(Last Updated On: October 31, 2020)

Three Weeks in North America

I’ve said it before and I’ll say it again – I am always in awe of how big and varied the USA actually is. I’ve been back four times now, but on this trip I managed to cross the northern border into Canada as well, making it my thirtieth country visited. The USA was actually the first ever international trip I ever went on when I spent time in New York City. Heading back again for three weeks in North America in winter allowed me to see a very different side of this part of the world.

In 2018, I visited Miami for the first time and in 2017 I spent time in Las Vegas, the Grand Canyon, California and New York City again. You can read my previous 2018 trip itinerary here.

This time around in 2019, I wasn’t alone. My boyfriend, Matt, and I hopped on a plane for our first ever holiday together, starting in Philadelphia before hitting up Washington DC, Chicago, Schomberg, Niagara Falls, Toronto, New York City and New Orleans. Three weeks in North America in winter was a wonderful way to start off the year with a bang.

Stop 1 – Philadelphia (2 days)

Philly has always been in the back of my mind as an awesome place to visit in the USA. Sure, it is the birthplace of the Declaration of Independence and there’s a whole heap of history and interest there on the formation of the United States of America, but Philadelphia is so much more than just the history. Under the surface, this town is a thriving foodie destination with eclectic street art and bars around almost every corner. I could eat at the city’s famous Reading Terminal Market for the rest of my life and be quite happy.

I spent two freezing cold winter days in Philly, but they were utterly perfect. I combined the history of the Liberty Bell, City Hall and Hall of Independence with the mosaic art of Philadelphia’s Magic Gardens, the creepiness of the decrepit Eastern State Penitentiary and the city’s best food found at Reading Terminal Market and the Italian Market.

Philadelphia Blog Posts:

Stop 2 – Washington DC (2 Days)

The political engine room of the USA, Washington DC is a beautifully and thoughtfully designed city that memorialises leaders of the past and celebrates American democracy. I spent two very busy days exploring the District of Columbia with a short sojourn over to Virginia to see Arlington National Cemetery as well. The more I learned about the layout of the city, the more amazing I found the geometrical planning of the region – many of the key monuments and memorials are designed to be in the sightline of each other and the memorials themselves are as grandiose and impressive.

My favourite memorial has to be the haunting Korean War memorial where grey statues of a US patrol lurk through the green bushes. On a beautiful day, the Jefferson memorial is also hard to top, with a beautiful rotunda overlooking the cherry tree lined Tidal Basin.


Washington DC Blog Posts:

Stop 3 – Chicago (3 Days)

Chicago has been top of my USA bucket list for a long time. There’s something magical about this city, even in the freezing cold depths of winter. In terms of beauty, I truly believe that Chicago is the most beautiful city in the United States and it also definitely has some of the best food I’ve tasted on my travels in America. I stayed around the Lakeshore area and seeing Lake Michigan frozen over was an incredible sight for an Aussie girl who has never seen a frozen lake in her life. 

Millennium Park was definitely a massive highlight, with the iconic Cloud Gate sculpture and an AV exhibit featuring diverse faces from around Chicago . The Rookery, a Frank Lloyd Wright designed building took my breath away with its opulent design and seeing Fleetwood Mac play at the United Centre on our last night in the city just made our time here even more special. 


Chicago Blog Posts

Stop 4 – Schomberg (1 Day)

Schomberg in Ontario, Canada, was a little off the beaten path compared to the other places we visited on this trip, but it had a super special sentimental reason. We stayed with Matt’s Maltese-Canadian family who he hadn’t seen for a long time and were able to pay a visit to his Nanu’s (Maltese for Grandpa) sister. Pair that up with the fact that we were able to go sledding on a neighbour’s hill and the town looked this pretty covered in fresh snowfall and that made our short but sweet Schomberg stop a very special one. Matt’s family are such a loving, welcoming family, so even though I was a stranger to them, they made me feel totally at home.


Schomberg Blog Posts:

Stop 5 – Niagara Falls (1 Day)

I’m such a sucker for a great waterfall that its hard to believe I’d never been to Niagara Falls in any of my previous trips to the USA. Luckily, Matt’s Canadian side of the family love the Falls and offered to take us there to see the amazing sight of a frozen wall of water, still miraculously gushing with force despite the frozen pool of water below. From the Canadian side of the falls, we were able to see the beauty of this incredible natural wonder and despite being frozen to our core, we didn’t mind at all because the sight of the Falls was so truly beautiful. I’d love to go back again when the Falls aren’t frozen to compare, but honestly, seeing them frozen and cloud-like was such a unique, special experience. 


Niagara Falls Blog Posts:

Stop 6 – Toronto (1.5 Days)

Toronto is such a great city. I absolutely loved the relaxed vibes, the snow covered streets and the love for food and street art everywhere we went. With only 24 hours in this Canadian city, Matt and I made the most of our time, heading up the CN Tower for birds-eye views of snow and ice, sampling poutine (hot chips with gravy and cheese curds), eating our body weight in Tim Horton’s doughnuts, wandering the amazing street art of Graffiti Alley and then finishing up at the gorgeous Victorian era Distillery District. We were here for a good time, not a long time, but I can truly vouch for the fact that we packed our 32 hours here to the max!


Toronto Blog Posts:

Stop 7 – New York City (5 Days)

I find it hard to visit the USA without adding in a stop in one of my favourite cities in the world, New York. This city heaves and thrives at all times, full of art, life, food and culture that is almost impossible to match. Every time I visit, there is something new to see or experience. This time around, I wasn’t alone and Matt and I were able to share our love for the city together. I’ve never visited in winter, so seeing Central Park transformed from its green splendour into a winter wonderland was mind-blowing. 

We also managed to win a Broadway ticket lottery, locate what we believe to be the best $1.50 hotdog stand in all of New York and eat all of the goodies at the Chelsea Market. I also ticked a couple of touristy things off my list too – would you believe in the three previous times I’ve visited NYC, I’d never seen the Statue of Liberty or walked over the Brooklyn Bridge?!


New York City Blog Posts:

Stop 8 – New Orleans (3 Days)

Another total bucket list item, New Orleans has been right up there with Chicago on my must-visit cities in the USA. I have to say, the incredible change of pace and scenery from New York to New Orleans really struck me. We went from freezing cold temperatures to a more tropical climate and for the first time in our trip we found ourselves wearing T-Shirts and jeans, rather than thermals, beanies and down jackets. New Orleans might be the most fun I’ve ever had in a city – the party vibes run strong here and music is everywhere. The southern-style Creole cooking is totally unique and unlike anything I’ve tasted anywhere else in the USA and several months later, I’m still craving a big cup of gumbo or red beans and rice.

Whether you’re a serious music-lover or just here to party, there is something for everyone in NOLA. The vibrancy and colour of this part of the US has me absolutely itching to get back and experience it all over again. This was the perfect end to our three weeks in North America.


New Orleans Blog Posts

There you have it. My full itinerary for my three weeks in North America in winter. Matt and I travelled together on our first big overseas trip, experiencing and sharing our love for different places across the US and Canada. We hit up some new places, some familiar and well-loved places and ticked some ultimate bucket list experiences off our list. Though we covered a lot of ground, we loved the itinerary we built – spending three weeks in North America when it was covered in snow was a really special experience.

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