We originally planned to spend the month of September in Toronto and had booked and paid for a fabulous apartment between Queen Street West and King Street West back in January for our September stay.

September is a popular month to visit Toronto, with comfortable temperatures and bright blue skies in abundance. September is also when Toronto hosts one of the world’s most attended film festivals, the Toronto International Film Festival (TIFF). It would have been great – but the owner of the Airbnb canceled our booking in July and there were no good Airbnb options available for re-booking for the entire month of September, so we shortened our time in Montreal by a few days and opted for five days in Toronto.

We’d been to Toronto multiple times in the past – mostly in winter – so, what to do in Toronto for our abbreviated five days in late August? Shopping, baseball and enjoying the perfect weather!

View the Toronto photo gallery

Bargains in Toronto

We seemed to find bargains everywhere we turned in Toronto during our stay. Soon after checking into our apartment at the corner of Spadina and Front Street, we walked a few blocks over to King Street West, where we found the first of our bargains.

King Street West

One of the oldest streets in Toronto, King Street dates back to Toronto’s beginnings and today is home to boutiques, large retailers, home goods and décor stores, restaurants, theatres, bars, and hotels. On our early evening stroll down Kings Street West, we happened upon The Red Tomato Bar, a basement-level bar with a killer happy hour deal.

The Red Tomato Bar is downstairs below Fred’s Not Here. While the bar is located in the basement, the front of the building is open the upstairs and the street, allowing plenty of light and openness into the bar area. The reward for sitting at the bar – Tomato Hour prices. We each enjoyed Cosmopolitans from the $5 (2oz) martini options and a $5 personal (6″) mushroom pizza. The pizza was topped with King Oyster, Enoki, Shataki, and Crimini mushrooms, caramelized onions, Fior di Latte (cheese), and truffle essence. The pizza was good, the drinks tasty, and our 4 martinis and 2 pizzas came with a price tag of $30 CAD, the equivalent of only about $24 USD. What a deal!

After dinner, we did a bit of browsing in the stores along King Street and stopped in an outdoor retailer with a “Retiring/Going out of Business” sale. The entire store was 40% off – everything included, with no exclusions. It was at this spot we were also reminded that Toronto has 13% sales tax, so purchasing decisions took on a bit of a math exercise. In other words… take the price of the item, calculate the price with the discount, add on the anticipated tax, calculate the exchange rate, and then evaluate if a better deal could possibly be had in the U.S. or Europe. Since some outdoor brands and/or items are rarely discounted, we found a few items we felt made the conversion rate+tax cut and were worth the limited space in our bags.

The next evening we once again found ourselves on King Street West for happy hour and this time found a martini deal at the swanky Luma on the 2nd floor of the TIFF Bell Lightbox. Luma holds Magic Hour every day (we were there on a Saturday) from 4 pm to 9 pm with $6 martinis and Manhattans (2 oz). We opted for a couple of classic martinis each and shared chips and dip and mixed nuts for $5 each for munching. Total: $34 CAD or about $27 USD.

Queen Street West

Queen Street West is a trendy district filled with boutiques, galleries, restaurants, bars, and a fabulous spot to spend an afternoon. On our visit to the neighborhood, we stopped for lunch in b.good, which sources local, fresh ingredients for its offerings. We opted for the house-made veggie burger with mushrooms, caramelized onions, smoked gouda, and bbq sauce and a power bowl, with kale marinated in lemon, canola oil, and Kosher salt, carrots, Brussel sprouts, roasted chickpeas, pepitas and topped with tomato vinaigrette and a local egg. Both were delicious and the flavors in the power bowl were amazing – great food and it didn’t break the bank.

After lunch, we shopped Queen Street West down to Trinity Bellwoods Park, then looped back the other side to Spadina. Along the way in the West Queen Street West section, we found an incredible sale in a clever little boutique named Logan & Finley. Already discounted items had an additional 20% off and we picked up Prana and Woolrich items at deep discounts – one of the Woolrich tops had a regular price of $45 and we got it for $8 CAD.

Uptown Yonge

While we’d found some great bargains, we were still in search of a good deal on a couple of waterproof shells. A bit of research turned up Sporting Life in the Uptown Yonge district that looked like they had a good selection of outdoor apparel. We hailed an Uber and headed north.

A good selection of outdoor equipment was an understatement and the best bargains of the trip were quickly uncovered. We picked up a Canada Goose black label waterproof shell and a Fjällräven waterproof shell, each for 50% off.

Bargains purchased, we strolled back towards downtown reveling in our good finds until we reached Terroni at Yonge and Price in Rosedale and decided we’d saved enough with our bargains to splurge a little. Terroni had been recommended to us by a friend so we headed in for a couple of Aperol spritz and some appetizers. Great bar, excellent food and they have a rooftop patio with views of downtown Toronto.

And, now for some baseball: Bluejays vs. Redsox

Our apartment was about a block from Rogers Centre, making it extremely convenient for catching a ballgame – and we caught two while the Redsox were in town.

Originally named the SkyDome, the Rogers Centre is located in downtown Toronto near the northern shore of Lake Ontario and next to the CN Tower. It has been the home of the Toronto Bluejays since June 5, 1989, and was the first stadium with a fully retractable roof. The roof is closed if the temperature is forecasted to be below 10° C/50° F, if the wind is predicted to be in excess of 64 km/hr, or if the risk of rain at start time is 75% or greater.

Game 1 was on a Monday evening. Monday was the one day out of five that was cloudy most of the day and, even though rain wasn’t in the forecast, I must confess I was hoping a few showers might come through so we could see the roof close. Didn’t happen.

The Redsox had been in a bit of a slump before arriving in Toronto having lost their last four games. The pitching matchup was Pomeranz for Boston and Stroman for Toronto and the over 35,000 fans showed up to cheer on their teams (ok, it was almost all Toronto fans, so team). The game went down to the wire, but in the end, Boston was victorious, winning 6-5.

On Tuesday, Sale took the mound for the Redsox and Anderon for the Bluejays. The Redsox once again took the win 3-0. It once again was a great game on a beautiful evening and Greg Hull evening walked away with a souvenir.

Toronto in Late Summer: Know before you go

Temperature. The average high temperature in Toronto in August is 75°F / 24°C and in September is 72°F / 22°C. Bring a sweater or a jacket and dress in layers in the evening as the average low in August is 63°F / 17°C and in September is 55°F / 13°C.

Rainfall. Rainfall in August and September averages 40mm-50mm, compared to the rainiest month of July at 60mm.

Bring the sunscreen. Toronto averages 9 hours of sunshine per day in August and 8 hours in September.

Getting to Toronto. Toronto has two airports – Toronto Pearson International Airport and Billy Bishop Toronto City Airport. If arriving by train, Union Station is conveniently located in the middle of downtown.

Back to top

Disclosure & disclaimer: The opinions expressed are entirely our own. Reviews are based only on our assessment and we accept no responsibility for how the information is used. We do not accept paid posts although some posts may contain information regarding businesses where we have previously been compensated