Tuscany 🍇 at $475 round-trip

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, amicoBolgheri'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)
Flight Details

Travel Dates

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Airline

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Standard Fare

From $700

Bags & Fees

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Flight Notes

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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.