Tuscany was made for road trips. What could be better than riding a classic Italian car down peaceful country lanes, olive groves and vineyards whizzing past you? Planning a road trip can be overwhelming, but lucky for you, the travel experts here at Plum Guide have all there is to know about travelling through Tuscany. Beginning and ending in Florence, our road trip itinerary is for those who want the classic Tuscany experience—the Tuscany you see in photographs with romantic hilltop towns shrouded in mist, pretty villages and fields of sunflowers. We’ve chosen all the best stops that the region has to offer (including a winery or two) and haven’t put a time limit on this itinerary—that way, you can spend as long as you like in each place. Ready to roll? Take a look at our itinerary for an unforgettable road trip through Tuscany.

Explore our exclusive collection of homes in Tuscany.

Begin your Tuscan road trip in its capital city, Florence. Known as the birthplace of the Renaissance, Florence is a fascinating place with endless churches, palaces and galleries, where you can see some of the finest artistic treasures from the likes of Michelangelo and da Vinci. Make your way along the winding cobbled streets and visit landmarks like the Cathedral and the Uffizi before crossing the Ponte Vecchio bridge, popping into its boutiques on the way over. Welcome to Oltrarno, the ‘newer’ part of Florence. A vibrant neighbourhood filled with art galleries, boutique stores, parks, gardens and trendy eateries, this is worth a wander. At sundown, climb up to Piazzale Michelangelo to take in magnificent views of the city.

Browse our selection of airbnb alternatives in Florence.

We recommend spending at least two full days here, giving you enough time to see all the major sights. Don’t worry if you don’t get to see everything—remember that this road trip ends back in Florence, so you can always add more days at the end.

Explore more of this home.

See our collection of serviced apartments in Tuscany.

The next stop on your road trip in Tuscany is Lucca. The distance between the cities is only 92 kilometres, taking you around one hour in regular traffic along the A11 and onto the E76.

Commonly known as ‘the city of 100 churches’, the charming, laid-back town centre is a great place to explore on foot. With its ornate churches, rustic cobblestone streets, Roman ruins and renaissance walls surrounding the city, you’ll find all the Tuscany checklist items. Walk or cycle around the walls before wandering through the town, popping into the shops and market stalls. Grab something to eat, as you’ll need the energy to climb the 233 steps up to the tree-topped Guinigi Tower. It’s worth the effort, as the tower offers spectacular views across the city. Back down, sip an aperitivo at a cafe that spills out onto the Piazza dell’Anfiteatro—an excellent spot for people-watching and soaking up the atmosphere.

Take a closer look at this home.

Browse our collection of short-stay rentals in Tuscany.

From Lucca, take a half-hour drive along the SS12 radd and S.da Statale 12 to Pisa, which is 20 kilometres away.

The city is home to the iconic leaning tower, and you can climb the 294 steps to the tilting top (don’t worry, engineers ensure it won’t topple over just yet). The surrounding historical complex of Campo dei Miracoli, or Field of Miracles, is worth visiting, with the Pisa Duomo and Baptistery being some of the finest examples of Romanesque architecture in Italy. Additionally, the Museo Nazionale is home to stunning artefacts, sculptures and paintings that go as far back as the 12th century.

It doesn’t take long to see Pisa’s top sights, so we recommend taking a quick detour to explore the nearby beaches. Tirrenia is one of the main seaside resorts, with a wide expanse of sand to sunbathe and opportunities for watersports. Marina di Pisa is another lovely town popular with families, with calm waters and plenty of facilities lining the seafront.

Explore this home.

See our collection of luxury vacation rentals in Tuscany.

From Pisa, drive along the SP11 to San Gimignano. The distance between the two cities is 80 kilometres and should take approximately an hour and 20 minutes, depending on traffic.

San Gimignano is one of the most visited places in Tuscany, famous for its majestic towers, which were built in the 12th century. Only 14 remain of the original 72, and they can be admired on a walk through the city. For those who like a challenge, see how many of the towers you can climb—the two most popular are the Torre Grossa (the tallest) and Torre della Rognosa (the oldest). Then, back on safe ground, reward yourself with a scoop (or five) of gelato from Gelateria Dondoli, one of Italy's most acclaimed gelato shops. San Gimignano also has its fair share of museums, including the Archaeology Museum, the Civic Museum and the Torture Museum, which provides a fascinating look into medieval torture.

Discover our range of luxury Tuscany villas.

From San Gimignano, take a 45-minute drive down the Raccordo Autostradale Firenze-Siena to the magical city of Siena, 42 kilometres away.

Siena has been Florence’s rival city for centuries, but that doesn’t mean it is second best. Start your Siena leg of the trip in Piazza del Campo, the city’s central square. It’s always a buzz of activity here, but if you’re visiting in the summer, you’ll get to witness the historical spectacle of Il Palio, Siena’s famous horse race. During the rest of the year, the city’s striped cathedral is the show-stopper—don’t forget to check out Piccolomini Library while you’re there, as well as the Porta di Cielo tour of the cathedral’s roof. For even more epic views, the Torre del Mangia is a slender, 14th-century tower offering gorgeous vistas across the whole town. It’s (only) 200 steps up to the top.

See more of this home.

Find the best Tuscany vacation rentals for a summer trip.

From Siena, head along the SR2 to the area of Val d’Orcia. This area is around 50 kilometres from Siena, taking approximately one hour.

This valley is the Tuscany of your dreams, the best place to soak up the idyllic views of gently rolling hills, olive groves, fields of grains and rows of cypress trees. This is where you’ll appreciate opting to take a road trip in Tuscany, as you can pull over to the many scenic spots whenever you like. We recommend taking it slow and savouring the region's beauty, visiting the many photogenic hill towns along the way, such as the UNESCO World Heritage town of Pienza, the spa town of Bagno Vignoni and the ancient Castiglione d’Orcia. Of course, no Italian road trip would be complete without a wine tasting. Stop at the town of Montalcino to taste the famous Brunello wine (just make sure you have a designated driver).

Explore our range of Airbnb alternatives in Tuscany.

From Val d’Orcia, take a quick 20-minute drive along the SP146 to Montepulciano, just 18 kilometres away.

The medieval hilltop town of Montepulciano is up there as having some of the most beautiful countryside views in all of Tuscany. Take a walk through the elegant historic centre, heading uphill towards the summit and Piazza Grande for blissful panoramas. As soon as you get here, you’ll feel like you’ve just stepped back in time, surrounded by Renaissance palazzos, artisan workshops and ornate churches, which are equally as beautiful inside. Montepulciano attracts wine enthusiasts far and wide, as the town and its surrounding area are considered one of the finest winemaking regions in the world. Don’t miss a visit to one of the wineries for a tasting—we recommend Boscarelli and De’ Ricci.

Find a home to work remotely from Tuscany.

From Montepulciano, drive along the SP327 towards Arezzo. The distance between the two is around 50 kilometres and should take one hour.

Your final stop on this Tuscan road trip is the gorgeous city of Arezzo. It’s often overlooked on road trips, but spend some time here, and you’ll find many things to see and do. There are Roman ruins to discover, as well as monuments, churches and monasteries. Arezzo is the wealthiest city in Tuscany thanks to its history in gold smithery, and traces of this can be seen in the buildings’ extravagant frescoes and Renaissance art like that in the Basilica San Francesco. See what treasures you can find in the town’s fantastic selection of antique shops, or if you’re visiting on the first Sunday of the month, peruse over 500 stalls which fill Arezzo’s main square, Piazza Grande.

From Arezzo, drive back to Florence along the A1/E35. It should take you around one hour to go the 77-kilometre distance.

Explore our exclusive collection of homes in Tuscany.