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The Ultimate Italian Road Trip: From Tuscany to Sicily

Updated: Nov 3, 2022

You have two to three weeks in May and you want to drive through the wonders of Italy, covering Pisa, Tuscany, Naples, Amalfi and ending up in the beauty that is Sicily.

With countless hidden gems in Italy, my best advice is follow your nose! But some of you will want a rough plan because you don't know where to start. So, the question is: coastal or in land? The coastal route south from Pisa would see you drive through Livorno, Piombino, Grosseto, Civitavecchia, Frosinone before then linking up to Caserta, Cosenza and Messina.

In this guide I have mapped out the scenic in land route, stopping at independent homestays or small hotels, enjoying the best local food and wine as you go.

Day 1: Pisa

Welcome to Italy!

Fly into Pisa or Florence, one of the closest airports, pick up your FIAT and your Italian roadtrip begins.

Spend your first day exploring the small town, questionably a village, ticking off the must sees and enjoying dinner in a local trattoria or osteria.

LUCCIOLA Loves: Poggio Al Casone.

Day 2: San Gimignano & Siena

Day 4: Montepulciano & Frascati

Day 6: Caserta

Day 7: Scala

Day 10: Cosenza

Day 11: Tropea

Day 14: Taormina, Sicily

Day 16: Siracusa

Day 17: Agrigento

Day 18: Marsala

Day 20: Trapani & Palermo

Day 23: Time to fly

Want to explore Italy but don't know where to start?

Pop me a message and we can map it out together.

Disclaimer: This page features affiliate marketing links, which means LUCCIOLA earns commission on sales of products when users click through a link from the site.

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