A popular tourist destination and posh neighborhood with evidence of First Nations encampments and artifacts dating back thousands of years, Old Montreal's past as a French settlement founded in 1642 is on copious display via its cobblestone roads, greystone buildings, and heritage sites, the closest mirage of Europe you'll spot this side of the pond.
Check Out the Churches
No visit to Montreal's historic district is complete without a tour of Notre-Dame Basilica, one of Canada's most stunning churches. Catch AURA while you're there, a multimedia light show initially created by Moment Factory in honor of Montreal's 375th anniversary.
Contrast Notre-Dame Basilica's ornate grandeur with the simplicity of Notre-Dame-Bon-Secours, the site of Montreal's oldest chapel which happens to house the body of a saint, Marguerite Bourgeoys. Only one other holy site in Montreal can lay claim to the same. A crypt, archaeological dig, and museum associated with the chapel are also on location.
Visit Its Museums
Pointe-à-Callière is a history and archeology museum built right over the birthplace of Montreal, what was once a tiny plot of land by the shores of the Saint Lawrence River where a small group of settlers led by Paul de Chomedey de Maisonneuve and Jeanne Mance landed their boat in 1642. Pointe-à-Callière specializes not only in urban archeological digs and history but also features international exhibits often relating to ancient cultures like those of Rome, Ancient Greece, Ancient China, and more.
Another history museum to drop by is Château Ramezay. Staff dress up in pioneer costumes for effect, in line with the museum's exploration of 500 years of history via exhibits, a French colonial style garden and multimedia portrayals of historical figures available in six languages.
And don't miss out on the Montreal Science Centre, an extremely family-friendly museum proposing fun interactive exhibits and IMAX science and nature films.
Finally, visit the Centre d'histoire de Montréal for an exhaustive history of the city and for a glimpse into upper crust Victorian life, drop by the Sir-George-Étienne-Cartier National Historic Site, where one of the founding fathers of Canada once lived with his family.
Catch a Festival
Old Montreal squares and the Old Port serve as regular –and notably picturesque– backdrops for a variety of Montreal festivals and annual events.
Most, if not all summer weekends see the Old Port come alive with activities, many of them free.
Catch June festivals like family science fair Eureka and foodie fest Taste of the Caribbean. Old Port fests in July include Canada Day activities and the massively popular Montreal International Fireworks Competition.
Come August, it's the Montreal International Reggae Festival and YUL EAT sets up food kiosks Labour Day weekend.
And in the winter, the Old Port and nearby Place Jacques-Cartier feature everything from Christmas markets to New Year's Eve fireworks to the outdoor dance wonder that is Igloofest through January and February.
Get a Room
Old Montreal's restaurant scene is filled with critic-approved upscale gems.
On the more affordable end of the scale, start with some of the best brunch in the city. Le Cartet and Olive and Gourmando are on the list.
Donut fans won't regret sampling BeaverTails down by the Old Port. For elegant chocolates, pastries and desserts, drop by Maison Christian Faure. Or stop by Ming Tao Xuan for tea and cheesecake. It's one of Montreal's top tea rooms.
As for dinner, options are off the charts.
For one of the finest meals in Canada, try Toqué's seasonal tasting menu composed of refined Québécois dishes featuring regional ingredients.
Le Bremner is an upscale ''kind-of-a-seafood-diner'' where all the cool kids go.
Le Club Chasse et Pêche is the place in the city for fish and game, one of Montreal's finest restaurants, period.
Diners rave about Le Robin Square, a family-owned restaurant located on the Main, especially over its decadent Mac&Cheese and pork belly dishes.
Fine French dining is easy to find in Montreal, but for a top-shelf experience with Quebec-sourced ingredients and desserts to die for, book a table at Les 400 Coups.
On a cold winter's night, Auberge Saint-Gabriel and its lush, cozy, centuries-old interior is a dream paired with authentic Swiss fondue and its seasonal menu including a handful of Thai delicacies courtesy of sous-chef Nongyao Truadmakkha, who grew up learning culinary arts in her mother's small restaurant in Buriram, a small town northeast of Bangkok. Head for the terraces in the summer.
Barroco makes killer cocktails, the best paella in the city, and has the kind of lively atmosphere that attracts all the beautiful people. No coincidence it's one of Montreal's most romantic restaurants. Also try Bocata, a wine and tapas bar adjacent Barroco. It's owned by the same people.
For live jazz and a choice rack of lamb, make a beeline to Modavie.
And there are at least a dozen more must-eats in Old Montreal that deserve a mention. It's remarkable how many solid upscale restaurants are crammed into one small neighborhood.
Enjoy Free Art
Old Montreal is teeming with artists and art galleries.
Start on the eastern side of the neighborhood in public square Place Jacques-Cartier where buskers and artists gather to showcase their talents and wares. Sketches, live caricatures, and paintings for sale liven up the area in warmer months.
Proceed along rue Saint-Paul, a cobblestone road connected to the square going west. You'd be hard-pressed not to find a slew of art galleries lining the street, like Galerie Got, who's represented acclaimed international photographers like Harry Benson and Steve McCurry. You could also head east toward Marché Bonsecours to browse through a couple of galleries in and around the heritage building beforehand.
Keeping west on Saint-Paul, you'll eventually reach rue Saint-Pierre. Take a right to go to PHI Centre, a multidisciplinary arts venue which nearly always features some sort of free art exhibit or digital art experience, often virtual reality film. PHI also features concerts, conferences, celebrity talks, theatrical presentations, and repertory film screenings, easily one of Montreal's most creative and forward-thinking spaces.
While you'll never, and I mean never find shopping malls in Old Montreal, boutiques are another story.
Marché Bonsecours houses a handful of shopping destinations showcasing everything from Inuit art to local leather designs to maple products and jewelry.
High fashion is brilliantly represented in Montreal's historic city centre. Outside of Paris, Montreal designer Rad Hourani's unisex designs --and the occasional art exhibit-- can be found on rue Saint-Paul. The first Canadian designer to present a collection at Couture Week in Paris, Hourani's 2013 invitation was groundbreaking. It was also the first time the Chambre Syndicale de la Haute Couture in Paris invited a designer to present a genderless, unisex collection on its exclusive runway.
For a well-curated selection of upscale menswear labels, including Neil Barrett, Yohji Yamamoto, and Montreal's own Want Les Essentiels, visit Michel Brisson on rue Saint-Paul.
And the most eclectic Old Montreal shop of all, Espace Pépin, also on rue Saint-Paul, sells everything from designer women's and men's apparel, footwear, accessories, bags, tea, housemade fragrances, housewares, kitchen accessories, and art.
Experience Exclusive Nightlife
Beautiful people take over Old Montreal when the sun goes down.
A chunk of them, including A-list celebrities, head to The Coldroom for its amazing cocktails and no-dicks-allowed house rules. First time? Try not to walk straight past it. There's no sign and the address is a secret but the street it's on, Saint-Vincent, is pretty short. Once you figure out which door it is, press the buzzer and someone will let you in. It's a small place though so don't get there too late or you won't score one of its 60 seats.
La Voûte is the historic district's hottest club right now. French for ''The Vault,'' the club is literally in one given that it's located in a former bank.
Philemon is a solid standby for wine, drinks and people-watching if you can score a spot near the window. Food –oysters, charcuterie– is sold earlier in the evening.
Velvet is hot, especially when the Canadian Grand Prix rolls through town. An underground club –as in literally underground– part of Auberge Saint-Gabriel, a building with roots dating back to the 17th century, patrons walk through an eerie, centuries old grotto hallway to get the dance floor and two bars manning the space.
Flyjin follows the supper club formula serving Japanese fusion and izakaya fare in the evening, turning up the music come midnight.
Three of Montreal's 12 most interesting spas are in Old Montreal, notably Bota Bota, which is basically a floating Nordic water circuit. It's a boat anchored at the Old Port near the corner of McGill Street, one of those things you have to try at least once in your life. And the view is spectacular.
But spas aren't for everyone.
Others like to bathe in the sun all day at the Clock Tower Beach.
Play at the Old Port
Perhaps the most popular activities at Montreal's Old Port are skating in the winter, and simply hanging out in summer. The waterfront is gorgeous. Droves of tourists and locals content themselves walking by the water. Some rent segways to zoom around. Others bike their way through.
Daredevils prefer ziplining by instead or enjoying a casual, controlled vertical descent head first. Whatever works.
Family-friendly fun includes access to life-size replicas of "a royal and a pirate ship of the 18th century of over 100 feet long" with aerial obstacle courses, climbing activities, and an inflatable park open April through October. And May through October features SOS Labyrinthe, a two-kilometre maze in a nearby hangar.
Water activities include dinner cruises as well as jet and speedboating on the St-Lawrence. I'd add the Clock Tower Beach to the list but no swimming is currently allowed.
A brand new observation wheel 60 meters high offering a panoramic view of the city debuted in the Old Port July 2017.
And there's food. Food trucks, food stands, restaurant terraces are all over the Old Port, and a farmer's market sets up shop Thursdays from 3 p.m.to 7 p.m. and Saturday from 9 a.m. to 2 p.m. Note that the schedule is subject to change without notice.