7 days in Windsor, Essex & Pelee Island Itinerary

7 days in Windsor, Essex & Pelee Island Itinerary

Created using Inspirock Ontario vacation planner

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

Windsor

— 2 nights
Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
On the 17th (Sun), steep yourself in history at Willistead Manor, learn insider's secrets on a distillery tour, then appreciate the extensive heritage of Olde Walkerville Neighborhood, and finally sample the tasty concoctions at Walkerville Brewery. Keep things going the next day: admire the natural beauty at Dieppe Gardens, walk around Assumption Park, deepen your understanding at Ojibway Nature Centre, take a stroll through Via Italia, then don't miss a visit to Windsor Riverfront, and finally stroll around Jackson Park.

To find ratings, where to stay, photos, and tourist information, use the Windsor itinerary maker.

Toronto to Windsor is an approximately 3.5-hour combination of ferry and flight. You can also drive; or take a train. In October, plan for daily highs up to 20°C, and evening lows to 9°C. You will leave for Essex on the 19th (Tue).

Things to do in Windsor

Historic Sites · Breweries & Distilleries · Neighborhoods · Parks
Find places to stay Oct 17 — 19:

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. 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 Aleksander Estate Winery, pick up some local products at Lee and Maria's, and take an in-depth tour of Canadian Transportation Museum & Heritage Village.

To find photos, reviews, and more tourist information, read our Essex itinerary builder app.

Essex is just a short distance from Windsor. In October, daily temperatures in Essex can reach 20°C, while at night they dip to 9°C. Finish your sightseeing early on the 21st (Thu) to allow enough time to drive to Pelee Island.

Things to do in Essex

Wineries · Shopping · Museums · Nature

Side Trips

Find places to stay Oct 19 — 21:

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 22nd (Fri): stroll through Fish Point Nature Reserve, do a tasting at Pelee Island Pavilion, then tour the pleasant surroundings at Lighthouse Point Provincial Nature Reserve, and finally explore the striking landscape at Stone Road Alvar Nature Reserve.

To see photos, more things to do, reviews, and tourist information, read our Pelee Island trip planner.

You can drive from Essex to Pelee Island in 2 hours. Plan for somewhat warmer nights when traveling from Essex in October since evenings lows in Pelee Island dip to 14°C. Cap off your sightseeing on the 22nd (Fri) early enough to go by car to Windsor.

Things to do in Pelee Island

Wildlife · Parks · Nature · Wineries
Find places to stay Oct 21 — 22:

Windsor

— 1 night
Start off your visit on the 23rd (Sat): stroll around Reaume Park and then see the interesting displays at Canadian Historical Aircraft Association.

To see traveler tips, where to stay, reviews, and more tourist information, you can read our Windsor online itinerary planner.

Getting from Pelee Island to Windsor by car takes about 2.5 hours. Expect slightly colder evenings in Windsor when traveling from Pelee Island in October, with lows around 9°C. Wrap up your sightseeing by early afternoon on the 23rd (Sat) to allow time for travel back home.

Things to do in Windsor

Museums · Parks
Find places to stay Oct 22 — 23: