5 days in Windsor, Essex & Pelee Island Itinerary

5 days in Windsor, Essex & Pelee Island Itinerary

Created using Inspirock Ontario route builder

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

S M T W T F S
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Windsor

Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
Kick off your visit on the 3rd (Sun): don't miss a visit to Windsor Riverfront.

For ratings, more things to do, maps, and other tourist information, read Windsor trip maker website.

Toronto to Windsor is an approximately 3.5-hour combination of ferry and flight. You can also drive; or take a train. In October, daytime highs in Windsor are 20°C, while nighttime lows are 9°C. On the 3rd (Sun), wrap the sightseeing up by early afternoon so you can drive to Essex.
Find places to stay Oct 3 — 4:
Highlights from your trip

Essex

— 2 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. Kick off your visit on the 3rd (Sun): take an in-depth tour of Canadian Transportation Museum & Heritage Village, do a tasting at Sprucewood Shores Estate Winery, and then don't miss a visit to Historic Essex Railway Station. On the 4th (Mon), you'll have a packed day of sightseeing: explore the wealth of natural beauty at Point Pelee National Park, then pick up some local products at Lee and Maria's, then learn about winemaking at Viewpointe Estate Winery, and finally learn about winemaking at North 42 Degrees Estate Winery & Bistro 42.

For reviews, photos, ratings, and other tourist information, you can read our Essex vacation planning tool.

Essex is very close to Windsor. In October, daily temperatures in Essex can reach 20°C, while at night they dip to 9°C. Wrap up your sightseeing by early afternoon on the 5th (Tue) to allow time for the car ride to Pelee Island.

Things to do in Essex

Wineries · Museums · Shopping · Parks

Side Trips

Find places to stay Oct 3 — 5:

Pelee Island

— 1 night
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.
To find out how to plan a trip to Pelee Island, use our trip itinerary maker.

Drive from Essex to Pelee Island in 2 hours. Expect a bit warmer evenings in Pelee Island when traveling from Essex in October, with lows around 14°C. Cap off your sightseeing on the 6th (Wed) early enough to go by car to Windsor.

Things to do in Pelee Island

Parks · Wildlife · Nature · Wineries
Find places to stay Oct 5 — 6:

Windsor

— 1 night
Start off your visit on the 7th (Thu): appreciate the extensive heritage of Olde Walkerville Neighborhood, indulge your taste buds at Food & Drink, then deepen your understanding at Ojibway Nature Centre, then stroll around Assumption Park, and finally take in nature's colorful creations at Dieppe Gardens.

To see traveler tips, other places to visit, maps, and tourist information, you can read our Windsor trip planner.

Traveling by car from Pelee Island to Windsor takes 2.5 hours. Plan for little chillier nights when traveling from Pelee Island in October since evenings lows in Windsor dip to 9°C. Wrap up your sightseeing on the 7th (Thu) early enough to travel back home.

Things to do in Windsor

Historic Sites · Breweries & Distilleries · Tours · Parks
Find places to stay Oct 6 — 7: