Tuscany
at $475 round-trip
Florence Schmorence, we're more interested in Tuscany off-trail.
And let me tell you, between the charming medieval towns of San Miniato, Lari, and Pietrasanta, you've got options, amico! Bolgheri's not to be missed either; it's Tuscany's wine capital, after all.
Most travelers fly into Pisa and make a beeline straight for the sparkling coast of the Cinque Terre. Not you, though.
Nope, you've done research. Meaning you've read my article on one of Italy's best-kept secrets, Sestri Levante!
And when you're back? Write me a postcard!
I'm dying to know how many jars of pesto can fit into a carry-on :-)
Taking off ✈️
Tip Published: Dec 18, 2025
To
- Pisa (PSA) - $475 (cabin bag)
From
- New York (JFK)
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.