliage at it’s finest and while away an afternoon reading a book in the sunshine. This area has a fascinating history which you can learn all about by taking a Freedom Trail tour. It also sits alongside Boston Public Garden, another beautiful area, and pretty Beacon Hill which is another highlight of the city.

Absolutely Lucy at Fenway Park, home of the Boston Red Sox, things to do in Boston USA

Catch a baseball game at Fenway Park

Whether you’re a sports fan or not – nothing quite compares to catching a live match or game when you travel. The atmosphere is electric and it’s a great way to really get into watching live sports. Boston is well-known for the Boston Red Socks for baseball and the Boston Celtics for basketball, so why not get tickets to watch? We went on a tour of Fenway Park stadium which was great if you’re a Red Sox super-fan, but I think if you’re just passing through the city it’s much better to get tickets to a game and see the team in action.

Dine on fresh seafood at Boston’s oldest restaurant

You simply cannot visit the city without stopping at Boston’s oldest restaurant where they serve the freshest and most delicious seafood. Union Oyster House is a great place to try the classic lobster roll, or clam chowder. They’re well known for their oysters which, while an acquired taste, you won’t find fresher. Not a seafood fan? They also serve New England specialties in a historic setting along the Freedom Trail, so it’s a perfect place to stop off for lunch before continuing on your journey through Boston’s history. I loved the lobster roll and the lobster mac & cheese!

Lobster roll at Union Oyster House in Boston

Explore beautiful Beacon Hill in the fall

This was an absolute highlight – prepare for ALL the house envy if you visit Beacon Hill. It’s a stunning part of the city with gorgeous residential homes with pretty door stoops lined with seasonal decorations. A great time to visit is around Halloween when this part of the city really comes to life, but I’ve no doubt the Christmas decorations are just as special. If you’re looking for things to do in Boston, this is definitely one you won’t want to miss. If you don’t have a few hours to spend exploring, speed up the visit by heading straight for Acorn Street which is considered one of the most aesthetic streets. Perfect for getting your Instagram-worthy snaps!

Spot some famous gravestones at the Granary Burying Ground

A bit of a spooky stop but Boston’s third-oldest cemetery, Granary Burying Ground, is hauntingly beautiful and the final resting place of some very well-known characters. It’s a stop along the Freedom Trail on Tremont Street and easily one of the busiest graveyards I have ever seen. Founded in 1660, it’s now home to the likes of Paul Revere and you’ll also find the graves of three signers of the Declaration of Independence: Samuel Adams, John Hancock, and Robert Treat Paine. As we were told rather comedically, there is a pub across the street which is the only place you can drink a cold Sam Adams while looking at a cold Sam Adams! You’ll see the graves of the five victims of the Boston Massacre, an obelisk in commemoration of Benjamin’s Franklin’s parents and even “Mother Goose” who has a very interesting story of her own.

Granary Burying Ground, Boston, USA

Eat a delicious lobster roll and try clam chowder

Two of my fave dishes I tried while visiting Boston. The foodie scene in the city is amazing with lots of fresh seafood, market-style food halls, fine dining experiences and much more. But often the simplest foods done to a high standard are the most memorable. Make sure you try the delicious fresh lobster rolls the city is known for and the tasty clam chowder. You can get these wherever you go and they’ll always be super fresh and yummy!

Tick Boston Time Out Market off your to-do list

After visiting the Time Out Market in Lisbon, I was very excited for this experience so I could compare with Boston Time Out Market. Boston’s has some delicious food on offer – I went for the truffle pasta and speciality garlic bread while lots of the group chose the Philly Cheese Steak sandwiches or sushi. You’ll also find lots of pizza, burgers, fish & chips and much more. It’s a great place to dine out with a group of friends, really informal and a great indoor area so it’s suitable for all weathers. There’s also a bar and lots of dessert options. We visited during the day so it was a bit quieter but I think the best time to visit would be a weekend or evening when it is a bit livelier.

Like what you read? Check out: The 33 best things to do in Lisbon, Portugal

Time Out Market Boston mushroom truffle tagliatelle and speciality garlic bread

Discover Boston’s Black Heritage Trail and Women’s Heritage Trail

For the history-lovers among us – Boston is jam-packed full of walking tours and historic trails to follow. If you’re looking for more things to do in Boston to learn about the fascinating history of the city look no further. Why not book on to a walking tour – our you could take a self-guided tour to learn about Boston’s Black Heritage Trail and Boston’s Women’s Heritage Trail. Again, the guides are really knowledgeable and it’s very interesting to learn more about the underground rail road, the time leading up to the abolishment of slavery and people of note, many of whom’s names you may have heard before. You also get to learn more about the jazz scene in Boston and much more.

Enjoy quirky market-style dining at High Street Place

Another fabulous informal food option and a great place to catch up with the sports as this venue is full of huge screens showing ice hockey, basketball, baseball and more. We loved the vibes with games outside, amazing food options lining the hall inside and lots of bars serving wine, cocktails and speciality beers. After a lot of deliberating, I went for the sushi and lychee sake-tini from the amazing Japanese stall. There were also tacos, sandwiches, pizza, burgers, vegetarian options, mezze platters and much more. High Street Place is a great place to bring a group of friends to gorge yourselves after a long day of exploring all the things to do in Boston.

Boston Chinatown, take a Boston Chinatown Tours

Take a food tour of Boston’s Chinatown

If you ask me, the ONLY way to explore one of America’s largest Chinese neighbourhoods, is by taking a food tour with an expert from the area. We met up with Jacqueline from Boston Chinatown Tours and we loved her knowledge, attention to detail and food recommendations. Visiting Chinatown felt like not only were we stepping into the Chinese quarter, but we were also stepping through the history of this area from formation right up to the present day.

We walked through the community, stopping off to visit eateries and learn about the history of Moon Cakes, boba teas, authentic Hong Kong barbecue and even herbal teas and medicine. We viewed street art with poignant messages, learned more about Chinese culture and stopped off for dim sum to finish. If you love Chinese food and culture, or simply want to explore and learn more – this is a great way to see a different side to Boston.

Visit the Monet collection at the Museum of Fine Art Boston

Did you know that Boston hosts the largest collection of Monet’s work outside of France? Visit the Museum of Fine Art to walk among the greats including works from Impressionist painter Claude Monet, Renoir and Van Gogh, plus exhibitions of Egyptian mummies, art from Ancient Greece and Rome, plus the Chinese Song Dynasty. Check online for the latest exhibitions and additions to the museum, and definitely plan to spend some time there to really get a taste for what the museum has to offer.

The Langham Hotel, The Fed bar with the flaming Gerri Halliwell cocktail

Head to The Langham hotel for a unique spin on cocktails

Have you ever tried a garlic cocktail? Head straight to The Langham Hotel where you’ll get the opportunity to try one while relaxing in the most beautiful setting. Take a seat in The Fed, the hotel’s gorgeous cocktail bar which was giving me all of the speakeasy vibes but mixed in with cosy dishes and snacks.

While the garlic cocktail was definitely an acquired taste and not for me – I was a big fan of the Gerri Halliwell which was tequila-based and gave quite the show as it was made and set alight! Highly recommend the cheese toastie but plan to share the dish with friends because it’s huge. The oysters were also really tasty. Head up the stairs and you can dine in the former Federal Reserve Bank’s grand hall. This gorgeous art-deco style hall is the perfect place to enjoy a meal with friends and feast on Italian family-style dishes.

Take in the grandeur of Boston Public Library

If you’re a bit of a bookworm like me, you’ll definitely want to add the Boston Public Library to your list of things to do in Boston. Just check out my pics and you’ll see why. Think all the Beauty and the Beast vibes! One of New England’s grandest and most historic venues, it’s often used for weddings and events, and you can see why. The architecture will blow you away, but it’s also a great spot to take photos and get a unique shot from the city. I recommend visiting in the early morning when the light would be pouring in the huge windows.

Like what you read? Check out: 10 unmissable libraries for the literary traveller

Boston Public Library

Visit the stunning Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum houses the personal art collection of Isabella Stewart and has a fascinating story behind it. I won’t give anything away now but definitely stop by this museum for a stunning location and skylit courtyard that is definitely Insta-worthy. But also an art collection that spans American, Asian, and European art plus old photographs, sculptures, furniture, and rare books.

Take a Boston Duck Tour

What is a Boston Duck Tour I hear you ask? Well, it’s a great way to spend an afternoon when you’re looking for things to do in Boston. This unique sightseeing tour takes you around the city of Boston and into the water to deliver breathtaking skyline views. With award-winning tour guides all sporting a unique character and personality, you’ll be laughing all the way around Boston. It’s a great way to see the city and to rest your legs after exploring the walking trails.

The Langham Hotel, Boston

Go whale watching from Boston Harbour

Another great tour you can do from Boston Harbour is whale watching! Spot humpbacks, finbacks, minke whales and dolphins from the comfort of a catamaran. It’s a great way to see the city from a different perspective.

Relax in Boston Public Garden

If the weather’s on your side, Boston is a beautiful city with lots of green spaces to relax in. If you’ve already explored Boston Common, why not grab a coffee and head over to its neighbour – Boston Public Garden? It’s a great place to chill and read a book, enjoy the sunshine, you could even take a swan boat out on the water.

Beacon Hill, Boston

Visit the Cheers Bar

Boston is known for the iconic Cheers bar, made famous by the TV show in the 80’s and 90’s. Well you can actually visit the bar and take photos there, for super fans of the show this is one of the must-do things to do in Boston. Just on the edge of Beacon Hill and sitting behind Boston Public Garden/Boston Common, it’s easy to find and well worth a stop.

Stop to shop at Faneuil Hall and Quincy Market

Need to shop for some last minute gifts? Swing by Faneuil Hall and Quincy Market to pick up delicious food, gifts, Boston merch and much more. There’s often live music and performers around this area, plus lots of restaurants and some market stalls so it’s a lively area. It’s also on the Freedom Trail so easy to stop off for a browse before continuing on your way.

Take the Harbour Walk

If you’re still in the mood for a walk after all of these activities, why not check out the Harbour Walk? This 43-mile park along Boston’s shoreline, the Harborwalk connects Boston’s waterfront neighbourhoods to Boston Harbour. A great way to get your steps up while taking in the skyline.

22 best things to do in Boston, USA

Travelling to Boston

When is the best time to visit Boston?

High season in Boston is considered June and July, this is the time to visit if you want to experience the best weather and sunshine. However, I visited Boston at the beginning of November and it was unexpectedly very warm. Although it can be very cold at this time of year, it was actually 24ºC and we were walking around in shorts, skirts and sandals. It was perfect weather for exploring the trails and walking around the city with barely a drop of rain in 5 days. We had the bonus of being there in great weather, but also getting to see the beautiful fall foliage and even some of the leftover Halloween decorations as we walked around Beacon Hill. Boston is truly spectacular in October and November, it’s really special to get to see the beautiful autumn colours as you stroll around the parks and green spaces.

Boston in the fall, fall foliage, autumn colours, Boston colours

How do I get to Boston?

It couldn’t be easier to travel to Boston from the UK right now, United Airlines has just started offering direct flights from London Heathrow to Boston. Their new daily service is available non-stop from Heathrow and makes it super easy to arrive on US soil within a matter of hours. Travel from the UK to the USA within 6-7 hours and enjoy extra space and more comfort in their new United Premium Plus so you arrive feeling well-rested and ready to explore Boston.

Or, why not upgrade to United Polaris Business Class for the best sleep in the sky? Trust me, I can vouch for how comfy those seats are – I managed to sleep through the desserts! Snoozing in luxury bedding from Saks Fifth Avenue, enjoying 96cm of legroom, dining from actual silverware at 3,000 ft while sipping on champagne. It’s an experience I won’t forget thanks to the faultless service and wonderful team who welcomed us onboard.

When you land in Boston, you also have the added bonus of the airport being just minutes from the centre of Boston which makes it super easy to get out exploring straight away. If you’re landing late, you can grab a late dinner at one of the many restaurants nearby. Or why not pop to your hotel for pancakes before you hit the trails?

22 best things to do in Boston, USA

Is 3 days enough for a first-time visit to Boston?

Absolutely! I was in Boston for 4.5 days and it was a wonderful introduction to the city. I’ve heard Boston described as the largest walkable city in the USA and I have to say I agree. It’s designed for visitors to explore on-foot with trails, walks and lots of great parks to explore. There are so many great things to do in Boston, I left feeling like I absolutely have to return one day because I have so much more I want to see there. But, it is definitely possible to get a great taste for Bostonian life in just a few days. Use my list above to pick out the things you want to see and do most and then plan an itinerary that suits you around those activities. Trust me, after one visit you will definitely want to go back in the future.

Flying business class with United Airlines