Canada – Ontario: Toronto & Windsor


Transportation: VIA Rail

Two of my friends and I took Canada’s VIA Rail from Windsor, Ontario to Toronto, Ontario. We sat in Business Class, and it was really nice! They served us bagels and drinks for breakfast, and for lunch we were able to choose from chicken, fish, or pasta. We brought some champagne on the train and made mimosas. It was a really fun way to begin our trip. Once we were in the city, we walked everywhere or used Uber.


Hotel: Renaissance Toronto Downtown Hotel

We stayed at the Renaissance Toronto Downtown hotel, which was in a great location right in the middle of downtown Toronto. The hotel was renovated, and the rooms were really nice, large, and very clean.



The Toronto Blue Jay’s stadium is connected to the hotel, and the Blue Jay’s happened to be playing the Los Angeles Dodgers on Friday and Saturday while we were there. We could watch the game from our hotel lobby, which was really cool!


Kensington Market Food Tour

The first day we were in the city, we took a Tasty Tours private food tour in the multi-cultural Kensington Market. The market has eclectic shops, cafes, victorian houses, and other attractions from a variety of cultures: French, Vietnamese, Chinese, Parisian, Thai, Canadian, American, etc. The tour was only $49CAD per person, and we stopped at 10 different places in the market.



Graffiti Alley

Graffiti Alley in The Fashion District runs south of Queen Street West from Spadina Avenue to Portland Street. There is graffiti art on every wall all along the alley in very vibrant colors. It is really beautiful and unique to walk along.

Queen Street 

Queen Street is a great place to walk with a very good selection of retail stores, little boutiques, restaurants, and bars. We stopped at a very cute Mexican restaurant and sat outside on the patio and ordered a pitcher Margaritas; it were very well priced.

Cabana Pool Bar

Cabana Pool Bar is a large outdoor pool bar with a pool and multiple cabanas, and some lawn games such as ping pong, bags, etc. The crowd is younger, and they play really fun music. We came on a Friday, so it was not super busy, which was really nice. Apparently the place is super packed on Saturday’s and Sunday’s. We grabbed a large shaded table and ordered some drinks and food and hung out. It was a great way to spend a Friday.




Wine Tours Toronto – Private Wine Tasting Tour

We booked the Urban Bachelorette tour, and we had a private bus that picked 12 of us up from downtown Toronto and brought us to Whitchurch-Stouffville. We worked with Lou on booking the tour, and he was very helpful and responsive. Our driver’s name was Dougall, and he was a great driver, and was willing to do anything to make us happy and have fun. He brought pastries and coffee / tea / water bottles for us when he picked us up. The tour visited two wineries in the greater Toronto Area (GTA).


Gallucci Winery

First, we visited the Gallucci Winery, which is known for their iced wines. Iced wine is where they make wine from a frozen grapes, so it is more expensive because they need more grapes to produce the same amount of wine. We were able to enjoy a tour of the vineyard’s property and wine making facilities, and we ended the tour with a wine tasting of 6 wines and cheese pairing. The grounds include a beautiful Italian inspired tasting room, a green house, the owners house, and a beautiful garden / gazebo. 

Applewood Farm Winery

Second, we visited this very cute little rustic fruit wine and cider producer. We tasted a variety of fruit wines and cidars, and then we bought some drinks and enjoyed them outside in front of the very cute barn tasting room.

Nathan Phillips Square 

On our way back to Toronto from the Wine Tour, we stopped by the City Hall and Nathan Philips Square, and we took a photo in front of the large and colorful Toronto sign. It was very busy there, but I am happy we stopped by to check it out.


Toronto Restaurants 

Kasa Moto

Kasa Moto is located in Yorkville, which is a really cute and fancy part of town. There are many boutiques and shops in the neighborhood. Kasa Moto is a very fun and hip contemporary Japanese restaurant and lounge, and we reserved a table on the rooftop, which had such a fun vibe with good music playing, and relaxing seating all around. There were many very good looking people at the restaurant. We had shots sent to us from some men at a table as well as the bartenders. I would highly recommend checking this place out if you are interested in dressing up a little fancy and enjoying some sushi.


Cactus Club Cafe

Very trendy and chic restaurant with multiple levels. We had a reservation on the 2nd level where we ate at a large table. Everyone loved everything that we ordered. The portions were large and reasonably priced. My fiancé had ordered us bottles of prosecco and rose, which was so nice! After we finished eating, our waiter moved us to a booth upstairs on their rooftop. The rooftop is a really fun environment with hip music, and lots of drinks. We really loved the restaurant.


Insomnia Restaurant and Lounge

We ate at Insomnia for dinner, and it was a really cute trendy spot. They have a lot of different table options: cozy chairs and couches in the back, high and low tables, and bar seating. They set up some large low tables in the front for us. The staff was so nice and friendly. One of my friends ordered a drink and they ran out of one of the ingredients, and the manager ran to the store down the street to buy it for them.


Pizzeria Libretto King West

Fun pizza joint with many different options of types of pizza. They start you off with awesome bread and oil before serving you your pizza. I would highly recommend checking it out if you’re in the mood for pizza.

Toronto Drink Spots

Thompson Hotel Rooftop

At the Thompson Hotel, they have a really beautiful rooftop bar. We visited the Thompson rooftop bar, where the drinks were nice and the view was amazing! Luckily for us, a gentleman bought us some shots and drinks, so we did not have to pay, but the drinks were really expensive. It is worth checking out for the view!


Right next to the Thompson Hotel was the Wildflower club. We were able to get in free, and we had a great time dancing the night away here. We met a bachelor party that had bottle service, and they invited us to join their table. They brought the bottles out with sparklers. It was a really fun time.


One of the nights we stopped by this secretive bar, which is on the upper level of Baro. They have a cool neon sign there that says ‘Pablo loves you’.


Growing up in metro-Detroit, we visited Windsor often once we turned 19 years old since the drinking age in Canada is 19. Some of our favorite bars were Voodoo Nightclub and the Boom Boom Room. The bars used to send us a limo or bus to bring us all over to Canada for free as long as we stayed at their bar all night. It was perfect for us because we didn’t have to worry about rides. One time we visited, I met Benni Benassi!


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