The highway that connects Rome to Florence – the A1 Autostrada – is a convenient ribbon of well-maintained, toll road. The full extent of the highway connects Milan with Naples, and hits Bologna, Florence, and Rome along the way. It’s the oldest European highway and the most important in Italy, also known as the Autostrada del Sole (The Sun Highway).

Cruising up to Florence will take you a good 3 hours, as long as you don’t hit traffic coming out of Rome or getting into Florence. But the journey is a vacation in itself. Dotted along the way are some charming towns that are worth a stop, like Orte, Orvieto, Montepulciano, Pienza, and Cortona. The A1 is a toll road, so every exit will require you to pay the toll, but the stops are well worth the few extra euros. Eat your way through the drive, starting with a rich cacio e pepe pasta in Orte, black truffles in Orvieto and a full-bodied glass of sangiovese wine in Montepulciano. Grab a wheel of pecorino in Pienza and a fine wool scarf or table cloth in Cortona to live out your Under the Tuscan Sun fantasy. It’s true what they say, half the fun is in the journey. Especially when you’re driving up the A1.

Orte

Orte is a small town built atop a rocky hill close to the border between Lazio and Umbria. Originally an Etruscan settlement, its strategic location meant that it fought for over the centuries and came under the Roman rule and subsequently ruled by the Ostragoths, Byzantines and Lombards. It was eventually incorporated into the Papal states and is home to many beautiful churches, including the Church of Saint Biagio and the Cathedral of the Assumption of Mary.

Orte is located at a crucial intersection off the A1 heading east into Umbria and Abruzzo. For this reason this is also an important rail hub for regional and express trains.

The quaint town is worth a stop and a short walk, and even for a quick bite of pasta. Here you’ll be able to savor some of your favorite Roman dishes, like cacio e pepe and saltimbocca. Pair your pasta with a local lazio wine with strong mineral notes.

Orvieto

Orvieto is one of the jewels of Umbria. You can admire the beautiful town perched atop the hill with rocky cliffs from the highway before you reach the exit and even clearly see the majestic cathedral at the far end. Orvieto has a long history as an important town which controlled the road between Rome and Florence. Like most towns in central Italy, it was originally an Etruscan settlement which was conquered by the Romans. It was one of the earlier towns to be governed by the Pope well before it was officially included in the Papal States.

The city of Orvieto was quite large even during the Middle Ages, and continues to be a highlight between Rome and Florence. The Cathedral is a main highlight, but even wandering the streets and popping into the little shops and restaurants is a real treat. Here in Umbria the truffle rules, so you’ll find them just about everywhere during truffle season which runs from about May through August.

Montepulciano

For real wine lovers, the city of Montepulciano is a haven. Tuscan wine is known for it’s rich, full-bodied reds and the robust sangiovese varietal from Montepulciano is no exception. The town sits high at the top of the hill and it seems that all the streets are on an incline, regardless the direction, but the trek to the top is worth the views, the food and the wine.

Many of the local restaurants are carved right into the rock of the hill, so venture deep into the back where the interior will take on a whole different appeal. Order yourself a hearty plate of pappardelle al cinghiale (pappardelle pasta with while boar sauce) and a large glass of red wine. Sit back, relax and take it all in.

Cortona

Feel free to live out all your Under the Tuscan Sun dreams in Cortona, the site of the best selling novel by American expat Frances Mayes and also the set for the blockbuster hit that was based on the book. Cortona is a charming Tuscan village that is still predominantly medieval architecturally. A stroll along the main corso is an exercise in window shopping local crafts, watching artisans work, and the aromas of local products like aged meats and cheeses. Since the release of the book and subsequently the film, Cortona has become a haven for American, Australian, and English expats seeking a place of refuge for the summer or all year long. It’s not uncommon to hear a conversation by “locals” in English, which just adds to the layers of history and complexity of this little Tuscan town.

Pienza

Albeit a bit off the beaten path from the A1, Pienza is another town that’s worth the visit. Originally the birthplace of Pope Pio, of the noble Piccolomini family, Pienza is a magestic borgo that seems to have remained untouched since the 1400s, a jewel of the renaissance. The town is becoming increasingly popular as a Tuscan stop for travelers driving around the UNESCO protected Val d’Orcia region, whose picturesque hills and seemingly fake cypress trees look taken straight from a post card.

The town celebrates its heritage not for the tourists that come to visit but for the vibrant community that live within its walls. Each summer a pecorino-rolling tournament – think lawn bowling but with wheels of cheese – are the popular attraction among locals and visitors alike in the main piazza in front of the cathedral.

Pienza has seen even more popularity arise as the set for the popular Medici series which originally appeared on the Italian public broadcasting channel, Rai 1.

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Have you visited any of these spots along the A1 from Rome to Florence? Share your experiences with us in the comments below!