Your perfect central Tuscany itinerary

If you’re planning to visit Tuscany and want to see more than Florence, this itinerary will take you to some of the most beautiful places in the region’s central part.

We live in the north of Tuscany, and driving towards Montepulciano, we were impressed by how different the scenery was.

As you leave Florence behind, the scenery changes, and rolling hills and those famous Tuscan sights greet you. Vineyards, medieval villages perched on top of hills, and the true countryside. That’s what central Tuscany is all about.

If you, too, are planning a trip here, I hope I can help you plan the perfect itinerary. One that won’t keep you in the car for too long. But one that will allow you to enjoy la dolce vita.

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Our Central Tuscany Itinerary

Our Central Tuscany Itinerary

Before we start, I would like to make a few remarks.

We didn’t visit Siena on this trip because we had already been there. However, I’ve added it to the map so you know you can include it on your itinerary when you have more time.

I’ve also included other places, such as Pitigliano or Orvieto, for when you want to extend the trip to one week or more.

We drove from Lucca and spent 3 nights in Montepulciano.

Central Tuscany itinerary map — Click on the map to open it in Google Maps

Where we stayed for our central Tuscany trip

After doing lots of research, we booked an apartment at the Tenuta Sant’Agnese in Montepulciano.

It was perfect for us because we were traveling by car and with a toddler. We had plenty of space for her to run around and play, a swimming pool overlooking the vineyards, and we were conveniently located near most of the places we visited.

The villa offers one-bedroom or two-bedroom apartments, making it an ideal retreat for those seeking relaxation after a long day of exploration.

Moreover, the owners run the oldest cellars in town and offered us a guided tour with wine tasting as well.

See more about Tenuta Sant’Agnese here!

On the other hand, if you want to be within walking distance to restaurants and shops, I recommend staying in Montepulciano.

Get the best prices for stays in Montepulciano!

For us, staying there was perfect because there is a large supermarket, and the town is big enough. Also, you are ideally located for exploring the whole region.

Getting around central Tuscany

I’m sorry, but there is no other way to experience these stunning landscapes except by driving around them.

We always recommend (and use when traveling) DiscoverCars. It is an aggregator that allows you to find the best prices and save on your rental. Check out prices here!

Our itinerary

Day 1 – driving from Lucca + stop in Monteriggioni, Montalcino, and drive along Val D’Orcia

Because we live here, we drove from Lucca, but you might be leaving from Florence or Pisa. No matter your starting point, you can still stop in these two beautiful villages along the way.

Stop in Monteriggioni

Monteriggioni is one of those places that feels like it’s been frozen in time. Just a short detour on the way to Val d’Orcia, this tiny medieval walled town offers a peaceful break from the more touristy spots in Tuscany.

Its perfectly preserved walls and quiet stone streets give you a glimpse of what the region looked like centuries ago — no crowds, no rush, just pure atmosphere.

It’s the kind of place where you can grab a coffee in the main square, look around, and feel like you’ve stepped into a different era.

A quick stop, but one that stays with you.

Montalcino

Famous for its Brunello, this small town has a relaxed, elegant charm — think winding streets, rustic stone buildings, and panoramic views over the Val d’Orcia.

It’s the perfect place to slow down, sip something exceptional, and soak in the beauty of the Tuscan countryside.

I must admit, finding a parking space wasn’t too easy, and we almost entered a ZTL. But, if you go to this parking area you will most likely find a place. And it is a short climb to the Fortezza di Montalcino.

The town is very beautiful and romantic, however, it is also very popular with tourists. This means that when we got there at around 2 PM we had a problem in finding a place to eat.

After a pretty rude encounter at the Vineria Le Potazzine, we finally sat at the Caffè Fiaschetteria Italiana 1888 and enjoyed a good (yet relatively small and pricey) meal.

Montalcino is not very big so you can eat and see it in around 3 hours without being in a rush.

Stop by the Fortezza di Montalcino, a 14th-century fortress offers incredible panoramic views over the Val d’Orcia. You can even do a wine tasting inside its walls.

We then went for a walk on Via Giuseppe Mazzini and Via Cialdini, and took pictures with every beautiful door or alley with a view.

If you don’t drive, step inside an enoteca (we recommend Tempio del Brunello) and taste Brunello di Montalcino at home!

Drive through Val D’Orcia

Driving from Montalcino to Montepulciano is one of those road trips that feels like it’s been designed just for the joy of it.

The route winds through the Val d’Orcia. And honestly, you’ll want to stop every ten minutes just to take in the views. Expect rolling hills, rows of cypress trees, and golden fields that stretch forever.

If you can, pull over near the Cappella della Madonna di Vitaleta – that little chapel framed by cypresses you’ve seen in postcards.

There’s also a gorgeous stop just before Pienza, with sweeping valley views that make for an epic photo backdrop.

It’s not a long drive, but don’t rush it – this is Tuscany at its dreamiest, and the road is part of the magic.

Dinner in Montepulciano

Check-in, relax by the pool and get ready to go out for a stroll and dinner in Montepulciano.

For dinner, we were recommended Il Covo, 3 stelle, and Ai 4 venti.

Day 2 – Cortona, Lake Trasimeno and wine tasting

Cortona

Cortona is the kind of Tuscan hill town that instantly makes you feel like you’ve stepped into a postcard. Or a movie, especially if you’ve seen Under the Tuscan Sun. It is a 45 minute drive from Montepulciano so you can drive there for coffee.

With its Etruscan roots, medieval walls, and narrow stone streets, Cortona blends deep history with that relaxed, sun-soaked charm people come to Tuscany for.

From the top of town, the views stretch all the way to Lake Trasimeno.

It’s small enough to feel intimate but full of character – artisan shops, cozy wine bars, and little piazzas where life slows down.

Lake Trasimeno

Cross over to Puglia and visit Castiglione del Lago on Lake Trasimeno. We loved this small town so much that we came back for dinner in the next day.

The drive from Cortona is 25 minutes long.

Lake Trasimeno, nestled between Tuscany and Umbria, is Italy’s fourth-largest lake — and a bit of an underrated gem.

It has a rich past, once the site of the famous Battle of Lake Trasimene in 217 BC, where Hannibal’s army defeated the Romans in one of the largest ambushes in military history.

Today, the vibe is far more peaceful. Think charming lakeside towns like Castiglione del Lago, quiet beaches, and ferries to Isola Maggiore, where time seems to stand still.

It’s perfect if you are looking to slow down, enjoy nature, and explore without the crowds. There are even beaches and beach clubs along the lake where you can go for a swim.

Wine tasting & dinner in Montepulciano

The evening will be reserved for doing wine tasting and a picnic in the vineyards. We loved to learn about the fabulous local Rosso di Montepulciano and Vino Nobile.

It is incredible how the same grapes produce differen wines depending on how they are kept and for how long.

Since we’re living in Tuscany we went on a few wine tasting tours and always had a great and interesting experience.

Booking a Winery Tour, Tasting, and Vineyard Picnic in Montepulciano is the perfect way to spend an evening in Tuscany.

You’re not just sipping wine – you’re walking through the vines that produced it, hearing the stories behind the cellar doors, and then enjoying it all with a picnic overlooking those dreamy rolling hills.

It’s relaxed, local, and incredibly scenic.

This is our recommandation for picnic

And this is a wine lesson with tasting and cold cuts at a winery close to Montepulciano

Day 3 – Bagni San Filippo and Pienza

Bagni San Filippo

Less than an hour drive south from Montepulciano, we discovered the wonderful termal baths of San Filippo.

While many know about Terme di Saturnia, Bagni San Filippo is one of those places that feels like a secret spot locals hope stays under the radar.

Tucked into the forests of southern Tuscany, this natural hot spring is famous for its steaming waters and dramatic white limestone formations, especially the striking Balena Bianca (White Whale).

It’s free to access, and unlike polished spa resorts, it has a wild, untouched feel that makes soaking here even more magical – especially in cooler months. Even though we visited in late July, it wasn’t very crowded.

Relaxed from the thermal baths, we enjoyed lunch in the small village. I recommend the wild boar pasta served at the only garden terrace in town.

Pienza

Magical Pienza is just 30 minutes north of Bagni San Filippo.

Designed during the Renaissance as an “ideal city,” it’s full of symmetry, soft golden stone, and views that spill out over the Val d’Orcia like a painting.

But it’s not just about the looks, Pienza is also the home of pecorino cheese, and you’ll smell it the moment you step into town.

The main street is lined with tiny shops selling local wine, honey, and of course, wheels of cheese.

It’s small enough to explore in a couple of hours, but charming enough to make you want to stay all day, especially if you catch the golden light near sunset.

Book a table for dinner at La Terazza del Chiostro!