7 days in Windsor, Essex & Pelee Island Itinerary

7 days in Windsor, Essex & Pelee Island Itinerary

Created using Inspirock Ontario trip planner

Make it your trip
Ferry to Billy Bishop Toronto City, Fly to Windsor
1
Windsor
— 2 nights
Drive
2
Essex
— 3 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
11
12
13
14
15
16

Windsor

— 2 nights
Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
Kick off your visit on the 10th (Sun): steep yourself in history at Willistead Manor, savor the flavors at Food & Drink, and then stroll around Jackson Park. On the 11th (Mon), you'll have a packed day of sightseeing: don't miss a visit to Windsor Riverfront, appreciate the extensive heritage of Olde Walkerville Neighborhood, then indulge your thirst for a good beer at Walkerville Brewery, and finally take in nature's colorful creations at Dieppe Gardens.

To find traveler tips, more things to do, ratings, and tourist information, refer to the Windsor itinerary planner.

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. You'll set off for Essex on the 12th (Tue).

Things to do in Windsor

Breweries & Distilleries · Historic Sites · Tours · Parks
Find places to stay Oct 10 — 12:

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: explore the striking landscape of Point Pelee National Park, do a tasting at Cooper's Hawk Vineyards and The Vines Restaurant, take in the exciting artwork at Chiaroscuro, and get engrossed in the history at Canadian Transportation Museum & Heritage Village.

To see photos, where to stay, more things to do, and other tourist information, you can read our Essex trip builder app.

Essex is just a short distance from Windsor. In October, plan for daily highs up to 20°C, and evening lows to 9°C. You'll have a few hours on the 15th (Fri) to wrap things up before traveling to Pelee Island.

Things to do in Essex

Wineries · Museums · Shopping · Parks

Side Trips

Find places to stay Oct 12 — 15:

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 15th (Fri), tour the pleasant surroundings at Fish Point Nature Reserve and then tour the pleasant surroundings at Lighthouse Point Provincial Nature Reserve.

To see reviews, traveler tips, where to stay, and more tourist information, go to the Pelee Island online holiday planner.

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 15th (Fri) early enough to go by car to Windsor.

Things to do in Pelee Island

Parks · Wildlife
Find places to stay Oct 15 — 16:

Windsor

— 1 night
Start off your visit on the 16th (Sat): see the interesting displays at Canadian Aviation Museum, deepen your understanding at Ojibway Nature Centre, and then visit Via Italia.

For reviews, ratings, more things to do, and other tourist information, you can read our Windsor trip itinerary maker tool.

Traveling by car from Pelee Island to Windsor takes 2.5 hours. Traveling from Pelee Island in October, Windsor is slightly colder at night with lows of 9°C. Wrap up your sightseeing on the 16th (Sat) early enough to travel back home.

Things to do in Windsor

Museums · Neighborhoods
Find places to stay Oct 15 — 16: