33 days in Toronto, Oshawa & Windsor Itinerary

33 days in Toronto, Oshawa & Windsor Itinerary

Created using Inspirock Ontario holiday planner

Make it your trip
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Toronto
— 15 nights
Drive
2
Oshawa
— 9 nights
Fly
3
Windsor
— 8 nights
Fly to Billy Bishop Toronto City, Ferry to Toronto

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Toronto

— 15 nights

New York City of Canada

Possibly the world's most diverse city, Toronto houses over 80 ethnic communities speaking nearly 150 different languages or dialects.
Get out of town with these interesting Toronto side-trips: Niagara Falls (Bird Kingdom, Journey Behind the Falls, &more) and Niagara-on-the-Lake (Memorial Clock Tower of Niagara On The Lake, Niagara College Teaching Brewery, &more). There's still lots to do: take in panoramic vistas at CN Tower, examine the collection at Hockey Hall of Fame, browse the eclectic array of goods at St. Lawrence Market, and get up close and personal with brilliant marine life at Ripley's Aquarium of Canada.

Plan a Toronto trip in moments using our itinerary builder.

Use the Route module to find travel options from your starting location to Toronto. In June, daily temperatures in Toronto can reach 27°C, while at night they dip to 17°C. You'll have a few hours on the 19th (Sat) to wrap things up before traveling to Oshawa.

Things to do in Toronto

Parks · Museums · Historic Sites · Nature

Side Trips

Oshawa

— 9 nights
Oshawa is a city in Ontario, Canada, on the Lake Ontario shoreline. Get out of town with these interesting Oshawa side-trips: Willow Springs Winery (in Whitchurch-Stouffville), Peterborough (Peterborough Lift Lock & Peterborough-Lakefield Rotary Greenway Trail) and Trenton (Trenton Greenbelt Conservation Area & National Air Force Museum of Canada). There's still lots to do: head outdoors with Joe Ford Fishing and Outdoors, tee off at Bunker Hill Golf Course, stroll around Lakeview Park, and view the masterpieces at L'Artisan Gallery and Boutique.

To see more things to do, ratings, reviews, and tourist information, use the Oshawa trip planner.

Getting from Toronto to Oshawa by car takes about an hour. Other options: take a train; or take a bus. Expect a daytime high around 26°C in June, and nighttime lows around 15°C. Finish your sightseeing early on the 28th (Mon) so you can fly to Windsor.

Things to do in Oshawa

Parks · Outdoors · Wildlife · Nature

Side Trips

Windsor

— 8 nights
Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
Change things up with these side-trips from Windsor: Sarnia (Artopia Gallery & Framing, Stones 'N Bones Museum, &more), Kingsville (Canadian Transportation Museum & Heritage Village, Aleksander Estate Winery, &more) and Chatham (Buxton National Historic Site & Museum, Kingston Park, &more). There's still lots to do: steep yourself in history at Willistead Manor, do a tasting at Oxley Estate Winery, get engrossed in the history at Mackenzie Hall, and explore the striking landscape of Point Pelee National Park.

To find maps, photos, where to stay, and more tourist information, refer to the Windsor trip itinerary builder website.

Fly from Oshawa to Windsor in 2.5 hours. Alternatively, you can drive; or take a train. When traveling from Oshawa in June, plan for a bit warmer days in Windsor, with highs around 30°C, while nights are about the same with lows around 17°C. Finish your sightseeing early on the 6th (Tue) so you can travel back home.

Things to do in Windsor

Parks · Museums · Wineries · Outdoors

Side Trips