10 days in Windsor & Leamington Itinerary

10 days in Windsor & Leamington Itinerary

Created using Inspirock Ontario itinerary planner
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Make it your trip
Ferry to Billy Bishop Toronto City, Fly to Windsor
1
Windsor
— 4 nights
Drive
2
Leamington
— 5 nights
Fly to Billy Bishop Toronto City, Ferry to Toronto

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Windsor — 4 nights

Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
Get some cultural insight at Olde Walkerville Neighborhood and Canadian Aviation Museum. Popular historic sites such as Willistead Manor and Sandwich First Baptist Church are in your itinerary. Explore Windsor's surroundings by going to Amherstburg (Amherstburg Freedom Museum, Amherstburg Navy Yard National Historic Site, &more). And it doesn't end there: make a trip to Windsor Riverfront, do a tasting at Sanson Estate Winery, indulge your thirst for a good beer at Walkerville Brewery, and get engrossed in the history at Mackenzie Hall.

For other places to visit, more things to do, ratings, and other tourist information, use the Windsor attractions planner.

Toronto to Windsor is an approximately 3.5-hour combination of ferry and flight. You can also drive; or take a train. In October, plan for daily highs up to 20°C, and evening lows to 9°C. Finish up your sightseeing early on the 24th (Mon) so you can go by car to Leamington.
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Historic Sites · Parks · Museums · Breweries & Distilleries
Side Trip
Find places to stay Oct 20 — 24:

Leamington — 5 nights

Leamington is a municipality in Essex County, Ontario, Canada. Your cultural itinerary includes sights like Oxley Estate Winery and Cooper's Hawk Vineyards and The Vines Restaurant. You'll find plenty of places to visit near Leamington: Harrow (Colchester Ridge Estate Winery, Viewpointe Estate Winery, &more). The adventure continues: explore the wealth of natural beauty at Point Pelee National Park, pick up some local products at Lee and Maria's, learn about winemaking at Colio Estate Winery, and indulge your senses at Grape Vine Tours.

To find ratings, maps, where to stay, and more tourist information, read our Leamington route planner.

You can drive from Windsor to Leamington in an hour. Another option is to take a bus. October in Leamington sees daily highs of 19°C and lows of 11°C at night. Cap off your sightseeing on the 29th (Sat) early enough to travel back home.
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Wineries · Parks · Tours · Museums
Side Trips
Find places to stay Oct 24 — 29: