Two days in Boston

Full disclosure, Boston is one of my favourite cities in the US. Mainly due to the fact that it feels a little like Europe and you can walk almost everywhere. I have been there a couple of times, so I thought I would create a little itinerary for 2 days in Boston, perfect for a weekend away or a stop while on a road trip on the East Coast.

Also if you are coming from NYC, I highly recommend taking the train from Pennsylvania Station as the views through New England and along the coast are lovely as you can see in the pictures below.

Weekend 2 days in BostonWeekend 2 days in Boston

Day 1 – Let’s make History!

You will need one big breakfast for this one as a lot of walking is involved. So first thing first head to Charlie’s for some authentic American breakfast. The place is like a time capsule, the staff, the furniture, the customers, everything seems to be like it was 40 years ago.

Order blueberry pancakes, they are to die for! And a side of bacon, because why not?

Weekend 2 days in BostonWeekend 2 days in Boston

Once you have cleaned your plate (if you can), head to Boston Common where the Freedom Trail starts. I recommend you follow the red line which will take you through the most iconic areas of Boston. It is quite a walk and with stops along the ways to the different sights, lunch and an afternoon snack/coffee it should take you 4/5 hours. I have done it twice and it really is the perfect way to enjoy Boston and its history, while ensuring you are not missing any of the main sights.

Weekend 2 days in BostonWeekend 2 days in BostonWeekend 2 days in Boston

Conveniently, the freedom trail will bring you to Quincy market which is the perfect place for a lunch break! The food options are endless and the venue beautiful!

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Enjoy the walk through Little Italy, the harbour, and stop by the USS Constitution Museum if you have an interest in sailing or if like me you are following your ship-obsessed boyfriendWeekend 2 days in BostonWeekend 2 days in BostonWeekend 2 days in BostonWeekend 2 days in Boston

Finish the day eating crab cakes while resting your little feet at Legal Seafood by the waterfront.

Weekend 2 days in Boston

Day 2 – Welcome to New England

Boston is a beautiful city. The architecture, the streets, the atmosphere, it will really give you a taste of New England.

For house watching, head to Beacon Hill and get lost in the cobbled streets. The neighbourhood is beautiful, even more in the spring or fall. Wander around, stop in a little coffee shop and try to pretend you are one of the very cool locals.

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For the second part of your day, head to Back Bay. Walk around the very grand Commonwealth Avenue to look at the beautiful Victorian houses and then head to Newsbury Street to explore all the little shops.

Weekend 2 days in Boston

You have another day in the city?

Here are a few things I recommend doing.

I apologise for the lack of pictures but last time I went to these places was in my pre-digital camera days (yeah, a while ago…)

Whales watching – depending on the season, see if you can go whales watching. Last time I went the whales were so close I could almost pet them!

Museum of Fine Arts – went there for an Edward Hopper exhibition which was fantastic!

Harvard – If you can, do a little day trip to Cambridge and wander around one of the most famous campuses in the world

Where to stay?

The two times I went to Boston, I stayed in the Back Bay area which is really well situated and convenient with plenty of restaurants in the area.

The Marriott which, well… Is a Marriott, the rooms are big and you get what you would expect.

The Eliot Hotel is my favourite. The place is beautiful and located on Commonwealth Avenue. Perfect for a couple weekend away!

I hope this 2 days in Boston itinerary helps you organise a memorable trip to Beantown!

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16 thoughts on “Two days in Boston

  1. I’ve heard such a lot about Boston, it sounds like a fantastic city. I’ve met quite a lot of students from there through my previous work, and they all loved the city life there! I’ll be saving your article for when we visit, which I hope will be very soon.

    Liked by 1 person

  2. Fantastic photos and really great travel information. Taking the train looks like a great way to see the scenery on the way


  3. This brings back such fantastic memories. I went to university in Boston, and have walked all of these places before. I cannot count the number of times I have walked the Freedom Trail, or stopped at Quincy Market, or journeyed in Back Bay. Thanks for reviving some memories.

    Liked by 1 person

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