Portugal & the Azores 🌞 in $570s-$730s RT

Portugal & the Azores 🌞 in $570s-$730s RT

Hold on tight—Lisbon’s hills don’t mess around. One minute you’re hanging off a vintage yellow tram, the next you’ve crested the peak, only to be rewarded with views so stunning you forget you’re sweating through your shirt.

You’ll wander cobbled streets lined with azulejo tiles and cafés that seem to exist solely to sabotage your diet. Follow the scent of grilled sardines to a back-alley tasca, raise a glass, and toast to “just one more"...

On Terceira Island, you’ll trade tram tracks for trails through emerald pastures, sip wine poured straight from a local’s cellar, and find yourself peering into the mouth of an ancient lava tube.

But, no matter where you are, by sunset, the country glows gold, the rooftops hum with Fado, and you’ll swear even the air smells romantic :-)

Taking off ✈️

Tip Published: Nov 10, 2025

Round trips to Lisbon (LIS):

  • Halifax (YHZ) - $722
  • Hamilton (YHM) - $672
  • Montreal (YUL) - $570
  • Quebec (YQB) - $734
  • Waterloo (YKF) - $672
Round trips to Terceira Island (TER):

  • Montreal (YUL) - $653
Flight Details

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Standard Fare

From $900

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How to Book

    This is a Takeoff-only Flight for Jack's Flight Club Takeoff members only. For step by step instructions on how to book it you'll need to login or upgrade to Takeoff membership.