A beautiful Boston, MA, itinerary for 2 days of fun and food

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Here are my personal recommendations for a 2 days in Boston itinerary if you’re spending a weekend or a couple of days in the city. Boston is the capital of Massachusetts in the New England region of the USA. It’s known for its tea-party history, the sitcom Cheers, its love of sports, and fresh local seafood. Clam chowder and lobster rolls are local delicacies that draw in foodies from around the world, but the city also prides itself on Italian food and has plenty of vegan places to eat too. The best thing about the city for me though is that it’s one of the few places in the US that you can easily do by public transport. There’s no need to hire a car in Boston, so if like me you don’t drive or don’t want to drive abroad, it’s perfect.

There are loads of things to see, do and eat in this vibrant and buzzing city. If you’re visiting from Europe and not too familiar with the USA in general, then planning your Boston itinerary can be quite overwhelming. I’ve put together this plan for how to spend 2 days in Boston, which is full of my personal recommendations so that you can make the most of your time there.

Side note: As this is a UK-based blog, I should probably add that I definitely mean Boston, MA, USA – not the one here in the UK!

Anyway, here’s my 2 days in Boston itinerary. I hope you find it useful as a starting point to plan your trip…

2 days in Boston itinerary: day 1

Morning: start off at Boston Common and the Public Garden

The first place I’d recommend seeing is the famous Boston Common, which is America’s oldest park. Boston is quite a built-up city, but it has this pocket of greenery that it’s very proud of. The Common is a really pleasing place to have a morning stroll and feel like you’re not really in the middle of a massive city. Also, it has excellent people-watching opportunities as all the locals flock here on a sunny day.

Boston Common is also next to the Public Garden, which has a beautiful lake with SWAN BOATS. Is it me or do you never see them anywhere these days? You know the things, those peddle boats in the shape of a giant swan that used to be par for the course at every little lake or water feature in the whole of the UK once upon a time. I can only assume they had their swan song (ahem) in the late 90s but I think we should bring them back. If you have time, you could go for a little ride on one (they only operate in spring and summer).

As it was May when I visited, the blossom was out in full force for my photographs. Bonus!

Make way for (in)famous ducklings…

From swan boats to more waterfowl, I have to mention these creatures that you might notice as you stroll round Boston Common. Apparently, this duck-and-ducklings statue is based on a ‘world-famous’ children’s book (that no one I know has heard of) called Make Way for Ducklings. I feel this may be an American thing referring to a ‘world-champion team’ when talking about American football, a sport only the USA competes in. The ducks seem to adopt seasonal headwear because they were all in Easter bonnets in May and I found photos of them in Christmas hats when I googled them to see what they were on about. That’s my kind of duck.

They’re quite cute, although sadly far too small to sit on for a photo and isn’t that the point of any animal-based statue? Anyway, keep an eye out for them if you’re walking through the Common as they do make for a cute photo even if you’re European so have never heard of the book.

Walk the Freedom Trail – a good way to get a feel for the city in your 2 days in Boston itinerary

Probably Boston’s #1 thing to do is the Freedom Trail. And handily, it begins in Boston Common.

The trail is a walk through the city, calling at various points of interest and historical landmarks. You follow a red-brick line along the pavements/roads, which guides you round on a 2.5-mile tour of American Revolution sites. It takes a few hours, depending on how many sites you call into (some of them aren’t free, though).

The ‘trail’ starts at Boston Common and ends at the Bunker Hill Monument. I must admit I’m not a huge fan of history unless it involves the Tudors. And I don’t know masses about American history at all. So I wasn’t expecting to find the trail that interesting but actually really enjoyed it. As well as the historical points, it’s nice just to see the different ‘neighbourhoods’ of Boston. I usually do a free walking tour to start off any city break, just to get a feel for the city. The Freedom Trail is a sort of alternative to that.

Plus, 2.5 miles of walking means you’ve earned a nice lunch…

Lunch: take your pick from the food stalls at Quincy Market

Quincy Market is a nice option for lunch on day 1 of your Boston itinerary. It feels quite touristy but is worth a visit just to enjoy the impressive building and bustling atmosphere. It’s a two-storey indoor food market, with loads of different stalls. This would be a good place to try one of the local dishes, like clam chowder. The food is on the expensive side but the stalls have plenty of options and the setting is stunning.

Quincy Market is set in a red-brick 19th-century building with a central rotunda section where a huge domed ceiling looks down onto the ground floor, lined with fairylights and surrounded by tall windows. All very impressive. If you sit on the upper floor for lunch, it provides some excellent people-watching opportunities.

Afternoon: a trip to the famous Harvard University

One of the area’s most well-known landmarks is Harvard University (they don’t seem to say ‘uni’ much in the US though, so if you’re referring to it, avoid that!). It’s their oldest uni and even if that seems like a strange thing to go and see, it’s worth doing. You can get there from the centre of Boston on the red subway line across to the neighbouring city of Cambridge. That takes about 20 minutes.

You can even do a guided tour of the uni with a current student if you’re interested in campus life and the student experience there. It’s enough just to wander around and admire the nice campus, though.

Honestly, I thought my uni was pretty (Lancaster ’til I die) but Harvard’s campus was on another level. The buildings are gorgeous and incredibly grand. The student accommodation was in sort of cute terraced houses set in very green and manicured grounds full of blossom trees. Serious National Trust vibes!

You can’t really imagine the students here doing Jagerbombs until they’re sick. It’s too fancy a setting for those kind of antics. But I suppose it must go on, or at least I hope it does for their sakes.

Pick up a couple of fresh cannoli – this should be a staple of any 2 days in Boston itinerary!

Until I visited Boston, I’d never even heard of cannoli. By the time I left, I had a borderline addiction to them. And my jeans were definitely feeling their effect on my waistline. WHY ARE THESE NOT A THING HERE IN THE UK?! 

If you don’t eat anything else in Boston, you have to get one (or two or three) of these bad boys. I’d really recommend the ones from Mike’s Pastry, which is a bit of a local landmark in Boston and well-loved by locals, judging by the queues outside. There are a few branches of Mike’s Pastry, including one handily located just next to Harvard. 

Cannoli are pastry tubes filled with delicious buttercream stuff. They come in loads of different flavours and sizes. I really loved just the plain vanilla ones, although I also enjoyed the lemon and pistachio. Delicious. Mike’s has about 20 different flavours to pick from, which is quite dangerous.

If anyone is going to Boston, feel free to try to smuggle a suitcase full of them back to the UK for me.

Evening drink and meal: discover Boston’s ‘Little Italy’, the North End

As the afternoon draws to a close, head to Boston’s Italian area, the North End. It has a bit of a tacky atmosphere, but it’s the oldest bit of the city and the best place to try American Italian food. If you’re used to eating Italian Italian food in (obvs) Italy, be prepared for something different from the American take on it. It’s much more saucy and chunky than normal Italian food but still very tasty. 

Before your meal, head for a drink somewhere in the North End. A good option in nice weather is Ward 8 Bar & Restaurant, which has an outdoor terrace area. As the name suggests, it’s both a restaurant and bar. But you’re fine just to stay for a drink and it doesn’t feel like you have to order food to be polite! They have an excellent cocktail menu. You need to sample at least two to appreciate it…

Once you’ve had some cocktails, you’ll probably want to head to eat. I really recommend La Famiglia Giorgio’s, which is worth booking if you’re visiting Boston in a busy period because it can have queues to get in. It’s only a 5-minute walk from the cocktail bar, handily (it’s almost like I planned this Boston itinerary carefully!). The pasta at La Famiglia Giorgio’s is lovely, with plenty of vegetarian and pescetarian options to choose from. Oh and they have a lovely selection of wines to pair with your meal. 

If you’re staying in a hotel so can’t take leftovers away to re-heat the next day (which is the norm in the USA), I’d recommend getting one pasta dish between two people, with a salad or mixed veg on the side. If you’re from Europe, you’ll be familiar with the USA’s reputation for crazy portion sizes. I have to say that Boston’s portion sizes seem particularly bonkers even for the USA! But sharing food does make eating out a bit cheaper, so you can’t complain. 

2 days in Boston itinerary: day 2

Morning: Breakfast at Boston Public Market

A lovely chap I’d met in San Francisco recommended Boston Public Market to me. And now I’m recommending it to you because it’s so good.

Boston Public Market is brilliant. It’s much, much better than Quincy Market, despite not having the impressive red-brick setting. It has a fantastic selection of food with far more emphasis on local produce and some incredible vegan and international options. It’s a good place to try a local lobster roll (which might work for breakfast, to be honest!).

One of the stalls specialises in the USA take on Yorkshire puddings, which are known as ‘popovers’. I really recommend trying one. You’re probably not expecting to be eating anything resembling a Yorkshire pudding for breakfast but it works. For something more breakfast-like, there are stalls doing crépes or bagels. The portion sizes, you’ll be pleased to hear, are much more European than American, so you won’t have to share one between two and can have different things.

An arty morning at the contemporary Museum of Fine Arts – an essential visit in any 2 days in Boston itinerary

Spend the second morning of your 2 days in Boston exploring the impressive Museum of Fine Arts. It’s quite a massive museum, so set aside a good couple of hours for it. It’ll definitely take you up until lunchtime.

Don’t be put off by the name like I was. ‘Fine art’ sounded like ‘old art’ to me, which is absolutely not my cup of tea. But actually, it’s got a huge amount of modern and contemporary art. I was thoroughly impressed by it, and I’ve been to art museums all over the world as I’m quite into art so always try to see one on every trip. The museum is home to one of the most memorable art installations I’ve ever seen. It was a video piece about the chronological history of the world through the perspective of different cultures, all interlaced. Very, very good. If anyone can tell me who it was by, answers on a postcard in the comments below.

The only downside to the Museum of Fine Arts is that it’s $25 for general admission and a further $5 for any temporary exhibitions. I’m so used to Europe’s museums being cheap or free that this surprised me. But it’s still worth doing. A really enjoyable and interesting must-see on any Boston trip.

Lunch at the best vegan chain ever, By Chloe

Is By Chloe slightly too hipster in its decor and wildly unhealthy in its calories? Yes.

Would I happily eat it for the rest of my life? Also yes.

I normally avoid chains like the plague, I won’t lie to you. But until recently, we didn’t have the famous vegan chain By Chloe in the UK. We do now have a couple of branches but they’re all miles away down in bloody London so may as well not exist for me at the other end of the country. I’m hoping they expand and move up north ASAP because I utterly love the food they do.

When I spotted that Boston ha a few branches, I got them saved on my Boston itinerary faster than you could say crispy tofu. And I recommend you do too. The food is unbeatable. They do the best vegan burgers, Caesar salad, tofu ‘fish’ and chips, and sweet potato skinny fries. Not to mention their delicious desserts. Even if you’re not vegan, you’ll love it. 

Afternoon: experience the Isabella Stewart Gardner Museum

The next port of call on your 2 days in Boston itinerary should be the interesting little Isabella Stewart Gardner Museum. If you’re going to go anywhere for photo opportunities that will make your Instagram happy, this is for you. Although it’s a museum, it seriously is a photography spot like nothing I’ve ever seen before. For the purpose of this post, I’ve only included one photo. But it could easily make a post of beautiful photos in itself.

Isabella Stewert Gardner was a prolific art collector shopaholic. I think I’d have got on well with her. She racked up a right old amount of eclectic paintings, sculptures and furniture from America, Europe and Asia over her lifetime and needed somewhere to show it all off. Behold, she commissioned this fantastic courtyard building that could be some kind of Venetian palace. You wouldn’t know you were in the USA, to be honest. It really feels Italian and is just absolutely gorgeous.

The collection itself is wide-ranging and absorbing to wander around and take in. One thing that sticks in my mind is that Isabella had bought a little piece of the bed (I think?) that Mary Queen of Scots slept in. Niche, but interesting.

You have to pay a general admission fee of $25.

Early evening: sample a local beer or three at Hopsters

If you’re visiting from Europe, you’ll probably be keen to try some American craft beer while in Boston, given that ‘New England IPA’ is a massive thing over here. However, you’ll probably come to the same conclusion as I did when I was planning this Boston itinerary: New England IPA isn’t a thing there! I did plenty of googling and research but concluded that it’s just marketed to us in Europe like that.

Anyway, Boston does do American hoppy craft beer, it’s just a bit different from what we’re marketed!

Hopsters Brewing Company is the place to try delicious local beers, brewed on site. It’s a brewery and restaurant combined, and you can also brew your own beer there if you book in online. Make sure you try their amazing milkshake IPA if it’s on. It’s a solid 10/10. The bar has a really nice atmosphere and pretty decor, so it’s the perfect place to sample some local beer before heading out for your evening meal. 

Evening meal: amazing Asian food at Myers + Chang – the best place to eat in your 2 days in Boston itinerary

Delicious food from Myers + Chang is the best thing you can put in your mouth in Boston (along with the endless cannoli, of course). I’m very fussy when it comes to Asian food, having been spoiled by experiencing too much good stuff in Japan. But I can assure you that Myers + Chang is absolutely spot on with everything it serves. You’ll have to book ahead because it’s really popular with locals so fills up fast, but it is absolutely worth it.

The crispy pancakes are unreal and they do the best gyoza I’ve had outside Japan. There are plenty of vegan, vegetarian and pescetarian options on the menu, which is brilliant. And the portions are much more normal and European-sized, so you won’t have to share one main between two and can have different things without worrying about wasting food.

I honestly adore this place and have recommended it to friends and colleagues who’ve been planning their own Boston itinerary. Everyone has fallen in love with it too. It’s a great one to save for your second of 2 days in Boston to end your trip on a high note.

2 days in Boston itinerary: other things to do (or skip)

If some things on this 2 days in Boston itinerary don’t tickle your fancy, here are a few things I wrote down before my visit but didn’t end up doing. You could squeeze them in or swap other things out for them.

• One of the biggest attractions in Boston is the Cheers Boston bar from the 80s/90s TV series Cheers, which was set in the city. Unless you watched and liked the series, it’s not really worth going inside in my opinion. Maybe just get a photo with the sign.
• Fenway Park is a famous baseball stadium in Boston. The locals love baseball and the atmosphere at a ‘game’ will be buzzing. But if you only have 2 days in Boston and don’t like/don’t know anything about the sport, it’s one you could give a miss.
• Another big attraction is the Boston Tea Party Ships & Museum, where fully restored 18th-century ships bob in the harbour. Tourists are led through an interactive Boston Tea Party reenactment by guides in costumes. If that’s your cup of tea (pun intended!), give it a go – you even get to chuck a cuppa into the water.

2 days in Boston itinerary: day trips to do if you want to stay for longer

If you’re staying longer than just a weekend or 2 days in Boston, you can elongate your trip with a few day trips out of the city and into the lovely surrounding areas in New England. After packing so much in, you’ll probably be wanting a break from the hustle and bustle. Here are my two recommendations for days out. You can do both by train, too.

Extending your 2 days in Boston itinerary: a day trip to Rockport

I love the adorable fishing village of Rockport so much. If you’re going to do only one day trip from Boston, this should be it. I cannot emphasise this enough. It is stunning and interesting and totally different to the city so makes a great little trip out.

I’ve done a separate blog post on how to do a day trip to Rockport from Boston, but I’ll briefly describe it here too.

The picture-perfect town of Rockport itself is on Cape Ann, a headland/promontory at the top of Massachusetts Bay. I didn’t really know what to expect from it but it was just beautiful – a total gem. There are loads of colourful wooden buildings, independent shops, fresh seafood and magnificent sea views from sandy beaches. It has an arty vibe to it and is overflowing with art shops and galleries, which is unsurprising given how beautiful the area is – anyone would be tempted to paint it.

Getting there: It takes just over an hour on the train from Boston’s North Station. Once you arrive at the station in Rockport, you’re only a five-minute walk from Rockport’s ‘downtown’ (the town centre).

Extending your 2 days in Boston itinerary: a day trip to Salem

I’ll be honest here. I was slightly underwhelmed by Salem. I’m very interested in witchy things, having been to uni in Lancaster (in the UK and where the famous Pendle Witch Trials happened). So Salem was naturally somewhere I really fancied going. But it was just ‘alright’. I would only recommend going if you’re absolutely determined to and really want to see the witchy stuff.

The Salem Witch Museum was mildly entertaining but not as good as any of the witch museums I’ve done in Europe, to be honest. It featured the story of the Salem witch trials being told while various mannequins were lit up. I actually preferred wandering around the town of Salem looking at pretty houses and having a drink out in the sunshine at BEERWORKS No. 2 Salem. Everything in the town centre was witch-themed too but there were a lot of tacky tat shops.

Getting there: It takes just over 30 minutes on the train from Boston’s North Station to Salem.

Useful information: 2 days in Boston itinerary 

How to get there

Flights to Boston are really doable from the UK. It’s only about 6 hours 30 mins from Manchester Airport to Boston Logan International Airport. You can spend almost as long flying just within Europe! I was impressed with this. Once you land in Boston, there’s a free shuttle bus (Massport Shuttle) from all airport terminals. This takes you the airport’s railway station, which is on the Blue Line. This then takes you into the centre of Boston.

Where to stay during your 2 days in Boston itinerary

Accommodation pricing is the real downside in Boston. It’s incredibly expensive for hotels/apartments: way worse than Paris or London even. It just doesn’t seem to have any mid-range hotels in the centre – you know like Premier Inn or Motel One where you pay like £80 a night for a nice modern room? Nope, none of that. Maybe it’s a USA thing because San Francisco was much the same.

Here are a few options for you. It’s worth remembering that when you’re browsing hotels in Boston online, the prices are usually listed as the room price only. When you dig deeper, there’s also tax (USA doesn’t list it as part of the price!), city tax, municipality tax and a ‘resort fee’. I’ve listed the prices with all of that included! All prices are correct at the time of writing. 

• Treat yo’self: If you want to really splurge, you can do so at The Godfrey Hotel Boston (about $215 a night).
• Mid-range: A great middle option is The Revolution Hotel (about $170 a night). The rooms are very stylish and really make the most of space to store all your stuff during your stay.
• Budget: My most affordable recommendation is Element Boston Seaport District (about $130 a night). It’s still not what I’d normally class as ‘budget’ on here, but that’s Boston. The rooms are modern and also include a microwave and coffee machine, so you could easily save money on breakfasts out.

How to get around

Boston has decent public transport by USA standards, which is the main reason I chose to visit as I don’t drive. It’s 100% doable without hiring a car. So if you don’t want to drive either, it’s a good place to go in the USA. But compared with Europe/Asia, public transport is not easy. I struggled to find a website/map that overlaid every type of transport so you could get your head around what the best combination to get was. There are buses and trains. Oh and of course Uber, which doesn’t work unless you have roaming data on so I’d recommend getting a SIM card that works in the USA.

If you are driving, perhaps as part of a wider USA road trip, Boston is well connected to other cities. A popular option is a Boston to Maine road trip, which would be beautiful in autumn.

When to go

I visited in May. Spring in Boston is sunny but cool and fresh, which I think is perfect for exploring a city. There weren’t too many tourists, but everything was open and bustling to a nice degree. So I’d recommend that as a good time to plan a trip.

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You might also like my other USA posts. I normally focus on UK, Europe and Japan posts, so I only have a couple of US ones. Watch this space for more in future, though.

• A fabulous San Francisco itinerary for 3 days of fun and food (without a car)
• 38 funny and interesting differences between the USA and Europe.

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