We've had the good fortune to visit Montreal several times. On each visit, we discover new neighborhoods, great restaurants, and cool shops.
Full disclosure: We've only visited Montreal in the summer months. Reviews of sites and activities reflect a summer-time bias. We are sure Montreal is also great in winter. Just not sure we have the fortitude to try Montreal in winter! Maybe someday!
Places to Stay: There are a lot of hotels as well as VRBO or AirBnB rentals in Montreal. We rented apartments in the Mile End and Plauteau neighborhoods. The advantage of these neighborhoods is that they are centrally located and easily accessible by public transportation. The downside is that they tend to be a bit more expensive.
Eats: Montreal has a fantastic food scene! All the options exist -- from fast food, to family style, to coffee shops, to Greek, to Canadian. You name it, you can find it!
A word about poutaine.....
Poutaine, a national delicacy, can be found on most menus. In fact, there are whole restaurants dedicated to poutaine. Essentially it is french fries and fried mozzarella covered in brown gravy. While it sounds a bit off-putting, it can be delicious!
Shopping: Montreal has both incredible malls and tiny boutique shops. As we tend to be a bit partial to boutique shopping, we'll focus on that.
If you like a good shopping stroll, we would recommend walking Boulevard Saint Laurent. The stretch of Saint Laurent between Sherbrooke Street and Laurier Avenue is a great city walk and home to lots of shops, restaurants, designers, boutiques, bars, furniture stores and nightclubs.
Honorable mention goes to Bonsecours Market in old town by the harbor. At more than 100 years old, this imposing structure with its silver dome was home to customs house as well as the Quebec legislature. Today it is a meeting or entertainment venue and has a really lovely shopping hall with lots of "made in Quebec" finds.
Good to Knows: These are a few tidbits that are just helpful (or fun) to know!
Good to Knows
Getting there: Montreal has a large, international airport just outside of town with lots of direct flights to the US daily. The otherwise excellent train system does not come out to the airport. To get from the airport to town you will need to take a taxi or public bus.
Getting around: Montreal has excellent public transportation. A good tidbit is that kids ride for free in summer (you should double check that this is still in effect). You can buy metro and bus tickets at kiosks at many train stations.
The STM (public transport system in Montreal) has a fantastic website that can help you plan your trip around town:http://www.stm.info/en
Montreal is really a bi-lingual town. The preferred language is French. If you have any French skills, this would be a good time to use them. However, note that the locals are likely to ID that you are not a native speaker and switch to English. Don't take it personally. They are trying to be nice.
French in this part of the world is a Quebecquois -- the words might be the same as French, but they sound a bit different.
Finally, you are likely to hear young people moving seamlessly between French and English -- within the same sentence. That kind of bilingualism is really a wonder to behold!
Once the long cold winter is over, Montrealers get outside and have fun!
All summer long there are outdoor festivals to meet every taste and interest--jazz, comedy, beer, fireworks, circus, food trucks, Grand Prix, Shakespeare, fringe, and on and on.
Most festivals have free as well as paid events.
https://www.mtlblog.com often keeps a running list of what is playing when.