Cobblestone streets and red car in Old Montreal

Your MONTREAL Itinerary: 5 Fantastic & VERY Different Days

Montreal has many sides to explore, and this 5-day Montreal itinerary will give you a very good sampling. My trip to Montreal was with four very different personalities, and they pushed me into trying things I wouldn’t have done on my own. So now I can share them with you!

5 fantastic itinerary ideas for Montreal, Canada

Limited time? Pin me for later.

This Montreal itinerary satisfies a lot of travel styles. The foodie. Nature lover. Sports fan. Culture and history buff. Adventurer (or wannabe adventurer). There are a lot of fantastic activities for families here, too. MORE than enough to keep you busy and satisfied for 5 days!

You may also like QUEBEC Getaways for Couples: Spas, Hotels and Cabins


This post may contain affiliate links. If you use these links to buy something, we may earn a commission at no extra cost to you. Thank you! For more info, please read my disclosure.

About Montreal

Montreal is rich in history, culture, food, art, scenic beauty and thrills for the adventure-seeker. It sits on an island in the lovely St. Lawrence River, is the largest city in Quebec, and gets its name from the three-peaked mount in the middle of the city.

For much of Canada’s early history, Montreal served as the launch-point for European expansion into the west, Canada’s economic and cultural hub, and its capital city. It was the first fortified settlement in the area, established as Fort Ville-Marie by the French, and served as a significant outpost for the Catholic church. Because of this, you’ll be charmed by Montreal’s lovely cobblestone streets, beautiful churches and fascinating museums.

Montreal has maintained its historical charm while evolving into an impressive modern city. In many ways, Montreal has led Canada on the global stage. It hosted the World’s Expo in 1967 (Expo 67) and the 1976 Summer Olympics, and continues to host tons of international festivals.

Experiencing Montreal means experiencing its art, its humor, its food, and its grit. Montreal has been at the forefront of pushing boundaries with its art, entertainment, political protests, strikes and marches. This is where some of the greatest moments in hockey history took place … very important to us Canadians. And it’s perfectly respectable to eat a LOT here: Montreal is second to New York City as having the highest number of restaurants per capita in North America, including some of Canada’s best. Then head underground to explore its 32km of tunnels, including underground malls!

You don’t need to learn French to enjoy this 5-day Montreal itinerary. Most Montrealers are fluent in English and generally happy to converse in English. That said, it’s always nice to learn a few customary phrases in the host’s language.

DAY 1 = Montreal Itinerary Classics: Mount Royal, Food, Comedy and Pubs

View from Mount Royal on your 5 Day Itinerary

Hike up Mount Royal for this great view

Get out your comfy shoes! Day 1 of your 5 day Montreal itinerary is all about hiking up Mount Royal for a fabulous view of the city and the St. Lawrence River. Then we fill in the rest of the day with food, comedy and drinks. 

Climb Montreal’s Mount Royal Park

Start your climb up Mount Royal at the Monument to Sir George-Etienne Cartier. On this little plaza, you’ll often find a little artisan market and some pretty fantastic buskers and street entertainers.

There are two trails behind the monument that start you up toward the summit. The Mount Royal trails are wide and well-groomed, but there are lots of options and offshoots so definitely take a map with you. We actually got impatient and hiked straight up through the trees. I suggest following the red Chemin Olmsted trail along the edge closest to the river, which is actually how the designer intended. But then I’d cut up through the stairs to the summit. End either at the lake on the south end or return to the monument.

Find everything you need to know about visiting the park, like trails and access points, at Here is the helpful PDF map.

Enjoy Montreal’s Amazing Food … Over and Over and Over

One of the many delicious coffees and desserts in Montreal

Coffee and dessert at Juliette & Chocolat

The Plateau area to the north of the Mount Royal monument has a ton of amazing places to eat. I fully recommend stopping in a few places before AND after your mountain trek … you need the fuel *wink, wink*

The popular streets for great food are Avenue du Mont-Royal, Rue Saint-Denis and St Laurent Blvd. Here are our favorites:

  • Juliette & Chocolat (3600 St Laurent Blvd): This is the perfect spot for a casual but scrumptious coffee and dessert treat. They also have an impressive selection of treats to take with you for a late-night sweet or picnic in the park.
  • Schwartz’s Deli (3895 St Laurent Blvd): One of the oldest delis in Canada, this iconic spot will have a line-up and is cash-only, but it’s totally worth it. I highly recommend the classic smoked meat sandwich meal.
  • Mache (1655 St Denis St): Poutine … mmm, poutine! Oh my goodness, this was SO delicious. I had mine with pulled pork. This spot is close to the pubs highlighted for tonight, so you could also make this one of your evening stops. The menu is only in French but the waiters will help you order.

I highly recommend eating at each of the spots above sometime during your 5-day Montreal itinerary.

After lunch, head up to Little Italy. The Jean-Talon Market (7070 Henri Julien Ave) is a great place to snag some picnic-worthy treats and the streets are cute for wandering. Here are three different but highly-rated Italian spots to enjoy dinner:

  • Bottega (65 Rue Saint-Zotique): Wood-fired pizzas with outdoor seating.
  • Restaurant Matterello (6950 St Denis St): A cozy, casual spot for homemade pasta, fresh ingredients and friendly service.
  • Quindici 15 (15 Rue Belanger): Delicious homemade pasta and dishes beautifully presented, with patio seating.

Experience Montreal’s Stand-up Comedy

Montreal is known for its stand-up comedy. I grew up watching “Just for Laughs” and comedians gracing Montreal stages on television. So taking in a real-life show definitely makes the classic itinerary for 5 days in Montreal.

Here are three very different styles of highly-rated comedy clubs in Montreal:

  • The Comedy Nest (2313 Saint-Catherine St, 3rd Floor of The Montreal Forum): Around for more than 30 years and featuring names like Jim Carrey and Russell Peters, this is a fantastic spot to take in a show. Shows are 1.5 hours Thursday through Saturday in a fun, cabaret-style setting with a full-service bar and snacks.
  • Montreal Improv (3697 Blvd St-Laurent): Enjoy some of the best improv comedy in Montreal. Prices vary depending on the night, but you’ll often find a free show and rarely pay more than $8.
  • The Blue Dog Motel (3958 Blvd St-Laurent): On Monday nights, this popular dance club turns into one of Montreal’s only pure comedy open mics. It’s free whether you perform or just watch.

Ideally, visit Montreal in July during the world’s largest comedy festival, Just for Laughs

Pub-Hopping in Montreal

Saint-Denis St (from Maisonneuve E Blvd to Sherbrooke St E) is fantastic for pub-hopping. Really, just wander this stretch and pop in and out of the ones that look most interesting to you.

Here were our favorites:

  • Bistro a Jojo (1627 St Denis St): A popular (and very loud) spot featuring nightly live blues and rock bands. It’s cozy but comfortable with outdoor seating options.
  • Le Saint Bock (1749 St Denis St): This brewpub has a fantastic list of craft beers and delicious food in a comfy setting. 
  • Les 3 Brasseurs (1658 St Denis St): A 3-story microbrewery with a rooftop terrace for great views, good food and drinks, and a fun vibe.

DAY 2 = Montreal Itinerary for Culture: Old Montreal, Notre-Dame, Art and Fine Dining

The grand Notre Dame Basilica in Old Montreal

Ahhh … the grand Notre Dame Basilica

Step your style up a bit on Day 2 of your 5-day Montreal itinerary! Discover the city’s history and culture by exploring Old Montreal, the lovely Notre Dame Cathedral and Montreal’s fine-dining.

Explore Old Montreal: A MUST for your Montreal Itinerary!

Old Montreal is a super-charming area with narrow, cobble-stoned streets lined with quaint shops, galleries and cafes. 

The most interesting street in Old Montreal is St Paul St E. I recommend starting from Barri St at the north end and following it to St Sulpice St (and then wrap around to the front of Notre-Dame Basilica). It only takes 10 minutes to walk this stretch, so take your time. Stop at every quaint artisan shop, gallery, cafe, pub or ice cream shop that intrigues you.

Place Jacques-Cartier is a bustling square between St Paul St E and Notre-Dame St E and with views of the St. Lawrence River. Daytime or evening, you’ll find interesting street entertainers, artists and local produce.

There are plenty of fantastic restaurants to pick from in the area, including some with patios in the Place Jacques-Cartier square. Check reviews beforehand, as they’re definitely not all equal. We really liked Jardin Nelson (407 Place Jacques-Cartier), including the view from its garden patio. Foodlab | Labo culinaire (1201 St Laurent Blvd) has a quirky menu with nice rooftop views.

Visit the Stunning Notre-Dame Basilica of Montreal

No Montreal itinerary is complete without stepping inside this beautiful basilica.

The Notre-Dame Basilica dates back to 1824 and features brilliant stain-glass windows, intricately carved wooden staircases, and a massive pipe organ. Its architect, James O’Donnell, was inspired by the two towers of Notre-Dame de Paris and Saint-Sulpice. Notre-Dame Basilica was the first Gothic Revival style church in Canada.

Most evenings, the Basilica puts on a pretty spectacular light show. It has two parts, each lasting 20 minutes: first, multimedia installations around the Basilica; then, an impressive show above the pews.

Between late May and late October during the week, you can also take a 1 or 2 hour tour. Experience its history and legend, and explore private areas including the second balcony and part of the crypt. Tours are limited to 25 people.

For information on visiting the Basilica, visit

Appreciate Montreal’s Rich Art Scene

Montreal is a city of artists. It’s definitely worth spending some of your 5-day Montreal itinerary appreciating its vibrant art scene. This includes a ton of public art and window installations in Old Montreal, but also a ton of fantastic Montreal galleries. 

Here are three very different styles of highly-rated art galleries in Montreal:

  • The Montreal Museum of Fine Arts / Musée des beaux-arts de Montréal (1380 Sherbrooke St W): This fine arts museum features local, Canadian and international works.
  • Parisian Laundry (3550 Saint-Antoine W): A 3-story industrial building with the best-of-the-best avant-garde works from Canada and around the world.
  • Station 16 Gallery (3523 St Laurent Blvd): Surrounded by excellent restaurants and bars near Mount Royal, this is a great spot to browse boundary-pushing urban art that likely wouldn’t appear in traditional galleries. It’s a small but fun space.

For more information, visit

Experience Montreal’s Fine-Dining Mastery

A city of artists, Montreal is also known for its amazing fine-dining restaurants featuring world-class chefs.

I’ve never savored a bite – nor spent as much! – on a meal as in Montreal. But, one of my travel companions was a foodie, so I thought, hey! Why not give it a try. And it’s important for you to know something, here. We arrived for our reservation after a spontaneous boat ride that left us drenched (see Day 4 of this Montreal itinerary!), and the staff still provided perfect, 5-star service. It was A-M-A-Z-I-N-G.

So, while there are PLENTY of very highly-rated fine-dining restaurants throughout Montreal, I strongly recommend this one:

  • Toqué (900 Jean Paul Riopell Pl): Exceptional food and service, and considered one of the top restaurants in Canada. I had their 7-course menu with amazing foie gras. Magnifique! They also have an a la carte menu.

DAY 3 = Montreal Itinerary for History: Clock Tower, Museums and Churches

The impressive Mary, Queen of the World Cathedral in Montreal

The regal and less touristy Mary, Queen of the World Cathedral

You’ve already tasted Montreal’s history by roaming Old Montreal, but here’s some more for the history buff in you. Day 3 of your 5-day Montreal itinerary goes deeper into the city’s early beginnings.

Climb the Old Port’s Clock Tower

The Old Port is a historic riverfront complex used as early as 1611 as a French fur trading post. We’ll explore the waterfront on Day 4, but for now, I want to point out a pretty cool historical landmark:

  • Clock Tower (1 Clock Tower Quay St): This iconic, 45-meter clock tower is a replica of London’s Big Ben and was built between 1919 and 1922. It marks the entrance to the port and is a memorial to sailors lost during wartime. In the summer, climb the narrow stairs up to fantastic views (free!).

Memorable Museums in Montreal

Montreal has many very well-done museums to explore. Dive into Montreal’s rich history at these memorable museums:

  • Pointe-à-Callière / Montreal Museum of Archaeology and History (350 Place Royale): This history and archaeology museum is built right on top of where Montreal began in 1642. The museum has seven pavilions and structures, and is officially designated a national historic and archaeological site. It features archaeological ruins along with international exhibits.
  • Château Ramezay | Musée et site historique de Montréal (280 Notre-Dame St. East): A  prestigious home that dates back to 1705 and is one of the oldest buildings in North America. It was built for Montreal’s governor and was where Benjamin Franklin tried to convince Montreal to become the 14th American state. Re-enactors give you a glimpse into life in the 1700s.
  • Sir George-Étienne Cartier National Historic Site (458 Notre-Dame St. East): Where one of the founding fathers of Canada once lived with his family. It’s small but nicely restored.
  • Redpath Museum (859 Sherbrooke St W): This small natural history and world cultures museum features dinosaur skeletons, extinct creatures and Egyptian mummies. Redpath Museum is on McGill University campus, is kid-friendly and free. McGill University is a great visit for history buffs, too, which was founded in 1821.

Beautiful Churches in Montreal

You’ve already seen the Notre Dame Basilica, but there are other beautiful historical churches also worth visiting in Montreal. Consider adding these lovely churches to your 5-day Montreal itinerary:

  • Saint Joseph’s Oratory of Mount Royal (3800 Queen Mary Rd): This 1904 Catholic shrine is one of the most visited in the world. Its dome was the largest in the world when it was completed in 1955. Come on a Wednesday evening for an organ recital and wander its lovely gardens, chapels and museum.
  • Mary, Queen of the World Cathedral | Cathédrale Marie-Reine-Du-Monde (1085 Rue de la Cathédrale): Although lesser-known and less touristy than Notre Dame, this elegant cathedral is stunning and larger. Building began in 1875 to create a scale model of Saint Peter’s Basilica in Rome. It features a fully hand-made reproduction of the Basilica’s elaborate ciborium, mosaics crafted from Italian marble, and paintings depicting historical events in Montreal. Outside along the top are statues of 13 patron saints from local parishes.
  • Notre-Dame-de-Bon-Secours Chapel (400 St Paul St E): This is Montreal’s oldest chapel, dating back to 1771. It’s known as “the sailors’ church” because of the sailing ships hanging from the vault, and because the founder intending it to be a place of refuge for sailors. The current chapel was built directly on top of the very first chapel in Montreal from 1675, which was destroyed in a fire. You can experience the archaeological dig yourself by taking the tour.
  • Christ Church Cathedral (635 Saint-Catherine St W): An Anglican church completed in 1859. Its design was inspired by 14th Century English cathedrals and features a 2778-pipe organ. Christ Church Cathedral literally sits right on top of a popular underground shopping mall, Les Promenades de la Cathedrale, and is surrounded by even more shopping.

DAY 4 = Montreal Itinerary on the Waterfront: Theme Parks, Cycling and Boats

Ferris wheel at Montreal's Old Port

Montreal’s ferris wheel lifts you 60m above the St. Lawrence River

Your Montreal itinerary HAS to include the waterfront. And ideally, getting out on the water! Day 4 of your 5-day Montreal itinerary does exactly that.

But don’t worry … I’ve included a bunch of different activities to suit your style (and stomach!).

New Fun at Montreal’s Old Port

Montreal has done a fantastic job of centralizing a ton of fun things to do along the Old Port. And many of these activities are geared towards families.

Here are the coolest things to do at Montreal’s Old Port:

  • Voiles en Voiles (Place des Vestiges): This outdoor pirate-themed family park is AWESOME!! Voiles en Voiles has life-size pirate ships, rope courses, climbing walls, inflatables, an archery tag arena, a 3D theater, and lots of winter activities when the snow flies. Their safety gear and patrol team make sure your little pirates don’t get too out of hand.
  • SOS Labyrinthe (Hangar 16 Vieux-Port, 360 Rue de la Commune E): A large indoor maze with 2 kilometers of passageways and 4 treasures to find while dodging obstacles and traps. Reservations are only required for groups of 20 or more.
  • Ferris Wheel | La Grande Roue de Montréal (362 Rue de la Commune E): Get beautiful, 360-degree views from 60 meters (20 stories) up. Cabins are enclosed and the ride takes about 20 minutes.
  • Zipline | Tyrolienne MTL Zipline (Hangar 16, 363 Rue de la Commune E): This 1200-foot zipline flies over the bustling Bonsecours Island in Old Port. It only takes 10-15 minutes and you don’t need to reserve in advance (though it’s recommended for groups of 20 or more).

You can also find more relaxed things to do at the Old Port. Take in an IMAX movie. Grab an ice cream and stroll the pathways. Or take the kids to the Science Centre or playground.

Cycling Along the Water in Montreal

Another fun, relaxing thing to do at the Old Port is simply rent a bike or book a bike tour. Extensive cycle paths give you terrific views of the St. Lawrence River and its canal.

Two great cycle routes along Montreal’s waterfront include:

  • Lachine Canal multipurpose path (15km one-way): Starting in the Old Port, follow the path along the still-functioning canal. Continue to the end, where you’ll come to the Musee de Lachine and Lachine Canal National Historic Site. Along the way, stop at the Atwater Market, which has been around since 1933 and is housed in a cool art deco-style building. You can continue into Monk Park and cycle a 3-kilometer loop past a couple of historic sites, and then cycle back the way you came. Or, follow a bike path through the lovely riverside neighborhoods of LaSalle and Verdun (be sure to pick up a map for this route).
  • Parc Jean-Drapeau bike paths (25km of paths): Expo ‘67 was hosted on the two scenic, man-made islands of île Sainte-Hélène and île Notre-Dame. Cycle through beautiful expansive gardens. Past lakes, Olympic training and competition sites, museums, public art, a casino, and little cafes. You can even cycle along a car racing track.

For bike rentals or tours with lots of options, check out the highly-rated Ça Roule Montréal | Montreal on Wheels (27 Rue de la Commune E).

Fun ON the Water in Montreal

Now that you’ve had your fun on land, head out onto the St. Lawrence River! Chose from a crazy boat ride, a relaxed cruise or something in between. I REALLY think you should spend some of your 5-day Montreal itinerary on the St. Lawrence River.

Here are five great options to get out on the St. Lawrence River:

  • Jet Boating Montreal | Saute-Moutons (1 Clock Tower Quay St): One of my travel buds twisted all our arms and got us all out. It was both terrifying and super-fun, and definitely memorable! Prepare for waves to hit hard unexpectedly, so hang on and know you’re gonna get soaked.
  • KSF (Watersports Pavilion, Ile Notre Dame): Experience the St. Lawrence by kayak, paddleboard or surfboard. Enjoy the river’s calm side or its surf-wave, whitewater-adrenaline side. Choose from rentals, tours and lessons. KSF also has locations in LaSalle and Verdun.
  • Le Petit Navire (Jacques-Cartier Pier): If you prefer a more relaxed cruise along the river, this is a great pick with fun, family-friendly options and strong reviews. Tour the Old Port or canal or head out to watch the fireworks during the international festival in July.
  • Amphi Tours (3-9 de la Commune St W): This land-water tour combo takes you through Old Montreal and then out onto the water. On certain evenings in July, you can take a 9 p.m. ride that gets you a terrific view of the fireworks.
  • Le Bateau-Mouche (55, Quai d’accostage): If you’re looking for a more sophisticated or romantic cruise option, this is for you. Choose from daytime, dinner and special event cruises.

Amusement Park plus Gardens

Now let’s head out to Ile Sainte-Helene, also called St Helen’s Island.

The north end of Saint Helen’s Island is for thrill-seekers at the super-fun La Ronde amusement park (22 Chemin Macdonald). This amusement park was built on St Helen’s Island for the World’s Fair in 1967 (aka Expo ‘67), and many of its rides date back to that time. La Ronde has the world’s oldest wooden carousel – the beautifully restored Galopant Carousel from 1885 – and the world’s tallest two-track wooden roller coaster – the terrifying, creaky Monstre (note that the cars are quite small and it jerks your head around quite a bit). You’ll also find heart-stopping Six Flags rides, a variety of candy and gift shops, and fun shows for the whole family.

If you’re here in late June or July, be sure to stay for the hugely popular and super-impressive International Fireworks Competition. Shows happen on Saturdays and the occasional Wednesday. Check for details.

The south end of St Helen’s Island is more relaxed. Stroll through its beautiful gardens and the Stewart Museum, which is a military museum and fort with costumed guides. Visit the Biosphere Environmental Museum that’s housed in a geodesic dome built for Expo 67, or have some fun at the outdoor pool. If you’re lucky, come for a festival or concert.

DAY 5 = Montreal Itinerary for Sports: Olympic Park, Auto Racing and Hockey

City and river view from Olympic Park Tower

Quite the view from Olympic Park Tower

Montreal has a rich history of sport. If you’re a sports buff, day 5 of this Montreal itinerary is for you.

Montreal is famous for its Montreal Canadiens hockey team and auto racing. Growing up, both were regulars on TV. Montreal also hosted the Summer Olympic Games in 1976. Although the stadium continues to be plagued with structural problems, it’s still a fascinating structure and area to explore.

Before deciding which day in your Montreal itinerary will be spent on Montreal’s sports scene, check to see which events are happening. There’s nothing that’ll take a facility tour up a few notches like experiencing a professional game.

Montreal’s Olympic Park and Botanical Garden

Montreal’s Olympic Park hosted the 1976 Summer Olympics. It features the tallest inclined structure in the world at 175 meters (574 feet) with a panoramic view of Montreal. The stadium has housed Montreal’s professional baseball and football teams, the Expos and Alouettes respectively. Unfortunately it’s been plagued with problems and is now only used for special events like concerts.

Ideally while here you should catch a Montreal Impact soccer game at the Saputo Stadium or a swim meet at the Olympic pool. The Biodome (formerly a velodrome cycling track) houses pretty cool replicas of 4 ecosystems and the Rio Tinto Alcan Planetarium features astronomy-related exhibits, shows and activities.

Walk through a short pedestrian tunnel under Sherbrooke St to Maisonneuve Park. This 290-acre park features the very pretty Montreal Botanical Garden and creepy-crawly Insectarium (I didn’t make it through it all … ick). It’s a great park for strolling, cycling and picnics.

Auto racing at Notre-Dame Island

If you love auto racing, head to the Gilles Villeneuve Circuit on Notre-Dame Island. This pretty riverside track hosts the Canadian Grand Prix, NAPA Auto Parts 200 and Grand Am Rolex Sports Car Series.

There are plenty of other things to check out while on the island. At the south end of the in-island lake, you’ll find a waterpark, beach and spot to rent various water equipment. Wander the pretty gardens, play a few rounds at the casino, and check out the rowing and dragon boat races at the Olympic Basin.

Montreal Canadiens Hockey at Bell Centre

If possible, catch a Montreal Canadiens game while visiting Montreal. The Montreal Canadiens are the oldest professional hockey franchise in the world and the most successful, with 25 National Hockey League titles. They helped found the NHL in 1917.

Montreal Canadiens games are held at the Bell Centre (previously called the Molson Centre). It has the largest arena capacity regularly hosting an NHL team. Since opening in 1996, it’s consistently been one of the world’s busiest arenas; in 2012, it was the fifth busiest based on non-sporting event ticket sales.

For tickets and tours, visit

Summary and Resources

Montreal should be on everyone’s travel bucket list. It’s SO rich in history, culture, scenery, culinary magic and FUN. In the spirit of this amazing city, I urge you to push your boundaries somewhere in your Montreal itinerary.

Hostel community wall in Montreal

Hostels capture Montreal’s spirit of community

When I visited Montreal, it was with four very different personalities. And we pushed each other to try new things. We stayed in a hostel (Samesun Montreal Central during the Olympics – SO fun!). Hung out on a rooftop bar in Gay Village. Got soaked on a jetboat right before our reservation at one of the most prestigious restaurants in Canada (and still got top-notch service). And screamed at the top of our lungs while flying over terrifying roller-coasters. Some of us even followed along on a student protest march. It was so classically Montreal.

Also check out QUEBEC Getaways for CouplesIncludes romantic hotels in and near Montreal.

In planning your own epic trip to Montreal, here are a few helpful resources:

Remember to SHARE this post with your TRAVEL COMPANIONS!

You may also like: 

Add a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.