8 days in Windsor, Essex & Pelee Island Itinerary

8 days in Windsor, Essex & Pelee Island Itinerary

Created using Inspirock Ontario trip itinerary maker

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Make it your trip
Ferry to Billy Bishop Toronto City, Fly to Windsor
1
Windsor
— 1 night
Drive
2
Essex
— 5 nights
Drive
3
Pelee Island
Drive
4
Windsor
— 1 night
Fly to Billy Bishop Toronto City, Ferry to Toronto

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Windsor

— 1 night
Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
Start off your visit on the 3rd (Sun): trek along Devonwood Conservation Area, then buy something for everyone on your list at Windsor Crossing Premium Outlets, and then examine the collection at Museum Windsor – Maison Francois Baby House. On your second day here, take in nature's colorful creations at Dieppe Gardens, then take a stroll through Via Italia, and then make a trip to Windsor Riverfront.

For reviews, photos, other places to visit, and other tourist information, use the Windsor route builder website.

Toronto to Windsor is an approximately 3.5-hour combination of ferry and flight. You can also drive; or take a train. October in Windsor sees daily highs of 20°C and lows of 9°C at night. Finish up your sightseeing early on the 4th (Mon) so you can go by car to Essex.

Things to do in Windsor

Shopping · Neighborhoods · Parks · Wildlife

Side Trip

Find places to stay Oct 3 — 4:

Essex

— 5 nights
Essex is a town with a population of 20,427 in Essex County in southwestern Ontario, Canada, whose municipal borders extend to Lake Erie. You'll discover tucked-away gems like Erie Shore Vineyard and John R. Park Homestead & Conservation Area. Colio Estate Winery and Amherstburg Freedom Museum are good opportunities to explore the local culture. There's lots more to do: do a tasting at Sanson Estate Winery, stop by Old Dutch Guys Chocolate, get a taste of the local shopping with Chiaroscuro, and look for all kinds of wild species at Holiday Beach Conservation Area.

For more things to do, maps, and more tourist information, read our Essex vacation planner.

Essex is just a short distance from Windsor. In October in Essex, expect temperatures between 20°C during the day and 9°C at night. On the 9th (Sat), you'll travel to Pelee Island.

Things to do in Essex

Wineries · Museums · Shopping · Wildlife

Side Trips

Find places to stay Oct 4 — 9:

Pelee Island

A vacation on Pelee Island allows you to get away from it all as well as to satisfy your appetite for adventure in beautiful natural surroundings.
Start off your visit on the 9th (Sat): tour the pleasant surroundings at Lighthouse Point Provincial Nature Reserve and then explore the striking landscape at Stone Road Alvar Nature Reserve.

To see photos, traveler tips, where to stay, and other tourist information, read our Pelee Island travel route planner.

Drive from Essex to Pelee Island in 2 hours. Expect somewhat warmer evenings in Pelee Island when traveling from Essex in October, with lows around 14°C. Finish your sightseeing early on the 9th (Sat) to allow enough time to drive to Windsor.

Things to do in Pelee Island

Wildlife · Parks · Nature
Find places to stay Oct 9 — 10:

Windsor

— 1 night
Kick off your visit on the 10th (Sun): stop by Whiskeyjack Boutique, then grab your bike and head to Ganatchio Trai, and then walk around Reaume Park.

To see where to stay, reviews, photos, and other tourist information, go to the Windsor journey builder.

Traveling by car from Pelee Island to Windsor takes 2.5 hours. Expect slightly colder evenings in Windsor when traveling from Pelee Island in October, with lows around 9°C. Cap off your sightseeing on the 10th (Sun) early enough to travel back home.

Things to do in Windsor

Parks · Outdoors · Trails · Shopping
Find places to stay Oct 9 — 10: