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
From Pisa to Siena, stopping at the gorgeous village of San Gimignano
Drive Time: 1hr 50min (126km)
LUCCIOLA Loves: Villa Elda, Palazzo Ravizza, Villa Curina Resort, Le Fontanelle, La Certosa di Maggiano, Borgo Lucignanello Bandini, Locanda di Fonterutoli, Fattoria San Martino, Argiano Posta, Il Battistero, Relais degli Angeli, Il Giardino di Pantaneto, La Chicca Siena, i Merli di Ada.
Day 4: Montepulciano & Frascati
Siena to Frascati, stopping at the second must see Tuscan village of Montepulciano.
Drive Time: 3hr 15min (265km)
LUCCIOLA Loves: Merumalia Wine Resort, B&B Theodora, B&B Al Borgo, Homescape Frascati.
Frascati, arguably best known among wine lovers, is a city in the Metropolitan City of Rome, so leave the car behind and catch a 30 minute train into the capital before returning to quieter hidden gem for a beautiful dinner and winetasting.
Day 6: Caserta
From Frascati to Caserta.
Drive Time: 1hr 50mins (176km)
LUCCIOLA Loves: Plana Hotel.
Caserta Royal Palace & Gardens is truly spectacular so as you pass through on route to Sicily, take a walk, hop on a bike or hose and carriage to observe the vast, hidden gem of Italian Baroque architecture in Campania.
Day 7: Scala
From Caserta to Scala on the Amalfi Coast.
Drive Time: 1hr 20mins (80km)
If you have the time, why not take a diversion to the historic town of Santa Maria di Castellabate on the Cilento coast where you will be warmly welcomed at the Hotel Palazzo Gentilcore within the ancient walls.
Continuing our journey to Scala, you may be wondering why I'm not suggesting Amalfi, Positano or Sorrento... These places are all within easy reach from Scala, but with crowds of tourists and inflated prices, enjoy somewhere calmer. You have gone away to relax right?
Scala and Ravello sit just above Amalfi so imagine the views!
LUCCIOLA Loves: Villa San Lorenzo, Casa Falcone B&B & Hotel Zi'ntonio.
Day 10: Cosenza
From Scala to Cosenza.
Drive Time: 3hrs 35mins (310km)
It's a longer drive today so notable stops on route for a coffee and lunch: the caves at Pertosa, beautiful village of Teggiano and the town of Padula.
LUCCIOLA Loves: Epoca Home, Agriturismo Trappeto Vecchio, Castello di Serragiumenta & Palazzo Lupinacci Dimora Storica.
Day 11: Tropea
Wind down in the beautiful Calabrian coastal town.
From Cosenza to Tropea.
Drive Time: 1hr 50mins (120km)
LUCCIOLA Loves: B&B Palazzo Mottola, Sui Generis, Hotel Piccolo Grand, Villa Paola, Rocca della Sena.
Day 14: Taormina, Sicily
From Tropea to Messina to catch the ferry to into Sicily.
Drive Time: 2hr 15min (109km)
Fifty minutes down the east coast of Sicily, you will arrive in Taormina.
LUCCIOLA Loves: Giovanni's B&B in Taormina, Hotel Villa Carlotta, Villa Fiorita, Hotel Villa Schuler, Hotel Villa Belvedere, Hotel Villa Taormina & Hotel Casa Adele.
Day 16: Siracusa
From Taormina to Siracusa.
Drive Time: 1hr (67km)
LUCCIOLA Loves: Palazzo del Sale, Borgo Pantano, Charming Ortigia Sea-View Apartment, Agriturismo Villa dei Papiri.
Day 17: Agrigento
From Siracusa to Agrigento.
Drive Time: 2hr 15min (125km)
Notable stops on route include the quaint lesser discovered gems of Noto and Modica before arriving in the Valley of the Temples with its striking Greek archaeological sites.
LUCCIOLA Loves: B&B Villa La Lumia, Foresteria Baglio della Luna, Azienda Agricola Mandranova, B&B Chiaramontano.
Day 18: Marsala
From Agrigento to Marsala.
Drive Time: 2hrs (135km)
LUCCIOLA Loves: Resort Baglio Oneto, Baglio Spana, Dimora dell'Olivastro & Dimora Cala del Pozzo.
Surrounded by the Sicilian specialities, stay in a vineyard and taste the best food and wine that Sicily has to offer.
Day 20: Trapani & Palermo
From Marsala to Palermo, stopping off in Trapani (40mins from Marsala).
Drive Time: 2hrs (140km)
LUCCIOLA Loves: Il Giardino di Ballaro', Porta di Castro, Palco Rooms & Suites, Casa Nostra, Palazzo Santamarina, Palazzo Natoli.
Day 23: Time to fly
Have a safe journey home and start dreaming up your next Italian adventure!
Want to explore Italy but don't know where to start?
Pop me a message and we can map it out together.
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