6 days in Windsor, Essex & Pelee Island Itinerary

6 days in Windsor, Essex & Pelee Island Itinerary

Created using Inspirock Ontario itinerary planner

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Make it your trip
Ferry to Billy Bishop Toronto City, Fly to Windsor
1
Windsor
Drive
2
Essex
— 3 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.
Start off your visit on the 3rd (Sun): wander the streets of Via Italia and then learn insider's secrets on a distillery tour.

For photos, maps, more things to do, and more tourist information, you can read our Windsor trip 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, daily temperatures in Windsor can reach 20°C, while at night they dip to 9°C. Finish up your sightseeing early on the 3rd (Sun) so you can go by car to Essex.

Things to do in Windsor

Neighborhoods · Tours · Breweries & Distilleries
Find places to stay Oct 3 — 4:

Essex

— 3 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. Essex is known for wineries, museums, and shopping. Your trip includes some of its best attractions: do a tasting at Oxley Estate Winery and explore the striking landscape of Point Pelee National Park.

To see traveler tips, photos, ratings, and other tourist information, refer to the Essex day trip tool.

Essex is just a stone's throw from Windsor. In October in Essex, expect temperatures between 20°C during the day and 9°C at night. Cap off your sightseeing on the 6th (Wed) early enough to go by car to Pelee Island.

Things to do in Essex

Wineries · Parks · Shopping · Nature

Side Trips

Find places to stay Oct 3 — 6:

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.
Start off your visit on the 7th (Thu): tour the pleasant surroundings at Fish Point Nature Reserve, learn about winemaking at Pelee Island Pavilion, then tour the pleasant surroundings at Lighthouse Point Provincial Nature Reserve, and finally explore the striking landscape at Stone Road Alvar Nature Reserve.

To see other places to visit, traveler tips, ratings, and other tourist information, read our Pelee Island trip tool.

Drive from Essex to Pelee Island in 2 hours. Plan for a bit warmer nights when traveling from Essex in October since evenings lows in Pelee Island dip to 14°C. Wrap up your sightseeing on the 7th (Thu) to allow time to drive to Windsor.

Things to do in Pelee Island

Wildlife · Parks · Nature · Wineries
Find places to stay Oct 6 — 7:

Windsor

— 1 night
Kick off your visit on the 8th (Fri): admire the natural beauty at Dieppe Gardens, sample the tasty concoctions at Walkerville Brewery, then appreciate the extensive heritage of Olde Walkerville Neighborhood, then deepen your understanding at Ojibway Nature Centre, and finally make a trip to Windsor Riverfront.

To see photos, more things to do, traveler tips, and more tourist information, you can read our Windsor vacation planner.

You can 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. Cap off your sightseeing on the 8th (Fri) early enough to travel back home.

Things to do in Windsor

Historic Sites · Breweries & Distilleries · Parks
Find places to stay Oct 7 — 8: