5 days in Windsor, Essex & Pelee Island Itinerary

5 days in Windsor, Essex & Pelee Island Itinerary

Created using Inspirock Ontario trip itinerary maker

Make it your trip
Ferry to Billy Bishop Toronto City, Fly to Windsor
1
Windsor
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
19
20
21
22
23
24
25

Windsor

Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
On the 19th (Sun), admire the natural beauty at Coventry Gardens.

For photos, traveler tips, other places to visit, and more tourist information, read our Windsor trip planner.

Toronto to Windsor is an approximately 3.5-hour combination of ferry and flight. You can also drive; or take a train. In September, daytime highs in Windsor are 27°C, while nighttime lows are 15°C. Wrap up your sightseeing by early afternoon on the 19th (Sun) to allow enough time to drive to Essex.

Things to do in Windsor

Parks
Find places to stay Sep 19 — 20:
Highlights from your trip

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. On the 19th (Sun), do a tasting at Cooper's Hawk Vineyards and The Vines Restaurant, explore the striking landscape of Point Pelee National Park, and then stroll around Seacliff Park. Get ready for a full day of sightseeing on the next day: don't miss a visit to Historic Essex Railway Station, do a tasting at Viewpointe Estate Winery, then do a tasting at Oxley Estate Winery, then do a tasting at North 42 Degrees Estate Winery & Bistro 42, and finally contemplate the long history of Fort Malden National Historic Site.

For where to stay, other places to visit, reviews, and tourist information, you can read our Essex holiday planner.

Essex is just a short distance from Windsor. Expect a daytime high around 27°C in September, and nighttime lows around 15°C. On the 21st (Tue), wrap the sightseeing up by early afternoon so you can drive to Pelee Island.

Things to do in Essex

Wineries · Parks · Historic Sites · Nature

Side Trips

Find places to stay Sep 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.
To see reviews, traveler tips, more things to do, and tourist information, you can read our Pelee Island travel route builder tool.

You can drive from Essex to Pelee Island in 2 hours. When traveling from Essex in September, plan for a bit cooler days and somewhat warmer nights in Pelee Island: temperatures range from 24°C by day to 20°C at night. Wrap up your sightseeing on the 22nd (Wed) early enough to drive to Windsor.

Things to do in Pelee Island

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

Windsor

— 1 night
Start off your visit on the 23rd (Thu): walk around Jackson Park, don't miss a visit to Windsor Riverfront, then get to know the fascinating history of Olde Walkerville Neighborhood, then learn insider's secrets on a distillery tour, and finally take in nature's colorful creations at Dieppe Gardens.

To see photos, where to stay, and more tourist information, use the Windsor online itinerary builder.

Drive from Pelee Island to Windsor in 2.5 hours. Expect little chillier evenings in Windsor when traveling from Pelee Island in September, with lows around 15°C. Finish your sightseeing early on the 23rd (Thu) so you can travel back home.

Things to do in Windsor

Historic Sites · Breweries & Distilleries · Tours · Parks
Find places to stay Sep 22 — 23: