7 days in Windsor, Essex & Pelee Island Itinerary

7 days in Windsor, Essex & Pelee Island Itinerary

Created using Inspirock Ontario vacation planner

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Make it your trip
Ferry to Billy Bishop Toronto City, Fly to Windsor
1
Windsor
— 1 night
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

— 1 night
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): steep yourself in history at Willistead Manor, then gain some tasty knowledge on a distillery tour, then indulge your thirst for a good beer at Walkerville Brewery, and finally appreciate the extensive heritage of Olde Walkerville Neighborhood. Get ready for a full day of sightseeing on the next day: stroll around Jackson Park, don't miss a visit to Windsor Riverfront, then examine the collection at Museum Windsor – Maison Francois Baby House, then take in nature's colorful creations at Dieppe Gardens, and finally walk around Assumption Park.

For maps, photos, traveler tips, and tourist information, go to the Windsor trip itinerary maker app.

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. Wrap up your sightseeing on the 4th (Mon) to allow time to drive to Essex.

Things to do in Windsor

Historic Sites · Breweries & Distilleries · Parks · Tours
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: learn about winemaking at Oxley Estate Winery and explore the striking landscape of Point Pelee National Park.

For other places to visit, photos, more things to do, and tourist information, refer to the Essex trip itinerary builder site.

Essex is just a stone's throw from Windsor. Expect a daytime high around 20°C in October, and nighttime lows around 9°C. Wrap up your sightseeing on the 7th (Thu) early enough to drive to Pelee Island.

Things to do in Essex

Wineries · Shopping · Nature · Parks

Side Trips

Find places to stay Oct 4 — 7:

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 8th (Fri): tour the pleasant surroundings at Fish Point Nature Reserve, then do a tasting at Pelee Island Pavilion, then tour the pleasant surroundings at Lighthouse Point Provincial Nature Reserve, and finally stroll through Stone Road Alvar Nature Reserve.

For traveler tips, maps, ratings, and more tourist information, go to the Pelee Island online trip planner.

Traveling by car from Essex to Pelee Island takes 2 hours. Expect somewhat warmer evenings in Pelee Island when traveling from Essex in October, with lows around 14°C. Wrap up your sightseeing on the 8th (Fri) early enough to drive to Windsor.

Things to do in Pelee Island

Wildlife · Parks · Nature · Wineries
Find places to stay Oct 7 — 8:

Windsor

— 1 night
Start off your visit on the 9th (Sat): see the interesting displays at Canadian Historical Aircraft Association, gain insight at Ojibway Nature Centre, then stop by Via Italia, and finally sample the tasty concoctions at Craft Heads Brewing Company.

To find more things to do, where to stay, photos, and other tourist information, read Windsor road trip planning tool.

Traveling by car from Pelee Island to Windsor takes 2.5 hours. Traveling from Pelee Island in October, plan for a bit cooler nights in Windsor, with lows around 9°C. Cap off your sightseeing on the 9th (Sat) early enough to travel back home.

Things to do in Windsor

Museums · Neighborhoods · Breweries & Distilleries
Find places to stay Oct 8 — 9: