Day One

  • Old Montréal

Take the subway to Place-d’Armes and make a beeline for the stunning Basilique Notre-Dame. Explore the cobblestoned streets of the old town, winding your way to the sailors’ church, Chapelle Notre-Dame-de-Bonsecours. Stroll up Place Jacques-Cartier with its many buskers and artists, into the Château Ramezay museum.

  • Lunch Grab a tasty baguette sandwich at Titanic.
  • Old Montréal

Deepen your understanding of the city’s history at the excellent Musée d’Archéologie et d'histoire Pointe-à-Callière before crossing Pl d’Youville to Fonderie Darling for its innovative contemporary-art installations.

  • Dinner Garde-Manger for a fun crowd, and tasty cocktails and dishes.
  • Old Montréal

Walk off dinner with a stroll into Chinatown (by the way, if you want cheap eats, slurp down some pho or grab some dumplings here) before catching a show at Cirque du Soleil in the Old Port. You might also consider watching the sky turn various colors at sunset while downing an old-fashioned on the rooftop patio at Terrasse Nelligan. Party the night away at scenester magnet Velvet or Philémon, which will rock you until 3am.

Day Two

  • Downtown

Start your tour of downtown Montréal at Musée des Beaux-Arts de Montréal for its excellent collection of Old Masters and contemporary art. Architecture aficionados will dig the contemporary Desmarais pavilion as well as the Claire & Marc Bourgie Pavilion in an 1890s church. Next stroll down Rue Sherbrooke Ouest, home to tiny shops and heritage mansions, toward McGill University.

  • Lunch Vegetarian-friendly Lola Rosa has great food and ambience.
  • Canal de Lachine

Hop on the metro to Lionel-Groulx and walk down to Marché Atwater for a look at the farmers’ produce, croissants and cheese. If you have the energy, rent a Bixi bike from a nearby station and pedal the Canal de Lachine. If not, consider a cruise on the canal.

  • Dinner For incredible Québecois fare, try Joe Beef if you can get in.
  • Downtown

Upstairs has nightly jazz performances, or better yet the jazz festival will be rocking the blocks around Place des Arts if your timing is right. Otherwise grab a postdinner glass at the Dominion Square Tavern or hear some beats at underground Bleury Bar à Vinyle.

Day Three

  • Little Italy, Mile End & Outremont

Make for Little Italy to explore the mouthwatering Marché Jean-Talon. Stroll down to the local church, the Église Madonna della Difesa, and be sure to spot Mussolini on the ceiling. Browse the old-world shops along Blvd St-Laurent before hopping a bus (or Bixi) to Mile End.

  • Lunch Enjoy market-fresh fare at the charming little Arts Cafe.
  • Little Italy, Mile End & Outremont

Ramble along St-Viateur and Bernard, visiting Drawn & Quarterly for its whimsical book selections, hipster curiosities at Monastiraki and artfully recycled objects at Galerie CO. Before dinner, grab a taxi to Parc du Mont-Royal for a panoramic view of the city from Kondiaronk lookout.

  • Dinner Inventive Vietnamese fusion and drinks at .
  • Plateau Mont-Royal

Head down to Casa del Popolo and see what the hipster kids are cheering for on stage. Afterward, take a late-night bar crawl down Blvd St-Laurent. Stop in Big in Japan for elegance and high-end libations, Majestique for oysters and cocktails, and Apt 200 for a loft-like house-party vibe.

Day Four

  • Parc Jean-Drapeau

A river runs through it, dividing Parc Jean-Drapeau into two isles. Begin at Île Ste-Hélène with a tour of remarkable buildings from yesteryear. Learn about the environment and our impact on it at the Biosphère, housed in Buckminster Fuller’s geodesic dome built for Expo '67. Not far away, the Musée Stewart is the site of an authentic British garrison.

  • Lunch Snacks along the forested paths.
  • Parc Jean-Drapeau

Wander the island’s walking paths, taking in the outdoor sculptures before kicking up your heels at Piknic Électronik, a summertime electronica dance fest. If it’s not on, try for some thrills on the world’s tallest wooden roller coaster at La Ronde. You can grab panoramic but decidedly slower views of the city from 45m up on the Ferris wheel.

The island is a perfect spot to watch the sky explode with fireworks during L'International des Feux Loto Québec. If not, the Casino de Montréal has everything you need for a good time; just bring luck. Or take a long walk or quick taxi ride to Habitat '67, the block-city left over from Expo '67. The winking lights of the Old Port will be beckoning you back across the water.