The Best Tuscany Itinerary – 6 Days, Day-by-day Tips

Ready to learn how you can explore this iconic region in Italy? Then hop on this Tuscany itinerary and prepare to be enlightened!

I lived in Italy a while back and explored Tuscany briefly (by bus) but more recently I had the chance to come back and explore more towns with a car and learn even more tips on how to make the best of a trip there.

In this post you’ll find everything you need to know from which routes to take, the best towns, hotels, attractions, costs and transportation.

I highly recommend booking your hotels and attraction tickets (especially in the bigger cities) in advance, as Tuscany is a tourist favorite, and it gets super crowded!

Quick Picks for Your Stay

Days: 6
Cost: around US$600 for budget & US$1200 for mid-range, as for luxury you can go as high as you’d like
Transportation: train, bus or car
Airport Towns: Florence, Pisa
Best luxury hotel: Palazzo Niccolini al Duomo
Best value for money: Luxury B&B La Dimora
Best affordable accommodation: Hotel Dali 

Here’s a map that will help you visualize all the locations that I will talk about in this Tuscany itinerary:

Day 1: Arrive in Florence & explore

● Distance & travel time: –
● Why visit: world-renowned art
● Key activity: Cathedral of Santa Maria del Fiore
● Estimated daily budget: US$80
● Where to stay: Palazzo Niccolini al Duomo ($$$), Luxury B&B La Dimora ($$), Hotel Dali ($)

There’s no better place to start your Tuscany adventures than the region’s capital, Florence!

Florence is home to the Amerigo Vespucci Airport (map), which is set around a 20 min drive away from central Florence by car and around 50 min away by public transport.

This airport isn’t so big, so there’s a high chance of not finding any flights directly to Florence. If that’s the case then you can check for flights to Pisa Airport (map) and from there take the train to Florence (the journey takes around 1h 30min or even 1h if you take the bus).

Or you could also look for flights to Bologna Guglielmo Marconi Airport (map) and from there take a bus and a train to Florence as it takes just 1h to get to the city.

Once you arrive in Florence (I’d suggest planning to arrive early in the day), you can do your check-in and start exploring! If you arrive too early and your room’s not ready, ask if you can leave your luggage. And if that’s not possible you can leave them in a luggage storage. There are tons across the city and one right inside the train station, like this one (map).

What you do on this day depends a lot on how much time you have left. I’d recommend starting in Piazza del Duomo (map) to see Giotto’s Tower, the Cathedral of Santa Maria del Fiore and its iconic Dome (you can even climb up to the top of the Dome). After that, I highly suggest you just explore the surrounding area as the architecture is stunning!

PRO TIP 1: I recommend booking your tickets for the attractions in Florence in advance, no matter the season, otherwise you risk standing in really long lines, waiting to get a ticket and visit. Trust me, this city is always crowded.

After you explore that Square and visit the attractions, if you have some time left before dinner, I’d recommend heading to Piazza della Signoria (map) which is only a 5 min walk away and visit the famous Palazzo Vecchio, the city’s town hall.

Right near it you’ll also find Loggia dei Lanzi (map), an open-air gallery filled with sculptures that you can explore for free!

PRO TIP 2: I don’t recommend renting a car in Florence! You’ll definitely not need it, as the main attractions are just a 10 to max 30 min walk away. Plus driving in the city center (ZTL Zone) is not allowed (I think it’s only for locals or those with a special permit). Since you’re exploring the region I’d recommend renting your car right when leaving Florence.

By the time you finish here, it’ll probably be time for dinner!

Hope you’re ready to drink some Tuscan wine and eat yummy food! If you’re looking for some fab dining spots, we have a whole post on the best restaurants in the city, so check it out! Il Ricettario (map) is a great one!

Where to stay in Florence

Here are a couple of hotels in Florence for each price range! If you want to check out more options, have a look at our post on where to stay in Florence, you’ll find many other places there:

• Palazzo Niccolini al Duomo ($$$)
• Luxury B&B La Dimora ($$)
• Hotel Dali ($)

Day 2: Visit the main attractions in Florence

● Distance & travel time: –
● Why visit: Renaissance architecture
● Key activity: Uffizi Gallery
● Estimated daily budget: from US$100

Ready for your second day in Florence? You’ve got lots to see today so buckle up!

First, I suggest a stop at one of the cafes and grab a strong espresso (or whatever tickles your fancy). Ditta Artigianale Neri (map) is a great spot and they also have some brunch options!

After that, I suggest going as early as possible to (drum roll please) Uffizi Gallery!

This is one of the most visited museums in the world (with works of art like Botticeli’s Birth of Venus and Da Vinci’s Annunciation) so book your tickets way in advance! We’ve got a whole post on how to get tickets for Uffizi, which includes lots of tips.

NOTE: You’ll definitely spend at least 2 hours in this museum so make sure you consider that when thinking about what other attractions you want to get tickets for and visit on that day.

After you get drunk on all the art at Uffizi, you can cure your hangover with some more art at Galleria dell’Accademia, another iconic museum (which is a 10 min walk away) where you can see Michelangelo’s famous sculpture: David! Of course, there are tons of other paintings there as well as plenty of beautiful sculptures.

By the way, if you have more than 2 days in Florence and you want to see all the sites, check our post with the best things to do in Florence, where you’ll find a much wider range of attractions and activities!

After enjoying all the art, you’ll probably be famished and if you want to grab a quick bite, then you can go to Mercato Centrale (map), set only a 10 min walk away from Galleria dell’Accademia, which is also a great place where you can get souvenirs. The food is so yummy there, and the place is also a sort of attraction, meaning you’ll kill 2 birds with one stone!

With your bellies full and hearts happy you can cross the iconic Ponte Vecchio (map), an ancient bridge that is packed with souvenir shops and head to Palazzo Pitti which is also home to the gorgeous Boboli Gardens. The Palace is huge with so much art and the gardens are also pretty big so I think you’ll definitely end up spending around 2h or more here.

End your 2 days in Florence with a delicious dinner at La Bussola (map) an amazing restaurant that serves Tuscan cuisine.

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Day 3: Head to Siena & explore the city

● Distance & travel time: 1h 20min by car, 1h 15 min by train
● Why visit: medieval architecture
● Key activity: Piazza del Campo
● Estimated daily budget: from US$50
● Where to stay: Palazzo del Papa ($$$), B&B Il Corso ($$), Al Mercato B&B ($)

Get your rented car or hop on the train and leave Florence early in the morning to head to Siena!

On the way from Florence to Siena, my husband and I found the most incredible winery, set just 30 min away from Florence, called Antinori nel Chianti Classico which had such stunning architecture!

PRO TIP: If you want to stop here and go on a tour of the winery book at least 2 months in advance, as this place is so popular! We actually wanted to do that, but everything was sold out.

So we only got to do the wine tasting which was US$39 and we also got to see a bit of the interiors but not the full thing that you’d see on a guided tour. They also have a restaurant (map) on-site which closes around 3PM, so arrive earlier than that if you want to eat and definitely make reservations in advance for that too.

After you’ve explored the winery, hop in the car and go to Siena, the gorgeous medieval city with beautiful architecture!

Once you arrive, you can drop the car at the accommodation and I’d recommend getting a hotel that offers parking (preferably free) so that you don’t go around the city looking for a place to park).

Then you can go straight to Piazza del Campo (map), the town’s main square, which is a UNESCO World Heritage Site, filled with stunning attractions like Palazzo Pubblico and Torre del Mangia.

From there you can go to Piazza del Duomo (map) which is only a 5 min walk away and visit the Siena Cathedral which is famous for its unique facade and stunning interiors.

If you didn’t get a chance to eat at the winery restaurant, then you’re probably famished! Luckily, Siena is packed with fab restaurants like Osteria Permalico (map) where you can indulge in the local cuisine!

By the time you finish, it’s probably going to be after sunset! So you can go for the regular passeggiata after dinner and maybe grab some gelato from Venchi Cioccolato e Gelato (map).

Where to stay in Siena

Looking for a fab hotel in the city? Then check out this short list with the top options in the center or have a look at our post on where to stay in Siena, you’ll find many other places there:

• Palazzo del Papa ($$$)
• B&B Il Corso ($$)
• Al Mercato B&B ($)

Day 4: Leave Siena and drive to Val d’Orcia region

● Distance & travel time: 1h by car
● Why visit: stunning scenery
● Key activity: exploring the rolling hills & medieval cities
● Estimated daily budget: US$100
● Where to stay: Castello di Velona Resort ($$$), Adler Spa Resort Thermae ($$$), Argiano Dimore Wine Relais ($$)

So for this, you will definitely need a car, as you can’t really explore the valley by bus. We rented a car and it was perfect as we got to stop in some of the amazing viewpoints that this valley has and admire everything!

Val D’Orcia is a UNESCO World Heritage Site famous for its rolling hills that are rich in vineyards, olive groves, cypresses, and chestnut groves! There are also lots of medieval villages with gorgeous castles and unique architecture!

PRO TIP: I’d recommend visiting Val d’Orcia in Spring or early Summer when everything is still green. We went in August and although it was beautiful, it was pretty dry and everything was harvested so there wasn’t that much to see.

It takes around 1h to get from Siena to Val d’Orcia, which is located in Southern Tuscany, close to the border with Umbria and on the slopes of Mount Amiata. As I mentioned, the valley is home to some gorgeous villages like Pienza (where we stayed), Montalcino, Castiglione d’Orcia and San Quirico d’Orcia.

Pienza is a gorgeous village, filled with so much history that it looks like it was taken out of a fairytale book! I loved exploring it! There are a few nice attractions that you can see there like Pienza Cathedral (map) and Corsignano Church (map).

Not too far from Pienza, we found some amazing spots and viewpoints that you should definitely check out!

1. Rolling Hills (map) – you can start in this spot, which is set only a 6 min drive away from Pienza! Here you’ll get a lovely picture of the fields and hills
2. Cappella di Vitaleta (map) – this is a super remote chapel, set a 20 min drive away from the first viewpoint which offers some amazing landscapes 
3. Gladiator Movie Scene viewpoint (map) – set a 15 min drive away from the chapel, this movie location from the Gladiator is actually closed, but you can drive by and look around, as you’ll still see something 
4. Cipressi di San Quirico d’Orcia, Circle of Cipressi (map) – it is here, but use this point otherwise it will take you on a not-so-good road, this one is set only a 5 min drive away from the Gladiator viewpoint 
5. Viale di Cipressi (map) – from the Circle of Cipressi you can drive down South for 12 min and stop at this beautiful road with cypress trees on each side of the road (the perfect spot for a picture)
6. La Foce (map) – from that road you can hop on the car again (drive for around 20 min) and get to this amazing site from where you can see the green rolling hills

PRO TIP 2: I recommend using the Google Maps links that I’ve included above for each of those viewpoints, as we actually had some issues with some of the places that we added as a stop on our navigator and we got sent to wrong locations. With those links, you can be sure that you’ll arrive where you’re supposed to.

In total you’ll probably spend around 2, maximum 3h (depending on how long you stay in each point) to explore all those viewpoints.

NOTE: If you’re visiting during the colder months, I’d recommend taking advantage of the amazing thermal baths that they have around the area. I found 2 great ones nearby, Terme di Chianciano (map) and Bagni San Filippo (map), which are a 30 min drive away from Pienza. There’s also Terme di Saturnia (map) but this one is set a 1h and 30 min drive away from the town.

After that, you can drive back to Pienza, or to the town that you picked as your base. Since I stayed in Pienza, these locations are centered around that place, so if you’re staying somewhere else, maybe up North of Pienza, make sure you check the locations on Google Maps so that they’re not too far.

If you’re looking for a place to have a bite (I’m sure you’re famished after driving and exploring all day long), then you can stop at Podere Il Casale restaurant (map), which is a lovely place. We had a meal there and everything was super yummy and the views were stunning (you can book your tables easily on their website).

Where to stay in Val d’Orcia         

As I mentioned I stayed in Pienza during my time in Tuscany (in this hotel Casale Le Querciole which I included below) and I loved it! But since the Valley is packed with numerous incredible hotels, I wanted to offer you some accommodations from other locations in the valley, so have a look below:

PRO TIP: I recommend booking your hotels in Val d’Orcia as this place is super popular and the prices are pretty high. And I’d recommend choosing an “agriturismo” type of accommodations, which are basically farm stays.

• Mastrojanni Relais ($$$)
• Castello di Velona Resort ($$$)
• Argiano Dimore Wine Relais ($$)
• Casale Le Querciole ($)

Day 5: Explore more of Val d’Orcia region

● Distance & travel time: –
● Why visit: stunning wineries
● Key activity: visiting old abbeys
● Estimated daily budget: US$100

Ready for another day in Val d’Orcia? Today is going to be pretty busy so buckle up and drink your coffee before hitting the road, or grab some to go!

The first stop is at Abbazia Sant’Antimo (map), a beautiful Romanesque abbey that’s surrounded by gorgeous landscapes. If you’re coming from Pienza, you’ll have to drive around 40 min.

You’ll find a parking lot there (map) and while there you can explore the gardens and admire the beautiful architecture and interiors of the abbey.

From there you can make your way to Biondi-Santi Tenuta Greppo winery (map), which is only a 10 min drive away. I highly recommend going on their website and making a reservation or calling them, rather than just turning up there, as they might not be able to accommodate you. 

Not too far from the winery, just a 3 min drive away you’ll find the town of Montalcino, which is one of the main villages in Val d’Orcia! The hilltop village is as charming as Pienza and it has a beautiful Old Town!

PRO TIP: There are a couple of parking lots around the town, like this one (map) and this one (map).

Get lost on the winding streets and visit some of its attractions like Museo Civico e Diocesano and the Fortress of Montalcino (map), before you leave for your next destination.

From Montalcino, you can hop on your car and head to another lovely abbey called Abbazia di Monte Oliveto Maggiore (map), which is set around a 30 min drive away. Tucked away between the hills, this unique monastery is much bigger than the first one, so you’ll probably need more time.

Monks still live here so you might to see them too (if they’re around)! Inside you’ll get to experience the library, cloister, a museum and some other spaces plus a lot of art!

Once you’re done at the abbey, hop on your car and head to a gorgeous viewpoint called Crete Senesi Vista (map), which is only 20 min away. Snap a pic, and stay there for a bit to enjoy the stunning scenery!

NOTE: If you have more time left from your second day and you’re not sure what to do, I have one more suggestion for you: Abbazia di San Galgano (map)! You’ll only see the remains of what used to be a Gothic Church, from the 13th century, but it looks really amazing!

Day 6: Set base in Pisa & take a short trip to Lucca

● Distance & travel time: 2h 30min by car
● Why visit: Unique architecture
● Key activity: Leaning Tower of Pisa
● Estimated daily budget: US$100
● Where to stay: The Rif ($$$), Villa Tower Inn ($$), Villa Martina Classic ($)

Alright, now that you’ve left the dreamy Val d’Orcia, I bet you definitely don’t want to go back home and leave Italy!

It’s okay, we all go through this, but luckily, you’ve got one more day in Pisa! Although mostly known for its Leaning Tower, this town has many other iconic attractions that you should check out while here!

Once you arrive, you’ll probably want to do your check-in. If you have a car, then my recommendation would be to go straight to Lucca (which is a 25 in drive away) or you could drop it off in Pisa, and take the train to Lucca as it takes the same amount of time. Up to you!

Better to explore Lucca in the morning so that you can spend the afternoon in Pisa and the night there, and get time at night to prepare for your flight home the next day.

Lucca is a gorgeous town, with a historic center, Renaissance architecture and a beautiful cathedral (map). If you don’t have much time I’d say stick to the central historic area, as most of the main attractions like Chiesa di San Michele in Foro (map) and Piazza dell’Anfiteatro (map) are set there. 

After you’ve seen that, you can go back to Pisa, where you can drop off your car (if you haven’t done it already and head to the hotel.

Then maybe you could grab a bite and some coffee, I’m sure you’ll need it! Ristoro Pecorino (map) is a great place, where they serve Tuscan dishes and yummy espressos!

From there you can head to Piazza del Duomo (map) where you can visit the Pisa Cathedral, the Battistero di San Giovanni church and the Museo dell’Opera del Duomo.

Of course, the Leaning Tower as well, but I wanted to leave the best at the end! You can also climb up the tower and admire the views! I know the climb isn’t very pleasant but the views are definitely worth it! You can get your tickets for all these attractions from this website.

I think these attractions will occupy most of your day but if you have some time left or you’re staying for more days, then I’d recommend reading our post with the best things to do in Pisa, where you’ll find many other fun attractions!

Just like in any other touristy town in Tuscany, I recommend booking your attraction tickets (and hotels) in advance!

Where to stay in Pisa

Here are some of the top hotels in the city! If you’re looking for more options, check out our post with the best places to stay in Pisa (you’ll find a breakdown of areas there, too):

• The Rif ($$$)
• Villa Tower Inn ($$)
• Villa Martina Classic ($)

Other itinerary ideas

I made this itinerary for 6 days, but if you’re staying for a longer time and you’d want to know which other places you could discover, then here are some ideas:

• + 1 or 2 more days in Florence: although you can see the main sites in just 2 days, Florence has much more to offer, so if you have the time, I’d definitely spend it there
• 1 day in San Gimignano: before you go to Siena from Florence, you can stop in San Gimignano (it takes 1h by car to get there from Florence) and spend a few hours or 1 day there. The medieval town is known for its towers and unique architecture
• 1 day in Volterra: from San Gimignano, you can easily reach Volterra, the drive is only 40 min. This is another medieval village with more art, ancient walls and a cathedral. From there you can drive to Siena which is 1h away
• + 1 of 2 days in Val d’Orcia: and lastly, I definitely recommend spending a few more days in Val D’Orcia and discover the other medieval villages

Transportation in Tuscany

You’re probably wondering if you should rent a car or not and that’s everyone’s thought when visiting Tuscany.

Unfortunately, to reach certain places like Val D’Orcia and all the medieval towns there, you will need a car, as you can’t really reach those sites by public transport.

However, if you want to stick to the bigger towns like Florence, Tuscany, Siena or San Gimignano, you could do without a car. You’ll just have to figure out the trains and buses that you need. For trains you can check Trenitalia and for buses you can check Autolinee Toscane

PRO TIP: If you’re using buses, make sure you check to see if they run during the time of your visit. Sometimes, usually in the summer, certain buses don’t run at all in Italy, so it’s better to be prepared.

We ended up renting a car and it was great as we got to see a lot of places, especially in Val d’Orcia.

NOTE: There are some tunnels and toll roads that you’ll need to pay for as you go down South from Florence to Val d’Orcia. We paid around US$8 to US$10/100 km depending if the road was flat or mountainous.

🤩 Best attraction:	Uffizi Gallery
🌲 Top area:	Val d’Orcia
🏨 Best hotel:	Mastrojanni Relais
🌞 When to visit:	Spring / early Summer

FAQs about Tuscany itinerary

Final thoughts on Tuscany itinerary

How dreamy is this region in Italy? You can never have enough of it!

I hope that this Tuscany itinerary helped you decide how you want to plan your trip and how you’ll get around.

Don’t hesitate to ask me any questions below! I lived in Italy for a while and I’ve explored Tuscany not only by public transport and also with a car, so I can definitely help you out!

Definitely book your hotels in Tuscany in advance, as they can get pretty expensive and also the good ones always go first.

Have fun exploring the region!

Happy exploring,

Yulia

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