5 days in Boston, MA, USA: things to see, do and eat

5 days in Boston itinerary, MA, USA | PACK THE SUITCASES

It’s taken me forever to write up this 5 days in Boston itinerary because there’s so much to include. I should add that I definitely mean Boston, MA, USA – not the local one here in the UK. I think you’d struggle to spend 5 days there…

Anyway, this was my first time visiting the USA (more on that here) and we went to Boston as the second half of our trip, having spent one week in San Francisco before it. Neither of us tend to drive and SF and Boston both have public transport, so that’s the main reason I picked them for my first trip to the USA.

So here’s what I got up to over 5 days in Boston – a bit of an itinerary, featuring everything I did/saw/ate each day (with emphasis on the eating, as usual). I hope it’ll be handy as a general travel guide for anyone else’s first time there or for anyone planning up to 5 days in Boston and feeling overwhelmed by everything there is to do…

5 days in Boston itinerary, MA, USA | PACK THE SUITCASES

Boston itinerary day 1: Exploring, ducks and Harvard

Boston Common

Having got rid of our luggage into our (frankly repulsive) Airbnb apartment, we headed out to get our bearings in Boston. The first place we headed to was the famous Boston Common, which is America’s oldest park.

It’s full of flowers, a lake and lots of greenery. A really pleasing place to stroll through to feel like you’re not really in the middle of a massive city. Also excellent people-watching opportunities. We saw a couple having a massive row AND a police horse.

As it was May, the blossom was out in full force, which was lovely… but I was more excited about the SWAN BOATS. Is it me or do you never see them anywhere these days? You know the beasts, 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.

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Make way for infamous ducklings…

Speaking of all things waterfowl, I have to mention these creatures.

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 like ‘world-champion baseball team’ when only Americans do baseball! We were just walking past and saw an actual queue of people waiting to have photos with the ducks, so naturally I joined the queue despite never having heard of the things.

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 were quite cute, although far too small to ride for a photo and isn’t that the point of any animal-based statue?

5 days in Boston itinerary, MA, USA | PACK THE SUITCASES

Lunch at Quincy Market

I’d picked out Quincy Market for lunch, which felt quite touristy but was worth a visit just to enjoy the impressive building. It’s a two-storey indoor food market, with loads of different stalls. I didn’t like it as much as the other market we went to (see further down) and it was a bit more expensive, but the setting was stunning.

It’s 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 yet more excellent people-watching opportunities.

A trip to Harvard University

One of Boston’s most well-known landmarks is Harvard University (they don’t seem to say ‘uni’ much in the US though). It’s their oldest uni and even if that seems like a strange thing to go and see, it’s worth doing. You can even do a tour from a student, although we didn’t bother as we just wanted to wander around. You can do this in about 20 minutes.

Honestly, I thought my uni was pretty (Lancaster ’til I die) but Harvard’s campus was 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. 

You can’t really imagine the students doing Jagerbombs until they’re sick in such a fancy setting, but I suppose it must go on.

Italian Quarter meal

I’d heard a lot about American Italian food. Having eaten a hell of a lot of Italian Italian food in (obvs) Italy over the years, I was ready to be disappointed. I actually liked it though! It is different – more saucy and chunky – but still very tasty. 

We ate at La Famiglia Giorgio’s, which apparently normally has massive queues but was fine. We were seated straight away, possibly because it was freezing cold in early May and not quite tourist season yet. The food was lovely and we also had a really good glass of red wine with it. 

Side note: Compared with San Francisco, which is of course the only American comparison I can offer, I found Boston’s portion sizes to be double as insane. And SF’s were pretty insane. Everywhere we went in Boston, we shared a starter and a main between us and it was still too much. There’s a big culture of taking leftovers home in the USA though, so hopefully food doesn’t get wasted as much as it seems.

5 days in Boston itinerary, MA, USA | PACK THE SUITCASES

Boston itinerary day 2: Markets and museums

Bizarre but beautiful breakfast at Boston Public Market

Having endured a night in our rancid Airbnb, we headed out very early for breakfast. This was mainly as I couldn’t stand another minute in the place.

A lovely chap we’d met in San Francisco had recommended Boston Public Market, which was conveniently right next to the bus station we came into. What an absolute treat that was. It was much, much better than Quincy Market, despite not having the impressive red-brick setting. It had a better selection of food – including incredible vegan options and Yorkshire puddings.

I was not expecting to be eating a Yorkshire pudding for breakfast on the other side of the world. But this is what it had come to. We shared one of those bad boys and then had a delicious vegan seitan sandwich.

I could have spent all day eating there, but I was already in deep trouble with my skinny jeans by this point, so we moved on.

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An arty morning

To force myself not to eat for a bit, we spent the morning exploring the impressive Museum of Fine Arts. It’s quite a massive museum, so if you’re going to go then set aside a good couple of hours for it. Don’t be put off by the name. ‘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 in there.

One of the most memorable art installations I’ve ever seen was here. 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 was that it was £20 each to get in. I’m so used to Europe’s museums being cheap or free that this felt like a lot, but it was still worth doing and we could’ve spent even longer there than we did.

5 days in Boston itinerary, MA, USA | PACK THE SUITCASES

More food in the form of the best vegan lunch ever

I normally avoid chains like the plague, but we until recently, we didn’t have the famous vegan chain By Chloe in the UK. We do now have one branch of it, but it’s miles away down in bloody London so may as well not exist for us.

So when I spotted that the city had a few branches, I got them saved on our Boston itinerary faster than you could say crispy tofu.

Was it 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.

5 days in Boston itinerary, MA, USA | PACK THE SUITCASES

An arty afternoon

Feeling and looking like an actual whale after lunch, the next port of call was the little Isabella Stewart Gardner Museum. It was about £12 to get in, which made me think maybe all museums/galleries in these parts were more expensive than I’m used to.

A friend who’d been to Boston raved about this (hi Hannah) and in her words, ‘If you’re going to go anywhere for the ‘gram, go here’. I suppose I went there more for photos for the blog rather than for Instagram but 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. 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, this fantastic courtyard building that could be some kind of Venetian palace. You wouldn’t know you were in the USA to be honest. Absolutely gorgeous.

Most of the collection itself wasn’t really my taste, but it was interesting nonetheless. I think the thing I remember most from it was a piece of the bed (I think?) that Mary Queen of Scots slept in.

5 days in Boston itinerary, MA, USA | PACK THE SUITCASES

A local beer or three…

Naturally, we were after some local beer with our evening meal.

After a week in San Francisco drinking some of the best beer I’d ever had, it didn’t seem like Boston had quite as many crafty places. I really struggled finding suitable places, which was a surprise considering how much ‘New England IPA’ is a massive thing in Europe/the UK.

Hopsters was the best place I found though. It was so good that we ended up going back twice (unheard of!).

It’s a brewery and restaurant combined, and you can also brew your own beer there. I had an amazing milkshake IPA, which was the first time I’d ever seen one of these although they’ve since started to become popular in the UK. I’d really recommend going there – lovely food, nice atmosphere and good decor.

Boston itinerary day 3: Seaside day trip on the train to Rockport

After two days in the city, you’ll probably be wanting a break from the hustle and bustle.

One of the reasons I picked Boston to go to was its trains as we don’t drive. So on day 3 of my Boston itinerary, we headed out on the train to the adorable fishing village of Rockport, on the coast of Cape Ann.

I’ve done a separate post on how to do a day trip to Rockport.

It was 100% worth doing (and was better than a day trip to Salem, too). If you’re going to do one day trip from Boston, this should be it. I cannot emphasise this enough. It was my favourite day of the whole holiday. GO!!!

5 days in Boston itinerary, MA, USA | PACK THE SUITCASES

Boston itinerary day 4: Trailing and more food

Waddling round the Freedom Trail

Probably Boston’s #1 thing to do is the Freedom Trail. This 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. Yes, it ends up a hill. If you’ve done lots of walking on your trip and you’re a bit tired by this point, that does feel unnecessarily cruel. But think of the food you’ll be able to eat without guilt…

I’m not a huge fan of modern history and don’t know masses about American stuff at all, so wasn’t expecting to find the trail that interesting. But I really enjoyed it. As well as the historical points, it’s nice just to see the different ‘neighbourhoods’ of Boston.

Oh and there was this donkey, who was obviously crying out for a photo.

A cannoli problem

Until we visited Boston, I’d never even heard of cannoli. By the time we left, I had a borderline addiction to them.

If you don’t eat anything else in Boston, you have to get one of these bad boys. I’d really recommend the ones from Mike’s Pastry. There are a few branches of this, including one near Harvard Uni. 

Cannoli are pastry tubes filled with delicious buttercream stuff. They come in loads of different flavours and sizes. I really loved just the plain ones, although if I’d not been the size of a house at this point then I’d probably have sampled a lot more.

If anyone is going to Boston (hi Ben!), feel free to try to smuggle a suitcase full of them back for me.

5 days in Boston itinerary, MA, USA | PACK THE SUITCASES

Cheers… or not

One of the other biggest attractions in Boston is the bar from the 80s/90s TV series Cheers. We walked past this on Beacon Hill several times, including after doing the Freedom Trail. Neither of us ever watched the series so it wasn’t of any interest to us, but if you want a photo with the sign or something, then seek it out.

The best evening meal of the trip

Myers + Chang was probably (other than endless cannoli) the best thing I put in my mouth in Boston. 

We shared two starters and mains for the first time in the fortnight because the portion sizes were almost normal (maybe they were meant to be like tapas…?!).

It was all top quality and I’m very fussy when it comes to Asian food, having been spoiled by experiencing too much good stuff in Japan. It needs booking because it’s really popular with locals, but is absolutely worth it.

The crispy pancakes were unreal and we had the best gyoza I’ve had outside Japan.

5 days in Boston itinerary, MA, USA | PACK THE SUITCASES

Boston itinerary day 5: Witchy day trip on the train to Salem

The fifth and last day was time for our second and final day trip out on the train. Having been really enamoured with lovely Rockport, I was slightly underwhelmed by Salem. I really wanted to go there as I’m very interested in witchy things, having been to uni in Lancaster (where the famous Pendle Witch Trials happened).

But Salem was just ‘alright’. The witch museum was mildly entertaining but not as good as any of the witchy stuff 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 in witchy scenes. 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 tat shops.

I’m still going to do a separate post on how to do a day trip to Salem as I know it’ll be one people are keen to visit. So again, I’ll crack the link in here when it’s published.

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How to get there (and away)

We flew from our previous destination in the USA (San Francisco, which I loved), but flights to Boston are actually really doable from the UK. It’s only about 6 hours 30 mins too, which was a lot less painful than double that to get to SF.

Where to stay

Accommodation was the real downside in Boston. I definitely can’t recommend where we stayed, unless I don’t like you and then go ahead and book that Airbnb (probably the worst place I’ve ever slept). Boston was incredibly expensive for hotels/apartments: way worse than Paris or London. It just didn’t seem to have any mid-range hotels – you know like Premier Inn or Motel One standard where you pay like £80 a night for a nice clean modern room? Nope, none of that. Maybe it’s a USA thing because San Francisco was much the same, although I did manage to get us somewhere for <£100 a night there.

How to get around

Boston has decent public transport by USA standards. It’s 100% doable without hiring a car. So if you don’t drive like me, it’s a good place to go in the USA. But compared with Europe, public transport is not straightforward. 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 so I’d recommend getting a SIM that works in the USA just in case.

When to go

We went in May. It was sunny but cold. May was a decent time to go though. Not too many tourists, but everything was open and bustling to a nice degree.

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  1. This is fab. I love Boston but you have highlighted plenty of places I’ve never been there, which is great. If you go again I’d say Kennedy’s birth place house is worth a look. It is the nearest thing in America to a National Trust experience ive seen, but don’t let that put you off! We have also found accommodation to be shockingly expensive and generally not very good, but found a nice Brownstone guest house that was good.

    1. Thanks Ruth! We actually nearly went in the Kennedy house but there was a queue and it was sunny so we wanted to make the most of being outside. The USA is crying out for a nice Premier Inn chain isn’t it?! x

  2. Great post Caroline! I’ve wanted to visit Boston for some time now hopefully this year! The food looks amazing – now I’m craving gyoza

  3. I recently visited Boston, and you took me straight back to this vibrant town with this post! Absolutely loved North End of Boston and yes cannolis are a sinful must in Boston. You were so lucky you got to visit Isabella Stewart Gardner Museum. When I visited it was closed for some maintenance. Hopefully will get to visit next time! 🙂

    1. Ah, it was really good although I preferred the building to the actual contents – I’m more into contemporary art to be honest. Definitely worth going back for though 🙂

    2. Hey! Great article. I’m thinking of visiting Boston next month so it was super helpful. Would you say a week is too long there? Also please let me Know which air BnB to avoid!!

      1. I can’t recall what the AirBNB was listed as now but it was in the Logan area (very handy for the airport).

        Yes, I would say a week would be a bit long. I thought five days, with two of them being day trips, was about right. Boston centre itself only needs a day or two at most, but there are plenty of good places you can get to on the train, like Rockport, which I also have a post on.

        Enjoy yourself!

  4. Boston looks so pretty! Definitely need to visit next time I’m on the east coast. Pinned this itinerary for later, so many great ideas on things to do & see 🙂 And I’ve also noticed that Americans don’t use the word Uni as much as Europeans and Australians do; people I’ve met over there usually say “college” – it’s very interesting!

  5. Boston is also famous for its beans, hence the nickname Beantown. We stayed in the Doubletrees hotel in the south of the city a short walk to the ‘T’. The main problem with hotels in the US is that they do not have restaurants. So, you have to go for a walk to find a diner for breakfast but, you can get takeaways delivered right to your room! You may have heard the tale of Paul Revere calling to the revolutionary troops that the “British are coming”. This is of course allegorical as he would not have cried that as EVERYONE there was British at that time. He probably cried “The redcoats are coming”.

    1. Interesting on the breakfasts! We stayed in apartments both times so missed that. I think the UK’s Premier Inn or TravelLodge would go down well there.

      I did hear about the beans but didn’t end up having any – did I miss anything?

  6. Thanks for the Itinerary. Got some great ideas. My wife and I are headed to Beantown in June along with a lighthouse and lobster tour in Maine. Was looking for a good Italian Restaurant in the North End and you were a big help with that.

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