The first tip to make this 10-day itinerary through Canada and the USA, is to buy a single ticket to Toronto and return from New York. Or the other way round. If not, you will need to spend more time and money on flights and accommodation.
This is a personal travelogue. I did this itinerary last year, travelling in September, with many train journeys. I took a flight from São Paulo to Toronto, with a connection in Newark. Then I went by train to Montreal and New York, from where I embarked back to Brazil. And here are all the tips: best time, how long to stay in each destination, where to stay, what to do and itinerary tips with the main sights.
How many days to stay in each destination
Toronto and Montreal are smaller cities, with fewer tourist attractions, so you can spend less time in them, dedicating more days to New York. That's what I did. But, if you prefer to spend less time in NY, which is understandable, due to the absurd prices and stresses, you can do it your way. Here's how I did it:
Toronto - 3 nights
Note that there are 10 nights in total. So 10 days of travelling, because there are 10 days of accommodation. If you count the day of the outward journey, which is usually a lost day, it will be 11 days of travelling. My way of counting, so a 10-day itinerary means a trip with 10 hotel days.
Best time to do this itinerary through USA and Canada
Avoid travelling in winter and summer. The winter months, from December to March, are extremely cold and snowy in Canada and the north-east of the USA. It's not cute, it's not Christmas weather, it's a nightmare impossible to leave the house and it's very inconvenient for tourists. Also avoid summer, especially July and August, as the heat in NY is unbearable and there are so many people on the streets that you will think you are sprouting tourists from the sewers. Prefer spring and summer, which are in the following months:
April
May
June - towards the end of the month the heat is already getting to you in NY.
September
October
November - it's going to be quite cold everywhere.
Accommodation
Toronto, Montreal and NY are not destinations with cheap hotels. That's why I stayed in different ways: hostel, airbnb and budget hotels. This itinerary will be best enjoyed if you stay in central neighbourhoods. Get straight to the point:
Where to stay in Montreal: best neighbourhoods
Manhattan or Brooklyn, where to stay in NY?
Toronto - Days 1, 2 and 3
Canada's largest city has a reputation for being boring and with nothing to do, but don't fall for it. Toronto, besides being beautiful, safe and organised, is full of natural, sporting and gastronomic attractions. (If you are thinking of staying more or less time in Toronto, check out our Toronto Itinerary : what to do from 1 to 4 days).
Day 1 - Toronto
On your first day in Toronto, explore the city centre attractions. Pass by the Old City Hall, the former city hall building. In front of it is the beautiful sign with the name of the city. Nearby is the Yonge-Dundas Square area, known as Toronto's Times Square: dozens of shops and buildings with big screens and lights. Then take the metro to Casa Loma, a medieval-style palace with period relics in its collection. To watch the sunset, head back to the centre and up to the CN Tower lookout.In the evening, head straight to the historic Distillery District, home to one of the country's best breweries.
Roger Centre, below the CN Tower
Distillery District and its Victorian-style buildings. Great place for photos and beer drinking.
Day 2 - Toronto
On the second day, if the weather is good, get up early and visit a small archipelago in Lake Ontario. On these islands are gardens, beaches, a children's playground, a so-called haunted lighthouse and beautiful views of Toronto. They are called the Toronto Islands and are a must-see tourist spot. Great place for photos. You have to take a ferry to get there, but it's only an 8 dollar, 20 minute journey. On the way back, take a train, bus or your hire car to Niagara Falls. It's only 130 kilometres there, but there's often traffic, so don't compromise on the return.
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Pan Pacific Toronto Hotel
For those seeking an unforgettable urban retreat in Toronto, the Pan Pacific Toronto Hotel stands out as a stellar choice. This elegant hotel boasts modern amenities, impeccable service, and a prime location in the heart of the city. Whether you're visiting for business or pleasure, the Pan Pacific Toronto Hotel ensures a delightful stay, with easy access to Toronto's iconic landmarks, cultural hotspots, and culinary delights.
Garden view near Chelsea Beach (yes, there is a beach on Toronto Island)
Boat trip to Niagara Falls
Day 3 - Toronto - Montreal
On the third day in Toronto, I went in the morning to visit the St Lawrence Market, the main public market in Toronto, a good place to eat well and without spending too much. There I ate Peamel Bacon, one of the typical Canadian foods that originate in Toronto. Then I walked to Union Station, where the train leaves for Montreal. I spent much of the day on the train from Toronto to Montreal. It was about 6 hours on board, travelling through ordinary landscapes. If you buy in advance, the plane ticket may be even cheaper. But I preferred to go by train to avoid the airports, far from the centre, and the hassle of waiting rooms.
Inside the train from Toronto to Montreal
Montreal - Days 4, 5 and 6
I think two full days was enough to explore the basics of Montreal. But I liked the city so much that I wanted to spend another week there, just walking through parks and eating the delicious typical food. And the nightlife is the best in Canada.
Day 4 - Montreal
On the fourth day of the trip, I woke up in Montreal and walked to try the most famous breakfast in the country, at Beauty's Lanchonete, where the typical Canadian breakfast was supposedly created, a well-served dish with scrambled eggs, boiled potatoes, bagels, pancakes and sausage. All topped with maple syrup. Afterwards, take advantage of the proximity and head to Mont-Royal Park. It's worth walking up the trail to the lookout point, where you'll have the most beautiful view of Montreal. By metro, head to St Helena Island and visit the imposing Montreal Biosphere. In the evening, relax in the lively bars and restaurants of Rue Saint-Denis.
Traditional Canadian breakfast at Beauty's
Squirrel in Mont-Royal Park
Day 5 - Montreal
On the fifth day of your trip, take the metro and go for breakfast on the other side of the city, at the Marché Jean-Talon, which has several typical food kiosks. Take the opportunity to walk in the area, in the Italian neighbourhood (Petite Italie) and in Mile-End. If you get hungry, head to Schwartz's, a traditional restaurant that serves the best smoked meat in Montreal and was once owned by singer Celine Dion. In the late afternoon, head to Vieux-Montreal and Vieux-Port, the historic city centre. The area, which looks more like Europe, has narrow streets, large squares and churches, restaurants and shops. Plus a large Ferris wheel.
Smoked meat sandwich at Schwartz's
Street in Montreal's historic neighbourhood, the Vieux-Montreal
Ferris wheel in Montreal's old harbour
Day 6 - Montreal - NY
On the sixth day I picked up, went to the station and boarded the train from Montreal to NY. It's a 10-hour journey, but the comfort and scenery make it worthwhile. The route is scenic and was once considered one of the most beautiful in the world.
Panoramic cabin on the train from Montreal to NY
New York - Days 7, 8, 9 and 10
I chose to spend 4 nights in New York because it is a huge city and full of attractions. But I regretted it, because I liked Canada much more. There, I followed most of the days of this 7-day itinerary in NY. Anyway, I will report what I liked best.
Day 7 - NY
On the seventh day of the trip and the first day I woke up in NY, I went for a walking tour in Manhattan. I got off the subway at Fifth Avenue, passed by the Coca-Cola headquarters, Trump Tower, saw the Empire State Building, Rockefeller Center and went to Central Park. There, I went to Bethesda Fountain, the setting for dozens of films, from Forget Me Not to John Wick. Then, again by subway, I headed to the tip of the island, where I saw the memorial to the victims of the World Trade Center and the new building erected on the site, the One Trade Center. Nearby is Wall Street, with the famous statues of the bull and the girl. To finish, I walked a few more minutes to Staten Island Ferry, where the free ferry departs from near the Statue of Liberty.
Bethesda Fountain in Manhattan's Central Park
Manhattan street near the Empire State Building
Statue of Liberty seen from the free ferry to Staten Island
Day 8 - NY
On the eighth day, I dedicated myself to getting to know Brooklyn, where I was staying. I walked in the centre (nothing interesting) and went to see the famous DUMBO area, where everyone goes to take that photo under the Manhattan Bridge. There are several parks by the canal, with great views of Manhattan, such as Main Street Park, where Jane's Carousel is located. Still in Brooklyn, I went to Williamsburg, the hipster neighbourhood, full of art shops, manufactured goods, vegan restaurants and alternative people with striped clothes and a mustache with gel.
Park next to the Brooklyn Bridge, overlooking Manhattan
Day 9 â NY
On the ninth day of travelling and the third full day in NY, I was tired of rushing around. I had already seen the main sights, so I went for a leisurely stroll around Manhattan. I tried some of the best hot-dogs in NY, went to Magnolia Bakery (which appears in Sex and The City) and didn't find it that good. I took the cable car to Roosevelt Island, a quiet island between Manhattan and Brooklyn. Without planning it, I went through three tourist hells called Little Italy, China Town and Times Square. At the end of the night, I decided to queue at Momofuku Noodle Bar, which is really tasty, but very expensive.
Roosevelt Island, a quiet place one subway or cable car station away from Manhattan
Hell on Earth, better known as Times Square
Day 10 - NY - BRAZIL
On the tenth and last day of travelling, I visited MOFAD, the Museum of Food and Drink, which was close to my Brooklyn hotel. It's worth a visit. Then I made the pilgrimage to Newark airport: Uber to the subway in Queens, subway to Penn Station and from there a train to the airport.
MOFAD kitchen, a museum in Brooklyn that not many people know about.
More tips on New York:
5, 6 and 7 day itineraries in NYC
23 free museums in NY
Brooklyn or Manhattan, where to stay?
More tips in Canada:
What to do in Montreal
