Toronto and Montreal Itinerary - 8-Day City Break

Toronto and Montreal Itinerary - 8-Day City Break

8-Day Toronto and Montreal Trip / Itinerary via rail! On this Toronto and Montreal Holiday, see Toronto’s iconic CN Tower and Niagara Falls before travelling via rail to Montreal for European charm and historic sites e.g Notre-Dame Basilica.

From £1195 pp
Above pricing is currently inclusive of local fees.
Travelling 20 April 2027
Maximum Occupancy

Duration: 8 Days
Quote CHH1681

Tell us your requirements and one of our travel advisors will contact you!

Toronto and Montreal City Break at a Glance

Itinerary Highlights:

  • All flights direct on Air Canada
  • Days 1 - 4 Toronto
  • Day 4 - fly form Toronto Montreal
  • Days 5 - 8 Montreal
We can tailor all hotels and durations to suit your requirements
Toronto and Montreal Itinerary - 8-Day City Break

Sample Itinerary of Toronto and Montreal City Break

Explore two of Canada’s most beloved cities with this 8-Day Toronto and Montreal Itinerary. This Toronto and Montreal City Break offers a blend of Toronto’s stunning natural landmarks and bustling city, with Montreal’s unique Canadian energy and European charm. Whether you want to see the stunning Niagara Falls, explore Toronto’s renowned art and culture scene, or wander Montreal’s historic streets and modern neighbourhoods, this Toronto and Montreal Holiday offers two unforgettable destinations. Fly Toronto on one of our airline partners like Virgin Atlantic / Air Canada! Plus, why not opt for a few extra days in Quebec City. 

Days 1-4 Toronto:

Enjoy 4 days for your Toronto City Break! Alongside being known for being the gateway to Niagara Falls, Toronto also offers top-tier museums, fun neighbourhoods and the iconic skyline marked by the CN Tower. Toronto offers a mix of city life and natural beauty. Whether you’re wandering the city’s historic markets, taking in panoramic views, or venturing out to the majestic Niagara Falls, Toronto is packed with memorable experiences.

Things to Do in Toronto:

  • Day Trip to Niagara Falls: Just 1.5 hours from Toronto, Niagara Falls is one of Canada’s most iconic natural wonders. Take a Hornblower Cruise to experience the falls up close, stroll along the scenic Niagara Parkway, or visit Clifton Hill for family-friendly entertainment. You could also opt for an overnight stay and enjoy the nearby Niagara-on-the-Lake.
  • CN Tower: An architectural marvel and Toronto’s most famous landmark, the CN Tower offers spectacular views from its observation deck. Be sure to try the EdgeWalk: a hands-free walk along the tower’s outer edge.
  • Kensington Market: This lively bohemian neighborhood is known for its eclectic mix of shops, cafes, and street art. Explore unique boutiques, sample international foods, and immerse yourself in the colourful local scene.
  • Toronto Islands: A quick ferry ride from downtown, the Toronto Islands provide a peaceful escape from the city’s bustle. Rent a bike or walk around the park’s scenic paths, relax by the beach, and enjoy beautiful views of Toronto’s skyline from across the lake.
  • Distillery District: Known for its cobblestone streets and historic buildings, the Distillery District is a pedestrian-friendly area filled with galleries, cafes, and unique shops. It’s a great place to spend an afternoon and explore Toronto’s art and cultural offerings.

Stay at: Chelsea Hotel, Toronto. Located in the heart of downtown, the Chelsea Hotel offers comfortable accommodations with modern amenities, an indoor pool, and a family-friendly atmosphere. With multiple dining options, a fitness center, and close proximity to Toronto’s main attractions, it’s an ideal base for exploring the city.

Day 4 - Fly from Toronto to Montreal

Fly on Air Canada from Toronto to Montreal.

Days 5 - 8 Montreal:

After experiencing Toronto, your City Break continues in Montreal; a city where Canadian hospitality meets European charm. From the historic streets of Old Montreal to the vibrant neighbourhoods filled with art, music, and culture, Montreal offers a dynamic blend of the old and the new. With five nights in Montreal, you’ll have time to delve into its rich history, try its famous culinary offerings, and explore its lively art scene.

Things to Do in Montreal:

  • Old Montreal: Step back in time in Old Montreal, where cobblestone streets, historic architecture, and vibrant plazas create a distinctly European atmosphere. Highlights include the stunning Notre-Dame Basilica with its breathtaking blue interior and the charming Place Jacques-Cartier lined with cafes and street artists.
  • Hop-On-Hop-Off Bus Tour: This convenient tour allows you to see Montreal’s top sights at your own pace, with stops including Mount Royal Park for panoramic city views, Jean-Talon Market for local flavors, and the bustling McGill University campus.
  • Mount Royal Park: Designed by Frederick Law Olmsted, the creator of New York’s Central Park, Mount Royal is the perfect spot for a scenic hike or a relaxed afternoon. Climb to the lookout point for breathtaking views of Montreal’s skyline and the St. Lawrence River.
  • Saint-Laurent Boulevard & Little Burgundy: Saint-Laurent Boulevard, often called “The Main,” is known for its vibrant street art, trendy cafes, and boutiques. In nearby Little Burgundy, you’ll find top-notch restaurants and jazz clubs, perfect for a night out to enjoy Montreal’s live music and dining scenes.

Stay at DoubleTree by Hilton Montreal. Centrally located downtown hotel connected to Complexe Desjardins, offering modern accommodations, an indoor pool, fitness center, on-site dining, and easy access to Old Montreal, shopping, dining, and entertainment.

Optional Extension: 3 Days in Quebec City

Why not extend your Toronto and Montreal Itinerary with 3 days in Quebec City, just a few hours from Montreal by train. Known for its well-preserved Old Quebec district, this charming city feels like a piece of Europe with its French-inspired architecture, cobblestone streets, and the majestic Château Frontenac overlooking the St. Lawrence River. Quebec City offers a deeper dive into Quebec’s rich history, culture, and culinary delights, making it an ideal addition to your Canadian adventure.

All our holidays are tailor-made and can be adapted by changing hotels durations and destinations to suit the individuals tastes and requirements – please do get in touch so we can start planning.


Toronto and Montreal Itinerary - 8-Day City Break FAQs

How many days do you need for Toronto and Montreal?

Eight days is a comfortable amount of time to see both cities properly, with four nights in Toronto and three nights in Montreal, plus a scenic rail journey between the two. That's enough time to fit in a day trip to Niagara Falls from Toronto and still explore Old Montreal at a relaxed pace. Every itinerary is tailor-made, so we can extend or shorten either city to suit you — including adding on Quebec City.

What's the best way to travel between Toronto and Montreal?

Flying is the fastest way to travel between Toronto and Montreal and your internal flight is included in this itinerary.

Is Toronto and Montreal a good city break for a UK traveller?

Yes — both cities are well connected from the UK, with direct flights from London on Air Canada and Virgin Atlantic taking around 7 to 8 hours to Toronto. The five-hour time difference makes it manageable for a week-long trip without heavy jet lag, and eight days is enough to properly experience two very different sides of Canada: Toronto's modern skyline and Montreal's European-inspired old town. It works well both as a standalone city break and as the start of a longer Canadian itinerary.

Can I add Niagara Falls or Quebec City to a Toronto and Montreal itinerary?

Absolutely. Niagara Falls is just 1.5 hours from Toronto and is easily added as a day trip or overnight stay within your eight days, with options like a Hornblower Cruise or a stroll along the Niagara Parkway. If you'd like to extend the trip further, Quebec City is a popular add-on, reachable by train in a few hours from Montreal, and brings an even deeper dose of French-Canadian history and architecture. Both can be built into your itinerary at the planning stage.

What's the best time of year for a Toronto and Montreal city break?

Late spring through early autumn (May to October) offers the most reliable weather for exploring both cities on foot and enjoying Niagara Falls at its best. September and October are particularly popular for the autumn foliage, especially around Mount Royal Park in Montreal. Winter has its own appeal too, with Montreal's Christmas markets and Toronto's ice-skating rinks, though you'll want to pack for cold temperatures and shorter daylight hours.

How much does a Toronto and Montreal trip cost?

hotels, and any add-ons like Niagara Falls or Quebec City, so every trip is quoted individually rather than sold as a fixed package. As a starting point, this gives us the flexibility to tailor flights, hotel category, and duration to your budget. Get in touch with our travel advisors for a free, no-obligation quote based on your exact requirements. This itinerary starts from £1195 per person.