Toronto in winter

I’ve been wanting to travel with our kids over New Year’s Eve for a few years now, and this year we finally made it happen! Toronto was on our short list of cities due to it’s proximity to Chicago—only a 90 minute flight!—and coolness factor. Once we saw affordable flights this fall we booked it! Reasons we loved this city and vacation:

Toronto was walkable, safe, and had great public transport. We easily learned the trolley system while we were there.
The food scene was lit! So much variety and food everywhere!
Plenty to do inside and out!

I’m going to share our itinerary with you for easy planning in case you want to duplicate our trip. For your reference, our kids are 15, 13, and 12 at the time of travel. And my intention for this vacation was to have equal amounts of relaxing and activities. I typically plan more activities than this, but I was going for RESTFUL. And it totally was.

Itinerary

Day 1:

We flew to Toronto from Chicago O’Hare. It was a super short 90 minute flight. We arrived around 5:30 pm and made our way to our AirBNB. It was perfect for our family! The area was in great proximity to everything, including restaurants and a little supermarket. There was even an Orange Theory about a mile away that we worked out at once. The only thing we didn’t love about our house was that there wasn’t a bathroom on the main floor (or the lower level) where two of our kids slept. This worked just fine for us, but it would have been challenging with little ones or with older adults who aren’t comfortable with stairs. Just something to be aware of. This is the house we booked. The communication was wonderful throughout and we had everything we needed to be cozy all week. Highly recommend.

After arriving and getting settled, we walked to a nearby restaurant. I won’t link it because it wasn’t sensational, but just wait for my link to the best NYE dinner ever!!

Day 2:

We all slept in and that was heavenly!! Chris and Owen walked to get a few grocery items for the week like milk and cereal and bread, and also picked up some pastries and coffee from a little bakery down the road. Once we were all ready we headed to the mall. This isn’t like any regular mall; this is THE MALL you want to go to! It’s called the CF Toronto Eaton Centre. We walked most of the way and took the trolley for part of it. The trolley was super easy to use; you hop on, swipe your credit card, stay on as long as you want, and hop off when you get close to/to your destination.

If all malls had food like this, I would have no money because I would be at the mall 24/7

Before shopping we headed to the food court. And again, this was not just any old food court with greasy, sub par food. This was the food court of my dreams. Have you ever been to Food Life in Chicago’s Watertower? This was super similar, but even better! Every type of food you can imagine was being freshly prepared within a fairly small area, so each member of the family can choose what they want for lunch. There was sushi, crepes, chicken, bbq, pizza, mediterranean, salads, pasta, and more. I passed money out to the kids and held our table while I decided on my stop. I eneded up at the salad/protein bar and it was SO DELICIOUS!

After eating we shopped! The girls and I found some awesome stores and fun fact, you pay the Canadian prices while you’re there, but later on your cc statement, you only actually pay the USD price! So it’s bascially like MAKING money (girl math!).

Once back at home, we rested (glorious!) and got ready for our New Year’s Eve dinner. We decided to go way fancier than we normally do and Uber to the restaurant. This was a great choice for us!

Shown here are our happy kids after shopping, my fancy outfit for dinner, and cute Mia and Chris at Enoteca Sociale!

We dined at Enoteca Sociale and it was perfection! The ambiance was intimate and warm. The servers were attentive and even worked with our pickiest eater to find a new favorite dish (gnochi!). And the food was delicous!! They have even been awarded a Michelin Star of distinction award! We all agreed that this dinner was a highlight of the trip for us. And get this: the cocktail Chris ordered (an Old Fashioned of some sort) came with a tiny bottle of cologne because they pair so well together!! Can you even?!! We were smitten and you will be too!

After coming home and wathcing a movie-literally WHO am I staying up this late?!-Chris convinced me to walk downtown to see the fireworks for NYE!! It was cold and rainy this night and I was very cozy in my jams, but I’m so glad he pushed me to do this! The kids chose to stay home and we walked the short 1 mile walk to the harbor and counted down the year with perfect strangers. It was an amazing day.

Day 3:

This was New Year’s Day! And OMG Chris and I slept until 10:30!!!! I don’t even know who I am at this point, but my body was loving the extra sleep. Once I got up and around I started on my 2025 Vision Board! I brought all the stuff with me to make this, much to Chris’s chagrin(!!), but I’m so glad I did. This ended up being a highlight for me (and maybe the kids too, although they likely won’t admit to that!) and was the perfect way to spend part of New Year’s Day. I purchased a “vision board clip art book” from Amazon, some 12 x 12 canvases, mod podge, foam brushes for spreading the mod podge, scissors, and some Elmer’s glue. They only took up a small bit of real estate in our luggage. After cutting out pictures for our vision boards, we glued them on and then spread mod podge on the whole thing to make it glossy. IT WAS SO FUN. The kids loved theirs too and talking about our goals and visions for 2025 was special.

P.S. The girls have their boards prominently displayed in their rooms now, so I know they enjoyed this project! Owen’s is in his room too, and “displayed” as a boy displays things, haha.

Later that day we headed out to go ice skating! Skating at an outdoor rink was a first for all of us and I was nervous about being too cold, but honestly, it was so fun! We were super bundled up and you do get some heat going from the movement. Our goal was to skate for an hour and that was perfect for us. Check out that picture! We were able to stay until it got dark and all of the holiday lights surrounded us. Beautiful!

For dinner, we walked down the road and happened upon the coolest dining experience! It’s a Japanese restaurant called Gyubee. You set around a grill and order your meats, vegetables, soups, noodles, accouchements, etc. and then you get cooking. The thin, marinated strips of beef were my favorite! You can eat them by themselves or use the lettuce to make wraps. I loved the sauces available, bean sprouts, mushrooms, miso soup, and noodles. It was an activity AND a delicious meal!

Day 4:

One of our favorite things to do when traveling to a new city is to book a food tour. It’s a great way to learn more about the culture, get some steps in, and try foods you might not even know to try. This is the food tour I booked and it was great! We met at 11 and ate our way around Toronto until 2 ish. Some of the things on our tour included: smoked salmon bites, a butter tart (insane!!), pizza, butter chicken (my favorite!), a pea meal bacon sandwich, and more.

We were full for hours and probably could have skipped dinner, but we walked down the street from our Airbnb to a local pub. Can you tell that we like eating??! LOL

Day 5:

On our last full day we booked a tour to see Niagara Falls! It’s about a 1.5 hour drive from Toronto and since we didn’t book a car, a tour was a great option. Before we left, we grabbed brunch at a super cute and delicious spot called The Morning After. And pro tip from parents of teens: to keep meals out enjoyable, try playing 20 questions or asking trivia questions from your phone. Our kids love this and it always helps keep attitudes at bay and gives some structure to what might otherwise feel like a frustrating conversation. We laughed and laughed during this brunch.

On the way there we stopped for a maple syrup tasting (did you know that Canada and the US are the only countries that produce maple syrup?!) and purchased some to take home. We got to the Falls a little bit later and went to something called Journey of the Falls. It allows you to walk BEHIND the Falls and take some pictures. It was cool and COLD, but honestly, I’m not sure I recommend for the money. I did really enjoy the high quality gift shop afterwords, where I purchased my Canada hat.

After the Journey of the Falls, we walked about a mile along the walkway that borders the Falls. It was stunning, but we were freezing! It was an unseasonably cold day there apparently. And because this tour boasted views of the lit up Falls at night, we had several hours to kill before it got dark. We found a brewery to eat a late lunch and kill some time because guys, the town that Niagara Falls is in is quite tacky. If you love Putt Putt and Ripley’s Believe it or Not Museums and haunted houses, you will LOVE this town. But that is not our idea of a good time, LOL, and it was too cold to simply keep walking around. After eating and grabbing coffee, we walked BACK to the Falls to see it at night with the LIGHTS. This is something they do in the winter via a light projector and it was stunning. So while the day was long, and COLD, it feels worth it to see the Falls lit up like that at night.

If I had this day to do again, I think I would hire a private driver to take us up and back. That way, we wouldn’t have to wait for the entire group and kill time. But our tour guide was lovely, the bus was super comfortable, and we didn’t have to make any decisions. I will link the tour we did in case you’re interested!

Our trip to Toronto was relaxing, fun, delicious, and adventurous. It is a great city and we will all have awesome winter memories from visiting. I highly recommend adding it to your list! Reach out if you have any questions when planning your trip to Toronto! XO

Rome and Florence