5 days in Kingsville & Windsor Itinerary

5 days in Kingsville & Windsor Itinerary

Created using Inspirock Ontario trip itinerary maker

Make it your trip
Drive
1
Kingsville
— 2 nights
Drive
2
Windsor
— 2 nights
Fly to Billy Bishop Toronto City, Ferry to Toronto

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Kingsville

— 2 nights
Kingsville is located in Essex County in southwestern Ontario, Canada, and is Canada's southernmost municipality with town status. Kingsville is known for fun & games, wineries, and shopping. Your trip includes some of its best attractions: explore the striking landscape of Point Pelee National Park, do a tasting at Aleksander Estate Winery, get engrossed in the history at Canadian Transportation Museum & Heritage Village, and pick up some local products at Lee and Maria's.

For other places to visit, traveler tips, ratings, and other tourist information, go to the Kingsville trip planner.

Toronto to Kingsville is an approximately 4-hour car ride. Expect a daytime high around 19°C in October, and nighttime lows around 9°C. Wrap up your sightseeing on the 25th (Mon) to allow time to drive to Windsor.

Things to do in Kingsville

Wineries · Shopping · Museums · Nature

Side Trips

Find places to stay Oct 23 — 25:

Windsor

— 2 nights
Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
Start off your visit on the 26th (Tue): see the interesting displays at Canadian Aviation Museum, deepen your understanding at Ojibway Nature Centre, then don't miss a visit to Windsor Riverfront, and finally wander the streets of Via Italia. Get ready for a full day of sightseeing on the next day: stroll around Jackson Park, learn insider's secrets on a distillery tour, appreciate the extensive heritage of Olde Walkerville Neighborhood, then sample the tasty concoctions at Walkerville Brewery, and finally admire the natural beauty at Dieppe Gardens.

To find photos, where to stay, more things to do, and other tourist information, you can read our Windsor journey planning website.

Traveling by car from Kingsville to Windsor takes an hour. Expect a daytime high around 20°C in October, and nighttime lows around 9°C. Finish your sightseeing early on the 27th (Wed) to allow enough time to travel back home.

Things to do in Windsor

Breweries & Distilleries · Historic Sites · Museums · Neighborhoods
Find places to stay Oct 25 — 27: