JFK Library and Memorial, Photo: Matthew Villemaire (me)

I should have written this blog like 3 months ago when I got back from my trip, but clearly, that didn’t happen… so here we are!

In June, I had the privilege of spending a week in the incredible downtown of Boston, Massachusetts. I went into the week with pretty low expectations and came home with an immense amount of love for a city I had never visited before.

My original plan was to visit New York… for like the twelfth time, but for whatever reason, my heart shifted towards somewhere new. I wanted to experience that rush of getting lost in an unfamiliar place again!

When I arrived, bags in tow, I could’ve easily hopped in a cab and zipped over to my Airbnb… but that would’ve been so boring! There is something so thrilling about touching your feet to the ground in an unfamiliar territory and navigating to your new home. I love experiencing public transit, the strange smells, the harsh lighting, the looks of disdain on the locals' faces, that I have when riding the subway here in Toronto.

Then there’s the rush of exiting the underground tunnels of Boston’s “T” (what they call their subway system) and emerging in the heart of downtown. Being surrounded by tall buildings, beautiful architecture, cars and pedestrians flying past you… it’s the perfect reminder of how small you are in this vast universe.

I could tell you all about the places I visited and give you a detailed description of my itinerary, but honestly, until you experience it for yourself, I’ll just bore you to death!

Instead, I’ll tell you a bit about how I travel and what made the trip special for me!

Firstly, it’s important to know that I’m not the kind of traveller who does a ton of research before I visit my destination. I don’t plan my days, I just go with the flow and see where the wind takes me. It’s my favourite way to travel because it feels organic, and rather than building high expectations based on what I’ve seen online, I get to be pleasantly surprised when things just fall into my lap!

This style of travel also keeps you open and allows you to be steered by what is around you. If you have a strict itinerary to follow and you only have an hour to explore the Boston Commons because you’ve gotta rush over to the Isabella Stewart Gardner museum for a guided tour… you miss out on the opportunity to sit and people watch in the Public Garden, or stop and listen to the busker singing by the pond (I got to do both of those things…just sayin’ ;p). When you’re on a tight schedule you’re limited to what are able to see and experience, and that, to me, is a missed opportunity.

I wasn’t able to see everything that Boston had to offer, and I’m okay with that. Boston will always be exactly where I remember it, and I know that I’m welcome anytime I wish to return!

That’s just my two cents on travelling more freely! Some people prefer to jam pack their schedules and see everything they can in one trip, if that works for you that’s totally fine too! :)

Watching the kiddies play in the park- Photo: Matthew Villemaire (me)

All of my favourite memories from the trip were spontaneously cultivated.

I met a lovely local online through a gay app called Grind’r, a great tool for meeting new people when you travel…so long as you’re safe and smart about it! We spent an evening at a bar chatting about life, our mutual love for musical theatre, our mutual hate for the current President, and what makes us both tick! Making genuine connections with strangers in foreign lands is what I live for! It feeds my soul and provides me with the knowledge that there are people like me all over the world, just trying to spread love and light!

I got to try the most amazing Cannoli at an Italian bakery on an afternoon stroll through the North End!

I toured Harvard’s prestigious campus in beautiful Cambridge and learned a lot about the schools rich history, from a very handsome 3rd year Psych student named Mike.

I experienced a vastly moving performance of Jagged Little Pill at the American Repertory Theatre. This show was all about inclusion, and giving space to people who’ve been jammed into the margins and who have experienced abuse and injustice. The performers left everything on that stage and the audience was LIVING for it! It was an unforgettable experience, one that doesn’t come around very often, and when it does you know you were apart of something special!

Audiences sharing their own stories outside the theatre ❤

If you’re looking to be swept off your feet by a city that is both larger than life but quaint and unpretentious at the same time…I’d definitely recommend Boston!

The city is compact and you can explore most of it by foot. But, be sure to bring good shoes, because though the cobblestone streets are pretty, they will f**k you up!

The city has the perfect balance of big city buzz, and peaceful respite to accommodate all your travel needs.

Most of all, if you’re willing to remain open, the city will take you on an amazing ride. There are opportunities to explore some of the United States’ rich history including the Freedom Trail and the first lending library (Boston Public Library). There are opportunities to explore arts and culture through a variety of museums, theatres, and amazing restaurants. There is truly something for everyone!

Oh! I almost forgot! If you can, stay at an Airbnb!! One of my favourite parts of travelling is the opportunity to experience a city like a local would. My host has been living in Boston for over 10 years and had an incredible condo in the South End. She had an amazing rooftop patio where I ordered pizza and drank beer and watched the sunset one evening. She recommended all her favourite local eateries and even offered to take me out to a drag show at one of the gay bars in the area! You just can’t get that kind of experience staying at a hotel.

If you have any questions about my trip, or wanna know what to check out, please shoot me a message!

With love,

Matt ❤

This cannoli from Bova’s Bakery in the North End was life changing! Check them out ;)

31, Toronto-Canada, LGBTQ+, Actor, Singer, Writer, Lover!❤

31, Toronto-Canada, LGBTQ+, Actor, Singer, Writer, Lover!❤