
One of my favourite things about what I do, is the ability to travel as part of my work.
On a recent project, I had the opportunity to spend a few days in Boston.
I LOVE Boston.
Everything – from it’s rich heritage and unique neighbourhoods, to the clean, wide-open green spaces and friendly locals, make Boston a phenomenal city to visit.
The city is also really easy to navigate making it the perfect city to explore on foot, and in case you get hungry or thirsty as you explore, the city also boasts an abundance of amazing restaurants, bars and pubs (due to it’s Irish heritage).
Here are a few of my tops tips to make your next trip to Bean Town a total hit.
(Be) A Good Sport
If you like sports, I guarantee you – Boston will not disappoint, there is literally something for everyone, be sure to check out a game.
The day after we booked our flights, my colleagues and I learned that the Toronto Maple Leafs were also going to be in town to kick off Round 1 of their playoff showdown against the Boston Bruins and tickets were insanely affordable (at least compared to what we would pay to see them in Toronto).
Long story short, a few minutes later, tickets were bought – we lucked out and got tickets right on the centre line.
I should probably mention that although I live in Toronto, and all of my colleagues are Leafs fans, I am a Bruins fan which led to lots of heckling back and forth in the run up to the game.
The game itself was amazing – aside from a couple of fights (mainly among the Bruins fans and the Bruins fans?!) a good time was had by all. The Bruins won 5-1 so I left very happy!
Here’s a quick video I shot of their first goal, as you can see and feel – the atmosphere is nothing short of electric.
Eat like a local
I really enjoy trying local cuisine when I travel and have become pretty good at searching out hidden gems in each city I visit.
Rather than re-visiting the same restaurants again and again (unless they are really good), I make it a point to try to find at least one new restaurant – ideally in a new neighbourhood – that I haven’t tried before.
After a quick search (I use Opentable) I came across Chestnut 75. A rustic American restaurant located in Beacon Hill – one of Boston’s most charming, quaint (and expensive!) neighbourhoods.
Although I have a shellfish allergy and likely missed out on – what I’m sure is – some of the freshest seafood on the eastern seaboard, I thoroughly enjoyed my meal.
The highlight (for me at least) was my dessert – a rich, decadent Tahitian Vanilla Creme Brulee served with seasonal berries which I particularly enjoyed paired with a phenomenal Petit Sirah by Michael David Winery.
Check out my full review of this wine in The Wine Vault.

I cannot recommend this restaurant highly enough!
Literally everything from the food and wine, to the attentive servers (who went above and beyond to accomodate my allergy) to the laid back ambiance made this one of my favourite Boston eats yet.
If you’re lucky enough to visit on the weekend, be sure to check out the Brunch Menu – I hear it’s to die for!