35 days in Windsor, Essex & Pelee Island Itinerary

35 days in Windsor, Essex & Pelee Island Itinerary

Created using Inspirock Ontario trip itinerary 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.
Step out of Windsor with an excursion to Bois Blanc Island Lighthouse & Blockhouse in Amherstburg--about 32 minutes away. And it doesn't end there: make a trip to Windsor Riverfront, tee off at Seven Lakes Championship Golf, stroll around Jackson Park, and gain some tasty knowledge on a distillery tour.

For other places to visit, where to stay, ratings, and other tourist information, you can read our Windsor vacation planner.

Toronto to Windsor is an approximately 3.5-hour combination of ferry and flight. You can also drive; or take a train. In August in Windsor, expect temperatures between 31°C during the day and 19°C at night. On the 17th (Tue), you're off to Essex.

Things to do in Windsor

Parks · Outdoors · Shopping · Golf

Side Trips

Find places to stay Aug 8 — 17:

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. Go for a jaunt from Essex to Lakeshore to see Tremblay Beach Conservation Area about 34 minutes away. Next up on the itinerary: explore the wealth of natural beauty at Point Pelee National Park, do a tasting at Cooper's Hawk Vineyards and The Vines Restaurant, stroll around Seacliff Park, and see the interesting displays at John R. Park Homestead & Conservation Area.

To find more things to do, photos, other places to visit, and tourist information, use the Essex tour itinerary maker site.

Essex is just a stone's throw from Windsor. August in Essex sees daily highs of 31°C and lows of 19°C at night. Wrap up your sightseeing by early afternoon on the 3rd (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 Aug 17 — Sep 3:

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: stroll through Lighthouse Point Provincial Nature Reserve, take in the dramatic natural features at Stone Road Alvar Nature Reserve, and do a tasting at Pelee Island Pavilion.

To see maps, where to stay, more things to do, and more tourist information, go to the Pelee Island day trip planner.

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. On the 10th (Fri), you're off to Windsor.

Things to do in Pelee Island

Wildlife · Parks · Nature · Wineries
Find places to stay Sep 3 — 10:

Windsor

— 1 night
Kick off your visit on the 11th (Sat): trek along Devonwood Conservation Area, examine the collection at Canadian Aviation Museum, then walk around Windsor Sculpture Park, then walk around Assumption Park, and finally sample the tasty concoctions at Craft Heads Brewing Company.

To find more things to do, photos, reviews, and other tourist information, read our Windsor trip itinerary planning tool.

Drive from Pelee Island to Windsor in 2.5 hours. Traveling from Pelee Island in September, plan for slightly colder nights in Windsor, with lows around 15°C. Finish your sightseeing early on the 11th (Sat) to allow enough time to travel back home.

Things to do in Windsor

Museums · Parks · Breweries & Distilleries · Outdoors
Find places to stay Sep 10 — 11: