2 days in Windsor & Kingsville Itinerary

Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.

For where to stay, maps, photos, and other tourist information, read our Windsor travel route builder website.

Calgary to Windsor is an approximately 7-hour flight. You can also drive; or do a combination of bus, car, and train. You'll lose 2 hours traveling from Calgary to Windsor due to the time zone difference. Prepare for a bit warmer weather when traveling from Calgary in October: high temperatures in Windsor hover around 20°C and lows are around 9°C. You will leave for Kingsville on the 9th (Fri).

Kingsville is located in Essex County in southwestern Ontario, Canada, and is Canada's southernmost municipality with town status. Kick off your visit on the 9th (Fri): stop by Old Dutch Guys Chocolate, then do a tasting at Viewpointe Estate Winery, then learn about winemaking at Oxley Estate Winery, and finally learn about winemaking at Cooper's Hawk Vineyards and The Vines Restaurant. Get ready for a full day of sightseeing on the next day: explore the wealth of natural beauty at Point Pelee National Park.

To find more things to do, maps, traveler tips, and tourist information, go to the Kingsville trip maker.

Getting from Windsor to Kingsville by car takes about an hour. In October, daily temperatures in Kingsville can reach 19°C, while at night they dip to 9°C. Wrap up your sightseeing on the 10th (Sat) to allow time to travel back home.