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Toronto and Windsor by Train

6 to 9+ Nights from $1,108*
* Sample price: priced within the past 7 days for a 5/28/2025 arrival, departing Miami MIA (FL), US. Choose departure city, cabin and dates.

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This 6 night sample itinerary includes:

  • Flight into Toronto and out of Windsor
  • Hotel for 3 nights in Toronto
  • Train from Toronto to Windsor
  • Hotel for 3 nights in Windsor

A Canadian trip along these two cities in Ontario Province!. Combine stays in Toronto (the capital of the province of Ontario, is a major Canadian city along Lake Ontario`s northwestern shore); and on Southwestern Ontario, in Windsor (Canada`s leading port of entry from the US; sits right along the Detroit River opposite the US city of Detroit. Is a city of history and culture, with its historic architecture, modern towers and multicultural residents) with a train.

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Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
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Flexible Itinerary

  • Toronto (Ontario)

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  • Windsor (Ontario)

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Canada

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Trip Summary

  • Toronto (Ontario)
    Toronto (Ontario)

    Multicultural and cosmopolitan, Toronto is a massive, sprawling city, made up of smaller, individual neighborhoods, and a fantastic, lively city to visit. This major Canadian city along Lake Ontario's northwestern shore boasts a dynamic metropolis with a core of soaring skyscrapers, all dwarfed by the iconic, tallest freestanding structure in the Western Hemisphere - the CN Tower. It also has many parks, world-class theater, shopping and plenty restaurants; and just a short drive away you will find the amazing Niagara Falls! Art, food, beaches, nightlife - in Toronto, you've got it all!

    Visit Niagara Falls, Toronto Islands, CN Tower Royal, Ontario Museum, Ripley's Aquarium of Canada, Rogers Centre, Art Gallery of Ontario, and so much more!

  • Windsor (Ontario)
    Windsor (Ontario)

    Known as the 'Automotive Capital of Canada', Windsor's industrial and manufacturing heritage is responsible for how the city has developed through the years. This beautiful city is Canada's leading port of entry from the United States; two tunnels, car ferries, and a suspension bridge connect it with Detroit, so you can't miss the amazing views of these two remarkable cities. National parks, museums, art galleries, and the imposing Ambassador Bridge are just some of the attractions offered by the ever eclectic Windsor.

    Visit and discover the amazing Art Gallery of Windsor, Ambassador Bridge, Willistead Manor, Windsor Riverfront, Adventure Bay Family Water Park, Jackson Park and so much more.

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