Where to Go in Tuscany
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Tuscany is truly blessed with an abundance of wonderful places to visit; there are countless beautiful towns, important cities, stunning countryside, wild mountains, and a lovely coastline. You could spend weeks here and still not see everything. I've been visiting for decades and still have more on my list!
I could easily have this made guide "100 places to visit in Tuscany" without exaggerating, but no one has unlimited vacation time (or money) and an endless list doesn't help you narrow down your options.
So what I've done below is create two lists: the first 10 places are what I consider "must visists” or "highlights". These are the places that I think every traveler to Tuscany should at least consider fitting into their itinerary, regardless of how many days they have. The second list contains 10 places that I think are equally wonderful, but that realistically will only make sense if you have an extended amount of time in the region. In some cases this is because they're far away f
Enjoy!
Table of Contents
Must-visit places
The following 10 places are a mix of cities, towns, and "sub regions” that I think should be included on any trip to Tuscany longer than just a few days.
If you'll be visiting the region for only 3 days, then I think realistically all you can do is visit Florence and take a day trip to Siena and the Chianti wine region. If you'll have 5 days, you can include many of these places, although not all of them. With one week, you could probably see everywhere on this list.
1. Florence
Ponte Vecchio
The Duomo
One of the most visited cities in the world, Florence really needs no introduction. The cradle of the Renaissance and home to many of Italy's most incredible works of art, this is an unmissable stop on any visit to Italy, let alone Tuscany.
Lying along the Arno River, for most of its history Florence was an independent city state, and one of the most wealthy and powerful places in Italy and Europe. Its powerful families, the Medici chief among them, sent Popes to the Vatican, dominated international trade, and raised and funded powerful armies engaged in conflicts around Eruope. With the wealth they earned they patronized and funded the works of incredible artists like Da Vinci, Michelangelo, and Botticelli, who made Florence into the masterpiece that it is.
Elegant palaces, incredible museums, and centuries-old churches are not all you will find in Florence. The city is also renowned for its fantastic food scene and some of the best shopping in the world.
For more info, check out my guide to Florence and 3-day Florence itinerary.
Palazzo Pitti
2. Siena
Piazza del Campo in Siena
The Duomo
A street in central Siena
An hour away from Florence, Siena is a gorgeous medieval town that sits at the intersection of two beautiful Tuscan landscapes; the Chianti wine region and the "Crete Senesi” badlands. Founded by the Etruscans over two millennia ago, the "modern” city is a medieval jewel. Although small, Siena is full of cultural landmarks and architectural marvels.
The town's main sights are the famous shell-shaped Piazza del Campo square and its black-and-white-marbled Duomo (cathedral). Each ranks as one of the most beautiful in the entire country. In terms of events, Siena is mainly known for its annual horse race, called the “Palio di Siena” which is held twice every summer, in June and August.
Although you'll often hear of a rivalry between the Florentines and Sienese, this is mostly a thing of the past; throughought the Middle Ages these two cities fought countless battles for supremacy of the region, but by the time of the Renaissance, Florence had fully emerged as the regional power. While this means that Siena's empire crumbled, for visitors it also means that the city is wonderfully different from Florence. In the place of grand palazzi and wide streets, Siena is all red brick, narrow pedestrian alleys, and hidden squares. It's incredibly atmospheric.
You can read more about Siena in my guide to Siena.
Piazza Salimbeni in the center
3. Lucca
A view over Lucca's rooftops
In western Tuscany and about 1.5 hours from Florence by train, Lucca is a lovely city. Its city center is almost entirely pedestrianized, it has among the best-preserved city walls in Italy (which you can walk along), and the architecture is a lovely mix of medieval and Renaissance.
Surrounded by green hills, the city also provides easy access to some gorgeous countryside and the wonderful Alpi Apuane mountains where you have excellent hiking and no crowds.
Besides the city walls, Lucca is home to elegant squares, centuries-old churches, and a couple of still-standing lofty towers. Most people visit on day trips, making it especially pleasant in the evenings when it's mostly locals out and about.
The town is also popular in Italy for hosting the Lucca Comics & Games, the country’s biggest comic event held annually between October and November.
Its location in the west of the region make it a convenient base for visiting Pisa (20 minutes away) and for day trips to the Cinque Terre.
I put together a detailed guide to Lucca with more information.
Piazza dell’Anfiteatro, Lucca's main square. Photo: Kasa Fue, CC BY-SA 4.0, via Wikimedia Commons
4. San Gimignano
San Gimignano's stone towers
Long a favorite among international visitos, you'll spot San Gimignano from a distance: the hilltop town is characterized by 14 tall medieval towers that create a totally unique skyline. Once 72 in number, the towers were commissioned by powerful families to show off their wealth. They're like medieval skyscrapers, if you will.
Although climbing the towers for breathtaking views over the Tuscan hills is the town's main draw, it also has a pleasant little historic center with Gothic and Romanesque buildings lining the streets and main square.
Located an hour southwest of Florence or 40 minutes northwest of Siena, the town is a bit out of the way, but easy to include as a day trip from either city or as a slight detour when traveling between the two of them.
5. Val d’Orcia
A typical Val d'Orcia landscape in the countryside near to Pienza
San Quirico's main street
A street in Montepulciano
Tuscany is beloved for its rolling hills, and the Val d’Orcia is quintessentially Tuscan in this sense. This fertile area of agricultural lands extends from the hills south of Siena up to the slops of Monte Amiata, Tuscany's most beloved and iconic mountain.
Here, it's all about enjoying the incredible panoramas that you get from the walls of hilltop medieval towns like Pienza, Montalcino, San Quirico d’Orcia, and Montepulciano. The roads that connect these little villages often offer even better vistas.
And of course, visiting the region’s wineries is an ever-popular activity. This is, after all, the land of Brunello di Montalcino, one of Italy's most famous wines.
Relaxing walks among olive groves, tall cypresses, and vineyards is another fabulous way to spend your time here.
These dreamy landscapes have been used for shooting scenes in many movies, with those of "Gladiator” probably the most well-known.
See my Val d’Orcia travel guide to learn more.
The Val d’Orcia in summer after the grain has been cut
6. Chianti Region
A vineyard near to Radda in Chianti
The stone church in Castellina in Chianti
A street in Castellina
Another unmissable area of Tuscany for any food and wine lover is the Chianti region. Located in a patch of hills and valleys in between Florence and Siena, this is Tuscany's premier wine-growing region.
Kilometers of rolling hills with fertile vineyards create not just a wonderful landscape to discover by bike, motorcyle, or car, but they also of course produce world-famous Chianti wines.
Having a wine tasting in the Chianti hills while sampling local foods and meeting local winemakers is a must-do experience in the area.
The region’s 9 stone villages are also lovely, with Greve, Radda, Castellina, Panzano, and Gaiole the prettiest of the bunch, and they are all worth a quick look around.
Chianti is easy to visit on a day trip from either Florence or Siena (30 minutes from either city) or when traveling between those two cities. That said, for the best experience I always recommend spending at least one night in one of the pretty towns or the gorgeous countryside that surrounds them.
To learn more about the region, see my Chianti travel guide and my article on wine and wineries in Chianti.
Hills and vineyards near to Gaiole in Chianti
7. Arezzo
Piazza Grande, Arezzo's main square
Sitting on a sloping hillside, Arezzo was once one of the 12 towns of the Etruscan League. Since medieval times, the city has been a major manufacturer of gold jewelry, earning it a reputation as a place of wealth. That's not entirely true any more (though the jewelry makers still exist), but it's a really pleasant little city with a compact historic core and an unassuming air.
Among the city’s highlights is the central Piazza Grande with the Vasari Loggia, the Palazzo della Fraternita dei Laici, Arezzo Cathedral, and Corso Italia, lined with boutiques and shops selling antiques.
Many scenes of the award-winning movie “La Vita è Bella” were shot in the town's center.
Traditionally, Arezzo has been almost totally ignored by visitors for whom it's just a blurr in the countryside while riding the fast train from Rome to Florence. That's started to change of late, which is long overdue. It's a very pleasant town to spend a half-day or day in, and the lack of major crowds and obviously tourist-oriented restaurants and shops is a welcome break from more touristy places.
8. Cortona
Lovely Cortona
Piazza Della Repubblica, Cortona's main square
Out for a stroll on a winter day in Cortona
Located in the Province of Arezzo, Cortona is set atop a hill full of Medieval and Renaissance buildings. Cortona’s main draw is the surrounding countryside, where the popular movie “Under the Tuscan Sun” was shot.
Besides the stunning landscape, Cortona has a long history dating back to Etruscan times, which can be learned about in its excellent Museum of the Etruscan Academy.
Despite being a very small city, it's a favorite among artisans and artists (both local and international) so has a very interesting cultural scene and great shopping.
Although Cortona itself only requires a few hours to explore if you're just stopping by, the surrounding countryside is lovely, Lake Trasimeno is only a few minutes away, and many of the Umbria region's prettiest cities are reachable on day trips.
More info in my guide to Cortona.
9. Pisa
Piazza dei Miracoli and the Leaning Tower of Pisa
I've included Pisa in my "top 10”, but whether it's actually worth visiting at all entirely depends on how you visit. If you're planning to come here on a multi-stop day trip from Florence just to see the Leaning Tower, prepare to be underwhelmed and to leave with an innacurate (and likely negative) opinion of the place. But if you plan your visit the right way, Pisa can make for a very nice stop on a Tuscan itinerary.
Known almost exclusively for its iconic Leaning Tower, Pisa actually boasts many other artistic and architectural treasures. One of the richest cities during the Middle Ages, here you can marvel at Romanesque palaces, Gothic churches, and Renaissance squares - with Piazza dei Miracoli being particularly beautiful.
Pisa is also a university town, so it has a lively vibe and hosts great bars, cafes, and cultural events.
Many people think of Pisa as the classic "tourist trap” with just one sight. There's some truth to that in the sense that the vast majority of visitors come here on overly rushed day trips from Florence or from cruise ships docked in nearby Livorno. Many tours try to squeeze Pisa, San Gimignano, Siena, and sometimes even Lucca into a single day trip and these visitors arrive on huge tour buses and descend en masse for the Leaning Tower to snap some pictures, maybe enter a church, and then zip off to their next stop.
From 10:00 am until 4:00 pm it's an absolute madhouse. But if you find yourself here in the early morning or after the day trippers have departed, the city returns to being a regular, and pleasant, place.
Learn more in my guide to Pisa.
Pisa along the Arno river
10. Hot springs and spa towns
The Terme di Saturnia
I realize that "hot springs and spa towns” is of course not a singular place, but I didn't want to list just one town as which will make sense for you to visit entirely depends on where you'll be going in Tuscany.
In general, Tuscany has many natural hot springs, some of which are pretty popular (and busy), while others are still totally under-the-radar. You will find both spa-style hot springs enclosed in resorts as well as beautiful natural pools, often deep in the woods.
The most famous hot spring in the region among foreigners is the Terme di Saturnia, which has become extremely busy and, in my opinion, not all that pleasant as a result.
If you prefer something less-frequented and much more natural, head to the Bagni di San Filippo hot springs located on the slopes of Monte Amiata mountain, near to Bagno Vignoni. Here, a series of small thermal pools is hidden within the forest, and it is characterized by white rocks that create a snow-like landscape. It's quite unique.
Bagno Vignoni, also in the Val d’Orcia, is another place to visit for thermal baths. It's been a spa town since Roman times and two hotels there carry on the tradition: Posta Marcucci and the Adler Spa Resort. You can visit the baths at Posta Marcucci without being a guest of the hotel.
Somewhat near to the town of Montepulciano is the spa town of Chianciano Terme, which was once a major destination but has fallen on rather hard times. There are a number of hotels here with thermal baths, though most have seen better days. I think it's an interesting place to visit because it has a rather strange atmosphere, but I'm not sure it makes sense for most visitors. It is quite cheap though…
And for one final entry on the list, we can't mention hot springs and spa towns and not include Montecatini Terme, one of the most famous spa towns in all of Italy. It's located in between the cities of Pistoia and Lucca.
The main square of Bagno Vignoni
Bagni di San Filippo, a natural hot spring in the Val d’Orcia
Other places to consider
These 10 places are some of my favorites, but I recognize that for a first trip to Tuscany, they probably won't (and can't) be priorities for most people. In some cases this is because they're just not as immediately impressive as the "must visits” while in others its because their out-of-the-way locations mean that you'd simply need more time than most people have in order to visit them.
So, consider these as places to include if you're planning an extended stay in Tuscany or are coming back for a return visit and have already seen the highlights.
11. Elba
A gorgeous beach on Elba
The town of Portoferraio in Elba
Elba is an island surrounded by the sparkling Tyrrhenian Sea. Famed for being the place of Napoleon’s exile, the island is much more than sun-kissed shores, beautiful beaches, and coves for a beach getaway.
Elba’s coastline is dotted with lovely towns where you can delve into the island’s cultural heritage, such as Portoferraio and Porto Azzurro.
The inner part of the island is home to fertile vineyards, and Monte Capanne, with a height of 1,018 meters, makes for an ideal hiking spot.
12. San Miniato
San Miniato. Photo: I, Sailko, CC BY-SA 3.0, via Wikimedia Commons. Cropped from original
A quaint village in the province of Pisa, San Miniato is the place to be to taste one of Tuscany's most prized food products: the rare tartuffo bianco (white truffle). To this incredible food is dedicated a whole cultural event, the “Mostra Mercato di Tartufi”, hosted every November. In San Miniato, you can do truffle tastings and also participate in truffle hunting.
The village is lovely to explore on foot, and its most stand-out feature is the medieval Piazza del Seminario.
San Miniato is also a stop on the historic Via Francigena pilgrimmage route.
13. Porto Santo Stefano
Porto Santo Stefano's waterfront
Cala Grande beach near to Porto Santo Stefano. Photo: Ceppicone, CC BY-SA 3.0, via Wikimedia Commons
Located on the Argentario Peninsula on Tuscany's southern Maremma coast, Porto Santo Stefano is a bustling little beach town.
All around town are striking coves whose waters look more like the sea that you find in Sardinia than the rest of Tuscany or even the rest of mainland Italy. Some coves are private while others can only be reached by boat or with a short hike. One of the best coves is Cala Gesso, which is a perfect snorkeling spot.
The town is also one of the main seaports of the area so it's always busy and you have daily transfers to Giglio Island, the next place on this list!
14. Giglio Island
The coast of Giglio island
Giglio Island lies within the Arcipelago Toscano National Park, just 16 km from Porto Santo Stefano.
This Mediterranean island offers visitors natural beauty and rich history. The narrow streets of the main town of Giglio Porto are lined with artisan stores and outdoor restaurants.
The island is home to stunning beaches for swimming and snorkeling - don't miss Campese Beach and Cannelle Beach.
Another highlight of Giglio Island is the town of Giglio Castello, on the island's highest point, where you can visit the medieval fortress Rocca Aldobrandesca to marvel at 360-degree landscape views.
15. Volterra
Volterra is one of the larger hill towns in Tuscany and, despite being a popular stop with visitors, its location a bit out of the way means that it doesn't get as crowded as many other places. It's rougly an hour northwest of Siena.
Enclosed within double walls whose origins date back to Etruscan and Medieval times, the town has a wonderful medieval atmosphere. If you like narrow streets, ancient walls, and towering fortresseses, you'll like Volterra.
Volterra is particularly known for high quality crafts made out of alabaster, and you can purchase decorative objects in the many artisan shops in town or visit the interesting Ecomuseum of Alabaster.
16. Monteriggioni
Photo: Maurizio Moro5153, CC BY-SA 4.0, via Wikimedia Commons. Cropped from original
Another walled town in Tuscany, Monteriggioni's main feature is the 13th-century castle that overlooks the entire landscape. You can walk on the medieval walls that are part of the castle to have a bird's eye view of the Chianti countryside. The town also has 15 still-standing medieval towers, two impressive doorways, and charming little streets.
Monteriggioni is located along the pilgrimage route known as Via Francigena, and it was featured in two famous movies, "The English Patient" and "The Gladiator".
It's not along any main routes you'll probably be driving, but it's only 20 minutes away from Siena, so any easy day trip. If you go, you can combine it with visits to Certaldo (great ceramics) and San Gimignano, making for a very nice full-day trip away from Siena.
17. Parco Naturale Migliarino San Rossore Massaciuccoli
A little inlet on Lake Massaciuccoli. Photo: Albarubescens, CC BY-SA 4.0, via Wikimedia Commons
The Migliarino Nature Park is a protected area that stretches from Pisa to Lucca. It covers 230 square kilometers and encompasses many habitats, including pine forests, wetlands, and coastal dunes.
The Migliarino Nature Park is perfect for discovering Tuscany’s natural beauty and biodiversity. The area also boasts the lovely Lake Massaciuccoli, which can be explored by bike or walking.
18. Orbetello
Orbetello is a seaside town in the Argentario, with a lovely center with shops, restaurants, and a lively weekly market selling local food products. But Orbetello is much more: the town boasts a lagoon, which makes the area geographically unique. The Laguna di Orbetello is rich in fauna of all kinds, which is protected by the WWF.
The lagoon is surrounded by a cycle-pedestrian path that you can go through to admire pink flamingos, white herons, and flocks of coots.
19. Livorno
Livorno is an important port town in Italy, where ferries depart for many other parts of Italy, including the Elba Island in Tuscany.
Embellished during the Renaissance by the Medici family, in Livorno, you can visit many attractions like a castle (the Fortezza Nuova), the beautiful Terrazza Mascagni (a sea view terrace), and the Nuova Venezia (the streets surrounding the castle, which are lined with canals).
20. The Tarot Garden
A statue in the garden. Photo: Simone Ramella from Roma, Italy, CC BY 2.0, via Wikimedia Commons
For a rather unusual attraction, check out The Tarot Garden (Giardino dei Tarocchi in Italian). This artistic garden is located right outside of Capalbio, a little village in the Maremma region of Tuscany, and about 20 minutes from Porto Santo Stefano. It was created by the incredible French artist Niki de Saint Phalle and is unlike anything else you'll find in Tuscany.
The park houses installations representing the 22 major “arcana of the divinatory tarot”, which are made of iridescent mosaic tiles and metal. The artist took almost 20 years to complete this project, and this magical attraction is open from the beginning of April through mid-October.
It's quite far from pretty much anything else you'll be visiting in Tuscany, but if it piques your interest or you'll be visiting the southern reaches of the region, it's very much worth seeking out.
More Tuscany travel info
For more advice on planning your trip to Tuscany and Italy, have a look at some of our other guides and itineraries!
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Hi, I'm Serena, and I've been a tour guide and travel consultant here in Tuscany for the last 25 years. If you're looking for some local advice on your trip, I'd love to help!
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