Toronto and Montreal

Check the tourist bureaus to see what is happening in each city during your planned travel dates. Both of them have many excellent music, entertainment, food and art festivals. If you are staying in the cities, no car is necessary because of great public transportation systems. When in Toronto I took a great day trip by car through the wine country on my way to Niagara Falls.

What time of year? If the Autumn, it may make a slight difference which to do first. Montreal and the region has beautiful Fall colours, but it only takes a bad storm to lose the leaves.
Personally, I would find a week in each city a bit long. I am tempted to suggest a 3rd city either Ottawa or Quebec City. Quebec City would give you a taste of Europe without the trans Atlantic flight and at a better dollar exchange. It is a little too far with a baby for a day trip, but if you could get a decent flight from there home, it could be a consideration. If you did Toronto - Quebec - Montreal it would work with your fly in and fly out plan, but the train between Toronto and Quebec is a longish day. Alternatively, look at a multi city flight of LA/SD - Toronto - Quebec City - LA/SD ( from Montreal) and train between QC and Montreal for the scenery.

Do not not not rent a car in Montreal. The entire city’s roads, highways, overpasses, underpasses and back lanes are under construction. I have lived here all my life and have never seen such chaos. The detour signage is confusing and in French only, thus making it even more difficult for strangers. On an outing yesterday, a drive that should have taken about 15 minutes took almost an hour.

On a cheerful note, the metro system and buses are very good.

I don't think it matters which city first - I would book based on flight costs and convenience. I too would add Quebec City to the mix. It only needs 2-3 full days or so, it's incredibly charming and much more compact that the large cities of Toronto and Montreal. You can get there by train to/from Montreal. Of the three, I would give most time to Montreal. I spent 5 full days there last time and it felt rushed. You don't need a car for any three, but it's nice to have if you want to go on day trips. There is so much to see even outside the cities, but with 2 weeks, I would stick to your city plan for a first trip.

We drove Montreal-Ottawa-Toronto (then back home near Boston via NY so we could see Niagara Falls) with our two year old daughter last spring. In addition, Quebec City is one of our favorite places in the world, my wife and I have been there (without kids) probably 7-8 times now.

With two weeks, I would suggest trying to add in Quebec City and Ottawa. Perhaps you could shoot for 4/5 nights in Toronto, 2in Ottawa, 4/5 in Montreal, and then ending in Quebec for a few nights?

You can do trains all the way in between. We had our car with us for our trip last year, but did not use it at all in Montreal and only in Toronto to go to the zoo (which is not centrally located). Also don't think you'd want one in Quebec (we only ever use ours to get out of the city).

Hello, we are going to Toronto this October, with our 11 year old son. My husband and I have passports but my son does not. We plan to fly into Toronto (from SC) and drive to Buffalo, hitting Niagara Falls on the way. What do I need to bring so my son can cross the boarder with us? Thanks so very much!!

All four cities (Toronto, Ottawa, Montreal and Quebec City) are great. To me Toronto felt a lot like a multi-ethnic US city (a clean New York). The others felt somewhat more foreign. I'm not sure I'd try all four in two weeks, but then again you probably won't be spending much time in museums with an infant.

Montreal has an annual jazz festival in late June/early July. I went to the festival many years ago and enjoyed it a lot. There was a lot going on outdoors and much was free; I don't know whether that has changed. The concerts were not limited to jazz.

Just to add to acraven's comments, don't go to Montreal during the Grand Prix (early June) weekend! The locals I've asked are not fond of the annual madness. Plenty of other festivals all summer, and also during the winter if you're hardy enough.

Do not not not rent a car in Montreal.

I agree with this wholeheartedly, and likewise for Toronto. I fly into both cities off and on, and have taken the inexpensive UP Express from Pearson Int'l to Union Station (Toronto) then walk to my lodging nearby. If you get a PRESTO card, you can load it up with a reasonable amount ($10 CAD minimum to load) and use it on the TTC-Metro and streetcars are excellent. In Montreal, I by a transit card at Trudeau Int'l and ride the 747 Express bus (not the most comfortable, it's basically a city transit bus) into the downtown core. For the $10 (CAD) fare, you have 24 hours from purchase to use the Metro. Very economical and efficient.

I recently visited Montreal and my flight arrived early evening. The 747 absolutely cruised into downtown, past all the construction. It was the quickest trip into downtown I've ever experienced (daytime, summer, not so much).

Hope this helps.

“The locals I have talked to are not fond of the annual madness” referring to the Grand Prix.

Well, the city loves, loves, loves the Grand Prix. The place is buzzing with excitement. The restaurants and bars are packed with all those big spending race car lovers, and there is a lot of fun to be had. The “locals” referred to above probably hate the jazz festival, too, but there are cranky pants everywhere.

As others have noted, with two weeks you should be able to cover Toronto, Montreal, and Quebec City. You should also be able to spend some time in Ottawa. It’s a great place to learn about our neighbor to the north, the true north, strong and free. In Ottawa, the Canadian Museum of History tells the story of the country. The Natural History tells the natural history of Canada. The Canadian War Museum starts with the first military operations in Canada to Canada’s role in Afghanistan and peace keeping operations around the world. Parliament hill is a great place to learn about Canadian government, although the Parliament building is undergoing major renovations. There is so much more to see.

I find the areas south of Toronto to be far more interesting than Toronto, so definitely rent a car for that part. I'm with the above posters that are recommending Quebec City and Ottawa. Quebec City is my favourite city in North America.