Boston city guide: Short break ideas to Boston

Boston city guide: Short break ideas to Boston

Boston city guide

When people think East coast USA cities, they think New York City. Right? But my Boston city guide will prove that NYC’s smaller (but much older) sister is the US city break you need to try.

I found myself celebrating my birthday there as part of a much larger 2-week East coast road trip and immediately fell in love with the city. Oozing vibrancy, culture, lovely people and fantastic seafood, Boston’s clash of history and modernity reminds me a lot of my hometown of London.

And trust me, it’s easy to get lost in the city’s welcoming warmth – whether it’s wandering the grounds of leafy Harvard University campus or strolling the cobbled Italian quarter of Boston’s North End area.


I firmly believe that whatever time of the year you choose to visit, you’ll have a good time. I visited in September and couldn’t have asked for a better climate. It was cool enough to walk around outside all day without getting really hot, and the trees were just starting to turn fiery shades of orange and red.

If Boston is part of a wider New England trip, I do recommend visiting in October to see the magical moment the thousands of trees turn from summer shades to autumn hues across the entire area.


Boston city guide

This list could go on and on, but below I’ve listed a few standout sightseeing things I did. Trust me, there’s way more you can do, and Boston is one of those beautiful cities you can wander through and never get bored.

  • The Freedom Trail: it’s important to know about the history of the place you’re visiting, and Boston is FULL of it. This 2.5-mile-long path passes by 16 important locations. Free on your own – I downloaded an app to give us more info as we went along.
  • Castle Island: The 1850 Fort Independence in South Boston is an overlooked sight – but also a fabulous one. In fact, on a lovely day the island is perfect for picnics, cycling and even a spot of fishing. Tours of the fort are free. 
  • Harvard University: I am SO glad I did this tour – and it was probably one of my favourite things I did in Boston. The tour was run by a university student and we got a fabulous insight into the history of Harvard, as well as current student life there. Tours are free but tips are welcomed. 
  • Fenway Park: Forget the Yankees, watch the Red Sox hit a bat around Boston’s baseball ground instead. The atmosphere is great, and I found that tickets were much more reasonably priced than watching NYC’s home team.
  • Salem: This historical town (known for the Salem Witch Trials), is a mere half hour train ride from Boston’s North station. While there’s not TONS to do there, there’s an eeriness about the place you need to experience to believe. The best way to see it all is via its tourist tram. The houses are stunning, the history is unbelievable and the area is as quintessentially New England as you can get.
  • Whale watching: This is a bit of a wild card, but I’m throwing it in anyway. If you’re visiting New England, I urge you to go whale watching. However, I chose to do a boat trip in Cape Cod rather than Boston (and saw SO many whales). If you can visit Cape Cod, I recommend you do the same. But if Boston is your only stop – then still give it a go, I just can’t guarantee what the trip will be like.


Row 34 restaurant boston

I loved the food so much in Boston, I dedicated an entire post to the dishes you need to eat there. In fact, it’s safe to say that foodies will be in heaven.

Gorgeous fresh seafood, stunning, home cooked Italian cuisine and proper American diners… you’re spoilt for choice.

For seriously good seafood, head to Atlantic Fish Company and Row 34, for Italian food we loved Villa-Francesca and for buttery pastry items worth the queue, head to Mike’s Pastry.

Lunchtimes were usually spent either grabbing a crab roll by the bay, or heading to one of Boston’s indoor markets like Faneuil Hall Market Place or Quincy Market.


Boston drinks guide

For us, this was pretty easy. In fact, we’re pretty easy drinkers who are just after a good wine list, a cold beer and a decent G&T.

Irish pubs are aplenty, and we loved Brendan Behan pub and Matt Murphy’s. For cocktails I loved the experience of Drink, where the bartenders created me the perfect gin cocktail based on my taste preferences.

Basically, get ready to fall in love with a city I’ll be returning to again…