How To Spend 48 Hours In Windsor – Essex

In desperate need to escape the city but not sure where to go or what to do when you only have 48 hours? No Problem! Windsor – Essex is the perfect escape for any traveler. I know. My first reaction was probably the same as yours. But what is there to do in Windsor? Windsor-Essex is an unexpected destination that will definitely pleasantly surprise you. Whether you are looking for a quiet and relaxing weekend with the family, or a fun bachelorette getaway to even exploring and seeing nature at its best. I had the pleasure to be invited to experience Windsor – Essex at first hand, and I am so happy I got the chance to go with some amazing bloggers (Dee from Liner, glitter, gloss, Kait from Teacups and Things, Kelsey from Kelsey Diane Blog and Marissa from Chic Darling. Here is what Windsor- Essex has to offer to the different types of travelers.

For The Culture Cruiser

I am definitely your typical tourist. Whenever I go somewhere I want to explore EVERYTHING. And I am talking- parks, museums, coffee shops, malls, you name it and I am there. Whenever though a city has a river, my number one suggestion is to always go on a boat cruise. Not only are boat cruises super fun with the DJ jamming the best beats, and food and drinks being served while sailing through the serene waters, they also give you a perspective of the city you have never seen before. The Detroit and Windsor skylines are breathtaking, and the cottages standing pretty at the edge of the shore are just as adorable. The Ambassador Bridge during the sunset is yet another gem you get to see up close when you take a boat cruise with Windsor River Cruises. Before you head on the boat cruise though stop by the Windsor Sculpture Park. Such a cute spot for a photo op with your squad.

For The Golfer Wannabe

This one was for the books. We spent one of our evenings at Rochester Place Golf Club and Resort in Belle River. I have gone mini golfing many times, but when it comes to real golfing, boy I am the worse. But I think that is also what made our visit at the Gold Club even better. I am pretty sure our instructor was probably laughing on the inside, but he was extremely kind and encouraging. Our group lesson, and riding the golf cart was pretty awesome. Just an FYI, driving a golf cart not as easy as you may think, but definitely just as fun. You hardly press on the gas and that thing flies off the pavement. Also, while driving the golf cart, do not get distracted by looking at the cute little cottages they have at the Resort. Definitely did that and almost crashed into the golf cart infront of me.

The Golf Club also has a restaurant onsite Parkside Grill. This is where we had a very relaxing dinner, and I am talking we were surrounded by fireflies. Like how romantic is that? The Chef put together a menu for us featuring the restaurant’s signature dishes. The menu features locally-sourced ingredient and my favourite dish was the Whole Roasted cauliflower stuffed with Mozzarella cheese, finished with manchego cheese topped with almonds and pomegranate seeds. Like ohemgee. I would totally drive all the way to Windsor just so I can eat that again.

For The Risk Taker

Stay and play go hand in hand when it comes to Windsor – Essex. AAA Four Diamond Award winning Caesars Windsor Hotel and Casino, is definitely the place you want to be if you love to gamble. The girls and I had the best time exploring and playing at the Casino. I am not much of a risk taker, but a very very conservative spender, but it was still so much fun. Just the energy of the casino is amazing. People winning, and yes people losing, but just the adrenaline rush you get from the whole experience is out of this world. I am going to do a more in depth review of the hotel in August so stay tuned! Also, read my review for the Iron Kettle Bed and Breakfast which is the perfect spot to stay at if you are going wine tasting or heading to Point Pelee National Park.

For The Wine Connoisseur

The Wine Country is located at the Southern tip of Ontario, at the Essex Pelee Island Coast, also known as EPIC. Of course it is not a getaway trip without some wine. So many different wineries to choose from to spend your day or late afternoon. We actually got to visit Cooper’s Hawk Vineyards at Harrow. If you are a wine connoisseur, you will not be disappointed. I definitely recommend grabbing a bite at their restaurant The Vines which overlooks the beautiful vineyard. The menu has lots of options to choose from all made with local fresh ingredients and substitutes are available for gluten free peeps.  As someone that loves fresh seafood, I could not help but order the Chef’s special, the Branzino dish which I paired with the 2013 Merlot Reserve which also happens to be one of the premium red wines the winery offers.

For The Nature Lover

Can’t think of a better place to visit while at Windsor-Essex than Point Pelee National Park. Emerge yourself in nature by walking through the 12km of trails the national park has to offer, discover the beauty of going bird watching, or even explore beyond the beautiful Marsh Boardwalk by canoeing or kayaking into the endless freshwater marshes. Two-thirds of Point Pelee National Park is actually composed of freshwater marshes and did you know that Point Pelee is actually classified as a world-class birding site with more than 390 species recorded in the park? Even more exciting is the fact that Point Pelee actually allows dogs as long as they are on a leash, and guys if you bring your dog, please, poop and scoop. There are bag dispensers at all main trailhead locations. No excuse! Your dog will also be allowed in all areas of Point Pelee Park including the beach, the visitor centre and the shuttle to the tip. Cool fact about Point Pelee is the southernmost point in Canada. It is a 10-kilometre sandspit with its southern point equal in latitude to the northern border of California. It is also really interesting how the weather actually gets much nicer as you move your way through the park, especially at the tip. Don’t forget to bring your little picnic basket! We packed some delicious goodies from Bradt’s Butcher Block for our lunch and it was the perfect day at the beach.

For The Coffee and Foodie Enthusiast

Just for your love for coffee, Windsor – Essex area is worth visiting. The Coffee Trail is such a fun adventure to go on. The girls and I were lucky enough to be able to squeeze in visiting 2 of coffee shops that are part of the coffee trail. The first spot we visited was Taloola Cafe in Walkerville. Taloola Cafe reminded me of a coffee shop that you would stumble upon in Turkey or Morocco. Taloola Cafe serves organic coffees and teas, but also a savouring menu that fills your tummy but makes you feel so healthy afterwords. I had their nachos which is far from the carbs filed nachos you are thinking of.

Another coffee shop we visited is Cafe March 21. This is such a cute little quirky spot. It actually got its name because the shop was first opened on March 21, 2015.If you find yourself here definitely have their cookies which are freshly baked by the owner. Their lemon cookie was my favourite. Cafe March 21 offers specialty and single-origin coffees. I tried their raspberry latte and it was so good.

For The Adventure Seeker

Windsor- Essex area has so many different activities available to you. One activity you must try is paddle boarding with Urban Surf Co. This is possibly the hippest and coolest spot in the Windsor- Essex area. The owners are truly inspiring, and they will tell you nothing keeps you as fit as paddle boarding, since you have to use those core muscles! Abs- galore! But there is more to this than just paddle boarding. The girls and I enjoyed some delicious fresh made refreshments at their smoothie bar, and from what I hear you can take fitness classes, go on a relaxing sunset paddle, or honestly just go and hang out with the owner, Danielle because she is so cool.

As you read, Windsor- Essex has something for everyone, and most importantly is a destination that appeals to every age. Thank you to Ontario’s Southwest and Tourism Windsor Essex Pelee Island for having us and for planning such an amazing trip.



  1. Kelsey Diane Blog
    2017/07 /

    had the best time on this little getaway with you and the other girls!! Great post <3

  2. Gabriella Pacifico
    2017/07 /

    Such a good post! I would never think to travel to Windsor. And all the food looks so good!xx

    • Eleni Kyri
      2017/08 /

      So many things to do!I think this goes to show that we shouldn't take a location for face value. There are so many things to do if you do the right research.

  3. Kristin
    2017/07 /

    This made my heart smile!! Windsor is home for me, and so many people think there is nothing to do there and no cool or exciting spots to visit! I love your post and glad you had such a fun time :)Kristin

  4. Elaine Sia
    2017/08 /

    So glad you enjoyed your visit – thanks for sharing all the fantastic ways to spend 48 hours here. That fabulous infographic summarized it all beautifully! We loved having you and look forward to your visiting again. ElaineTourism Windsor Essex Pelee Island

    • Eleni Kyri
      2017/08 /

      Thank you so much for having us Elaine! It was the perfect trip for our girls getaway.

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