8 days in Essex, Pelee Island & Windsor Itinerary

8 days in Essex, Pelee Island & Windsor Itinerary

Created using Inspirock Ontario route planner

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

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Essex

— 4 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. Your cultural itinerary includes sights like Oxley Estate Winery and Cooper's Hawk Vineyards and The Vines Restaurant. For shopping fun, head to Cindy's Home & Garden or Lee and Maria's. There's lots more to do: explore the striking landscape of Point Pelee National Park, do a tasting at Sprucewood Shores Estate Winery, take an in-depth tour of Canadian Transportation Museum & Heritage Village, and make a trip to Historic Essex Railway Station.

To find where to stay, photos, maps, and other tourist information, read Essex tour itinerary maker tool.

Toronto to Essex is an approximately 3.5-hour car ride. In September in Essex, expect temperatures between 27°C during the day and 15°C at night. On the 13th (Mon), you're off to Pelee Island.

Things to do in Essex

Wineries · Shopping · Museums · Nature

Side Trips

Find places to stay Sep 9 — 13:

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 13th (Mon): stroll through Fish Point Nature Reserve and then stroll through Lighthouse Point Provincial Nature Reserve.

For more things to do, ratings, photos, and tourist information, use the Pelee Island trip itinerary tool.

Getting from Essex to Pelee Island by car takes about 2 hours. While traveling from Essex, expect a bit cooler days and a bit warmer nights in Pelee Island, ranging from highs of 24°C to lows of 20°C. Wrap up your sightseeing on the 13th (Mon) early enough to drive to Windsor.

Things to do in Pelee Island

Parks · Wildlife
Find places to stay Sep 13 — 14:

Windsor

— 3 nights
Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
Satisfy your inner culture vulture at Olde Walkerville Neighborhood and Willistead Manor. There's much more to do: don't miss a visit to Windsor Riverfront, indulge your thirst for a good beer at Walkerville Brewery, take a stroll through Via Italia, and walk around Jackson Park.

To see where to stay, traveler tips, and more tourist information, read our Windsor vacation planner.

Traveling by car from Pelee Island to Windsor takes 2.5 hours. Traveling from Pelee Island in September, plan for little chillier nights in Windsor, with lows around 15°C. Wrap up your sightseeing on the 16th (Thu) early enough to travel back home.

Things to do in Windsor

Breweries & Distilleries · Historic Sites · Tours · Shopping
Find places to stay Sep 13 — 16: