10 days in Windsor & Leamington Itinerary

Created using Inspirock Ontario itinerary planner
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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 Bois Blanc Island Lighthouse & Blockhouse. 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). There's lots more to do: don't miss a visit to Windsor Riverfront, wander the streets of Via Italia, learn about winemaking at Vivace Estate Winery, and examine the collection at Canadian Aviation Museum.

For where to stay, more things to do, other places to visit, and other tourist information, read Windsor itinerary 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 your sightseeing early on the 24th (Mon) to allow enough time to drive 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: