Solo Trip to Toronto: Part 1

This is a long one, so grab a glass of  Pinot Grigio, a snack, and settle in.

I had toyed with the idea of a solo trip for a few years, but never had the balls to actually take the plunge and go. I have always enjoyed being by myself (I consider myself an extroverted introvert) but wondered how it would be to travel alone. I’ve always read and been inspired by solo bloggers liked Nomadic Matt and how enlightened they were after traveling alone.

During this phase of my life when I finally became so comfortable being alone (and have never been so single), had a little money in my pocket I knew now was the perfect time to take a solo trip. I wanted to go somewhere international, but wasn’t ready to go somewhere so far that I didn’t speak the language. In case I wasn’t comfortable being alone, I wanted to be able to be on the time zone as my friends and family, and be able to communicate. Canada seemed like the perfect middle ground, a place where I could go for just a few days,  but required my passport to get there.

I booked a trip from LGA to Toronto from a Wednesday to a Friday,  with my flight getting in around 11 am. I’m someone who likes to make plans in every aspect of my life – making a to do list every day, and travel is no different. Even if I don’t stick to the plan (which I usually don’t) I need to have it written. So that is what I did.

Day 1

I am super weird in the sense that I love airports. I love the idea of being in this hub when you’re able to soar thousands of feet in the air, around thousands of other people jet setting to different states and countries, and are gearing up to go somewhere different   – and the fact that airports are a totally no judgement zone.  I hopped on the plane and landed in the Toronto airport around 12 pm.

After getting through customs I planned to take a cab from the airport, but I kept seeing signs in the airport for the Up Express and decided to take the train to downtown, where I was staying. The train was super easy to take, and cost around $12.50 CA instead of the $70 or so a cab would have been. I took the train to the DoubleTree Downtown Toronto where I stayed and of course, was greeted with a warm cookie. I definitely recommend the Downtown Doubletree if you’re staying – it was a central hub for everything and there was so much in walking distance. And the hospitality of the staff and crew was welcoming and great.

I didn’t stay long before I was eager to hit the town and explore – and I was super hungry at this point. I took a long walk down to the St Lawrence Market, a really cool indoor marketplace famous to Toronto with over 100 vendors, everything from meat and cheese vendors, to live oyster shucking, to classic Italian vendors – and of course, tons of maple syrup. As soon as I walked in, I was greeted by amazing aromas, but what caught my eye right away was a wine tasting (obv.) I chatted with the vendor as I tried a few different wines from the 13th Street Winery. I ultimately settled on a delicious Italian salad from. After walking around the market a little while I headed on my way.

Coming from New York City, I am used to walking, and especially when I’m traveling I love to walk everywhere I can – it’s such an amazing way to see a city and find hidden gems. On my walk, I took in the beautiful glass buildings and cool architecture.

I walked down to the Harbourfront, which took me around 30 minutes to get to. There, I saw where the Ferry takes you to Toronto Island – an item that was on my list but I didn’t get a chance to do. All the locals I talked to said it was a must-do, so I definitely recommend if you have the time! Here, I was able to sit by the water (the Harbourfront overlooks Lake Ontorio) reflect and relax. I felt so at peace in that moment – water views always gives me a sense of serenity and there was something about the calmness around me. I brought a book with me and headphones if I wanted to listen to a podcast, but I found myself restricting my time on both of those things.

Then, I walked another 15 minutes or so other to the Amsterdam Brewhouse, a large lakefront brewery, with dark wood everywhere and a fun atmosphere. I sat at the bar and tried their Space Invader IPA – a delicious and hoppy beer. I ubered back to my hotel to get ready for dinner. I didn’t know where I wanted to go, and I will admit that eating out so the one thing I had trouble adapting to. I walked around the town and stopped into a bar called Duke’s of Richmond. I didn’t end up eating at this bar, but chatting with some gentleman at the bar. Everyone at the bar seemed to be locals who knew each other and the bartender. It was so interesting chatting with a gentleman named George about his background. He was a bit older than me, maybe in his 60s, and we just had an interesting conversation about how he grew up in Prague, his past, and I was able to share about New York. In New York, I never would have just sat at a bar and had the pleasure of these conversations.

Then, I went to this little Italian wine and tapas bar for dinner. Had my go-to Pinot Grigio and some pasta at the bar. I was going to head to bed after this, but a little pub called the Village Idiot that I passed on the way caught my eye. I’m so glad I went – I had a blast, I chatted with the bartender who was this VERY attractive man from France – he had such an interesting background and story, and another man came and joined us. We all had so many interesting stories to share and had a blast. I got back to my hotel a little drunk, at 12:30 am.

Read part 2 for my adventure to Niagara Falls, the rest of my trip, and my travel tips and learnings from this trip.

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Author: Chasing Wine and Waterfalls

Welcome to Chasing Wine and Waterfalls, a lifestyle site where you will get a little bit of everything. I started this blog as a creative outlet apart from my day job, which I was desperately craving during a bit of a rut shortly after I turned 26. On Chasing Wine and Waterfalls, you will find some travel stories and tips, NYC living, and probably a whole lot of complaining. Thanks for hanging out with me - grab a glass and stay a while.

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