From the exciting urban life and density of Toronto and Ottawa, to the wilds of the Great Lakes and Northern Ontario, the possibilities are endless in Ontario. In Vacations of the Brave, Dallas ice cream shop owner Tom and his star employee, Kalin, venture to Ontario, Canada, where they freestyle in the Caribbean Carnival, hoop dance at a First Nations Pow Wow, explore underwater shipwrecks, and come to a powerful realization about the power of inclusion.


Has the episode inspired you to plan your own trip to Ontario? This list of local experiences will help you get started.

Dancers at the Wiikwemkoong Cultural Festival on Manitoulin Island.

Welcoming cultures


There are a lot of stereotypes about Canada we would love to shed (it actually gets really hot here in summer, we promise) but Canadians being friendly isn’t one of them. When you travel to Canada, you won’t just be welcomed by the locals; you’ll often be invited to live the local culture. Tom and Kalin experienced this on a visit to Manitoulin Island, where they took part in the 58th annual Wiikwemkoong Cultural Festival. One of the largest and longest running Pow Wows in North America, the event allows you to experience the history, cultural lifestyles and traditions of the Anishaabek people, through dance, cuisine, arts and crafts, and more. Manitoulin Island is also part of The Great Spirit Circle Trail, an inclusive cultural experience that puts you in the hands of a local guide, who will walk you through the history of the island, its nature and its peoples. Hear their stories, share in their food and even take part in a traditional ceremony.


Of course, Ontario’s major cities are filled with cultural communities from around the world ready to invite you in. If you don’t know where to start, look to the markets. Ottawa’s ByWard Market features cuisine from Mexico, Vietnam, Poland and just about everywhere in between, while Toronto’s Kensington Market perfectly captures the city’s diversity, from Latin America to Asia to Europe, through fusion restaurants, ethnic stores, and more. Also make some time for Toronto’s Bloor St. Culture Corridor if you can. This arts and culture district that offers museum experiences, films, performances, classes, and culture talks related to the local French, Jewish, Italian, Estonian, Japanese, and Indigenous communities, among others.

The Caribana Festival, in Toronto Ontario.

Toronto: A city of festivals


Tom and Kalin were also welcomed with open arms by the performers at Toronto’s Caribana festival, where Caribbean music, dancing, and food take center stage. Each August, the festival ramps up Toronto’s already stellar nightlife with a weekend of parties and events. And it all culminates in the Grande Parade, a show like no other filled with the music and costumes of Caribana Mas Bands. In addition to being another example of Ontario’s welcoming cultures, Caribana is a perfect illustration of the city’s unbelievable festival cultures.


No matter when you visit Toronto, you’re basically guaranteed a festival. For indie music fans, NXNE is Canada’s counterpoint to SXSW, while Canadian Music Week sees about 1,000 artists from across the country perform at more than 40 venues in Toronto. Drake’s OVO fest is a hip-hop extravaganza hosted in “the 6ix,” while the TD Toronto Jazz Festival has three decades of great events to its name.


Beyond music, Toronto attracts the world’s biggest movie stars thanks to The Toronto International Film Festival (TIFF). TIFF turns the entire city into a 10-day party during which you can view cutting-edge cinema, meet filmmakers and celebrities, or just enjoy the celebration with the entire community. Luminato is another annual event that transforms theaters, parks, and public spaces into homes for all kinds of art. And you can’t talk about Toronto festivals without mentioning Toronto Pride, which celebrates the LGBT community each year through a number of events and an amazing parade. There are so many more festivals to discover, that it’s not hard to see why Toronto’s called “Canada’s Downtown.”

Kalin preparing to scuba dive in Tobermory, Ontario.

Life on the water


Surrounded by three oceans and with over 60 percent of the world’s lakes, you can bet any trip to Canada usually involves some time spent on, in, or near water, and Ontario is no exception. For Kalin, this meant strapping on scuba gear and exploring the unbelievable shipwrecks of Tobermory while Tom hung out on the boat. In the 1000 Islands region, which borders Ontario and New York State, you can also scuba dive among shipwrecks, or view them on a helicopter or boat tour of the region. These tours are a great way to learn about the region’s history, from real pirates and bootleggers to the politicians and business people who built mansions — and even one castle — on these islands.


Elsewhere in Ontario, the Ottawa Valley is known as the Whitewater Capital of Canada. Choose one of the local rafting companies and, with experienced guides at the helm, safely splash and roll through one of the world’s great whitewater routes. On Lake Huron, you can actually go freshwater surfing, which many people don’t even know is possible. Or, for a more relaxed time, Muskoka serves as much of Ontario’s cottage country. It’s the perfect place to rent a cottage on a lake and waterski, canoe, kayak, cliff jump, or just go for a swim. 


Want more information on the beautiful province of Ontario?

Return to the Vacations of the Brave page to discover more of Canada.

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