The pretty towns and winding roads of Tuscany offer the perfect views for any road trip. With plenty to explore on your route, what better way to explore central Italy.

With its picturesque rolling hills and nestled towns, Tuscany is a region of endless postcard material, with each turn of the road promising a blissful day of car tunes, yummy Italian food and the chance to explore another of Tuscany’s charming towns.

Saying that, real life can get in the way and suddenly our leisurely cruising becomes a rushed panic to get everything done in time before heading home again. If this is the case, don’t worry, you can still make the most of your Tuscan road trip with this golden itinerary. With each place separated by a 90minute drive at the most, this itinerary will take you to seven beautiful destinations in Tuscany. Our variety of spots allows you to experience a bit of everything, from the Tuscan countryside to medieval towns, this road trip will take you round Tuscany in a nice neat circle. With only one detour, to the area of Val d’Orcia, it’s to time to pack your bags and start up your engine.

Before your trip:

It’s a good idea to get a gist of where you’re going before you start your trip and grasp an idea of what you want. Remember to consider time, budget, attractions and how long you’ll want in each place. This will help you in preparing for your epic road trip. This quickly brings us to your vehicle. What do you hire? Where? And for how much? Do your research to find the best value car that suits your needs, especially if you’ve got young ones with you. After that quick prelude, it’s onto the exciting stuff…your itinerary.

Below is a list of seven wonderful places that will give you a taste of the real Tuscany, just as varied as the region itself.

  • Florence

    Where better to start your Tuscany road trip than in the region’s Capital. A great place to start if you’re flying into Italy. You can hire a care from Florence Airport on your arrival and return it when you fly home. Prices will vary depending on the number of car seats, how long you rent it for, and of course how much petrol you use. From the airport it’s a quick 20-minute drive into the centre of Florence when you can begin your exploring! Another option if you’re looking to save some dollar is to check budget airlines for flights into Rome or Venice, as these larger international airports are likely to have cheaper flight prices. You can get to Florence by train from either of these two cities, just check the Trenitalia site, the main train operator in Italy, for more information regarding departure times and ticket prices.

    Renown for its Renaissance art and historical buildings, Florence is a relaxed city compared to the larger Italian cities like Rome and Milan, but with just as much to offer. Enjoy a few days exploring this beautiful city. Browse the masterpieces in the Galleria Degli Uffizi, before taking a stroll in the Boboli Gardens, finishing off with a visit to the iconic Duomo di Firenze.

    To see a full list of Florence’s top attractions, check out our article 9 Masterpieces You Must See in Florence.

  • Siena

    Distinguished by its medieval brick buildings, Siena is technically a city, although its quiet hum makes it feel more like a town. If Florence was too crowded for you then Siena is the place to be. Small enough to be explored in a day, Siena’s centre has been declared a World Heritage Site by UNESCO for its stunning Romanesque-Gothic architecture. To see this for yourself, take a trip down the cobbled streets until you arrive in the Piazza del Campo, the town square. A great piece of artwork itself, from here you are in the perfect place to explore the Siena Cathedral, or Duomo, and the Palazzo Salimbeni, a gothic style palace which houses one of the oldest banks in the world.

  • Val d’Orcia

    A 55-minute drive from Siena is an area called Val d’Orcia. Broken only by the picturesque towns of Pienza, Radicofani and Montalcino, this drive is surely to be the most scenic of your life. From Siena, take the SR2 road to San Quirico d’Orcia and wonder at the curling hills that extend down from Siena to Mointe Amiata. A mix of green, gold and blue will overwhelm you as you desperately try to take in the vast expanse of varied landscape. From golden wheat fields to olive groves, this stop is worth it for the feeling of being dropped straight into a Tuscan postcard.

  • Volterra

    After exploring the towns of Pienza and Montalcino, you get to enjoy the same scenic route for a second time as you head back towards Siena and make a left towards Volterra. A walled town dating back to before the 8th century BC, Volterra’s well-preserved sights offer a truly authentic view of Italy and a romantic experience for tourists. Spend some time exploring the Medicean Fortress and the great Roman theatre, discovered in the 1950s by archaeological excavations.

  • Pisa

    This road trip wouldn’t be complete without visiting the iconic city of Pisa. Filled with stunning and unusual architecture, you can brave the crowds of Pisa in a day or take your time by having two full days in this bustling city. Just make sure you don’t leave without taking a quick cheesy tourist picture in front of the Leaning Tower of Pisa. A great one to add to your Tuscany Road Trip Scrapbook!

  • Lucca

    Right next to the Serchio river, Lucca is a pretty, quaint town, popular for its broad tree-lined pathways that can be explored on foot or by bike. Lucca’s main landmark is its 16th century ramparts that mark the city’s walls creating a cosy atmosphere, which each year welcomes a host of musical events. Inspired by the composer Giacomo Puccini who was born in Lucca, the city celebrates the Puccini family’s talent for music with the Lucca Summer Festival (LSF), Blues Festival and the Lucca Jazz Donna. If you manage to time your trip with one of these events, even better!

  • Pistoia

    Before heading back to the busy crowds of Florence, savour one last bit of Tuscany by stopping off in Pistoia. Although still popular with tourists, Pistoia is one of the least visited towns in Tuscany, which only becomes it even more. Regarded a ‘little Florence’ without the crowds, the relaxing vibes of Pistoia is the perfect way to end your Italian road trip. Enjoy your last bit of Tuscan architecture by climbing up the Piazza del Duomo and admire the sea of terracotta roofs. Next, pick out some sweet souvenirs by visiting Bruno Corsini’s antique sweet shop. Opened in 1918, it has an excellent selection of the best quality chocolate. The perfect accompaniment to a delicious glass of wine, both to be enjoyed in the intimate, candlelit square of Piazza della Sala.

And that’s a wrap! We hope this article has helped to convince you that a road trip through Tuscany is one of the best ways to experience Italy in all its diverse natural and man-made glory. Check out our Tuscany site for more inspiration on things to do and where to stay, as well as our range of tours.

Related article: The Best Day Trips from Florence

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