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It’s the Summer of the Staycation – and this summer we want you to stay in Windsor Essex and enjoy everything in your own backyard.

As businesses continue to open, it is more important than ever to support our locally owned businesses. From restaurants and bakeries to boutiques and markets, our local businesses need your ongoing support.  There are strict regulations to enter commercial businesses in Windsor Essex, and strict guidelines establishments need to follow to be open. You can check out our COVID-19 hub for more details. 

We’re making it super easy for you to plan – as well as giving you the chance to WIN your own staycation day trip itinerary.

  1. Click on the icons below for some pre-planned day trip itineraries to help you explore Windsor Essex.
  2. Click here for details on how to plan your own day trip itinerary using our MyTrip digital itinerary builder.
  3. WIN your custom day trip itinerary worth $500. Just send us the link for your chance to win!

This week we’re featuring our food & drink itineraries. Check back weekly to see new ideas! 


Our itineraries are easy to use. Click on any of the icons below to see all our suggested 1 day itineraries for locals to explore their own back yard. 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.

All of our itineraries are designed as day trips – but you can easily add an overnight stay to make it a true staycation. Check out all of our hotel options by clicking here – and just add your reservations details into your itinerary before you export it!

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 Staycation Guide, blogs, promotions, special event guides, offers and much more!


Your next #staycation should most definitely include a few nights at @themagnoliaranch! Enjoy some quiet time in this stunning B&B nestled right in @epicwineries wine country! #YQG #WindsorEssex #DiscoverYQG #DiscoverON #DiscoverCanada #OntSouthwest #winecountry ...

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So many beautiful shades of green across our #WindsorEssex golf courses! If the sun is out then you could be too - grab your family bubble and make you way to the greens. #YQG #WindsorEssex #DiscoverYQG #DiscoverON #DiscoverCanada #OntSouthwest ...

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If on the water activities don't float your boat, @urbansurfco has got you covered with some two-wheeled fun! Rent one of their electric beach cruisers to explore #YQG in a different way #WindsorEssex #DiscoverYQG #DiscoverON #DiscoverCanada #OntSouthwest ...

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