Travel from Toronto to Montréal on a two-week family road trip that leaves room for both city exploring and long afternoons by the lake. Spend time in Toronto’s neighbourhoods, settle into a private cottage in the Haliburton Highlands, visit Canada’s capital, and stay off-grid at Kenauk Nature before finishing in Montréal. With paddling, hiking, museums, guided experiences, and free days built in, the journey gives families plenty to do without filling every hour.
DAY 1: ARRIVE IN TORONTO
Pick up your rental car and settle into your hotel in Toronto’s Annex neighbourhood. The University of Toronto, museums, shops, cafés, and restaurants are all nearby, making it easy to explore on foot. Keep your first day simple with a neighbourhood walk or an early dinner before your Ontario and Québec road trip begins.
Accommodation: Kimpton Saint George (or similar)
DAY 2: EXPLORE TORONTO’S NEIGHBOURHOODS
Spend the day getting to know Toronto beyond its skyline. Explore neighbourhoods such as Kensington Market, browse independent shops in Queen West, seek out the city’s multicultural food scene, or spend time around the University of Toronto and Bloor-Yorkville. With no fixed sightseeing schedule, you can follow your family’s interests and change plans as you go.
Accommodation: Kimpton Saint George (or similar)
DAY 3: TORONTO OR NIAGARA FALLS
Choose another day in Toronto or make the drive to Niagara Falls. At the falls, viewpoints provide different perspectives on the Niagara River and Horseshoe Falls, while experiences such as Journey Behind the Falls and seasonal boat tours take you closer to the water. A quieter alternative is Niagara-on-the-Lake, known for heritage architecture, compact streets, and lakeside paths.
Accommodation: Kimpton Saint George (or similar)
DAY 4: TORONTO TO THE HALIBURTON HIGHLANDS
Leave Toronto and drive north into the Haliburton Highlands, where your home for the next three nights is a private lakeside cabin. Settle in, head down to the waterfront, or simply enjoy the change of pace after several days in the city. This marks the first of two longer nature stays built into the journey.
Accommodation: Haliburton Post House
DAY 5: ONTARIO LAKE LIFE
There is nowhere you need to be today. Swim from the waterfront, take a canoe, kayak, or paddleboard onto the lake, spend time on the dock, or settle into the easy rhythm of an Ontario cottage stay. The region also offers artisan studios, local shops, and outdoor sculpture installations for those who prefer gentle exploration.
Meal: Continental breakfast basket
Accommodation: Haliburton Post House
DAY 6: A FREE DAY IN THE HALIBURTON HIGHLANDS
Enjoy another day by the water or head out to see more of the Haliburton Highlands. Hiking and cycling trails, local communities, studios, shops, and outdoor art provide options away from the cottage. Or stay exactly where you are for another day of swimming, paddling, games, and time together by the lake.
Meal: Continental breakfast basket
Accommodation: Haliburton Post House
DAY 7: HALIBURTON HIGHLANDS TO OTTAWA
Drive east to Ottawa, with the option to make a longer journey through Algonquin Provincial Park for a walk or scenic stop along the way. After arriving in Canada’s capital, spend the evening exploring the compact downtown core. Parliament Hill, the Rideau Canal, and surrounding streets are all easy places to begin.
Meal: Continental breakfast basket
Accommodation: Lord Elgin Hotel (or similar)
DAY 8: OTTAWA TO THE QUÉBEC WILDERNESS
Start the morning at one of Ottawa’s national museums or galleries, with choices spanning Canadian history, nature, art, science, aviation, and technology. Pick up groceries before leaving the city and continue into Québec. Families interested in wildlife can consider an optional stop at Parc Omega before arriving at their private cabin retreat surrounded by forest and lakes.
Accommodation: Kenauk Nature (or similar)
DAY 9: A DAY TO DISCONNECT
Wake up with a full day devoted to the outdoors. Explore the lakes by canoe or kayak, follow trails through the surrounding forest, go swimming, fish, or simply spend time around your cabin and waterfront. The remote setting and lack of a sightseeing schedule make this a chance for the whole family to slow the pace of the trip.
Accommodation: Kenauk Nature (or similar)
DAY 10: GUIDED ADVENTURE & FREE TIME
Add a guided outdoor experience such as fishing or climbing, with the rest of the day left open. Depending on your family’s interests, spend the afternoon hiking, paddling, swimming, or relaxing back at the cabin. The combination of a guided activity and unstructured time allows family members with different interests and energy levels to enjoy the day their own way.
Accommodation: Kenauk Nature (or similar)
DAY 11: QUÉBEC WILDERNESS TO MONTRÉAL
Leave the forest behind for the relatively short drive to Montréal. After checking into your centrally located hotel, spend the afternoon getting acquainted with the city. Walk through the downtown core or Old Montréal, find a neighbourhood restaurant for dinner, or simply follow whatever catches your attention on your first afternoon in the city.
Accommodation: Hotel Bonaventure Montréal (or similar)
DAY 12: DISCOVER MONTRÉAL WITH A LOCAL GUIDE
Meet a local guide for a private walking tour tailored to your family’s interests and pace. Depending on the route, you might explore areas such as Old Montréal, the Plateau, Mile End, or Little Italy while learning about the people, food, architecture, and cultures that have shaped the city. The private format allows the experience to adapt to the people travelling with you.
Accommodation: Hotel Bonaventure Montréal (or similar)
DAY 13: MONTRÉAL OR THE EASTERN TOWNSHIPS
Keep your final full day open. Stay in Montréal to revisit a favourite neighbourhood, explore a museum or public market, or spend time in one of the city’s parks. Alternatively, take a day trip into the Eastern Townships, where small communities, rural landscapes, and local food producers offer a very different perspective on southern Québec.
Accommodation: Hotel Bonaventure Montréal (or similar)
DAY 14: DEPART MONTRÉAL
Enjoy an easy final morning in Montréal before returning your rental car and making your way to the airport for your flight home