The Perfect 3-Day Windsor-Essex Itinerary: Where to Stay, Eat & Explore

Looking To Visit The Windsor-Essex Area In 2026? Keep Reading For All The Info!

If you’re looking for a fun Ontario getaway filled with award-winning wineries, scenic waterfronts, and incredible local restaurants, then check out this 3-day Windsor-Essex itinerary!

Whether you’re visiting for the first time or looking to see a different side of the region, this itinerary takes the guesswork out of planning.

Over three days, you’ll explore some of the area’s top highlights.

Including Point Pelee National Park, local wineries and cideries, historic landmarks, boutique shops, and delicious restaurants.

If you’re wondering where to stay, what to eat, and the best things to do in Windsor-Essex, this guide has everything you need for an unforgettable trip.

Where Is Windsor-Essex Located?

Windsor-Essex is located in the southwestern corner of Ontario, Canada, along the Detroit River and the shores of Lake Erie and Lake St. Clair.

The region includes the city of Windsor and the surrounding Essex County communities.

Including Amherstburg, Kingsville, Leamington, Essex, Lakeshore, LaSalle, and Tecumseh.

It sits directly across the river from Detroit, making it the southernmost region in Canada.

Also, Windsor-Essex is an easy road trip destination from many major Ontario cities.

It’s approximately a four-hour drive from Toronto, about two hours from London, and just one hour from Chatham.

If you’re visiting from Niagara Falls, you can expect the drive to take around four and a half hours.

3-Day Windsor-Essex Itinerary – Day 1: Drive To The Area + Point Pelee National Park

The first half of your day will most likely be spent getting to the area unless you live somewhere close by.

Iron Kettle Commissary

The Iron Kettle Commissary is a bakery, café, and specialty food shop located in the small community of Comber, about 35 minutes east of Windsor.

It was created by the owners of the beloved Iron Kettle Bed & Breakfast, which is no longer operational.

However, it has now transitioned into the perfect place for artisan breads, flaky pastries, handcrafted baked goods, and ready-to-heat meals made with locally sourced ingredients whenever possible.

You can stop by on your way into the area and enjoy fresh coffee and pastries.

And on the way out, stock up on sourdough bread, croissants, cookies, butter tarts, and seasonal treats, or pick up prepared meals to take home.

Get the Iced Maple Oat Latte or Iced Vanilla Latte; both were outstanding. For bread, go for the Jalapeno & Cheese Curds Sourdough (it is not too spicy) or the Apple & Rosemary one.

I got a selection of the sweets, and honestly, I cannot choose a favourite. You can’t go wrong with any of them.

Point Pelee National Park

The Point Pelee National Park is Canada’s second smallest national park and one of its most ecologically diverse.

Located on a narrow peninsula extending into Lake Erie near the town of Leamington, it’s best known for being the southernmost point of mainland Canada.

Also, the park features more than 20 kilometres (12 miles) of trails and boardwalks that wind through marshes, forests, and beaches.

Popular attractions include the iconic Tip, where visitors can stand at the southernmost point of mainland Canada.

As well as the Marsh Boardwalk, the observation tower, and the park’s sandy beaches.

The Tip

The Tip is the most iconic attraction in Point Pelee National Park and a must-see during your visit to Windsor-Essex.

As the southernmost point of mainland Canada, this narrow sand spit stretches into Lake Erie, creating a unique landscape where the waters on either side of the peninsula meet.

Not only that, but the color of the water is different too. On the left, the water is darker blue, while on the right it is lighter blue.

Also, the shape of the Tip is constantly changing due to wind, waves, and water levels, so no two visits are ever exactly the same.

To reach the Tip, you should take the park shuttle to the southern end of the park.

Then follow a short boardwalk through the forest to the shoreline.

Drive to the Visitors Center and park your car there, then hop on the free shuttle. You can also walk, instead of taking the shuttle, but it is about 2.5 km (7-8 mins ride) each direction.

I would recommend doing The Tip first as the shuttle schedule ends long before the whole park closes.

You can find the shuttle schedule here.

Tip Observation Tower

The Tip Observation Tower is a viewing platform located near the Tip of Point Pelee National Park.

Climbing the tower provides a bird’s-eye view of the park’s unique geography.

This allows you to see the narrow peninsula stretching into Lake Erie and the surrounding shoreline from above.

From the top, you’ll enjoy panoramic views of Lake Erie, the park’s forests, beaches, and the famous sand spit.

Unlike viewing the park from ground level, the tower lets you appreciate just how narrow the peninsula is and how dramatically it extends into the lake.

In addition, there are information boards on the top of the tower, providing more info about the area.

The tower is free to access and does not seem too difficult to climb, but it is made of metal that you can see through.

Therefore, if you are afraid of heights, you may want to skip that one.

There are bathrooms right behind the tower, and that is also where you will find the shuttle stop.

The Marsh Boardwalk

The Marsh Boardwalk is a 1-kilometre floating boardwalk that winds through the park’s largest wetland.

As you stroll along the boardwalk, you’ll pass through tranquil waters lined with cattails, lilies, and reeds.

Also, keep an eye out for turtles sunbathing on logs, frogs, fish, muskrats, and countless species of birds.

I saw a beaver munching on lily pads as well as a blue heron standing in the middle of the marsh.

At the beginning of the boardwalk, you’ll find a viewing platform that offers beautiful panoramic views of the surrounding wetlands.

In addition, benches along the route provide the perfect place to stop, relax, and soak in the sounds of nature.

The Main Grill and Ale House

For dinner, stop at The Main Grill & Ale House, which is located in the heart of downtown Kingsville.

The Main Grill & Ale House is a welcoming restaurant that combines the relaxed atmosphere of a neighbourhood pub with elevated Canadian cuisine.

The menu features a variety of locally inspired dishes, like hearty burgers and shareable appetizers.

As well as fresh salads, pasta, and comforting main courses, along with a selection of craft beers, wines, and spirits.

Whether you’re dining indoors or enjoying the patio during the warmer months, it offers a delicious and laid-back dining experience in one of the area’s most charming small towns.

The Cajun Beef Tips and the Garlic Shrimp were outstanding!

Colchester Beach and Harbour

Stop by the Colchester Beach and Harbour to watch the stunning sunset before checking into your accommodation.

Colchester Beach and Harbour is a scenic waterfront destination located along the shores of Lake Erie in the charming community of Colchester.

Known for its peaceful atmosphere and beautiful lake views, it is a lovely place to take a break and enjoy the natural beauty of the Windsor-Essex region.

Also, you can walk along the pier, admire the boats in the marina, relax by the water, or enjoy the park beside the beach.

You can even go in for a quick dip if you feel like it, but then make sure you check in at the motel first so that you can change.

The Grove Motel

For a unique place to stay in Windsor-Essex, check into The Grove Motel, a stylish boutique motel located in the lakeside community of Colchester.

It is located just a short walk from Colchester Beach and Harbour.

This retro-inspired property combines a relaxed, nostalgic atmosphere with modern comforts.

One of the motel’s standout features is its collection of 27 individually designed rooms, each with its own fun theme and personality.

From bold colours and playful décor to creative details and unexpected touches, every room offers a different experience and provides plenty of photo-worthy moments.

The motel also has a shared space lounge that has board games, comfy couches and a fun toilet.

I stayed at The Little Blue Box room, which is inspired by Tiffany’s, and I loved it!

Room themes:

• The Wink – a fun, colourful room with a playful retro feel
• The “I Do” Crew – designed with weddings, celebrations, and group getaways in mind
• The Happy Camper – a cozy, camping-inspired room with a nostalgic outdoor theme
• The Little Blue Box – a bright room inspired by the classic blue-box aesthetic
• Life at the Woofhaus – a dog-themed, pet-friendly room with whimsical details
• The Entourage – a bold, social space that works well for a friends’ getaway
• Let’s Flamingale – a vibrant room inspired by flamingos and tropical fun
• Hope on the Orient Express – a travel-inspired room with vintage railway touches
• Whatever Floats Your Boat – a nautical-themed room that reflects the motel’s lakeside location
• The Great White North – a playful Canadian-inspired room
• Straight Outta Coolchester – a fun tribute to the motel’s location in Colchester
• Welcome to the Circus – a colourful and quirky circus-themed room
• The Bucket Wish – a whimsical room featuring a wishing-tree experience
• Ready Player One – a gaming-inspired room for guests who enjoy a nostalgic, playful atmosphere

3-Day Windsor-Essex Itinerary – Day 2: Spa + Drinks + Shopping

The next day will be a full-day itinerary with a lot of experiences and activities.

JOE Hot+Cold Coffee

After a restful stay at the Grove Motel, stop at JOE Hot+Cold Coffee, which is a coffee shop located inside the motel.

JOE. Hot+Cold Coffee (Colchester) is a vibrant café that serves specialty coffee, fresh breakfast, and baked goods.

With locally roasted coffee, house-made syrups, creative drinks, and a relaxed, welcoming atmosphere, it is the perfect place to start your day.

Also, I have never seen a coffee shop that offers more options for flavour shots before – Salted Caramel & Maple Pancake are my favourite.

Their food is really good; I have been to Joe a few times, and it has been excellent.

The iced latte with any of the flavour shots is a must, and the sausage breakfast sandwich is great!

Wilderness Retreat And Nordic Spa

The first stop of the day is the Wilderness Retreat and Nordic Spa, which is located just outside Kingsville.

It offers a peaceful wellness experience focused on hydrotherapy, combining heat, cold, and relaxation in a beautiful wooded setting.

The spa experience follows the traditional Nordic cycle of moving between hot and cold temperatures before taking time to rest and relax.

You can enjoy a private sauna, cold plunge, and tranquil relaxation areas surrounded by the natural beauty of the property.

The contrast between the warmth of the sauna and the refreshing cold dip is designed to leave you feeling refreshed and rejuvenated.

I spent 2 and a half hours there and did the cycle a few times, and it felt amazing.

Unlike larger, busy spas, Wilderness Retreat and Nordic Spa offers a more intimate and private experience.

Making it a great option for couples, friends, or anyone looking for a peaceful wellness break.

There are a few Muskoka chairs and two hammocks that were perfect to relax in the forest. I even saw a deer!

Quick Shopping Break

For a unique shopping experience in Windsor-Essex, check out Anna’s Garden, Home & Wellness and The Local Maker Shop in Kingsville.

Anna’s Garden, Home & Wellness is a thoughtfully curated shop filled with nature-inspired décor, cozy home accents, candles, plants, and wellness items.

Also, they have local produce and different pies, in case you are looking for some to take home.

It is a great place to get plants, plant seeds or garden-inspired items.

Located in the heart of downtown Kingsville, you will find The Local Maker Shop.

This charming boutique showcases the creativity and craftsmanship of local makers while offering a beautiful selection of home décor, wellness products, gifts, and unique finds.

From jewelry and artwork to handmade soaps, pottery, food products, and one-of-a-kind gifts, the shop is a great place to discover unique items you won’t find anywhere else.

The Goose Kitchen+Bar

For lunch, make your way to The Goose Kitchen + Bar, a local favourite known for its farm-to-table cuisine, welcoming atmosphere, and creative menu.

Located in a historic building in the heart of downtown, this restaurant combines a cozy gastropub feel with elevated dishes inspired by the flavours of Essex County.

The menu features regional favourites like Lake Erie perch, along with creative mains, shareable appetizers, and comforting Canadian-inspired cuisine.

Also, the restaurant offers a selection of Ontario wines, craft beers, and cocktails.

I would highly recommend the Artichokes Parmesan and the Kung Pao Brussels Sprouts – both were delicious.

If you’re looking to extend your stay, the restaurant is also connected to the accommodations at Inn 31.

Allowing visitors to enjoy a complete food-and-stay experience in the heart of Kingsville.

👉 Check availability for your dates: Inn 31

Black Bear Farms Of Ontario Estate Winery

Next, make a stop at Black Bear Farms of Ontario Estate Winery.

Located on a family-run farm near Kingsville, this winery offers something a little different from the region’s traditional vineyards.

It specializes in handcrafted fruit wines made from berries and fruits grown right on the property.

The Rondelez family grows a variety of fruits on their farm before transforming them into distinctive wines.

Visitors can stop by the tasting room to sample their creative selection of fruit wines.

As well as browse the farm shop and discover unique bottles that you won’t find at many other wineries in Ontario.

Also, you can find their wines only here; they don’t sell to the LCBO.

It’s the perfect stop for travellers looking to explore a smaller, family-owned winery and try something beyond the traditional red and white wine experience.

Priscilla’s Presents & Here’s the Scoop Ice Cream Parlour

Priscilla’s Presents in Harrow is a unique country gift shop which is more than just a place to pick up souvenirs.

It’s an experience filled with carefully curated gifts, home décor, fashion accessories, wellness products, and unique treasures for every type of shopper.

From cozy home accents and bath products to gifts, clothing, and seasonal décor, the shop offers a little bit of everything and is a great place to find something special to take home.

One of the highlights of visiting Priscilla’s Presents is that it combines shopping with a nostalgic sweet treat experience at Here’s the Scoop Ice Cream Parlour.

After browsing the shop, you can enjoy a scoop of ice cream in the charming farm-themed parlour or relax outside on the shaded silo patio.

They had a large selection of flavours and a fun, family-friendly atmosphere.

Carolinia Cider Co. and The Fruit Wagon

For a true taste of Essex County’s agricultural roots, make a stop at Carolinia Cider Co. and The Fruit Wagon.

Located on the same family farm in Harrow, these two destinations offer the perfect combination of fresh local produce and handcrafted cider.

The Fruit Wagon has been a beloved farm market since 1984.

It offers a seasonal selection of homegrown fruits, vegetables, herbs, flowers, and other local products.

Carolinia Cider Co. takes the farm’s apple harvest and transforms it into small-batch, estate-grown ciders.

The family-owned cidery specializes in dry, sparkling ciders made from apples that are planted, harvested, and carefully crafted on the property.

You can stop by the tasting barn to sample their unique ciders, enjoy a glass in the orchard, and experience a relaxed farm-to-glass experience.

North 42 Degrees Estate Winery And Serenity Lavender

For a beautiful combination of wine, food, and seasonal blooms, visit North 42 Degrees Estate Winery and Serenity Lavender in Colchester.

It is located along the Lake Erie North Shore wine route and is a family-owned winery.

It combines a working vineyard, award-winning wines, a farm-to-table restaurant, and a picturesque lavender farm.

The estate produces wines made from grapes grown on the property, with visitors able to enjoy tastings, explore the vineyard, and dine at Bistro 42.

The restaurant’s scenic setting overlooking the vineyard makes it a perfect place to enjoy a leisurely lunch or dinner paired with a glass of local wine.

Located alongside the winery, Serenity Lavender Farm offers a peaceful escape surrounded by fragrant lavender plants.

During the summer bloom, you can stroll through the gardens, take photos among the purple flowers, and browse the shop.

Which is filled with lavender-inspired products, including culinary items, bath and body products, and locally made gifts.

Wolfhead Distillery & Restaurant

For dinner, stop at Wolfhead Distillery & Restaurant, which is located in Amherstburg.

It is an award-winning craft distillery and is famous as the first premium craft distillery in Essex County.

The distillery produces small-batch spirits including whisky, vodka, and gin.

It focuses on creating bold, unique flavours using local inspiration and has become a must-visit destination for spirit lovers exploring the region.

More than just a place to sample spirits, Wolfhead offers a complete experience with an on-site restaurant, cocktail bar, retail shop, and guided tours.

Popular drinks include their whisky, barrel-aged gin, grapefruit vodka, and coffee whisky liqueur.

The restaurant is another highlight, serving a menu inspired by local ingredients with creative dishes that pair well with Wolfhead’s handcrafted spirits.

Get the espresso martini and the Portabello fries and thank me later!

Walnut Grove B&B

The Walnut Grove Bed & Breakfast is located in Harrow and is set on a beautiful 10-acre property surrounded by trees, gardens, and farmland.

This adults-only B&B is housed in a beautifully restored 1902 farmhouse, which combines historic charm with modern comforts.

Each of the three guest rooms has been thoughtfully designed with a spa-like feel.

They feature luxurious linens, cozy furnishings, and private ensuite bathrooms.

Also, Bob and Leslie are absolutely amazing hosts and love what they do!

You can relax on the property’s outdoor spaces, enjoy the heated pool, unwind by the koi pond, or explore the peaceful wooded trails surrounding the B&B.

Also, they have a hot tub!

One of the highlights of staying at The Walnut Grove is the farm-to-table breakfast experience.

The hosts focus on using local ingredients, with many items sourced from the property’s gardens and nearby producers.

With Leslie’s background as a chef and sommelier, breakfast becomes more than just a meal — it’s a memorable part of the stay.

👉 Check availability for your dates: The Walnut Grove BnB

3-Day Windsor-Essex Itinerary – Day 3: Peche Island + Mansions + Planes

Day 3 is mostly focused on activities around Windsor, so after breakfast at the Walnut Grove, head towards it.

Peche Island

For a unique outdoor adventure in Windsor, visit Peche Island, a peaceful 86-acre island located just off the eastern edge of the city in the Detroit River.

It is home to wetlands, peaceful woodland trails, historic ruins, and beautiful views of both the Windsor and Detroit skylines.

The island was once the private summer retreat of Canadian whisky entrepreneur Hiram Walker.

You can still find the ruins of his house along one of the trails.

Today, Peche Island is a popular destination for nature lovers, history enthusiasts, birdwatchers, and anyone looking to experience a quieter side of Windsor.

Peche Island is accessible by boat, with seasonal self-guided tours departing from Lakeview Park Marina.

There are two walking loops, so it would take you a couple of hours to see everything.

Washrooms can be found near the boat docking area, but there are no other facilities of any kind on the island.

Harbour House Waterfront Eatery

The Harbour House Waterfront Eatery is located at Lakeview Marina along the Detroit River, directly across from Peche Island.

This coastal-inspired restaurant offers beautiful views of the water and a relaxed atmosphere that makes it a great place to enjoy a meal or drinks.

The menu features a variety of seafood-inspired dishes, shareable appetizers, burgers, salads, and other casual favourites, along with cocktails, beer, and wine.

One of the highlights is the spacious waterfront patio.

Where you can dine outdoors while taking in views of the marina, passing boats, and the Detroit River.

Get the Peach Brown Sugar Margarita and the lobster roll, which can come with fries, salad or both.

Also, it comes as a half or full size, and you can get it hot or cold.

Make sure you park across the street from the restaurant and not in the marina parking lot, as you will get a ticket.

Willistead Manor

Located in Windsor’s historic Walkerville neighbourhood, Willistead Manor is a beautiful 36-room heritage mansion surrounded by the scenic grounds of Willistead Park.

It was built in 1906 for Edward Chandler Walker, the son of Canadian whisky entrepreneur Hiram Walker.

Step inside and you’ll find grand rooms filled with intricate woodwork, ornate fireplaces, carved details, elegant staircases, and historic architectural features.

The manor’s impressive Great Hall, library, drawing room, dining room, and conservatory offer a fascinating glimpse into the luxurious lifestyle of one of Windsor’s most prominent families during the early 1900s.

Today, Willistead Manor is a cultural landmark and popular venue for weddings, special events, and tours.

Also, you can enjoy a stroll through the surrounding 15-acre park, which features different trees, landscaped pathways, and the peaceful Paul Martin Gardens.

The Coach House across the manor is also accessible to the public. There is a new exhibition, so make sure to check it out.

Canadian Aviation Museum

If you are an aviation and history enthusiast, a visit to the Canadian Aviation Museum is a fascinating stop on this trip through Windsor-Essex.

It is located at the west end of Windsor International Airport.

The museum is housed inside a historic Second World War-era hangar that was once part of No. 7 Elementary Flying Training School.

During the war, the site helped train thousands of pilots through the British Commonwealth Air Training Plan.

It was an amazing opportunity to explore such an important piece of Canada’s aviation history.

Inside, you can see a collection of vintage aircraft, aviation artifacts, and interactive displays while learning about the people and stories behind Canada’s aviation heritage.

One of the museum’s highlights is the opportunity to see restoration projects in progress.

Including historic Second World War aircraft such as the Avro Lancaster and de Havilland Mosquito.

I recommend doing a guided tour because it provides a closer look at the history of the planes and the facility.

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Conclusion: The Perfect 3-Day Windsor-Essex Itinerary: Where to Stay, Eat & Explore

Windsor-Essex is full of unique places to explore!

Spend your days exploring Point Pelee National Park, visiting local wineries, shopping in charming small towns, and relaxing along the shores of Lake Erie.

Also, enjoy delicious meals, discover local attractions, and stay at one-of-a-kind accommodations.

This 3-day Windsor-Essex itinerary includes a mix of outdoor adventures, food and drink experiences, relaxing activities, and hidden gems.

With so many places to stay, eat, and explore, Windsor-Essex is the perfect destination for your next Ontario getaway.