How To Spend 36 Hours In Boston

How to spend 36 hours in Boston

Last weekend, Lewis and I rented a car and drove down through beautiful New England to Boston. Our main motivation for going was for a long-awaited opportunity to see one of favourite musicians play who we kept missing in Europe due to our constant relocating this year. Of course, I also could not wait to get back to Boston, a beautiful city with lots of history and European feel that we had visited almost exactly four years ago. After a long (but worth it) drive, we arrived in Boston on Friday evening and we spent a whirlwind 36 hours in Boston before heading back at midday on Sunday. It is totally worth taking quick weekend trips because you can get a lot done in a short space of time so here’s how to spend 36 hours in Boston.


Regina Pizzeria - how to spend 36 hours in Boston
Regina pizzeria - how to spend 36 hours in Boston

After a 7 hour drive with just car snacks and a stop off at the Ben & Jerry’s factory (more on that another time), we headed straight to The North End, which is like the Little Italy area of Boston, for pizza, of course! We stumbled across a rather large queue for a pizzeria off the main strip and after checking out other options on Salem Street, I persuaded Lewis that we should go back to the first one – a queue is always a good sign right?! And right we were! We waited about half an hour for a table at Regina before we were seated in a cute wooden booth right next to the kitchen. We ordered a 16 inch margarita with extra ricotta to share for 20 bucks, which we enjoyed amongst the bustle and noise of this charming Italian restaurant. The queue was definitely worth the wait and it was the perfect start to our weekend in Boston.

Mike's Pastry cannoli - how to spend 36 hours in Boston
Boston skyline at night - how to spend 36 hours in Boston

From Regina, we strolled though the lively North End to Mike’s Pastry on Hanover Street – the best place to get cannoli in town. If you don’t know what a cannoli is, it’s crispy tube of pastry stuffed with a creamy filling of which there are many flavours. We chose a plain cream filling with chocolate chips and went to heaven while eating these watching the Boston skyline at night. We also picked up another cannoli each on Saturday afternoon because if you can’t indulge on holiday, when can you?!


Beacon Hill - how to spend 36 hours in Boston
Beacon Hill - how to spend 36 hours in Boston
Beacon Hill - how to spend 36 hours in Boston

Located just west of the centre of Boston, Beacon Hill is an affluent, residential and beautiful area of town that is great for a calm weekend stroll admiring the gorgeous red brick buildings so this is exactly where we headed on Saturday morning. We were particularly taken by Louisberg Square and while taking some photos, an American couple pointed out John Kerry’s house. As well as being home to important men of power, Beacon Hill also has lots of cute independent shops and cafes along Charles Street and although they can be pricy, it is always nice to have a little look.


Boston Common - how to spend 36 hours in Boston
Boston Common - how to spend 36 hours in Boston
Boston Common - how to spend 36 hours in Boston

From Beacon Hill, just cross over Beacon Street and you are in Boston Common, a vast and diverse park smack bang in the middle of the city. The weather was stunning for our whole weekend in Boston so we took the opportunity to wander through this lovely park, taking some time to reflect whilst sitting on the bench that features in the film Good Will Hunting. The bench has a great view of the lagoon and is just perfect for people watching.


Quincy Market - how to spend 36 hours in Boston
Quincy Market - how to spend 36 hours in Boston

Last time we were in Boston, we spent a lot of time around Quincy Market (and taking full advantage of the free Mac n Cheese samples) so we knew this was the place to head to to fill our stomachs before the gig. Quincy Market is in a beautiful old building that sits next to the equally stunning Faneuil Hall (where the Freedom Trail starts, which I highly recommend too) and is a lovely bustling retreat from the skyscrapers that surround it. Quincy Market offers lots of hot and cold meals including seafood, pizza and asian but we were there for one thing only – the cheesiest and most moorish Mac n Cheese. We certainly did not feel too healthy eating it and we definitely ate too much but it was the perfect way to get energised for the evening entertainment.


Brian Fallon at Royale - how to spend 36 hours in Boston

I often plan city breaks around going to a particular event and although your dates might not always match up with your favourite artist, going to a gig, musical or show is great way to make a trip extra special. I had been dying to see Brian Fallon (lead singer of the Gaslight Anthem) play all year so this has to be the highlight of my weekend. He played at the gorgeous Royale venue on Tremont Street, right in the heart of theatre district, and he was amazing! We had such a magical night and we even managed to meet him afterwards by hanging around the tour bus after the show – I’m a fan girl and proud ok?! 


Trident Booksellers Cafe breakfast - how to spend 36 hours in Boston

On Sunday morning, having rinsed our money on cannoli and other deliciously unhealthy food, we wanted to stock up on a hearty American breakfast before hitting the road. Our Bostonian friend Bella, recommended the Trident Booksellers Cafe in the Back Bay area, which was great as we got to see another lovely area of town and the breakfast was just insane! We had to wait about 20 minutes for a table in this cafe located within a bookshop but it was so worth it. I went all out and chose the lemon ricotta stuffed French toast topped with blueberry coulis and maple syrup – and trust me it was a much as a mouthful to eat as it is to say! The portion was absolutely enormous – probably double the amount that I really needed – but Lewis was happy to help me out once he had finished his scrambled eggs and home fries. Great recommendation Bella!

So there you have it – how to spend 36 hours in Boston! If you have the time or it is your first visit to the city, it is worth spending a good four or five days there, which is what we did when we went four years ago. Thankfully we managed to squeeze in our top favourite things to do in Boston in just 36 hours – of course the only other must-do is see the Red Sox at Fenway Park but they were unfortunately playing away last weekend.

I hope you have enjoyed this post and watch out for the vlog coming on Sunday. I will certainly be doing more of these posts as I explore Canada and the USA so let me know if you have any recommendations. Next stop…New York in December!

Izzie x