Pisa: The Perfect Start to Your Tuscany Road Trip
Your Tuscany trip starts in Pisa — and honestly, it’s more than just that famous leaning tower.
Thanks to its international airport, Pisa is a super easy place to begin your adventure. And while you’re here, it’s definitely worth sticking around a little to explore before diving deeper into Tuscany.
Of course, you can’t skip the classic stop at the Leaning Tower of Pisa. Try to get there early if you can — it gets crowded fast, and it’s way easier to snap that must-have tourist photo (yes, the cheesy ones are the best).
This park is a real local favorite — people come here for morning runs, horseback rides, or just to chill out. It stretches all the way to the sea, and if you’re lucky, you’ll spot some wildlife too. (The animals here aren’t shy — you’ll probably make a few new furry friends.) Whether you’re wandering through the woods or sticking closer to the coast, it’s just one of those places that makes you feel good. Fresh air, nature, and a little piece of Tuscany all to yourself.
Pisa is the perfect starting point for your road trip — a little bit iconic, a little bit unexpected.
Next up? Lucca. It’s just a short drive away and honestly, it’s one of those towns you’ll wish you had more time in.
Lucca: a Hidden Fortified Gem!
Lucca is one of those places that feels almost frozen in time.
The whole historic center is wrapped up in perfectly preserved Renaissance walls, and as you wander through the narrow streets, you can see layers of history everywhere you look. The heart of the city, Piazza dell’Anfiteatro, is especially cool — it’s shaped like an old Roman amphitheater, a little reminder of Lucca’s ancient roots.
When we visited, it was raining, but honestly, that made it even better.
Walking through those little alleys with the cobblestones shining from the rain — it felt like stepping into a storybook. Getting a little lost among the cozy cafés and quiet corners ended up being one of the highlights of our whole trip.
When it comes to food, Lucca definitely delivers. If you’re looking for a great meal, check out The Allabona Experienceor Sottosotto — both spots serve up amazing local dishes that really capture the flavors of Tuscany.
Quick tip: Lucca’s famous Renaissance walls aren’t just for show — you can actually walk or bike right on top of them, which is such a fun way to see the town.
If you’re driving, just a heads up: cars aren’t really allowed inside the walls unless you have a special permit. It’s best to park outside the city center and walk in. (And trust me, you’ll want to — fines are no joke, and they’ll track you down even after you’re back home.)
Florence: an Open Air Museum
Florence is the heart of Tuscany, and honestly, it feels like an open-air museum. The history here is just everywhere — from the Medici family to Michelangelo and all the little pieces of the Renaissance that are still woven into the streets. You don’t even have to try that hard; just wandering around, you’ll feel it
Wandering through Florence honestly feels like stepping back in time. You can easily get lost (in the best way) among the narrow, cobbled streets, where every corner seems to hide something new — a cozy café, a beautiful old building, or a quiet little piazza that’s perfect for people-watching.
And of course, you can’t leave Florence without treating yourself to some real Italian food.
Find a spot with a view of the Duomo or a lively square, and just take your time. Soak it all in, one delicious bite at a time.
Don’t miss the city’s big landmarks — they’re famous for a reason.
Start with the Cathedral of Santa Maria del Fiore (the Duomo) and its stunning dome, then wander over to Piazza della Signoria where the Palazzo Vecchio towers over the square. And of course, make time for the Ponte Vecchio, the old bridge lined with little shops that’s straight out of a postcard.
If you love art, the Uffizi Gallery is a must — you’ll find masterpieces by Botticelli, Leonardo da Vinci, Michelangelo, and so many more.
San Gimignano: City of Beautiful Towers
As you continue your journey south, you’ll arrive in the enchanting town of San Gimignano, famously known as the “City of Beautiful Towers.” In its heyday, this charming medieval town had 72 towers, each a symbol of the wealth and power of the families who built them. Today, 14 of these impressive structures still stand, offering a unique skyline that overlooks the rolling Tuscan hills.
The towers weren’t just displays of wealth; they were status symbols in a fierce competition among the town’s noble families. The taller the tower, the more important the owners appeared to be.
San Gimignano is a true gem, with its picturesque streets, inviting shops, and simple yet delicious food that captures the essence of Tuscany. We had the best panini ever at Boboli1909, a local favorite that’s not to be missed. Their porchetta and pecorino cheese panini, served in freshly baked focaccia, is the stuff of foodie dreams—we come here each time we pass throughout this region as it’s that good! Also they have the worlds most famous gelato in the world with some of quirky flavours.
Also, don’t miss the chance to climb the ruins at the back of the town, where you’ll be rewarded with a breathtaking panoramic view of the Tuscan hills. It’s the perfect viewpoint to pause and take in the beauty of this magical region.
Take a Detour to Volterra
Though it might be a slight detour from your main route, Volterra is definitely worth the extra miles. Perched dramatically on a hilltop, this town is steeped in mystery and ancient history. Famous for its Etruscan roots and well-preserved medieval architecture, Volterra gained even more fame as the setting for the Twilight series, where it served as the fictional home of the Volturi, the powerful vampire coven in New Moon. As you wander through its narrow, winding streets, you’ll discover hidden treasures, from Roman ruins to alabaster workshops that have been crafting beautiful pieces for centuries. The town’s elevated position provides stunning views of the surrounding Tuscan countryside, making Volterra not just a feast for the eyes, but a journey back in time.
Monteriggioni: Medieval Fortress
As you journey from San Gimignano to Siena, take a quick detour to town of Monteriggioni. Just 20 minutes from Siena, this medieval fortress town offers a unique experience that can be fully explored in about 30 minutes. You can literally walk a full circle around the town along its ancient walls, you’ll feel like you’ve stepped back into the era of the Assassin’s Brotherhood, with views that have remained largely unchanged for centuries.
Despite its small size, Monteriggioni is full of character. In the evenings, the town comes to life with a few cozy restaurants that open their doors, inviting you to sit down and enjoy some homemade pasta. It’s the perfect spot to unwind, savor authentic Tuscan flavors, and soak in the peaceful ambiance that makes Monteriggioni such a special stop on your road trip.
Siena: Charming Hilltop Town
Siena is arguably Italy’s loveliest medieval city, and it’s a must-visit, even if you’re only in Tuscany for a few days. Known for its stunning medieval brick buildings, Siena’s charm is best experienced in its fan-shaped central square, Piazza del Campo. Here, you can simply lay back, relax, and soak in the city’s unique atmosphere.
For a memorable dining experience, we highly recommend Osteria il Carroccio and Osteria degli Svitati. We had the best lunch at these spots, where the food was incredible, and the service went above and beyond to make our meal special.
And don’t miss the Siena Cathedral (Duomo di Siena). As you gaze at its striking black and white facade, you might find it reminds you of something familiar—perhaps another famous cathedral you’ve already seen on your journey?
Arezzo: The Best Kept Secret
Arezzo is one of Tuscany’s best-kept secrets! It has managed to retain its authentic charm, making it a fascinating stop for those looking to explore Tuscany beyond the usual hotspots.
Arezzo also served as the backdrop for Roberto Benigni’s Oscar-winning film, Life is Beautiful. You can walk through the same piazzas and streets where the film’s most memorable scenes were shot.
Every first weekend of the month, Arezzo hosts one of Italy’s largest and most famous antiques fairs, Fiera Antiquaria. The fair transforms the town’s historic center into a bustling market, with vendors offering everything from vintage jewelry to rare books and furniture.
Arezzo’s main square, Piazza Grande, is another highlight. This sloping piazza is surrounded by beautiful medieval and Renaissance buildings and is famous for hosting the Giostra del Saracino, a traditional medieval jousting tournament that takes place twice a year. We always seem to miss this event but it’s on our wishlist for next time for sure!
The town is known for its excellent restaurants and trattorias where you can savour Tuscan specialties, such as pappardelle al cinghiale (wild boar pasta) and acquacotta (a hearty vegetable soup).
Pienza: Place From a Postcard
When you picture Tuscany, you’re likely envisioning Pienza, the postard of Val d’Orcia. This charming town is not only stunning but also the home of the famous pecorino cheese. If you’re a cheese lover, don’t miss the chance to go on a cheese-making tour and see firsthand how this delicious delicacy is crafted.
And Pienza is our favourite place in Tuscany, we always return to this place and just have the best days here!
And speaking of food, we had the best meal in Tuscany at Trattoria Latte di Luna. This small, family-owned restaurant is where Nonna still cooks with love, creating dishes that are as authentic as it gets. The food is simply delicious, and the owners are incredibly warm and welcoming. You can’t get much fresher than this—imagine the chef stepping out to the garden to pick basil and then using it in your dish. Dining here is an experience! P.S. We stayed in Val d’Orcia for 6 days and 4 of them had lunch at this place, it is that good!
San Quirico d’Orcia: a Foodies Haven
Often overlooked, San Quirico d’Orcia is a serene and picturesque town that perfectly captures the essence of the Val d’Orcia region. The town’s medieval streets are lined with stone buildings and beautiful gardens, including the Horti Leonini, a splendid example of Renaissance landscaping.
One of the most iconic sights around here is just outside town — a cluster of cypress trees perched perfectly on a small hill, the kind you’ve probably seen on a postcard or two from Tuscany.
San Quirico d’Orcia is the kind of place where you can just take your time. Wander the historic center, check out the beautiful Romanesque Collegiata Church, or simply relax and soak in the peaceful atmosphere.
It’s a timeless little town that really stays with you — and the food scene is incredible too. Some of the best restaurants here are even featured in the Michelin guide.
We returned here 2 nights in a row as the food in Ristorante Trattoria Osenna was so delicious!
Montepulciano: Hilltop Film Set
A visit to Montepulciano is an absolute must on your road trip. As you make your way uphill through the town’s ancient walls and along its charming streets, you pass trough unique little shops offering handmade products. The streets will lead you all the way up to the stunning Piazza Grande, the heart of Montepulciano.
As you make your way uphill through the town’s ancient walls and along its charming streets, you’ll pass by unique little shops offering handmade products, from artisanal crafts to local delicacies. The streets will guide you to the stunning Piazza Grande, the heart of Montepulciano, where Renaissance palaces surround you on all sides. The town is perched on a hill, offering incredible views over the Val d’Orcia and Val di Chiana.
Montepulciano’s cinematic charm has caught the eye of filmmakers, serving as the backdrop for films like Under the Tuscan Sun and The Twilight Saga: New Moon. As you wander through the town, you might even recognize some of the scenes from these films, adding a touch of Hollywood magic to your visit.
Val d’Orcia: The Iconic Heart of Tuscany
Val d’Orcia is the image of Tuscany that comes to mind when you think of this beautiful region. With its gently rolling hills, sprawling vineyards, tall cypress trees, and medieval hilltop towns and castles, this area perfectly captures the essence of Tuscany that is recognised across the world. It’s the ideal place to get lost and explore winery’s and eat great food.
If You Have Time: Other Amazing Places to Visit
If your schedule allows for a bit more exploration, Tuscany has plenty of other incredible spots that are well worth a visit. Each of these destinations offers its own unique slice of Tuscany, adding even more depth to your journey through this enchanting region. They are a bit off route but totally worth it:
Pitigliano
Pitigliano, often referred to as “Little Jerusalem,” is one of Tuscany’s most striking and unique towns. Perched dramatically on a cliff of tufa rock, Pitigliano’s stone buildings seem to rise organically from the landscape, creating a breathtakingly scenic silhouette. This ancient town is rich in history, with roots that trace back to the Etruscans, and it offers a fascinating blend of cultures, particularly its significant Jewish heritage.
Pitigliano’s narrow, winding streets are perfect for wandering, with every turn revealing something new—whether it’s a hidden courtyard, an ancient archway, or a panoramic view of the surrounding countryside. The town is also known for its charming wine cellars carved into the tufa rock, where you can sample some of the local vintages.
Saturnia
The natural hot springs of Saturnia are one of Tuscany’s relaxing destinations. These thermal waters (37 degrees) are free to visit and have become an iconic spot for both locals and tourists seeking a soothing soak. However, the popularity of Saturnia has led to some serious overcrowding, making it a bit tricky to enjoy the experience fully.
To beat the crowds, it’s best to arrive early in the morning, though even then, you might find it busy. The warm, mineral-rich waters are certainly inviting, but be aware that there are some small red worms or other bugs in the water, which might take away from the experience. We didn’t quite like it, stayed only for a couple of minutes inside the water. We best appreciated it from a distance.
How Much Time Do You Need
Allow yourself at least 7 days to fully enjoy this road trip. If you have more time, consider stretching it to 14 days for a more relaxed journey, where you can explore every bit of Tuscany without rushing. This extended time frame lets you dive deeper into each town’s unique charm, savoring the landscapes, food, and culture at your own pace.
If you’re short on time, you can still experience the best of Tuscany by focusing on the northern part of the region. A 4-5 day itinerary will allow you to explore highlights like Pisa, Lucca, Florence, and San Gimignano. This shorter route gives you a taste of Tuscany’s rich culture and stunning landscapes, while still leaving you time to savor the local cuisine and visit some of the region’s most iconic sights.
Best Time to Visit Tuscany
The best times to visit Tuscany are during the spring (April to June) and early autumn (September to October). During these months, the temperatures are comfortable, making it ideal for exploring the region’s beautiful landscapes and historic towns. Plus, the crowds are smaller, allowing you to enjoy the sights without the peak-season hustle.
In the summer months, both the temperatures and the number of tourists can be quite high, which might make sightseeing a bit more challenging. So, if you prefer a more relaxed experience, aim for the spring or fall when Tuscany is at its most welcoming.
Best Way to Travel Through Tuscany
The best way to explore Tuscany is definitely by car. Having your own car gives you the freedom to stop whenever a stunning view catches your eye—and trust us, you’ll be making plenty of those impromptu stops!
While on the road, you’ll find that most gas stations are self-serve, and the prices are usually cheaper if you fill up yourself. Toll roads are fairly priced, and if you’re on a tight schedule, the highways will get you from point A to point B quickly. However, if you have the time, take the scenic routes. The breathtaking landscapes and charming towns along the way make the journey as enjoyable as the destination, and before you know it, time will have flown by.
We hope this guide helps you plan an unforgettable road trip through Tuscany. Enjoy every winding road, every little town, and every plate of pasta along the way. Until next time, be mesmerized! 🧡