Your Essential Tuscany Itinerary: Must-See Cities and Scenic Tours

This post contains affiliate links, meaning I may receive a commission if you make a purchase through my links, at no extra cost to you.

Tuscany is a bigger area than one might think. It regrouped many big cities and smaller towns. You can easily spend two complete weeks just in Tuscany or you can choose 1-2 towns to add to your Italy itinerary.

From north to south, I recommend you start from Bologna or Florence, depending on your arrival flight, both being good options. I would start from Bologna then go to Florence (or Florence then Bologna if your plane arrive in Florence), Lucca and finally pass a few days in the Val d’Orcia region. You can travel between Bologna, Florence and Lucca by train, but I strongly recommend traveling between towns in the Chianti area by car. If you prefer you can also exchange 1-2 days from this itinerary or add 1-2 days to see Sienna which is also accessible by train. If you do so, see Sienna after Lucca and before Val d’Orcia. 

Bologna: 2 days 

Bologna is not technically in Tuscany but it is close and fits perfectly in a Tuscany trip. While planning my trip, I learned that Bologna is a must for food lovers and is even known as ‘’the food capital of Italy’’. I found a food tour with incredible reviews and decided I could not miss it. It was a great decision! Bologna is not only a foodie’s dream, but it is also packed with gorgeous historic architecture! 

How to go to Bologna: 

Train : Like many big cities in Italy, the best way to get to Bologna is by train. It takes around 2h from Rome, 1h15 from Milan and 40 minutes from Florence.
Plane : You can come by plane directly to Bologna or land in Florence, Pisa, Rome or Milan and then take a train.
Car: I don’t recommend visiting Bologna by car, the streets are very narrow and there’s people everywhere. However, you can rent a car after visiting Bologna if you want to go straight to Lucca, the Chianti region or Val D’Orcia. Otherwise, I don’t think it’s necessary. 

Where to stay: 

I suggest you stay near the historic city center and awalking distance of the Piazza Maggiore.

What to do: 

Bologna is known in Italy as ‘’La Dotta, La Rossa, La Grassa’’ which means ‘’The Erudite, The Red, The Fat One’’. It’s a reference to The University, the beautiful red rooftops and of course the delicious food. So no surprise, the things to do are related to this nickname. 

I spent a day and a half in Bologna which is not enough to see everything. I got just enough time to have a good feel of the city and do my absolute must which include an amazing food tour. So here is a list of the things I choose to do after my research and would do again. Then I’ll give you some idea of more things to do if you want to stay longer. 

1) food tour: The Tour I recommend is from Taste of Bologna, the classic Bologna food tour, but they have other tours if you prefer. I can not recommend this tour enough! We tried coffee, meat, wine, cheese, balsamic vinegar, pasta, ice-cream…everything was delicious! Our guide was very nice, knowledgeable and interesting. The tour was a good mix of food and history, it was simply amazing! 

There’s other similar tours if you want other options: 

Bologna: Local Food Tour with Authentic Tastings and Wine

Bologna: Walking Food Tour with a Local Guide

2) Eat: If you don’t want to do a food tour, eat as many things as you can. The city is known for its delicious tagliatelle al ragù and I confirm it’s a must. The region, Emilia-Romagna, is also known for its balsamic vinegar, parma ham and parmesan. 
You can visit the market, Mercato delle Erbe, where you can find fresh fruits, seafood, meats, pasta and more.

3) Piazza Maggiore: The Piazza is vast and surrounded by architecture dating to different time periods. On the south side, you have the Basilica di San Petronio, Bologna’s most important church. This stunning gothic Basilica has a very peculiar facade because its initial construction was stopped and deferred due to the construction of the Archiginnasio Palace. The Result is a lower part carved in marble and an upper half in bricks, a unique architecture. Then you’ll see the Palazza d’Accurso, now Bologna’s city Hall. Continue walking and you’ll find Piazza Del Nettuno and the Fontana del Nettuno. 

4) Walking under the arcades: Bologna is also named the ’’city of porticoes’’. In fact, it has 62 km of beautiful arcades which are included in the Unesco World Heritage.  They were built to expand the already present buildings and solve the housing problems. It’s not only impressive, strolling under the arcades is actually quite charming.

5) Le Due Torri: You can easily see two towers above the other building while walking in the city. It’s the Garisenda and the Asinelli towers, built in the 12th century. The short one, the Garisenda, is leaning a lot, so of course you can’t visit this one. 
The other one, the Asinelli, is almost 100m tall which corresponds to 498 steps. You can go up to see the view and admire all the beautiful red rooftops. It’s worth it but it’s really narrow so I would not recommend this to claustrophobic people!
I strongly recommend you book this one in advance online or at the office at the entrance. 

Other options: : 

  • University of Bologna. ‘’La Dotta’’ means ‘’the Erudite’’ and refers to the University of Bologna which is the oldest University in the western world, dating all the way back to 1088, and has the longest continuous operation in the world. The university is now in the Archiginnasio Palace which was built in 1563 to include the different schools, and rebuilt after WWII bombing.  The Palace includes among others the Anatomical Theater where they used to teach anatomy using a marble dissecting table in the center of the room. 
  • Sanctuario Madonna di San Luca
  • Santa Maria Della Vita 
  • Cattedrale Metropolitana di San Pietro 
  • Museo Civico Archeologico
  • Museo Internationale e Biblioteca della Musica

Florence: 3 days

It’s well known that Florence is a fascinating city and a prime destination for art adepts. The city is stunning with its Renaissance architecture, charming red roofs, beautiful churches and art everywhere. It’s definitely a must see while visiting Tuscany and you need to stay at least two days but I would recommend three days if you love art. 

We only had time for 2 days in Florence, so we didn’t get to see everything we wanted. We only got to do a wine tour (so worth it!), the duomo, the Palazzo Vecchio and the Ponte Vecchio. 

Here is a plan that I would recommend for 3 days in Florence.  

How to go to Florence:

Train: You can easily come to Florence by train and it’s definitely what I recommend to skip the traffic, which can become really heavy. It’s only 1h30 from Rome, 2h from Milan, about 2h30 from Venice or La Spezia. 
Plane:  You can come by plane to Florence, then take a 30 minute tramway to Florence historic center. 
Car: I don’t recommend visiting Florence by car. However, if you want to do a roadtrip in Tuscany from Florence, you’ll easily find a car to rent from Florence.

Where to stay: 

Day 1: 

Chianti Region and wine tour : Just south of Florence you’ll find the Chianti region, which is famous for its wines and beautiful landscapes. So it’s no surprise that I strongly recommend doing a wine tour. Choose one that includes exploring some of the Chianti area

Before choosing which tour to go to, I did a lot of research and found the perfect one for us! I was in Italy with my husband and a couple of good friends and it just fit with our personality. It’s a fun and upbeat tour, with a lot of great wines. We had a blast and it is to this day one of our favorite Italian memories! I’ve done a couple of wine tours in Italy in the last few years and this one is by far my favorite! You’ll have more than enough wine and things to nibble on. You’ll also visit the beautiful San Gimignano where you’ll find the best Gelato in Italy, Gelateria Dondoli. Don’t miss out on this one, it’s amazing. This is a 7h tour from 9h45 to 17h so you have to reserve a full day for this tour, but it is absolutely worth it! 

So this is the tour that I strongly recommend:  

Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence

Day 2 : 

1) Duomo (Cathedral de Santa Maria del Fiore)

I recommend starting the day with the Duomo because it takes more energy and is better to do when the heat is not at its peak.  

Florence Duomo is known all around the world as one of Italy’s landmarks and is in my opinion a must see. It has outstanding gothic architecture and a beautiful panoramic view of the city from the dome! It is known for its impressive brick dome, which is in fact the world’s largest. Its marble facade is also breathtaking with the green, pink and white embellishments and sculptures. It is definitely one of a kind.

You can just take a walk around this beautiful church if you don’t want to visit the interior. However, I recommend you climb up the dome to admire the view of Florence’s beautiful red rooftops. I personally loved it! Have some good shoes and a bottle of water, and be prepared to do some cardio! But don’t worry too much, the pace is not too fast and gives you the time to take some pauses. If you want, you can even reserve a guided tour to learn more about the cathedral’s history.

If you want to go inside the Duomo, you absolutely have to reserve it online beforehand because the waiting line can be more than an hour long and there’s a limited number of people allowed inside at the same time. You’ll need at least an hour. 

Those are some of the tickets you can reserve: 

2) Accademia Gallery

This one is for the art lovers. That’s where you’ll find Michelangelo’s David and a beautiful plaster gallery by Bartolini and Pampaloni. It’s full of stunnings paintings and sculptures. I strongly recommend you also book this one in advance, otherwise you’ll need to wait in line a long time. The visit is around 1 to 2 hours long. However, if you only want to see the David, know that you can find a replica in the Piazza della Signoria. 

3) Piazza della Signoria 

It’s located in front of Palazzo Vecchio. If you’re not going to the Accademia Gallery, it is worth a visit to see the beautiful replica of Michelangelo’s David. You’ll also find other statues like Fontana del Nettuno. 

4) Palazzo Vecchio

We visited the palace at the end of our day when it was already dark so we didn’t get to see the view from the Torre d’Arnolfo. Also, we also had limited access to the Salone dei Cinquecento which is the biggest and most impressive room in the palace. We saw it from afar and it truly looked amazing. Maybe we were too tired for this visit but from what we saw of the whole palace we found it kind of empty. It was not a must for either of us, but if you’re a true fan of architecture and history maybe do this one sooner in the day. 
From there you can also go see Basilica Santa Croce. 

Day 3: 

1) The Uffizi Gallery 

If you love art, don’t skip this one! The Uffizi Gallery is a national monument well known for its legendary art collection primarily from the renaissance period. You’ll find artwork from Michelangelo, from Botticelli like The birth of Venus and from Da Vinci. If you really love art, you’ll need at least 2h to appreciate everything. It’s the most visited museum in Italy, so I strongly recommend buying your ticket in advance. You can buy a combo ticket to also see the Accademia Gallery. 

2) Ponte Vecchio

Ponte Vecchio is the oldest Bridge in Florence. Its unity comes from all the shops along it which are mostly jewelry shops. You’ll found it between Piazza della Signoria and the the Palazzo Pitti 

3) Pitti Palace and boboli Gardens 

4) Piazzale Michelangelo: This beautiful Piazzale give you a amazing view of Florence, you’ll be able to admire The Duomo, the Palazzo Vecchio and Santa Croce Basilica. 

Lucca: 1 day/2 nights

Lucca was the biggest surprise of my trip. I pretty much only chose to go there because I found a nice wine tour departing from there. The central part of Lucca is the walled city. It’s full of charming yellow houses surrounded by beautifully preserved historic walls. We’ve spent two days here and it was perfect! There’s not a lot of things to do but it’s ideal to have a few relaxing days or it can be used as a base camp for a wine tour like us or for day trips to Pisa or La Spezia.  

What to do: 

Take a walk or a bike ride on the top of the historic walls where you can admire the view.  

Wine Tour: We loved the tour we did ! Our guide Massimo was incredible! Full of stories and historic facts! The wine was delicious, we even bought some to bring home with us. The vineyard was beautiful, and we were really lucky to have beautiful sunny days so we got some amazing pictures of this day! If you are looking for a great day with good wine don’t hesitate!

This is the tour:

From Pisa or Lucca: Half-Day Tuscany Chianti Wine Tasting

Piazza dell’Anfiteatro: Take a drink or have dinner in the beautiful Piazza dell’Anfiteatro.

Admire the Torre Guinigi, a peculiar tower topped by trees from the XIVth.

Torre delle Ore: You can take a tour up the tower to see the view and the old clock. I personally didn’t do this one because we’d gone up the tower in Bologna just a few days before and my claustrophobic friend didn’t want to go up another small tower. But if you’re up to it and interested in clocks you might want to try!  

Val D’Orcia : 5 days 

The first time we came to Italy, we only passed through the hills of Tuscany for a day trip. We instantly regretted not staying for a few days, so we decided to come back on our next trip. We chose specifically to visit Val d’Orcia because of all the viewpoints and the multiple little towns that can easily be visited from a base camp. This Tuscany’s area is so charming, with beautiful cypress, hills as far as the eye can see, and cute little towns atop those hills. So dreamy. 

Where to stay: 

I recommend staying in an agroturismo with a pool to really get a good feel of all the charm Val d’orcia has to give. Surround yourself with olive trees, cypress and vineyards and just relax.

We stayed in the beautiful Poggio ai Gelsi. It has olive trees, gardens and most importantly  a pool with a truly breathtaking view of the valley. I can’t recommend this enough! Once we got there, we never wanted to leave!
https://www.booking.com/Share-oDPEVt

What to do: 

Your days here are gonna be relaxing and fun. It’s just a series of amazing viewpoints and charming little towns on top of hills. Take pictures, eat everything you want, drink some wine and spritz, admire the view, spend a lot of time in the pool and relax!

So here are a few places you can visit during your stay in Val d’orcia: 

Viewpoints: 

If you look on all the blogs, instagram or other, you’ll find a lot of little viewpoints to go see in the region. We’ve gone to a few of them and taken some beautiful pictures, but honestly the view from our place was so amazing that it trumps all the other viewpoints. 

You can do a little road trip and go see all of them in about half a day. It’s a nice activity during which you can take very nice landscape photos. So here are a few: 

  • Gladiator Avenue De Cypresses: On google maps: Il cammino del Gladiatore. When we got there, we had to park in a free parking lot and then walk down to reach the road, so maybe choose a day when it’s not too hot and have good shoes. We didn’t go all the way, but just enough to have a good angle to view the complete road.  
  • Cappella Madonna di Vitaleta: There’s a cute chapel surrounded by green or golden fields depending on the season. You need to park a few hundred meters before and then walk if you want to see it upclose. Or some people recommend seeing it from Strada Provinciale 146 for a more panoramic view. 
  • Podere Belvedere: If you stay on Strada Provinciale 146, you’ll see two other viewpoints close to one another. 
    • SP146, bivio Alteta 52, 53027 San Quirico d’Orcia SI, Italie 
    • St.Pienza Rodellosso, 53027 San Quirico d’Orcia SI, Italie
      From there look in the direction of Podere Belvedere.  
  • Cipressi di San Quirico d’Orcia: It’s a cute circle of cypress on the tops of fields, once again green or golden depending on the time of the year. 
  • Viale di cipressi: Be respectful, the road to the agriturismo is private.
  • Cipressi di Monticchiello: This zigzag road has tall cypress on both sides and leads to the small town of Montichiello. 

Towns:

As I said, Val d’Orcia has a lot of little towns atop of hills, it makes for great little day trips. We choose to see one or two towns in the mornings, eat there and then spend the afternoon by the pool. I can’t recommend this enough!

The towns are mostly pedestrian, so you’ll have to park just outside and sometimes walk a little.  
Here are a few suggestions: 

Pienza: Our agriturismo was near Pienza so we took a few walks there. It’s of course small but you can find great restaurants and viewpoints. You will need to park outside the main area. For some beautiful views, go behind Monastero Maria Tempio dello Spirito Santo on via S. Caterina, then walk on via Gozzante, pass in front of Duomo di Santa Maria Assunta and take via del Casello until Camminata Panoramica.  
If you plan to have dinner here, I recommend La Bandita Townhouse, we all loved it! 
We only eat in Pienza once, but I wish we had time to try Podere Il Casale which is a farm to table experience that seems to have amazing views. 

Montechiello: Come visit at the same time you go see the cipressi di Monticchiello/the zigzag road. We came at dinner time and caught the sunset over all the beautiful hills and vineyards, beautiful. 
A local recommended us to have dinner at Daria and it was indeed delicious ! I had pici and it was the best I had the whole trip! The plates can be small so it can become a little pricey but if you love perfect pasta, don’t miss this one.  

Montalcino: Come visit the Fortezza di Montalcino, admire all the viewpoints, then have a Brunello tasting which is an amazing wine that originated from the region. 

Montepulciano: I don’t want to just repeat myself, but again, amazing views and beautiful piazzas.  You can climb the clock tower for an even better view, but we didn’t do this one. 

Other options : 

  • Wine tasting. There’s winery all around the region so you won’t run out of options. We already had two wine tours on this trip so in Val d’orcia we chose to taste wines by ourselves in the different towns and communes. 
  • Bagni di San Filippo or Terme di Saturnia: Those are two different thermal springs with natural pools. Both are free. Bagni di San Filippo is smaller, but less crowded and closer to Val d’Orcia. I did not do either of them, I didn’t have time and it was in my opinion too hot outside to enjoy. Reviews are really split on this one, so I would say only do it if you don’t have anything else to see or if you really love thermal springs. . 

I hope this helped you plan your trip so once you’re there you can relax and enjoy!