Though I’m originally from Ottawa, I’ve lived a combined ten years in Montreal and the city has become a second home. Even after all that time, it still has a lot to offer. As you’d imagine, it would be impossible to experience all of Montreal’s gifts in three days, yet a three day itinerary will give you enough time to sample many of its top attractions and certainly give you a good sense of its charms and character.

That said, it should be noted that—like much of Canada as a whole—Montreal enjoys four seasons, each with its own distinct feel, benefits and challenges. For this reason, I’ll mention when sites or activities will differ from one season to the next, particularly between winter and summer. Let’s just say that, when it comes to your trip to Montreal, timing matters.

Okay, so, as with most of these itineraries, we’re assuming three full days in Montreal, meaning four nights, with day one beginning when you awake from your first overnight in the city, and day three ending when you head to bed for your last night. In other words, you’d be arriving on day zero and departing on day four.

One final note before we jump into this three day itinerary for Montreal: the order of days is largely up to you, meaning if it’s more convenient for you to do the Day One activities on day Two, go nuts; the days are listed in no particular order.

Montreal is often described as Canada’s most European city and this is due largely to Old Montreal, which certainly does feel like parts of the old world. Though touristy and dotted with crappy gift shops, Old Montreal is also genuinely quaint, features some excellent dining and shopping options, and is a great place for a stroll. And this is true regardless of the season, though in the winter be mindful of the ice on the cobblestones.

A short walk from Old Montreal takes you to the Old Port. In the winter this area is often quiet, though it is the setting for a few winter events. In the summer, though, is when it truly comes to life. There are plenty of dining options, many of them with outdoor seating. This is also an excellent place to learn about the city’s history, as it is the site of the Museum of Archaeology, set directly on the original entrance to the colonial-era fort that served as the city’s first settlement, back when it was called Ville Marie.

A quick glance at a map will guide you from the Old Port’s Museum of Archaeology to the Notre Dame Basilica. As its name suggests, the basilica is modelled on its famous sister in Paris and is home to an enormous pipe organ. It was also where Celine Dion married her long time manager. Just across from the Notre Dame are more historical sites of potential interest, including Canada’s first bank.

Start the morning with a coffee and some pastries at one of many excellent cafes sprinkled throughout the city, then head for Parc La Fontaine. This is a truly lovely place to walk around and see Montrealers enjoy their leisure time outside. If you’re into cycling or jogging it’s also an excellent spot to get in a run or ride. That said, Parc La Fontaine is wonderful at any time of year, perfect for a picnic in the summer, quite lovely in spring or fall (the image above was taken in the park in autumn) and features a skating rink during much of the winter.

Note that, near the northwest corner of the park, steps from the intersection of Rue Rachel and Avenue du Parc La Fontaine, you’ll find La Poule Mouillee (literally The Wet Chicken, but don’t let the less than appetizing name throw you) which serves some of the best chicken in town, while across the street is La Banquise, considered by many as the best place to try poutine, the city’s—and arguably Canada’s—most famous dish (though I personally think La Banquise is overrated; it’s mostly popular as a post-drinking spot to eat). Either is a good option for lunch—though keep in mind that poutine is quite heavy.

From Parc La Fontaine, head to Square Saint Louis to get a look at some of Montreal’s iconic architecture. This is a truly photogenic area but more just a spot to see on the way to other sites. Just a block over from Square Saint Louis, though, you’ll find Mama Clafoutis, known as one of the top spots in the city to grab some pastries.

Now head southeeast-ish, using the Berri-UQAM metro station as a goal. This will bring you to Saint-Catherine, much of which is pedestrianized, especially in the summer and during major festivals. In fact, head right from here in winter and you’ll be taken into the city’s Christmas Village where you can shop for unique gifts and enjoy a hot chocolate. Turn left and you’ll enter the part of the city known as The Village, a predominantly gay neighbourhood that also features some excellent cafes and bars, most of which offer outdoor seating in the summer.

Place des Arts is also not far and the site of some of the city’s major festivals, including the Jazz Festival.

For dinner, explore le Quartier Latin which is also a great place to try some local brews. One of my favorite places for a drink is in the area, too: L’Ile Noire (the Black Island), a scotch bar with a massive list of scotches. They also serves excellent gin and tonics.

Parc Mont Royal is set nearly in the centre of the city and was actually designed by the same guy who designed Manhattan’s Central Park. The city’s name is also a mispronunciation of Mont Royal (say it fast enough and you get…Montreal, which is pronounced Mun-tree-ALL in English, by the way, not MONN-tree-ALL). The park is draped overr a squat mountain and crissed and crossed with trails that are perfect for a walk, a run or, in the winter, even a cross-country ski. Upon reaching the top you’ll be rewarded with some great views of the city. On flank of Mont Royal is covered by a sprawling cemetery that can be interesting and evocative to explore, if you’re into that. Oh, and that massive cross visible from nearly anywhere in the city? Yes, you can reach it as it stands atop Mont Royal.

From the top of Mont Royal head down through the McGill campus, which will take you right downtown. Here you can try a smoked meat sandwich at one of two iconic spots (though many will say THE place to try the famous dish is at Schwartz’s Deli, on St Laurent, which is nearer Square Saint Louis), Reuben’s and Dunn’s, though I prefer the latter.

If you have shopping to do, Montreal has an entire underground city that is mostly interconnected shopping malls, from the modest to the high end. The tunnels that join these malls also connect them to hotels and the city’s train station, not to mention it’s entire subway system, of course, meaning that you could potentially spend days exploring without ever heading outside. The Eaton Centre has an especially good food court, while Simon’s—though primarily a clothing store—offers some rather unique housewares and home decoration options.

Even during the winter months, you should head outside to wander the area, which has its own hectic energy. The downtown area also has several decent bars and restaurants to check out. You’ll find several Irish-style pubs on Crescent, as well as Brutopia, another great place to try some local brews.

The city has plenty to offer year round, but its weather can be extreme. In the depths of winter—especially around January and February—temperatures can be as low as -30 degrees Celsius (-22 Fahrenheit), while in July and August temperatures can rise to +30 Celsius (86 Fahrenheit), so dress accordingly.

Autumn can be nice, cool without being cold, and the turning of the leaves gives the city a completely different look and feel, though there are fewer events on tap. Spring is also an option though it can rain a lot, especially in April.

I’d recommend staying in or near the Plateau area and ensuring that you’re an easy walk from a metro station, especially if visiting Montreal during the winter as you may not want to do as much walking. The metro is dingy and ugly but generally clean and truly convenient.

Last time I was in Montreal I stayed with a friend at Hotel Manoir Sherbrooke, in the Plateau area, walking distance from Square Saint Louis and the Sherbrooke metro station. The hotel is also housed in a beautiful mansion and has the feel of a guesthouse with all the conveniences and services of a hotel.

Well, obviously the aforementioned poutine is a must. Ask ten Montrealers where you should try a poutine and you’ll get ten different answers, but here’s my advice (which will have many locals cry havoc): start at La Belle Province. Why? It’s basic and no nonsense. It’s just a poutine. The platonic ideal of the dish: good fries topped with cheese curds and smothered in gravy. Nothing more and nothing less. Start there.

Once you’ve tried the most basic version, you can mess around with the weird and the fancy and the artisanal. I’ve mentioned La Banquise, which is a favorite of many and offers several varieties of the dish. But if you want variety and prefer a more family restaurant atmosphere, check out Poutineville, which not only offers its own house variations but allows you to build your own poutine, choosing from a long list of toppings as well as cheeses and sauces.

In February you can also time your visit for Poutine Week, when restaurants all over the city offer their own unique takes on the dish, so a Vietnamese restaurant might add a Vietnamese poutine to their menu for that week alone, for example. This is especially great for the foodies and adventurous eaters, but be sure to try the basic poutine first.

You should also try the Montreal-style smoked meat sandwich, which I’ve also mentioned. Montreal is known for its bagels, and many will agree St Viateur has the best in the city, with Fairmount a close second (though opinions on this are as strong as they are regarding the best poutine).

I’d say Montreal is also a great place to try local beer. There are microbreweries all over the city, from the divey, like Le Cheval Blanc (also the first in the city, already over 30 years old), to the more relaxed and creative, like Dieu du Ciel. Other places to grab a beer include Brutopia, mentioned above, and Benelux, with its sprawling summer terrace.

Lastly, any trip to Canada should include a taste of the Nanaimo bar (created in British Colombia, nowhere near Montreal, but a key dessert to try regardless of location) and any pastry featuring maple syrup, especially a maple sugar pie or maple tarts.

Of course, you could stay longer in Montreal and still have plenty to see and do, but this taster is a great place to start.