7 days in Essex, Kingsville & Windsor Itinerary

7 days in Essex, Kingsville & Windsor Itinerary

Created using Inspirock Ontario route planner
Make it your trip
Drive
1
Essex
— 1 night
Drive
2
Kingsville
— 3 nights
Drive
3
Windsor
— 2 nights
Fly to Billy Bishop Toronto City, Ferry to Toronto

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Essex — 1 night

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 31st (Tue), do a tasting at Muscedere Vineyards, learn about winemaking at Sprucewood Shores Estate Winery, then don't miss a visit to Amherstburg Navy Yard National Historic Site, and finally steep yourself in history at Fort Malden National Historic Site. On the 1st (Wed), you'll have a packed day of sightseeing: make a trip to Historic Essex Railway Station, do a tasting at Colchester Ridge Estate Winery, learn about winemaking at Viewpointe Estate Winery, then learn about winemaking at Oxley Estate Winery, then do a tasting at Cooper's Hawk Vineyards and The Vines Restaurant, and finally learn about winemaking at North 42 Degrees Estate Winery & Bistro 42.

To see traveler tips, ratings, where to stay, and tourist information, refer to the Essex trip itinerary website.

Toronto to Essex is an approximately 3.5-hour car ride. Expect a daytime high around 31°C in August, and nighttime lows around 19°C. Cap off your sightseeing on the 1st (Wed) early enough to go by car to Kingsville.
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Wineries · Historic Sites
Side Trip
Find places to stay Aug 31 — Sep 1:

Kingsville — 3 nights

Kingsville is located in Essex County in southwestern Ontario, Canada, and is Canada's southernmost municipality with town status. Start off your visit on the 2nd (Thu): pick up some local products at Lee and Maria's, stroll around Seacliff Park, then explore the striking landscape of Point Pelee National Park, and finally do a tasting at Aleksander Estate Winery. On your second day here, take in the exciting artwork at Chiaroscuro, then take an in-depth tour of Canadian Transportation Museum & Heritage Village, then look for all kinds of wild species at Jack Miner Bird Sanctuary, and finally stroll around Lakeside Park.

To see reviews, more things to do, photos, and tourist information, refer to the Kingsville attractions planner.

Kingsville is very close to Essex. In September, plan for daily highs up to 26°C, and evening lows to 15°C. Wrap up your sightseeing on the 4th (Sat) to allow time to drive to Windsor.
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Parks · Shopping · Museums · Nature
Side Trip
Find places to stay Sep 1 — 4:

Windsor — 2 nights

Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
Windsor is known for sightseeing, parks, and breweries & distilleries. Your trip includes some of its best attractions: don't miss a visit to Windsor Riverfront, walk around Assumption Park, take in nature's colorful creations at Dieppe Gardens, and gain insight at Ojibway Nature Centre.

For more things to do, photos, traveler tips, and other tourist information, refer to the Windsor trip builder app.

Traveling by car from Kingsville to Windsor takes an hour. In September, daily temperatures in Windsor can reach 27°C, while at night they dip to 15°C. Wrap up your sightseeing on the 6th (Mon) early enough to travel back home.
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Historic Sites · Breweries & Distilleries · Parks · Museums
Find places to stay Sep 4 — 6: