We drove to Montreal, and honestly—it was a cool experience. There’s something special about crossing borders by car and watching the scenery (and language!) slowly shift. That said, you can absolutely fly into Montreal if you prefer; it’s a well-connected city either way.

There is a bit of a line at the border; they’ll ask why you’re visiting and where you are staying. If you speak French, use it. They’ll love hearing it. The only downside I’ll say is the fact that they don’t stamp your passport; they just scan it. And, as someone who loves to collect stamps on my passport, I was a bit disappointed. But Montreal made up for my disappointment.

Montreal turned out to be vibrant, welcoming, and full of incredible food—and even in August, the weather was cool enough that light jackets were a must.

Here’s how we spent four full days in Montreal.

Day 1: Arrival, Shopping & Skyline Views

Afternoon: Sainte-Catherine Street

After the 2-hour 45-minute drive from Lake George, we check into our hotel and headed straight to Sainte-Catherine Street, one of Montreal’s main shopping arteries. It’s busy, energetic, and lined with everything from major retailers to local boutiques.

Dinner: Garde Manger

For dinner, we went to Garde Manger, a lively, trendy spot known for creative takes on comfort food. The atmosphere alone makes it worth the visit.

Evening: Mount Royal

We ended the day at Mount Royal Park, heading up to the Kondiaronk Belvedere for sweeping views of the city skyline at sunset. It’s one of those views that instantly makes you fall for Montreal. Get there before sunset so you can find a place as there will be a lot of people wanting to enjoy the views as well.

Day 2: Markets, Neighborhoods & Montreal Classics

Morning: Bagels & Markets

We started with breakfast at St‑Viateur Bagel—a Montreal institution. The bagels are smaller, denser, and baked in wood-fired ovens, and yes, they live up to the hype. Keep in mind that there is always a wait to enter this place; it’s a popular spot. Also, bring cash as they sometimes don’t take American cards.

Next stop: Jean‑Talon Market, one of the city’s largest and most vibrant markets. Fresh produce, local treats, and an unmistakable neighborhood feel. We got soaked with the sudden rain that came in while walking here, but it was so worth it.

Of course, we got ourselves some Canadian maple syrup. That was the best part about driving up there; we didn’t have to worry about transporting the syrup. We kept the cute maple bottle and keep refilling it because we love it so much.

From there, we wandered through Little Italy, popping into cafés and visiting the Church of the Madonna della Difesa. (which unfortunately closed that day, so we didn’t go inside)

Lunch: Smoked Meat Classic

Lunch was at Schwartz’s Deli, home of Montreal’s famous smoked meat sandwich. It’s iconic for a reason.

Afternoon: Space for Life

We spent the afternoon at Montreal Botanical Garden, exploring beautifully designed gardens and greenhouses. This place is huge and you can walk for hours, especially if you’re interested in reading every description like my hubby. It’s also a great place for the kids to run around and burn some energy.

Right nearby is Espace pour la vie, where we visited the Insectarium and Biodome—both fascinating and especially engaging if you’re traveling with kids. We all loved it, it’s a huge space.

Evening: Bistro Dinner & Free Performances

Dinner was at L’Express, a classic French bistro with a timeless feel.

Day 3: Art, Trendy Neighborhoods & Indulgent Dining

Morning: Coffee & Contemporary Art

We grabbed breakfast at Café Myriade, then headed to the Montreal Museum of Contemporary Art for a dose of modern creativity.

Notre-Dame BasilicA

We visited Notre-Dame Basilica, and it’s important to note that you’ll need to purchase your tickets ahead of time. The interior is stunning, with deep blue ceilings, intricate gold details, and a dramatic, almost theatrical feel that sets it apart from other churches. It ended up being one of the most memorable stops of our time in Montreal.

Plateau & Mile End

We spent the late morning wandering Plateau Mont‑Royal, known for colorful murals, leafy streets, bookstores, and cafés.

Lunch

Lunch was at Au Pied de Cochon, famous for indulgent Québécois cuisine.

Day 4: Old Montreal & Waterfront Strolls

Breakfast & Old Montreal

We started the day at Olive et Gourmando, then explored Old Montreal once more.

Cobblestone streets, historic architecture, and European charm make this area feel worlds away from the rest of North America. It kind of reminded me of Rome.

Old Port

We wrapped up the trip at the Old Port of Montreal, strolling along the river, checking out the Clock Tower, and enjoying views of the St. Lawrence River.

I made it a point to try all the very Canadian things while we were there. I tried poutine—which I didn’t love, but I’m still glad I tried it—grabbed a drink from Tim Hortons, and even sampled a Canadian cocktail, just to fully lean into the experience.

Where We Stayed

We stayed at Holiday Inn Montreal-Longueuil (900 Rue St-Charles East). The biggest reason? Our hotel stay was free, booked with points, and since we had a car, driving into Montreal’s neighborhoods was simple and convenient.

Longueuil ended up being a great base—quieter, practical, and well connected to the city.

Final Thoughts

Montreal exceeded our expectations. It’s cultured but relaxed, foodie-focused without being pretentious, and incredibly walkable—even if you’re staying outside the city like we did. Driving made everything easy, and even in August, the cooler temperatures made exploring comfortable (just don’t forget a light jacket).

Whether you road-trip like we did or fly in, Montreal is a city that offers something for everyone—and we’d happily go back.

Yours,