5 days in Windsor, Essex & Pelee Island Itinerary

5 days in Windsor, Essex & Pelee Island Itinerary

Created using Inspirock Ontario sightseeing planner

Make it your trip
Ferry to Billy Bishop Toronto City, Fly to Windsor
1
Windsor
— 1 night
Drive
2
Essex
— 2 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
17
18
19
20
21
22
23

Windsor

— 1 night
Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
Kick off your visit on the 17th (Sun): appreciate the extensive heritage of Olde Walkerville Neighborhood, then gain insight at Ojibway Nature Centre, and then don't miss a visit to Windsor Riverfront.

To find more things to do, other places to visit, maps, and more tourist information, use the Windsor trip itinerary 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, daytime highs in Windsor are 20°C, while nighttime lows are 9°C. You'll set off for Essex on the 18th (Mon).

Things to do in Windsor

Historic Sites
Find places to stay Oct 17 — 18:

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. Start off your visit on the 18th (Mon): do a tasting at Sprucewood Shores Estate Winery, learn about winemaking at Cooper's Hawk Vineyards and The Vines Restaurant, and then explore the wealth of natural beauty at Point Pelee National Park. On the 19th (Tue), you'll have a packed day of sightseeing: make a trip to Historic Essex Railway Station, then do a tasting at Viewpointe Estate Winery, then learn about winemaking at Oxley Estate Winery, and finally pick up some local products at Lee and Maria's.

For photos, traveler tips, ratings, and other tourist information, you can read our Essex journey app.

Essex is just a short distance from Windsor. October in Essex sees daily highs of 20°C and lows of 9°C at night. You'll have a few hours on the 20th (Wed) to wrap things up before traveling to Pelee Island.

Things to do in Essex

Wineries · Shopping · Nature · Parks

Side Trips

Find places to stay Oct 18 — 20:

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 20th (Wed): stroll through Fish Point Nature Reserve and then tour the pleasant surroundings at Lighthouse Point Provincial Nature Reserve.

To see traveler tips, photos, maps, and other tourist information, read Pelee Island trip website.

Traveling by car from Essex to Pelee Island takes 2 hours. Traveling from Essex in October, plan for somewhat warmer nights in Pelee Island, with lows around 14°C. Finish your sightseeing early on the 20th (Wed) so you can drive to Windsor.

Things to do in Pelee Island

Wildlife · Parks
Find places to stay Oct 20 — 21:

Windsor

— 1 night
Kick off your visit on the 21st (Thu): stroll around Assumption Park, gain some tasty knowledge on a distillery tour, then indulge your thirst for a good beer at Walkerville Brewery, and finally take in nature's colorful creations at Dieppe Gardens.

Find out how to plan Windsor trip without stress by asking Inspirock to help create an itinerary.

Traveling by car from Pelee Island to Windsor takes 2.5 hours. Plan for slightly colder nights when traveling from Pelee Island in October since evenings lows in Windsor dip to 9°C. Finish your sightseeing early on the 21st (Thu) so you can travel back home.

Things to do in Windsor

Breweries & Distilleries · Tours · Parks
Find places to stay Oct 20 — 21: