Tuscany Itinerary: 5 Days In The Paradise You Want [2026]

Tuscany is one of my favorite parts of Europe (not just Italy). There is something unique about how locals live and treat their land, which is perfectly reflected in the food and wine they’re preparing and the hospitality they offer.

I’ve visited Tuscany many times while guiding my groups through Italy, and also made this road trip on my own, researching the most beautiful parts. I’ve created this Tuscany itinerary for 5 days for you to experience the highlights of Tuscany.

So, take it, and enjoy this unique trip – probably a bucket-list moment for so many of you, as it was for me.

Enjoy!

Tuscany Itinerary: 5 Days – Overview Road Trip

DAY:	DESTINATION:
1.	Florence – Greve In Chianti – San Gimignano
2.	San Gimignano – Siena – Val d’Orcia
3.	Val d’Orcia: Pienza & Montepulciano
4.	Val d’Orcia: Truffle Hunting & Wine-Tasting
5.	Val d’Orcia – Arezzo – Florence

I’ve designed this road trip for you to explore the most charming parts of Tuscany – exactly as you picture the Tuscany vacation to be – rolling hills lined up with cypres trees, cute agroturismo houses with pools, sunsets over the countryside, little stone towns, delicious wine and food.

Tuscany is quite a big Italian region and includes major cities such as Florence and Pisa. However, I think the majority of us, when we think about Tuscany, we think of the countryside.

That is why I didn’t include any major cities in this itinerary, and I’m taking you to the most stunning Tuscan landscapes and hidden gems.

You can add Florence and Pisa at the beginning or end of your itinerary.

The best way to explore it is by car, no doubt. So, I suggest starting in Florence, renting a car there, and driving around.

I suggest Discover Cars for car rental services – you can click on the button below and search for many cars.

Tuscany Itinerary For 5 Days: Map

Here is a map of the itinerary/road trip – you can follow it to visit all the places:

1. DAY: Florence – Greve In Chianti – San Gimignano

Start your trip in Florence – pick up your rental car in the morning (I recommend the main train station, Santa Maria Novella, as a pick-up point), and set off.

Take it easy, enjoy driving through the winding Tuscan roads, and pay attention as they can be quite narrow at times. Enjoy the stunning views. This is a very slow-paced itinerary, so you’ll have plenty of opportunities to stop by, take pictures, and soak it all in.

First, we’ll be driving through an area called ‘Chianti‘. I suggest stopping in a town called ‘Greve in Chianti‘ for lunch and to stretch your legs.

Distance Florence ⇒ Greve In Chianti: 50 minutes by car (28 km/17 miles)

Greve In Chianti & Castello Di Verrazzano

Greve is the gateway to Chianti wine region, and the famous wine produced here is called Chianti Classico (with the famous black rooster sign). It’s one of the oldest wine-growing regions in the world.

First, I recommend visiting Castello di Verrazzano – one of the most beautiful castles in the area, set on the hill, with breathtaking views. You can book a guided tour of the wine cellars and then enjoy some tasting and delicious meat platters on the terrace.

This place is pure magic. They also have olive oil and balsamic vinegar to taste.

After, stop in Greve town and hang around the main square, Piazza Matteotti. You can even visit their famous butcher shop, Antica Macelleria Falorni, which has been in operation since 1729.

Enjoy lunch at a local bar/restaurant, and then set off again. Drive to San Gimignano, which will also be your overnight stop.

Distance Greve In Chianti ⇒ San Gimignano: approx. 1 hour by car (40 km/25 miles)

San Gimignano

San Gimignano has become quite popular among tourists over the past few years, but don’t worry. That’s why I suggest staying here for the night – it’s mostly day tourists or cruise ships, leaving in the afternoon. And you’ll get to enjoy the town by yourself with locals in the evening.

In addition, it offers some of the most beautiful sunsets in the area, so don’t miss it.

San Gimignano is one of the most stunning medieval towns in Tuscany (it’s awesome, no wonder it’s become so famous). Back in the 13th and 14th centuries, royal families competed to build the most towers and fortifications. This town had 72 towns at its peak; now, you can still see the remaining 14 towers. I mean, that’s pretty impressive for such a small town.

You can wander around the stone streets, climb the highest tower – Torre Grossa, try local Vernaccia wine, and visit their award-winning gelateria – Gelateria Dondoli. It’s such a good gelato.

DID YOU KNOW? Have you heard about Via Francigena? It’s a pilgrimage route from Canterbury to Rome, and San Gimignano is one of the stops. You can walk parts of it, if you’re interested. I’ve walked Camino de Santiago 3 times in my life, and Via Francigena is still on my bucket list. Let me know once you walk it and how it was.

2. DAY: San Gimignano – Siena – Val d’Orcia

Good morning to San Gimginano – I hope you had a lovely first evening in Tuscany yesterday, exploring the town and enjoying its sunsets.

Today, we’ve got even more beautiful places on the list. So, enjoy a slow morning with breakfast, and then set off.

First, drive to Siena – one of the major cities in Tuscany.

Distance Greve San Gimignano ⇒ Siena: approx. 50 minutes by car (42 km/26 miles)

Siena

Welcome to Siena – one of my favorite cities in Italy.

Historically, it was a major banking center and is home to the oldest bank in the world, Monte dei Paschi bank.

The University of Siena is one of the oldest continuously operating universities in the world, founded in 1240.

Below are the main sights in Siena you shouldn’t miss and to make the most of your time.

• Siena Cathedral
• Santa Maria Della Scala– one of Europe’s first hospitals
• Piazza Del Campo – main square in Siena full of cafes and medieval buildings
• Palazzo Pubblico – town hall and seat of Siena’s government, you can enter its inner courtyard for free
• Civic Museum – inside Palazzo Pubblico, you can pay entrance on the spot and see beautiful fresco paintings
• Torre Del Mangia – the tower rising up from Palazzo Pubblico – climb 400 stairs and get stunning views of Siena
• Via di Città – shopping street
• Via Dei Montanini – also a great shopping street full of local shops and boutiques

Whenever you’re ready, keep driving from Siena to your accommodation in Val d’Orcia.

Distance Siena ⇒ Val d’Orcia: approx. 1 hour by car (60 km/37 miles)

Val d’Orcia

Val d’Orcia is a spectacular valley in southern Tuscany, stretching between Siena and Monte Amiata. It’s THE PLACE when we picture Tuscany, as I mentioned above – rolling hills, pretty sunsets, stone towns, cypress trees, and agroturismo accommodation with pools.

So, I recommend you pick an agroturismo/hotel in the area for the next 3 nights and make it your base. From there, we’ll explore the most beautiful parts of Val d’Orcia together.

Here are the agroturismo accommodations and hotels I suggest for your stay. I stayed at Poggio ai Gelsi, and it was unforgettable – in the middle of nowhere, with hill views, a pool, and a perfect location to explore:

📍 Agriturismo Bonello
📍 Poggio ai Gelsi
📍 Agriturismo Palazzo Conti A
📍 Agriturismo Lunadoro
📍 Agriturismo Marinello
📍 Casa d’Orcia

Enjoy your first night at your agroturismo apartment, and ask your staff whether they provide dinner and a wine-tasting. You can enjoy it on the terrace overlooking the countryside.

Then, have a romantic evening while watching the stars on the grass, next to the pool.

3. DAY: Val d’Orcia – Pienza & Montepulciano

Good morning to Val d’Orcia. I hope you enjoyed your first night in this beautiful place. Enjoy another slow morning with breakfast, and soak up the sun (hopefully it’s sunny).

Today, we’ll do a little road trip visiting some of the most charming towns in the area, learn about the history, and enjoy wine-tasting.

First, I recommend driving to Pienza and exploring the town in the morning.

Pienza

Pienza is one of the loveliest towns in Val d’Orcia (Tuscany), and it’ll be your first stop today.

It’s the birthplace of Pope Pius II – he decided to build a small town at this place and it was named Pienza (which means city of Pius).

My favorite thing to do in Pienza is to wander around, stroll through its streets, walk the city walls, and soak up the atmosphere. It’s also famous for the Gladiator Shooting Spot.

Here are a few sites that you can see during your visit:

• Corso il Rossellino – main street in the historical center
• Palazzo Piccolomini – a palace from 15th century, you can see its interior & beautiful botanical gardens with great views
• Pienza Cathedral – you can also visit a crypt inside with a labyrinth (maze of narrow, brick tunnels)
• Walk The City Walls – Via del Casello is a beautiful part of the city walls
• Try Pecorino cheese – many shops will let you try this local cheese
• Cute shops – Pienza is a great place to go into local shops, see the artwork and home made goods
• Gladiator Viewpoint – this famous viewpoint was used in the movie, featuring Russell Crowe. The scene where he is walking towards his home, through a field of grain, was filmed here.

Scenic Tuscan Drive

After Pienza, I recommend driving to Montepulciano. Make a detour and drive via 2 scenic points.

• Cipreces En Zigzag
• Cypress Road

Montepulciano

Welcome to Montepulciano, famous for its historical wine cellars. Enjoy the vibe, have some lunch, wander around, and visit local shops.

I suggest doing a wine-tasting in one of the cellars here. Check out ‘De’Ricci Cantine Storiche‘ and book a tour with tasting.

Besides, you can visit these sights:

• Historical town center – main street is called II Corso
• Piazza Grande – main square – here you’ll see Town Hall, Cathedral of the Assumption, Contucci Palace, Palazzo dei Capitani del Popolo, and the Well of the Grifi and the Lions
• Palazzo Comunale & Clock Tower -climb the tower for the views
• Taste Vino Nobile di Montepulciano – local wine – you can taste in any wine shop in the city (e.g. in Pulcino Di Matassini Ercolani Gabriella Fattoria)
• Visit an underground wine cellar– you can go to De’Ricci Cantine Storiche (they have a tour with tasting) or you can visit Cantina Contucci wine cellar without tasting
• Temple of San Biagio – outside of Montepulciano

Whenever you’re ready, drive back to your accommodation and enjoy a relaxing evening there.

4. DAY: Val d’Orcia – Truffle Hunting & Wine-Tasting

Today will be a relaxing day dedicated to some extra activities like truffle hinting and wine-tasting in the countryside. You can choose what you want to do. You can enjoy both, or just one of them, and spend some time relaxing at the pool at your agroturismo, enjoying the vibe.

If you’d like to go truffle hunting, I recommend these 2 suppliers:

🔅 Podere Il Casale
🔅 Montalcino Wine Tours

If you like to experience wine-tasting in the countryside, I recommend booking with:

🔅 Montalcino Wine Tours

They offer various packages, so look at them and choose the one you like. You can even enjoy a cooking class with them.

Or ask your accommodation for more options and what they recommend on the spot.

5. DAY: Val d’Orcia – Thermal Baths – Arerzzo -Florence

On your last day, I suggest enjoying some thermal baths in the area, stopping in Arezzo for some more history and charm, and driving back to Florence.

In the morning, you can visit some of the thermal baths in the area. I recommend the following:

📍 Bagni San Filippo – natural
📍 Antiche Terme Romane Libere – natural
📍 Terme di Chianciano – commercial

After, start driving towards Florence, you can stop in Arezzo and explore the city:

Distance Val d’Orcia ⇒ Arezzo: approx. 1 hour by car (70 km/43 miles)

Arezzo

Arezzo is one of the oldest Tuscan cities, even older than Florence. It used to be an Etruscan settlement called Arretium and became an important Roman town, famous for producing red Roman pottery.

It was a filming location for the movie ‘Life is Beautiful’ or ‘La Vita è Bella’, as the Italians say.

And if you’re lucky, you might catch their medieval festival, which locals organize twice a year, called ‘Joust of the Saracen‘.

So, explore, wander around, and do some people-watching on the main square (Piazza Grande). Here are the sites to see:

• Piazza Grande
• Basilica of San Francesco
• Fortezza Medicea
• Visit Vasari’s house – famous Renaissance artist and architect

Whenever you’re ready, drive to Florence and return your rental car.

Distance Arezzo ⇒ Florence: approx. 1 hour by car (75 km/46 miles)

Florence & Pisa

Now, it’s time to enjoy Florence – the pearl of Tuscany. I suggest spending 2 – 3 days. You can explore Florence for 2 days and on the last day, make a day trip to Pisa (just 1 hour by train).

Florence is wonderful – stunning Renaissance architecture and buildings, the Medici family, Piazzale Michelangelo and views of the city, delicious gelato and a focaccia sandwich (you need to try), jewelry shops, leather products, Leonardo da Vinci museum, do it all.

I’ve written a separate article about Florence and the best things to do in the city, so check it out and plan your stay.

Practical Tips For Visiting Tuscany In Italy

I’ve got some more tips to help you plan your trip to Tuscany, so check them out below:

Getting To Tuscany

Florence is the main city in Tuscany and the best place to start your Tuscan road trip. So, fly to Florence, and start there. Alternatively, you can also start in Pisa and then make your way down south.

If you want more affordable flights, fly to Rome or Venice, and then take a train to Florence.

Getting Around Tuscany

The best way to get around Tuscany is by car. There isn’t really any public transportation, and the towns are scattered around. You’ll be most flexible and enjoy the landscape fully if you have or rent a car.

Where Is The Best Place To Base Yourself In Tuscany?

Val d’Orcia or Siena. Val d’Orcia is the place that perfectly matches one’s expectations of what Tuscany looks like. Base yourself somewhere around Pienza and explore the area for a couple of days.

Another great base is Siena, as it’s kind of in the middle and you can make day trips to Chianti, San Gimignano, or Val d’Orcia. So, base yourself in Siena if you prefer to stay in a city for multiple days and make day trips, rather than road tripping.

Best Time To Visit Tuscany

June and September are the best months to visit Tuscany. The weather tends to be great, and nature is in its full beauty. September is also the harvesting season, which adds the extra special touches.

October, April, and May can be tricky with the weather – there are sometimes quite torrential rains in Tuscany at this time of the year. That’s what I experience when I was there once in early October – so, check the weahter beforehand, if you plan a last-minute visit at this time of the year.

How Many Days In Tuscany Is Enough?

5 days in Tuscany is the perfect amount, enough to explore it all without rushing.

FAQs

I’ve also answered some frequently asked questions about Tuscany for you:

What Is The Best Town In Tuscany To Stay In?

Pienza and Siena are the best towns to stay in Tuscany. You can reach all other highlights from these towns on day trips.

Where To Go In Tuscany For The First Time?

Val d’Orcia is the place to go in Tuscany. It’s everything we imagine Tuscany to be – golden landscape with agroturismo buildings, wine-tasting, truffle hunting, cypress trees, and lovely valleys with stone towns.

Is It Better To Visit Florence Or Tuscany?

Florence is in Tuscany. But I know what you mean – it depends whether you want to explore a city with sightseeing or have a quiet vacation in the countryside.

I would honestly do both, start your trip in Florence, explore the city for 2 days, and then head to Tuscan countryside for 3 – 5 days to enjoy its breathtaking countryside.

What Is The Prettiest Part Of Tuscany?

Val d’Orcia is the prettiest part of Tuscany – rolling hills with cyprees trees, agroturismo buildings with pools, hundreds of wine-tasting spots and wine cellars, stone towns, and peace in nature.

WRAP-UP: Tuscany Itinerary 5 Days

This is my ultimate Tuscan road trip itinerary for 5 days for you. I’ve created it based on my experience traveling around Tuscany on my own and with tour groups – so, enjoy the highlights. It’s truly one of the most beautiful road trips you can make in Europe.

If you need more help planning your trip, I’ll be happy to design a customized travel itinerary for you. Or book this 1-on-1 travel chat (consultation) with me to ask me any questions in real-time, and I’ll provide you with all the tips.

Happy Tuscan Travels!

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