Why Visit One City When You Could Visit Two?

Montreal to Taipei. Roughly 15 hours in the air, probably with a connection somewhere. You land wrecked, need a full day to recover, and by the time you feel human again, you’ve burned through a quarter of your trip doing nothing.

What if that connection wasn’t just a layover?

Airlines already figured this out

Icelandair lets you stop in Reykjavik for up to seven days at no extra airfare. TAP Portugal does the same for Lisbon and Porto. Turkish Airlines actively encourages Istanbul stopovers. They know their hub cities are worth visiting — and that breaking up a long journey makes the whole experience better.

But you don’t need an official program. Book two separate flights, spend a night or two in a city along the way, and keep going.

Montreal to Taipei, the interesting way

A direct Montreal–Taipei routing doesn’t exist. You’ll connect somewhere no matter what — Vancouver, Tokyo, a US hub. The usual drill: sprint through the terminal, grab a bad sandwich, sit in another plane.

Or: stop in Istanbul.

Direct flights from Montreal. Well-connected to Asia. You land, check into a hotel, walk through the Grand Bazaar, eat by the Bosphorus, visit the Hagia Sophia. Next morning, you catch a flight to Taipei. Total trip is one day longer, but you arrive having actually done something instead of just surviving transit.

How to find your stopover city

The hard part is figuring out which cities sit on a reasonable path between A and B with direct flights from both. Most people give up at this stage because manually cross-referencing airline routes is tedious.

Midway makes this simple. Enter your origin and final destination — it shows every city with direct flights from both. Those are your stopover candidates.

Other options that work between North America and Asia:

• Paris or London — always well-connected to both continents, and a day in either is never wasted
• Dubai or Doha — major hubs with modern airports, direct flights to most of the world
• Tokyo — if you’re already heading to Taipei, adding Tokyo first gives the trip a completely different feel

Why a real stop beats a layover

A 3-hour airport layover and a 24-hour city stop are completely different things.

You actually sleep. A hotel bed vs. an airport chair — obvious difference, but it compounds. You show up at your final destination functional instead of destroyed.

Your body adjusts. Montreal is UTC-5. Istanbul is UTC+3. Taipei is UTC+8. Stepping through the time zones gradually is easier than jumping 13 hours at once. Your first day in Taipei is usable instead of lost.

It can cost less. Two one-way flights sometimes beat a single round-trip with connections, especially with flexible dates. Budget carriers on European or Middle Eastern legs often run deals that don’t show up in multi-city searches.

It works on shorter routes too

This isn’t only for 15-hour hauls. Flying New York to Rome? Stop in Lisbon. Los Angeles to Tokyo? Honolulu splits it in half and gives you a beach day. Even within Europe — Paris to Athens could include a night in Milan.

The connection was going to happen anyway. The only question is whether you spend those hours in an airport or in a city.

How to book it

1. Use Midway to find cities with direct flights from both your origin and destination.
2. Pick somewhere you’d actually want to spend a day. Not every hub is interesting — choose one that is.
3. Book two separate flights. Origin → stopover, then stopover → destination. Give yourself at least one night.
4. Don’t overplan the stop. A hotel near the center, one good meal, and a walk. That’s enough.

Next time you’re booking a long flight, before searching for the fastest connection — ask yourself what city you’d want to wake up in along the way.