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How I fell in love with Montreal Add to ...

As we sit beneath a canopy of trees in Montreal’s Parc La Fontaine, my tour guide pours me a paper cup full of sparkling cider and gently knocks it – “Salut!” – against the side of his own. We had been leisurely cycling through residential streets, parks and alleyways all morning, and this informal picnic of effervescent cider and delicious, gourmet salmon wraps is the perfect coda to my introduction to the city.

I’m in love.

Montreal has always reminded me of an unapproachable crush – it’s arty and sophisticated, and, to me, seems to possess an impenetrable coolness. In recent years, the rise of its indie music scene, trendsetting street fashion and unapologetically rustic comfort cuisine has only added to its mystique.

On previous visits, I had felt every bit the awkward outsider. I’d wander the streets of Old Montreal or take in the view from atop Mount Royal, keenly aware that those who lived here were going to the better bars, eating fabulous food and participating in all sorts of amazing activities that I couldn’t even begin to imagine.

This time, I wanted to crack that barrier. So I joined a tour.

Guided tours are typically the antithesis of cool. But Shea Mayer’s Fitz & Follwell Co. is a different kind of tour company. As the Montreal resident explains, his cycling tours aren’t just meant to take visitors to the most popular tourist attractions. Rather, they’re based on his idea of a perfect day in the city.

“That’s how I designed the routes: What’s my favourite bagel place? Where do I think the best coffee is? What do I do when I go down to the market?” he says.

His Bike & Yoga tour, for example, takes visitors through the bohemian neighbourhood of Le Plateau, with a break along the way for smoothies at his favourite juice bar and stops for yoga sessions in three of the area’s tranquil parks. His all-day Mountainside to Riverbank package offers a more challenging ride for seasoned cyclists up to the top of Mount Royal, then down along the St. Lawrence River to Saint-Helen’s and Notre Dame Islands.

I chose to tag along on his ’Hoods and Hidden Gems tour, lured by the promise I would be immersed “in the local hangouts of the city’s hippest habitants.”

Upon my arrival at his Mount-Royal West Avenue shop, Mr. Mayer sets me up with a sleek black city cruiser, which he has christened “Jeanne,” after the pioneering Montreal nurse Jeanne Mance. (All of the bikes at his shop are similarly named after the city’s historic figures, like “Molson” after the beer tycoon, and “Lili” after the legendary burlesque dancer Lili St Cyr.)

Montreal is renowned for being a bike-friendly city, with designated cycling lanes throughout the side streets and thoroughfares. It’s also the launching pad for the now-famous Bixi, a bike-sharing system that allows users to rent a vehicle from one of the many stations scattered around town and deposit it at another station when they’re finished riding. The system has proved so popular that cities around the world, from Toronto to Melbourne, have adopted it.

But because Bixi bikes are meant for only short commutes, they’re not ideal for longer, leisurely trips. My Jeanne offers a smoother ride.

Mr. Mayer leads our small group through the tony francophone enclave of Outremont and Le Plateau. Along our route, he stops to point out quirky details, not always found in guide books, such as where larpers (live action role players) gather to enact their fantastical battles or where resident bohemians hold their “tam tams,” or drum sessions.

We stop to pick up freshly baked bagels at the Montreal institution St. Viateur Bagel, and tote them across the street to Mr. Mayer’s neighbourhood hangout, Café Olympico, where he orders us the café’s specialty espresso coffees.

The next part of the tour takes us through Little Italy and Mile End, before we wind our way over to our next stop, the Jean-Talon Market. As we wander around exploring the smorgasbord of fresh produce, meats, cheeses and baked goods, Mr. Mayer picks up our lunch at the eatery Milliner Creativite Gourmand for our picnic.

We then hop back onto our bikes and take a detour through several of the city’s so-called green alleyways, the results of a civic initiative to beautify gritty, residential back lanes. Planted with flowers and greenery, they’re a hidden, urban oasis. Then, it’s off to Parc La Fontaine, where we enjoy our picnic on a grassy slope overlooking the pond.

While that concludes Mr. Mayer’s itinerary for a perfect day in Montreal, my ideal day is incomplete without a trip to the spa. I make my way over to the restored industrial, waterfront district of Vieux-Port for a massage at Bota Bota.

Bota Bota, which opened last year, is actually a moored ferryboat, transformed into a chic, modern facility. Co-owner Natalie Émond explains that she and sister Genevieve had been scouring the city for a site for their new spa, but were unable to find a location that was easily accessible to downtown clients, yet still close to nature. The revitalized waterfront, with its park-like setting, was as close to that ideal as they could get. When they heard that the 1951 ferryboat was for sale, they knew they had found their solution. The sisters snapped it up and commissioned Montreal’s Sid Lee Architecture to redesign the vessel.

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