Window Seat

Window Seat

The underrated city that feels like Europe without the jet lag

Where to stay, eat, shop, and linger in the most charming city just 45 minutes from New York

Tori Simokov's avatar
Tori Simokov
Mar 18, 2026
∙ Paid

This is From the Window Seat, a series of deeply researched, design-forward dispatches for people who believe in the art of traveling well. From immersive itineraries to standout hotel reviews, each one offers everything you need to experience a place—or a property—with intention and great taste.

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I love a destination that makes me feel like I’ve traveled far. But I love it even more when I haven’t.

Montreal is a 45-minute flight from New York. You’re barely in the air long enough to finish a coffee, and yet when you land, it feels like you’ve crossed an entire ocean. Suddenly you’re walking past stone facades and wrought iron balconies, ordering in French, and lingering over wine like you’re somewhere much older than North America.

It’s charming in a way that feels effortless, with cafes tucked into corners, vintage shops hidden down quiet streets, and restaurants that hum late into the night. It feels European, but approachable. Romantic, but relaxed. And somehow, I still think it’s underrated. Montreal is the easiest way to feel half a world away without actually going anywhere at all.

Read on for:

  • The boutique hotels worth booking in Old Montreal and beyond

  • Where to eat, from unlimited cornichons to charcoal-grilled pastas

  • The coffee shops and vinyl bars I would fly back for

  • The fashion and design stores that feel distinctly Montreal

  • The spa-on-a-boat experience that feels straight out of Europe

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