Italy
in $600s-$750s RT
Fresh spring dates have officially bloomed in Italy.
And like any good bouquet, we’ve picked a handful of cities that look perfect together — Florence, Rome, Milan, and Napoli.
Think: the Colosseum glowing in moonlight, dancing in the streets when the accordion inevitably comes out, and fields of flowers fresher than a bowl full of pasta.
From art that pulls you in to espresso strong enough to power a revolution, every stop is a love letter written in sunlight and sauce.
And if you need more time to stop and smell the roses, don’t worry — we know plenty of tucked-away villages and coastal corners where you can linger just a little bit longer :-)
Taking off ✈️
Tip Published: Nov 05, 2025
To
- Florence (FLR) - $729 (cabin bag)
- Milan (MXP) - $600
- Naples (NAP) - $755 (cabin bag)
- Rome (FCO) - $647 (cabin bag)
From
- Toronto Pearson (YYZ)
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.