8 days in Windsor, Essex & Pelee Island Itinerary

8 days in Windsor, Essex & Pelee Island Itinerary

Created using Inspirock Ontario route planner

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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

S M T W T F S
10
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17
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23

Windsor

— 1 night
Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
On the 10th (Sun), enjoy the sea views from Bois Blanc Island Lighthouse & Blockhouse, then stroll through Devonwood Conservation Area, and then visit a coastal fixture at Pelee Passage Lighthouse. On your second day here, see the interesting displays at Museum Windsor – Maison Francois Baby House, walk around Reaume Park, then stop by Via Italia, and finally admire the natural beauty at Bert Weeks Memorial Gardens.

For other places to visit, ratings, reviews, and other tourist information, read our Windsor road trip tool.

Toronto to Windsor is an approximately 3.5-hour combination of ferry and flight. You can also drive; or take a train. In October in Windsor, expect temperatures between 20°C during the day and 9°C at night. Finish up your sightseeing early on the 11th (Mon) so you can go by car to Essex.

Things to do in Windsor

Historic Sites · Parks · Neighborhoods · Wildlife

Side Trip

Find places to stay Oct 10 — 11:

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. Explore hidden gems such as Erie Shore Vineyard and Kingsville Golf & Country Club. Next up on the itinerary: learn about winemaking at Sanson Estate Winery, brush up on your knowledge of spirits at Wolfhead Distillery, see the interesting displays at John R. Park Homestead & Conservation Area, and relax in the rural setting at The Fruit Wagon.

To see other places to visit, ratings, and other tourist information, read Essex day trip tool.

Essex is very close to Windsor. In October in Essex, expect temperatures between 20°C during the day and 9°C at night. On the 16th (Sat), you'll travel to Pelee Island.

Things to do in Essex

Wineries · Outdoors · Golf · Museums

Side Trips

Find places to stay Oct 11 — 16:

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.
On the 16th (Sat), tour the pleasant surroundings at Lighthouse Point Provincial Nature Reserve and then stroll through Stone Road Alvar Nature Reserve.

To find where to stay, other places to visit, traveler tips, and tourist information, refer to the Pelee Island tour planning app.

Drive from Essex to Pelee Island in 2 hours. Traveling from Essex in October, plan for a bit warmer nights in Pelee Island, with lows around 14°C. Finish up your sightseeing early on the 16th (Sat) so you can go by car to Windsor.

Things to do in Pelee Island

Wildlife · Parks · Nature
Find places to stay Oct 16 — 17:

Windsor

— 1 night
Start off your visit on the 17th (Sun): stop by Whiskeyjack Boutique, then walk around Assumption Park, then make a trip to Sandwich First Baptist Church, and finally walk around Malden Park.

For where to stay, reviews, traveler tips, and other tourist information, go to the Windsor trip planner.

Drive from Pelee Island to Windsor in 2.5 hours. Traveling from Pelee Island in October, expect little chillier with lows of 9°C in Windsor. Finish your sightseeing early on the 17th (Sun) so you can travel back home.

Things to do in Windsor

Shopping · Parks · Historic Sites
Find places to stay Oct 16 — 17: