Where to Stay in Tuscany - 7 Best Bases
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Everyone has heard of Florence and you've undoubtedly seen pictures of some of Tuscany's highlight places. Names like Montepulciano, San Gimignano, Volterra, Pisa, and Lucca are sure to be familiar to you, but all these names aren't much help when it comes time to figure out where to base yourself.
Tuscany is big and for anyone staying more than a few days, you'll need to look beyond just Florence. There is no singular town or city in which you can base yourself and do day trips to the rest of the region, so you'll need to plan on having at least a couple of bases.
For example, while Florence makes for an ok base from which to visit Chianti and San Gimignano, places like Montepulciano, Cortona, and the Val d’Orcia are really too far away for day trips.
Another consideration is whether you want to spend all your trip in cities, or if you want to enjoy a taste of small town life and rural Tuscany. Whether this is even an option for you will depend on how you plan to get around; you can't do everything by train!
In short, there's a fair deal to consider. I get into all this and more below!
Table of Contents
Tuscany's main areas
Before we discuss the best places to base yourself in, let's go over a bit of Tuscan geography. Like I said before, this is a big region and its attractions are spread all over, so before you decide where to stay, you need to think about where you'll be visiting.
For most first-time visitors, I think you should consider the following areas when planning your trip:
Florence metro area
Chianti
Val d’Orcia
Lucca and the northwest
Grosseto and the Maremma coast
Florence metro area
This is exactly what it sounds like - the area immediately surrounding the city of Florence, Tuscany's capital. Despite being home to Tuscany's largest city and one of the most visited places in Italy, the surrounding area doesn't actually have very many places of touristic interest. The main places that you're likely to be interested in are the Chianti wine region, the charming little village of Fiesole, and the medieval city of Pistoia.
Other places within day trip range of Florence are San Gimignano, Volterra, Siena, Pisa, Lucca, and Arezzo.
Chianti
The Chianti area, sometimes also called the "Chianti Classico” is a hilly region that lies in between Florence and Siena and is famed for its production of Chianti wine (made of Sangiovese grapes). It's made up of 8 little medieval towns that dot the forested hilltops, the most famous of which are the ones whose names end with “in Chianti": Radda in Chianti, Castellina in Chianti, Panzano in Chianti, Greve in Chianti, and Gaiole in Chianti. While the towns themselves are very cute, the main reason to visit this part of Tuscany is to see vineyards, taste wine, and enjoy the rural countryside.
For those who want to enjoy a bit of rural Tuscan life, staying in/around any of these little towns can be very nice. However, the entire region is also easily visited from Florence or Siena, taking 30-60 minutes to get to. Note, however, that you will need a car to visit.
Val d’Orcia
The Val d’Orcia is a rural region of rolling hills and valleys in southern Tuscany. It begins about 45 minutes to the south of Siena and includes famed towns like Montalcino, Pienza, and Montichiello. Montepulciano, although not technically within the "valley”, is right on its eastern edge and usually included as part of it.
Like Chianti, this a major wine-producing area and it's home to some of Tuscany's most prized wineries, some of which produce that most famous of nectars, Brunello di Montalcino.
Although the villages here are, as with Chianti, quite small, both the architecture and the surrounding terrain is quite different. Where the Chianti towns are predominantly medieval and rather humble in scale, the towns of the Val d’Orcia feature grander buildings, Renaissance flourishes, and they overlook wide open plains of golden wheat and grains.
Lucca and the northwest
The main cities of northwest Tuscany are Lucca, Pisa, and Livorno. Just a bit west of Lucca, you also have a clutch of seaside resorts that are quite popular with Italians and wealthy foreign visitors - Viareggio, Forte dei Marmi, etc. The surrounding countryside has many serviced villas as well as a number of large resort-style hotels.
Although millions visit the beach towns, cities, and resorts, the countryside here is almost entirely unknown to foreign visitors.
And even visitors to the cities rarely stick around for long. Livorno is a major port of call for cruise ships, but almost everyone who arrives immediately heads off for more famous parts of Tuscany. Visitors to Pisa tend to come on day trips from Florence or just stop over to see the Leaning Tower while on their way to the Cinque Terre. Lucca receives some overnight visitors, but is also primarily a day trip destination.
The Maremma coast
The Maremma coast is Tuscany's southern coastline (and its most beautiful). Many of the beaches here are gorgeous and some look more similar to what you find in Sardinia than the rest of mainland Italy. Much of it also lies within protected nature reserves, so provides access to a relatively unspoiled coastline.
The area's main city is the pretty Renaissance town of Grosseto which, perplexingly, receives very few visitors. Other places that you may have heard of are the town of Pittigliano, the Terme di Saturnia thermal baths, and the Monte Argentario peninsula and its main beach town of Porto Santo Stefano.
Florence
Tuscany's capital city and its main transit hub, almost every visit to the region starts in Florence.
A Renaissance masterpiece filled with more art and architecture than you could see in a dozen visits, Florence is home to the world renowned Accademia and Uffizi museums, monuments from the Medici family, and works of art by masters like Michelangelo, Donatello, Caravaggio, Botticelli, and Giotto. To soak all of that up, you need a minimum of 2 days in the city.
Florence also makes for a convenient base from which to explore much of the surrounding region. Places like Lucca, Pisa, and Siena are all reachable via public transport within 1.5 hours. If you'll have a car or plan to book tours, you can also take easy day trips to the Chianti countryside, Volterra, and San Gimignano.
Siena
Located about 1.5 hours south of Florence, Siena is one of Tuscany's most beautiful cities. A stunning example of medieval architecture, the city's red brick buildings and narrow pedestrianized streets are an absolute pleasure to wander. An evening in Siena is one of the most atmospheric experiences you can have in Tuscany. The city's cathedral is also one of the most impressive in all of Italy.
Although many tourists just visit the city as part of a day trip from Florence, this is a real shame and I always recommend spending at least one night here.
Siena is also a really good base for making day trips. Getting to the wineries of Chianti takes as little as 20 minutes, and you're only 1-1.5 hours from all of the following: San Gimignano, Volterra, and the Val d’Orcia towns of Montalcino, Pienza, and Montepulciano. It's an ideal choice for those who will have a car, are happy to do day trips, and want to avoid changing home bases frequently.
With a population of about 50,000 people and a major university (Università di Siena), Siena is also always lively and never feels overwhelmed by tourism. Because most people only visit during the day, staying here gives the added benefit of getting to enjoy the city in the mornings and evenings when there are few tourists and the streets of the old town are surprinsgly empty.
Chianti
Covering a small area of hilly and forested countryside between the cities of Florence and Siena, Chianti is Tuscany's premier wine-growing region. If you've seen photos of wavy hillsides carpeted in neat rows of grapevines, you've almost certainly seen Chianti.
The area comprises 8 little medieval villages: Gaiole, Radda, Panzano, Greve, Castellina, Barberino Val d’Elsa, San Casciano in Val di Pesa, and Castelnuovo Berardenga. Half of the villages are closer to Florence, while the other half are nearer to Siena.
The appeal of staying in Chianti is to enjoy the bucolic countryside, tour vineyads and do wine tastings, and spend time leisurely hopping between the pleasant little towns. With a great network of gravel and paved roads, cyclists have fantastic biking opportunities and hikers also have a good selection trails. When in the car, the winding country lanes make for great road trips. Photographers will also find themselves with simply too many panoramas to capture.
A few of these towns are bigger than others and have a little more to see and do in them, but it really doesn't matter which you stay in. Moreover, most of the good accommodation options are actually in the surrounding countryside (not in the towns themselves), often housed in renovated castles and noble palazzi.
You have an excellent choice of hotels here, ranging from rustic farmhouses and small B&Bs to really luxurious estates. Many high-end properties also have their own wineries, so you can do tastings on-site and your room is likely to overlook vineyards.
I really do think that for Chianti you should choose where to stay based on the hotel and its general location and not by specific town, but here are some pointers anyways:
Greve is the largest of the Chianti towns and has ta decent selection of hotels, restaurants, and bars. It's closer to Florence than to Siena, and therefore busier. You have a few hotels in the town itself.
Radda and Castellina are right next to each other and both are tiny, but very charming. They have a few restaurants and bars, so you'll have a few options in the evenings. They are both also just 15-30 minutes to Siena and you have a couple of hotels in both towns’ centers.
San Casciano is a rather work-a-day place. Its countryside is lovely, but the town itself is neither historic nor charming.
Barberino is cute, but just one road and far from the rest of the Chianti towns. The only reason to base yourself here is if there are specific wineries you want to visit nearby (like Antinori) or if you want to stay at the 5-star Castello del Nero hotel.
Panzano is the smallest town in Chianti (just 1,000 inhabitants), but it has a gorgeous location and is actually one of the more visited towns, in large part due to the fame of Dario Cecchini's famous butcher shop and restaurant.
Gaiole is the most rural and "wildest” place in Chianti. It has just a handful of restaurants (although one my favorites - La Gorgia), two bars, and a couple of hotels. It has good wineries nearby though, some charming stone hamlets that don't even count as towns, and is deep in the woods. There are also 2 or 3 excellent 5-star hotels just 15 minutes away. It's not the right choice for most people, but is great if you're looking to get away from it all.
Castelnuovo Berardenga is a pleasant partialy walled village just 20 minutes from Siena. It sits in an interesting location where the forested hills of Chianti give way to the dry "badlands” of the Crete Senesi. It's also home to the impossibly pretty hamlet of San Gusmé. You have no hotels in town and most people who chose to stay here do so at the nearby 5-star Borgo San Felice Hotel.
Val d’Orcia
While not an official adminsitrative area, the Val d’Orcia is defined as the small southern Tuscan territory that encompasses five main towns: Pienza, San Quirico d’Orcia, Montalcino, Bagno Vignoni, and Radicofani. The region begins about 45 minutes to the south of Siena (1.5 hours from Florence) and is a sparsely populated agricultural zone. Although wine is grown on the hillsides around Montalcino, the defining characteristic of the Val d’Orcia is really its undulating fields of grain which are watched over by hilltop towns.
Montepulciano sits on the eastern edge of the area, technically at the start of the Valdichiana, but is usually considered part of it for tourism purposes. The hamlet of Montichiello, not large enough to be considered its own town, is another famous place in the region.
The main reason to visit the Val d’Orcia is really to enjoy its unique panoramas. The countryside, and the way the farmland has been subdivided among small landowners, has earned it a UNESCO World Heritage designation and the landscapes are both unique and quintessentially Tuscan.
In addition to great views, the small towns are pretty and historic, and their proximity to one another makes it very easy to visit many of them in a single day. For wine lovers, spending a day touring vineyards and tasting famous wines like Brunello di Montalcino and Vino Nobile di Montepulciano is another highlight. The restaurants of the region are also excellent and many of them are located in stunning settings, offering phenomenal views and al fresco dining.
To get a taste for the region, I generally recommend spending 1-2 days here.
As for where to base yourself, I personally think that you should choose a hotel in the countryside, focusing on somewhere that offers great views. Because this part of Tuscany can get very hot, having a pool can also be a major benefit.
If you want to stay in a town instead of the countryside, consider the following:
Pienza has the most going on, but is also the most touristy.
San Quirico d’Orcia has a few hotels and a nice center, but feels sleepy.
Bagno Vignoni is miniscule, but it has two very nice hotels, both of which have their own on-site thermal baths.
Montchiello is a tiny walled hamlet with a few streets, a couple excellent restaurants, and great sunset views.
Radicofani is your best bet for staying a bit more “off the beaten path".
Montepulciano
Sitting at an elevation of almost 2,000 feet and overlooking vineyard-carpeted valleys on all sides, Montepulciano is perhaps the classic “Tuscan hill town". Located at the eastern edge of the Val d’Orcia and the western edge of the Valdichiana (two agricultural valletys), Montepulciano has a population of around 14,000, making it the largest town in the area. It also has the most impressive architecture, with a substantial city center made up of grand stone and marble buildings in a mix of medieval and Renaissance style.
Its strategic location, easily defendable on a hillside and surrounded by fertile farmland, has made it an important regional center since the Middle Ages. Like with Chianti and the Val d’Orcia, the hills around town also produce prized wines, in this case "Vino Nobile di Montepulciano".
You can visit the town itself quite easily in half a day (a morning or an afternoon is plenty), but if you're planning on also spending some time in the Val d’Orcia or visiting Cortona, you could use Montepulciano as your base for a couple of nights. Montalcino in the far west of the Val d’Orcia is a 40 minute drive, Cortona is the same, and even Siena is only an hour.
You have a good selection of hotels in the town center as well as a few just outside it. There is decent bus service to the Val d’Orcia towns, meaning if you won't have a car, this is really your only sensible base. You also have a couple of taxis here, so arranging transfers without the need to hire a driver is a possibility, unlike in any of the other towns.
I think there are five primary things to think about when considering Montepulciano as a base:
It's the largest town in the area with the best selection of restaurants, bars, and hotels
You have the best transit connections (although they're still not good) and there are taxi services
It's by far the most touristy and most visited town
It's very hilly
Parking can be an absolute nightmare
Lucca
In the northwest of Tuscany, Lucca is a lovely mid-sized city that sits on flat terrain along the banks of the Serchio River. Near to the coast and about 1.5 hours from Florence, it's also close to the cities of Pisa and Livorno.
Blessed with wealth since medieval times, Lucca is an elegant city of 90,000 with walkable city walls, cobbletone streets, pretty churches, and gorgeous villas in the hills beyond town. Located at the beginning of the impressive Apuan Alps (Alpi Apuane), the gentle rolling hills that you see elsewhere in Tuscany are replaced here by actual mountains.
There are no major “must visits”, but it's a very pleasant city, quite a bit less touristy than other Tuscan cities you'll visit, and the sensible place to base yourself if you're planning on visiting it, Pisa, Livorno, or the Cinque Terre. If you're here in the summer, it's also only 30 minutes to the coast, so you can combine some beach time with sightseeing.
One of its other major benefits is that it's well connected by train, with regular service to the rest of Tuscany and the city of La Spezia, the jumping off point for visits to the Cinque Terre. If you're planning to visit the Cinque Terre on a day trip from Tuscany, this is really the only city from which it makes sense to do so.
Cortona
Cortona sits on a high hill in the southernmost part of Tuscany, in the province of Arezzo, just north of Lake Trasimeno, Italy's 4th largest lake. It's 105 kilometers southeast of Florence, about 2 hours by train. It is also essentially on the border with the region of Umbria, and it's just 45 minutes to its capital city of Perugia.
Originally an Etruscan city, Cortona is one of the only places in Italy that has preserved the Etruscan city layout and urban design. Visibly, it's not that distinct from other medieval cities, but as you explore the town you'll probably perceive that something simply feels "different". It's a neat town and simply a pleasant place to spend time.
The city's main square is lined with restaurants and wine bars, steep and narrow staircases lead off in all directions, and a number of viewpoints offer vistas that extend as far as Lake Trasimeno. This is also a favorite town for local and foreign artists and artisans, so it has a good cultural scene (galleries, events, shows, etc.), is surprisingly cosmopolitan, and has lots of good shopping. Despite being small, it also has many good restaurants.
Cortona itself can be visited in half a day or even just a couple of hours if you don't stop to eat, but it can also be used as a good base for a night or two. Although Montepulciano and the Val d’Orcia are less than an hour away, I don't really recommend using Cortona as your base for visiting those places. Instead, I consider it somewhere to get a bit off the beaten path and to use as a base for visiting the western parts of Umbria. The under-the-radar Tuscan city of Arezzo is also 30-60 minutes away by train or car.
More Tuscany travel info
For even more advice on planning your trip to Tuscany, have a look at some of our other guides and itineraries!
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