Italy is my absolute favourite country to visit, and I love going back again and again. There are several regions in Italy that have stolen my heart through the years, and Tuscany is one of them. The Tuscan countryside is full of charming villages and picturesque towns to explore, and so I decided to start writing this guide to the best villages and towns in Tuscany to visit before you die.
These are the towns and villages I have come across in Tuscany that I have absolutely loved, for various reasons, and I hope this guide helps you in deciding where to go when planning your Italy trip! Of course, I’ll make sure to add new places and areas in Tuscany to visit as I explore the region more myself, but I’d also love to hear from you. Feel free to leave a comment below this post on your favourite towns to visit in Tuscany so I can add them to my list of places to see some day!
Italy is a large country, and I assume you have already considered whether to visit Northern or Southern Italy before landing on Tuscany and the North (since you’re reading this post). If you are still a little undecided, make sure to check out this guide comparing Northern Italy vs Southern Italy as destinations. Hopefully that guide will make the decision a little easier for you, as it lists popular destinations in both ends of the country.
Now, I believe it is safe to assume you have decided to visit beautiful Tuscany since you are still here! So let’s dive into this guide to the best places to go in Tuscany. I will mainly focus on specific towns and villages I have been to and loved during my Italian adventures.
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The Best Towns in Tuscany to Visit and Explore
Tuscany is a rather large region in Northern Italy, with almost 4 million inhabitants. Amongst the most popular things to do there is (obviously) to go wine tasting, visit vineyards and wineries, and explore the Tuscan wine culture in the region (they specialise in red wine, but also have some incredible whites).
Another reason people visit Tuscany is to go cycling along the coastline. I learned during my most recent visit that cycling is a very popular activity amongst locals, but also that there are lots of group cycling tours in Tuscany you can join if you are into cycling.
History is another reason people visit Tuscany, and a word you might see repeated in this guide is “Etruscan”. The Etruscans were a civilisation that lived along the Tuscan coast and across the region, and the Etruscan period lasted from around 800 to 100 BC (yes, that’s before Christ), and there are interesting excavations found all across Tuscany from the time. Especially along the part of the coast known as the Etruscan Coast.
I have first and foremost focused on unique and perhaps unknown places to visit in Tuscany, but at the bottom of the post I have included the best cities in Tuscany as well. This is mainly because you are likely to fly into one of these for your trip – unless you fly to Rome and drive north (which I don’t recommend unless you are doing a road trip).
For each town and village, I have included a few things to do there, as well as advice for where to stay and how to get there. Hopefully this will make planning your Tuscan holiday a little easier!
#1 Castiglione della Pescaia
On my recent trip to Tuscany with Danitacom, we started our first day in the picturesque Tuscan town of Castiglione della Pescaia. It is located in the Southern Maremma region of Tuscany, along the coast.
This is a town and municipality with around 6800 inhabitants. It is a beach town and fishing village with a rich history (excavations dating back to the Etruscan period has been found all over the coast).
Why visit and things to do
Personally, I felt like walking around a movie set – like something out of a cheesy romcom where the main character goes to Tuscany, or a mafia movie of some kind. Every corner we turned in the old town was more beautiful than the next, and I could have spent the whole day walking around the old town of Castiglione della Pescaia.
I mean, just saying the name of the town sounds good, doesn’t it?
As with the rest of the Tuscan coast towns, biking is a popular activity here, as there are 140 km of cycling trails nearby. These are known as the Sentieri Castiglionesi.
In addition to this, horseback riding is also a fun thing to do in the area, and of course to sample all the wine. There is great wine all over Tuscany, as I am sure you already know. So make sure to try several of the local varieties.
Castiglione della Pescaia is home to the Diaccia Botrona, a wetlands nature reserve. There, you will find an old building from the 18th century, known as Casa Rossa (“the red house”). The building was built to separate the swamp water from the ocean water, and to control the water coming in and out from the sea. By creating movement in the water they could avoid the problems that followed with the stagnant water and swamplands (insects, mosquitoes and in turn, malaria).
The nature reserve is particularly popular amongst bird watchers, as a lot of birds stop here as they migrate north or south for the season. In the summer you can find more than 2000 flamingos here!
There is a 15-kilometer pathway around the entire perimeter of the park. Even if you are not a bird fanatic, you will enjoy walking around it, or making your way around by bicycle or horseback.
The reserve is open 24/7, and as a nature reserve it is free of course. There is a small museum inside the Casa Rossa, which has opening hours, and it costs €3 to enter. Guided tours are available during opening hours, but they also have a great app in English.
Where to stay in Castiglione della Pescaia
For such a small town in Tuscany, you will find that there are plenty of places to choose from when looking at where to stay in Castiglione della Pescaia. Some of my favourites are below.
- If you are looking for a luxury experience in the Tuscan countryside, surrounded by vineyards and olive farms, the stunning L’Andana Tenuta La Badiola is just a 10-minute drive out of town.
- The Roma Hotel is centrally located in Castiglione della Pescaia, with just a short walk to the beach.
- If you are traveling with a friend group or your family, you might want to consider renting a holiday home for your visit. The Casa Acqua Marina is perfect for this.
- Find more places to stay here!
#2 Bolgheri
I will say this right away, and stand by it forever: Bolgheri might just be one of the most beautiful towns in Tuscany. I was blown away by the charm of this little town, its cobbled buildings, (many) enotekas, and cute restaurants.
I absolutely fell in love with this place, and it might have had something to do with the long lunch we enjoyed whilst opening bottle after bottle of Bolgheri wine, or just because I felt like time really slowed down whilst we were there.
Wine is obviously a big reason to visit, as the area around Bolgheri is known for it. Therefore, you will find some great wine shops (enotekas) around this town, in addition to a great ice cream place called Bolgheri Ti Amo (find it at Largo Nonna Lucia 1).
A fun little thing about Bolgheri, and one of their claims to fame is that Giosue Carducci, the first Italian Nobel price for literature spend a lot of time in the town, because his grandma lived there.
Where to stay in Bolgheri
Like with Massa Marittima, Bolgheri is a small Tuscan town, with more holiday homes, bed & breakfasts and apartments for rent than hotels. Head this way to see a selection of them!
#3 Massa Marittima
Another favorite on this list of small towns in Tuscany is Massa Marittima (not to be confused with Marina di Massa below, as I first did).
This medieval village is perched on a hill overlooking the countryside surrounding it, a little further in from the coast than some of the other Tuscan towns on this list.
Why visit and things to do
Cultural tourism is the main reason for visiting Massa Marittima, much due to the Etruscan history and excavations from the area surrounding the town. If you are curios about this site of the town’s history, make sure to visit the Archaeological Museum, located right in the town center.
Also located in the town center you will find the breathtaking Cathedral of San Cerbone, a large stone cathedral towering over the piazza in front of it. The church is beautiful, and sitting on the steps in front of it with an ice cream just watching the world go by might just be the perfect way to spend some time.
There’s more to Massa Marittima’s history than just the Etruscan excavations and findings. Just a short walk from the Piazza Garibaldi (town center) you will find some very famous frescoes, that weren’t discovered until around the year 2000.
The reason these are so famous, is that the biggest (and best-preserved) of the frescoes depict a Tree of Fertility. This medieval fresco is basically (and there is no better way to say this) a tree of penises.. Obviously, we know that in ancient and medieval times, the male reproductive member was a sign of fertility, but it’s still quite the sight to behold.
Where to stay in Massa Marittima
Massa Marittima is a small town in countryside Tuscany, so there isn’t a vast amount of options for where to stay. However, there are some really charming bed & breakfasts and guest houses in the historic center, so if you want to spend a night getting a true feel of that slow Italian lifestyle, I recommend staying here.
Booking.com#4 San Gimignano
San Gimignano is not only a beautiful town you need to see in Tuscany, but also a UNESCO World Heritage Site (since 1990, to be exact). Located in the center of Tuscany, just a little over an hour’s drive from Florence, it is known for its many towers peaking out from above its rooftops.
In addition to the many towers (65 of them, to be exact), don’t miss the town cathedral, dating back to 1148. Get your ticket in advance, paired with a trip up to the top of the Torre Grossa, for epic views of the city’s rooftops and towers. The Torre Grossa is the tallest tower in San Gimignano, and dates back to 1310.
Fun fact: its towers has given San Gimignano the nickname of “medieval Manhattan”.
San Gimignano is a popular day trip from Florence, often paired with wine tastings and a visit to the town of Chianti. But it is also possible to spend the night there, in one of the many great hotels in town.
#5 Populonia
All the way out on the Tuscan coast you will find Populonia, known for being one of 12 Etruscan settlements along what is known as the Etruscan Coast. As mentioned, the Etruscan era dates back over 2000 years, and was an empire, like the Greek and Roman Empires.
There is a very interesting Etruscan Museum at the top of the hill in Populonia, right next to the castle and tower. From the top of the tower you can see the entire coastline stretching both north and east, and I recommend climbing it after visiting the museum.
From the tower, you can almost see the excavation site where they have found (and are still finding) tombs and graves from the Etruscan era. This Necropolis (city of the dead) contains tombs of several sizes, one of which is almost completely intact (yes, you can go inside it).
Exploring these tombs and learning about how the Etruscans buried and handled their dead made me realise just how real this civilisation was. The official name is the Archaelogical Park of Baratti and Populonia, and it should be on your list if you want to explore some of Tuscany’s ancient history during your stay.
Where to stay in Populonia
A bonus for those wanting to spend the night in Populonia: you can actually stay in the castle apartments! Head this way to learn more and to book it. Whilst the castle and museum is a short drive away from the beach, you will find more places to stay closer to the coast and the town called Baratti. This is also where you will find the Etruscan Necropolis.
#6 Marina di Massa
I visited Marina di Massa for the first time with my family when I was a teenager, and I remember loving this beach-side town for its great ice cream, long beaches and relaxed vibe. If you are looking for a beach holiday in Tuscany, Marina di Massa should be on your list. Or, if you are visiting some of the more cultural or non-touristy towns in Tuscany, you might find that a few days lounging on the beach in Marina di Massa is the perfect way to end your trip.
This town has lots of great resort-style hotels to choose from, you are guaranteed to find a place to stay that fits your preferences (and budget).
Booking.comCities in Tuscany to keep in mind
This article has mainly focused on villages and small towns, but there are a couple of cities I feel deserve an honorable mention, as they are very likely to be destinations you end up visiting during your trip to Tuscany. Or, you will probably fly into either of these cities for your holiday under the Tuscan sun. Therefore, I decided to include a short introduction below.
Florence / Firenze
Together with Pisa (below), Florence is likely the most well-known city in Tuscany. And that’s with good reason. This beautiful city should definitely be on your Italian bucket list. It is located right in the middle of the country, and is a 3-hour drive from both Rome and Venice, 4 hours from Genova and 3,5 hours from Trento.
Side note: If you are trying to decide wether to visit Florence or Verona in the Veneto region – Florence often ends up pulling the longer straw.
Florence is a beautiful city with ties back to (you guessed it!) Etruscan times (the city was actually built on top of a former Etruscan settlement. Since then, it has been Italy’s capital, home to the famous Medici family, and the inspiration of many an artist and architect.
Amongst the most famous sights and attractions in Florence are the Cathedral of Santa Maria del Fiore, the Giotto’s Bell Tower and the Palazzo Vecchio, in addition to the beautiful bridge Ponte Vecchio – one of the oldest bridges in the city.
From Florence, the Tuscan countryside and the towns I have included in this guide are within easy reach. If you don’t have a rental car for your trip (so you can drink all the wine, of course), you’ll be happy to hear that there are plenty of great day trips from Florence to the countryside. Here is a selection of a few of them:
Pisa
Pisa is located close to the coast in Tuscany, and spending a few days in this beautiful city will show you that there’s more to it than the Leaning tower of Pisa. Of course, the tower itself is worth a visit (get skip-the-line tickets in advance here), but don’t miss the beautiful Piazza dei Miracoli surrounding it – which has been on UNESCO’s World Heritage List since 1987. The beautiful Cathedral of Santa Maria Assunta (from 1063!) is worth a visit as well.
Pisa has lots to offer visitors, so before you head out of the city to explore the villages in the countryside, make sure to go on a tour of the tower and cathedral, and explore some of the city’s architecture as well.
Towns in Tuscany: Map
Below is a map to give you an idea of how far away from each other each of these towns, villages and cities are. I have included both Florence and Pisa on the list (as number 7 and 8), as you are likely to start or end your trip in either of them. This map should also be helpful if you are planning a road trip in Tuscany, and want to make sure you include some (or all) of these towns.
Time to visit Tuscany!
There you have my favourite villages and small towns in Tuscany, and I hope you have discovered some new destinations for your Italy bucket list. There are many other beautiful towns I could mention, such as Siena, Chianti (wine, anyone) and Montepulciano. One day I am sure I will expand this list to include even more places to visit, but for now I’d love to hear from you!
Have you been to any of these places? What’s your favourite destination in Tuscany? Tell me in the comments below!
Read more Italy guides:
- 27 Things to do in Palermo, Sicily
- Northern vs Southern Italy: Which is better to explore?
- Castles to visit in Trentino, Italy
- A guide to evenings in Venice, Italy