35 days in Windsor, Essex & Pelee Island Itinerary

35 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
— 9 nights
Drive
2
Essex
— 17 nights
Drive
3
Pelee Island
— 7 nights
Drive
4
Windsor
— 1 night
Fly to Billy Bishop Toronto City, Ferry to Toronto

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Windsor

— 9 nights
Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
When in Windsor, make a side trip to see Bois Blanc Island Lighthouse & Blockhouse in Amherstburg, approximately Amherstburg away. There's still lots to do: make a trip to Windsor Riverfront, steep yourself in history at Willistead Manor, get to know the fascinating history of Olde Walkerville Neighborhood, and stroll around Jackson Park.

To see more things to do, reviews, traveler tips, and tourist information, read Windsor trip itinerary website.

Toronto to Windsor is an approximately 3.5-hour combination of ferry and flight. You can also drive; or take a train. Expect a daytime high around 27°C in September, and nighttime lows around 15°C. You'll set off for Essex on the 21st (Tue).

Things to do in Windsor

Outdoors · Parks · Shopping · Golf

Side Trips

Find places to stay Sep 12 — 21:

Essex

— 17 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. Step out of Essex with an excursion to Tremblay Beach Conservation Area in Lakeshore--about 34 minutes away. And it doesn't end there: explore the wealth of natural beauty at Point Pelee National Park, steep yourself in history at Fort Malden National Historic Site, do a tasting at Sprucewood Shores Estate Winery, and make a trip to Amherstburg Navy Yard National Historic Site.

For ratings, photos, where to stay, and other tourist information, use the Essex day trip planning app.

Essex is just a stone's throw from Windsor. Expect a daytime high around 27°C in September, and nighttime lows around 15°C. Wrap up your sightseeing by early afternoon on the 8th (Fri) to allow enough time to drive to Pelee Island.

Things to do in Essex

Outdoors · Parks · Wineries · Wildlife

Side Trips

Find places to stay Sep 21 — Oct 8:

Pelee Island

— 7 nights
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.
Pelee Island is known for wineries, parks, and childrens museums. Your trip includes some of its best attractions: tour the pleasant surroundings at Lighthouse Point Provincial Nature Reserve, learn about winemaking at Pelee Island Pavilion, and take in the dramatic natural features at Stone Road Alvar Nature Reserve.

To see traveler tips, ratings, reviews, and more tourist information, refer to the Pelee Island online vacation planner.

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. On the 15th (Fri), you're off to Windsor.

Things to do in Pelee Island

Wildlife · Parks · Nature · Wineries
Find places to stay Oct 8 — 15:

Windsor

— 1 night
On the 16th (Sat), hike along Devonwood Conservation Area, examine the collection at Canadian Aviation Museum, walk around Windsor Sculpture Park, then stroll around Assumption Park, and finally sample the tasty concoctions at Craft Heads Brewing Company.

To see ratings, where to stay, other places to visit, and more tourist information, use the Windsor day trip planning tool.

You can drive from Pelee Island to Windsor in 2.5 hours. Expect little chillier evenings in Windsor when traveling from Pelee Island in October, with lows around 9°C. Cap off your sightseeing on the 16th (Sat) early enough to travel back home.

Things to do in Windsor

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