Windsor Holidays

A historical town on the Detroit River

Overview

Windsor sits on the southernmost peninsular of Ontario, on the shores of the Detroit River. A city with an important history, its downtown is an interesting blend of new and old, with many pretty parks and a lovely waterfront – a perfect blend for your next holiday.

Although perhaps best known for its casino, Caesars, there is more to the city than just blackjack tables. The vast complex does provide a large part of the city’s entertainment - with a 5,000 seat concert venue and several restaurants and bars - but Windsor also has a thriving arts scene, with theatres, galleries and a great calendar of events and festivals throughout the year. From the colourful Balloonapalooza and exciting Dragon Boat Festival, to the creative Art in the Park and entertaining Bluesfest International, there is always something going on, whatever the season.

The Olde Walkerville neighbourhood is the city’s oldest district. Built by the family of Hiram Walker, the founder of Canadian Club whisky, the charming area still retains its village-feel with well-preserved houses and mature trees lining the pretty streets. The grand Willistead Manor and park provide the delightful centrepiece to this thriving part of the city, which offers a range of great boutique stores and restaurants, and regular art events in the landscaped park.

Windsor boasts several large shopping centres including the Devonshire Mall, which is excellent for seasoned shoppers with over 175 stores of all kinds, while the downtown area has a good blend of shops, restaurants and bars. If you are travelling with children you must visit the huge water park, Adventure Bay, which covers an entire downtown block and features water slides, a wave machine and surfing fun on the flow rider. The waterfront area is a well-maintained part of the city and a popular place to relax, with many beautiful gardens, flower displays and sculptures as well as the impressive city skyline of Detroit across the river. There is also a great cycle trail which hugs the coastline for 8km with beautiful views out over the river and lake.

Windsor has a rich and fascinating history as an important stop – or ‘terminal’ - of the Underground Railroad freedom movement which transported fugitive slaves between safe houses across the border to freedom in Canada. The family-run John Freeman Walls Historic Site just outside Windsor, is a good place to get a real sense of this terrible struggle, with a collection of buildings and exhibitions telling the story of John Freeman Walls, who escaped to freedom in 1846.

The city is also the perfect base from which to explore some of the lovely coastal scenery, in particular Point Pelee National Park. Although one of Canada’s smallest national parks, it is a beautiful oasis of forest and marshland with several sandy beaches. The wildlife is plentiful, especially the birds, and it is a great place to spot the elegant Monarch butterfly. For a pleasant day away from town, you are also just a ferry ride from stunning Pelee Island where you can explore the pretty countryside, tour the winery or simply sit back and soak up the sunshine on one of the lakeside beaches or tasty restaurants.

Surrounded by water and peppered with pretty parks, Windsor is a friendly city with plenty to offer for your holiday whether you visit in the heat of summer or the frosty winter.

Things to do

Holidays

Browse our amazing range of holidays in Windsor

Top tips

Top tips for visiting Windsor

Top Tip 1

• The long coastline on Windsor’s peninsular provides some fantastic cycle trails. If you prefer to take a tour there are several available, including the unusual Bike & Beer tour which winds through the city, stopping at local restaurants for refreshments.


Top Tip 2

• A walk around Walkerville, the city’s oldest neighbourhood is a must, with its leafy avenues and the beautiful Edwardian Willistead Manor. The house is open for tours and is particularly charming during the Christmas period when it is filled with lavish decorations and lights.


Top Tip 3

• Often overlooked, Colasanti’s, (the local’s favourite!) is a great find. Just a short drive from the city it boasts a lovely tropical greenhouse full of exotic flowers, birds and plants as well as a small petting zoo and playground. Open throughout the year it is a great place to brighten up a cold winter’s day.


Top Tip 4

• The region is a real hotspot for birds with a huge number of visiting birds flocking to the area as well as many resident species – from bald eagles and gulls to tiny wrens and even woodpeckers. Take your cameras to one of the national parks or take part in one of the popular birding events in spring or autumn.


Top Tip 5

• As the site of the outbreak of the 1812 war, the area is rich in military history, and there is no better place to relive the battles than at Fort Malden just along the coast at Amherstburg. Walk along the trenches, see the lively re-enactments and explore the fascinating museum.


Top Tip 6

• The city also played a significant part in the Underground Railroad freedom movement. From the John Freeman Walls historical site, to the North American Black Historical Museum, you can uncover the often harrowing stories of this period. Perhaps most moving is a tour around Sandwich church in Windsor. Hand built by escaped slaves in 1840, it provided them with a safe haven and you can still see the tunnels where escapees were hidden by the congregation from the American bounty hunters.


Top Tip 7

• Downtown Windsor has a good variety of shops and restaurants, as well as the towering Caesar’s Casino, and fantastic Adventure Bay Water Park. Take a walk around the city and see the remarkable murals on the walls, depicting cars and workers from the local Ford factories.


Gallery

At a glance


  • Important history with the Underground Railroad
  • Beautiful riverside location
  • Fly direct to Toronto from Birmingham, Glasgow, Manchester and Gatwick in approx. 7 hours. Then it's under 4 hours' drive to Windsor

Trusted travel partner


Winner of British Travel Awards 2020 - Gold award for Best Holiday Company to Canada (Large)
Winner of British Travel Awards 2020

Gold award for Best Holiday Company to Canada (Large)


Fully protected - We are members of ATOL, ABTA and IATA
Fully Protected

ATOL, ABTA and IATA logos

We are members of ATOL, ABTA and IATA.

Price Match Guarantee
Price Match Guarantee

If you find the same tour cheaper through another operator, we'll match the price.

Talk to us

Speak to our travel experts to book or tailor-make this holiday.

Canadian Affair Travel Expert

020 7616 9949

 

At a glance


  • Important history with the Underground Railroad
  • Beautiful riverside location
  • Fly direct to Toronto from Birmingham, Glasgow, Manchester and Gatwick in approx. 7 hours. Then it's under 4 hours' drive to Windsor

Trusted travel partner


Winner of British Travel Awards 2020 - Gold award for Best Holiday Company to Canada (Large)
Winner of British Travel Awards 2020

Gold award for Best Holiday Company to Canada (Large)


Fully protected - We are members of ATOL, ABTA and IATA
Fully Protected

ATOL, ABTA and IATA logos

We are members of ATOL, ABTA and IATA.

Price Match Guarantee
Price Match Guarantee

If you find the same tour cheaper through another operator, we'll match the price.

Maple leaf

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