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6-Day Itinerary in Windsor, Canada

Sunday, August 27: Exploring Downtown Windsor

Start your trip by exploring the vibrant downtown area of Windsor. In the morning, visit the renowned Windsor Sculpture Park along the Detroit River, which showcases more than 30 large-scale contemporary sculptures. In the afternoon, head to the Windsor Riverfront, a beautiful waterfront promenade with walking trails and parks. As the evening sets in, enjoy a delicious dinner at one of the many restaurants in the downtown core, offering a variety of cuisines.

  • Windsor Sculpture Park: Free, 2-3 hours
  • Windsor Riverfront: Free, 1-2 hours
  • Dinner in Downtown Windsor: $20-$50 per person
Monday, August 28: Windsor Casino and Distillery Tour

Start your day with a visit to Caesars Windsor, a popular casino and entertainment venue offering a wide range of gaming options. In the afternoon, take a guided tour of the Hiram Walker & Sons Distillery, where you can learn about the process of whiskey production and enjoy tastings. In the evening, relax and try your luck at the casino or explore the nearby bars and nightlife.

  • Caesars Windsor: Cost varies, 3-4 hours
  • Hiram Walker & Sons Distillery Tour: $15-$30, 1-2 hours
  • Evening at the casino or local bars: Cost varies
Tuesday, August 29: Explore Windsor's History and Culture

Start your day by visiting the Canadian Club Heritage Center, which offers guided tours of the historic distillery and allows you to discover the legacy of Canadian Club Whisky. In the afternoon, explore the Chimczuk Museum, known for its exhibits on local history, culture, and natural sciences. As the evening approaches, take a stroll along the Dieppe Gardens, a beautiful waterfront park with stunning views of the Detroit skyline.

  • Canadian Club Heritage Center: $10-$15, 1-2 hours
  • Chimczuk Museum: $5-$10, 2-3 hours
  • Dieppe Gardens: Free, 1-2 hours
Wednesday, August 30: Windsor-Essex Wine Country Tour

Embark on a wine tour in the Windsor-Essex region, known for its award-winning wineries. Spend the morning visiting vineyards and wineries, such as Pelee Island Winery or Colio Estate Wines, where you can enjoy tastings and learn about the winemaking process. In the afternoon, indulge in a leisurely lunch at one of the winery restaurants, offering delicious local cuisine paired with their wines. Wrap up the day with a scenic drive along the Lake Erie coastline.

  • Winery visits and tastings: $10-$20 per winery, 4-6 hours
  • Lunch at a winery restaurant: $20-$50 per person
  • Scenic drive along Lake Erie: Free, 1-2 hours
Thursday, August 31: Outdoor Adventures in Windsor

Start your day with a visit to Point Pelee National Park, a nature reserve located on a peninsula extending into Lake Erie. Explore the park's diverse ecosystems, hike the trails, and spot unique bird species. In the afternoon, head to Ojibway Park, a nature preserve known for its walking trails and wildlife viewing opportunities. As the evening approaches, enjoy a picnic at the park or visit a local restaurant for dinner.

  • Point Pelee National Park: $7.90 per person, 4-6 hours
  • Ojibway Park: Free, 2-3 hours
  • Picnic or dinner at a local restaurant: $15-$40 per person
Friday, September 1: Windsor Waterfront and Adventure

Start your day by exploring the Windsor Waterfront Trail, a scenic pathway that spans along the Detroit River. Rent a bike or go for a leisurely walk while enjoying the beautiful views of the riverfront. In the afternoon, venture to Adventure Bay Family Water Park, where you can cool off and have fun on the water slides and lazy river. As the evening sets in, treat yourself to a delicious dinner at one of the waterfront restaurants.

  • Windsor Waterfront Trail: Free, 2-3 hours
  • Adventure Bay Family Water Park: $15-$30 per person, 3-4 hours
  • Dinner at a waterfront restaurant: $20-$50 per person

Hidden Gems and Local Favorites

While exploring Windsor, make sure to check out Willistead Manor, a historic mansion with beautiful gardens and frequent events. For nature enthusiasts, consider visiting the Ojibway Prairie Complex, a protected area home to diverse plant and animal species. Windsor also offers a vibrant local food scene, so be sure to try some of the local specialties, including peameal bacon sandwiches and butter tarts.

For hotel and flight prices, click here.

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