We landed in Montreal on Thursday around 5:30p.m. and decided to take it easy that evening. After settling into our hotel room, we ventured into Vieux Montreal (Old Montreal) and had a scrumptious dinner at Le Robin Square—a family-owned eatery with a cozy yet stylish ambiance and elevated comfort foods. For starter, we ordered a kale salad (the best he’s ever had at a restaurant, according to Drew) and a charcuterie platter with warm, melting brie. The mains were truffle flavored mac n cheese with a generous portion of maple syrup spiced ham, as well as a sirloin steak cooked to perfection. For a decadent finale of our first meal in Montreal, we shared a slice of dark chocolate and ganache cake.

Montreal is pretty easy to get around, as there are no shortage of transportation options. On Friday we decided to take advantage of Montreal’s self-serve bike sharing system to explore the city*. We biked through the busy streets of downtown Montreal to Old Montreal, where we spent the morning/early afternoon strolling through the charming cobblestone streets lined with restaurants, side-walk cafes and shops. The brick-facade buildings adorned with hanging potted plants as well as the relaxing atmosphere felt distinctively European, and for a moment, we thought we were walking through the streets of a French city!

*We paid $5 CAD (roughly $3.82 USD) each for an one-day pass that allowed us to rent bikes from bike stations located throughout the city for an unlimited number of trips. The only caveat is you only have up to 30 min for any given trip from point A to point B before incurring extra charges. We were definitely cutting close a few times!

In the afternoon we went “Underground.” Montreal’s Underground City is a series of downtown office towers, hotels, shopping centers, residential and commercial complexes, convention halls, universities and performing arts venues, connected by a network of tunnels and metro stations—a rather ingenious planning by the city government, considering the brutal weather in the winter. Although we were a bit perplexed by the name “Underground” as most of the commercial centers were at the ground level… 🤔

For dinner, Drew, the Chief Dining Officer, picked Hoogan et Beaufort, about a 30-min bike ride from our hotel. The ride gave us a workout and took us through a sketchier part of the town, but the restaurant—one of the city’s top 30—did not disappoint! We worked off the excess calories with a post-dinner ride back to downtown and enjoyed a few Montreal Jazz Festival* performances before finally returning to our hotel.

*Montreal’s annual Jazz Festival is a spectacle in and of itself and we were lucky to be in town for it. The one-week event features 3,000+ artists and 350+ concerts across multiple stages (many of which were outdoor and free), and brings together hundreds and thousands of visitors. Many of the streets are closed off to accommodate vendors and pedestrians and the city is buzzed with energy. What’s amazing is that this wasn’t the only festival going on at this time. There were also the Circus Festival and Mural Festival, and somehow, Montreal pulled them all off seemingly effortlessly.