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As the cooler fall weather creeps in and the sun sets a little earlier it’s the perfect time to explore the back roads and plan a Windsor Essex Road Trip. Discover more about the home of Canadian whisky, the Southern mainland tip of Canada, the birthplace of bubble in Canada, Canada’s best pizza, the start of the underground railroad and more.

Whether you’re staying close to home or taking advantage of our exclusive offers or deals, Windsor Essex is open and ready for you to visit!

Check out our guide below – we’ve created easy-to-download itineraries you can use when you plan to visit – or create your own (and you even have the chance to win it!). We’ve also included great trip inspiration pieces – like our blogs, our 2021/2022 Official Visitor Guide and more.


Get rewarded when you visit Windsor and stay in a hotel! Book a 2+ night trip to Windsor now – and you’ll get rewarded for your stay.

Click today and book a 2+ night stay through November 30th, 2021 at a qualifying hotel in Windsor and you’ll instantly be rewarded at check in with $75 in upgrades:

  • $50 VISA gift card valid at any City of Windsor business
  • $25 Windsor Pizza Club gift voucher valid at Arcata Pizzeria, Armandos Cabana Road or Capri Pizzeria Dougall Avenue.

You’ll also get rewarded for stays in the county, including qualifying hotel stays in:

  • Kingsville and receive a $50 in Eat Drink Dine Kingsville voucher
  • Lakeshore and receive $50 in Belle River BIA dollars
  • Leamington and receive a $50 VISA gift card valid at any Leamington business

Book today – supplies are limited. Black out dates and other restrictions may apply. Tourism Windsor Essex Pelee Island may cancel this promotion at any time. Click here for additional details and restrictions.


  1. Check our our MyTrip Digital Itinerary Builder and create a step-by-step itinerary for your trip (or use one of our pre-designed trips)
  2. Order your EPIC Tasting Pass and get an exclusive tasting experience at 8 different wineries for $50 bucks
  3. Order a Barrels Bottles & Brews Flight Log 7 Day Pass – for $40 bucks you can get a tasting experience at 12 different wineries and 2 distilleries
  4. Check our our Hotel Packages for all-in exclusive offers at select hotels including awesome experiences
  5. Book an Experience of Tour to add on to your itinerary


We’re making your next Road Trip super easy – and giving you the chance to WIN your own Road Trip itinerary worth $1,000!

  1. Click here for details on how to plan your own day trip itinerary using our MyTrip digital itinerary builder.
  2. WIN your custom road trip itinerary. Just send us the link for your chance to win!


Our itineraries are the easiest way to plan a trip to Windsor Essex. Check out our suggested and pre-designed itineraries below, or create your own using our MyTrip Digital Itinerary Builder.

This week we’re featuring our food & drink itineraries. 


Click on any of the icons below to see ALL of our suggested 1, 2 and 3 day itinerary ideas to make the most of your trip to Windsor Essex. Select an itinerary then click the ‘Download Here‘ button to explore the itinerary in three easy way – by timeline, by calendar view, or through google maps. You can export the itinerary to your phone, and the itinerary can sync with your phone to take you step-by-step and minute-by-minute to each stop.


Blogs are a great way to learn about what others have experienced when they came to Windsor Essex. Check out our top blog posts below: 

Influencer Essentials


More resources to help you plan your trip to Windsor Essex: 

Additional Resources

Additional Resources

Use these resources to help plan your trip! Our top picks feature our Official Visitor Guide, promotions, offers and much more!



Celebrate the Queen's Platinum Jubilee with a stop @blimeys 👑 in Essex #ShopYQG #YQG #WindsorEssex #DiscoverOn #DiscoverCanada #DiscoverYQG #OntSouthwest ...

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Celebrate #NationalWineDay by checking our some of our @epicwineriers - including a stop at @crewinery 🍷 #epicwineries #YQG #WindsorEssex #DiscoverOn #DiscoverCanada #DiscoverYQG #OntSouthwest #wine #winery #vineyard ...

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Let's roll to @funkychowkitchen #YQG #WindsorEssex #DiscoverOn #DiscoverCanada #DiscoverYQG #OntSouthwest #dineYQG #foodie ...

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