Best places to stay in Tuscany 2019 [without a car or with it]

Where to stay in Tuscany

Last updated on February 12th, 2019 at 05:31 pm

I have spent a considerable amount of my life in this region. I just love it. So many friends asked me where to stay in Tuscany. It was time for me to write a guide on it (not sure why I waited so long).

I have visited this region with a car or uniquely with public transportation. They are two different kinds of experience.

There is no better one, just different.

I found the driving experience very relaxing, once outside the cities, however, very stressing when driving inside them.

I have organised this guide with a few possible itineraries, both with a car and without a car, updated in 2019 (no old stuff)

If you want to experience both the culture offered by the cities as well as the typical Tuscany landscape then you may also opt to rent the car when visiting the hills and vineyards.

Tuscany rolling hills

Tuscany rolling hills

For local events and news about Tuscany, I suggest reading The Florentine and La Nazione (Italian only, Google Chrome translator works great on it)

But let’s start with a map of the Tuscany towns and cities. This will help to have a better idea of the trip

Where to stay in Tuscany: Map of towns and cities

To make things easier, I always suggest seeing Tuscany as divided into 6 areas

  • the Central area with Florence and the wineries around
  • the North with a mountain landscape (less characteristic, I would leave this area on a third or fourth trip to Tuscany)
  • the West with cities as Pisa (main touristic airport) and Lucca. They are both connected with a quick train to Florence and the beach.
  • the Coast with some good beaches great for a day tour in that hot days but I would not stay there
  • the South, from the Chianti area to Siena and other beautiful villages
  • the East with Cortona and Arezzo (opening more to the tourism in the last few years)
Best villages to stay in Tuscany, including the major cities

Best villages to stay in Tuscany, including the major cities

Best towns in Tuscany to stay

With a map in hands, it’s probably easier now to discover the major towns and see the differences between them.

In the next two chapters, I focus on possible short and long holidays that can be done renting a car or just using public transportation.

If you know already all about the cities and villages I suggest to skip the part below and jump straight to the best places to stay in Tuscany without a car (or with a car).

Here below a short description of the major cities/towns

Florence, the city of art

Florence, the city of art

Florence, the capital of culture

Florence is the only real city in Tuscany. It is very well connected to Rome, Milan and Venice with a quick train (under 2 hours)

It has also an airport, used mostly by the major airlines.

There are so many things to do and places to see that you can be busy for a week or more. Cultural events, museums, churches, amazing architecture, parks and so much more.

Florence it’s a magical city, however, I highly suggest to NOT visit it by car.

The centre is open only to the residents and finding parking is a real challenge.

If you are visiting on a day trip, you better park your car close to a train station outside the city and take a short trip to the centre. It will save you a big headache, besides some money.

From Florence, you can easily reach Lucca and Pisa with a short train trip, and Siena by bus (1.5hours).

If you plan to visit the Chianti area or the South of Tuscany then you better rent a car or join an organised tour.

Accommodation in Florence can be quite expensive but it’s a unique city and unmissable in any trip to Italy.

The leaning Tower of Pisa

The Leaning Tower of Pisa

Pisa and the leaning tower

Pisa has the most popular airport for low-cost airlines (and now also for a few big names).

It’s an interesting university town with one of the most famous attractions in the world, the Leaning Tower of Pisa.

This tower is located between the Arno and Serchio rivers. It is said that it was planned in that place because the soft soil would preserve it from possible earthquakes’ damages.

Unfortunately, one side of the soil is much softer, which explains the leaning.

It has been secured in the last 10-20 years and today it’s a much safer attraction that it used to be.

I really wonder if Pisa would be so world famous with a straight tower, by the way !!

The town itself is interesting, with a local young feeling, but not as spectacular as the others.

I would personally stay in Pisa only if I had a late arrival flight or/and early morning one.

Lucca main square

Lucca main square

Lucca, the Renaissance town

It is one of my favourite town, if not my favourite, in Tuscany. Here are the main reasons.

  • the architecture is different from the other places in Tuscany, more from the Renaissance era and not the medieval time
  • if you spend weeks and months in Tuscany, as I did, you get used to the medieval towns and villages. Lucca is definitely something else.
  • the centre is still designed in a grid, as in the original plan from the Roman Empire. Different from the square concept
  • the town is still protected by the original Renaissance wall, all around the perimeter
  • best of all, the entire wall has been reorganised as a pedestrian area with a bike path. You can literally walk all around town, without the worry of any car. Fantastic if you are travelling with kids (my suggestion is to rent a bike, plenty of options around)

More information about Lucca can be read on this interesting article on Traveller magazine titled ” Lucca, the most overlooked town in Tuscany”

Arezzo dressed up square

Arezzo dressed up square

Arezzo, the Etruscan town

Arezzo was one of the most important Etruscan cities and you can see evidence of it all around town.

Interesting enough, Arezzo joined the Tuscany “touristic revolution” only in the last few years. It used to live only of agriculture and handcraft.

And this comes to a surprise because the town is really beautiful, with the main square, Piazza Grande, and the Cathedral being the top attractions.

Arezzo is somehow still off the beaten path and if you are looking for more of a local experience then it can be the best town to stay in Tuscany.

It has still that nice local feeling that places as Siena has somehow lost.

View of beautiful Siena

View of beautiful Siena

Siena, as beautiful as touristy

How can you not fall in love for Piazza del Campo and the whole historic centre around Siena?


In fact, it has been added to the UNESCO World Heritage Site list.

Siena has also probably the oldest horse race in the world, the Palio, that started in the medieval time and still runs on the 2nd of July and the 16th of August.

This is the race that stops the nation. Everyone in Italy is in front of the TV, watching this crazy event where the horse wins, doesn’t matter if the jockey is still riding it.

Every horse represents a neighbourhood of Siena and all the locals are absolutely crazy about it.

Piazza del Campo is the stage for the race, changed and reorganised just for the event.

It has been used also in famous movies, as 007 Quantum Of Solace.

There is however something to be said about Siena.

It is today one of the most visited sites in Italy and it suffers the same issue as Venice and other popular Italian destinations.

It can be really really busy with tourists, up to a point where the small lanes become too crowded.

The best time to enjoy Siena is at sunrise and in the night when most of the tour buses have left.

June to August is the high season, expect plenty of people everywhere.

Winter is instead a great season to visit Siena, more livable, although it can be quite cold as well.

There are other towns as Pistoia, Livorno, Piombino, Grosseto that can be visited, but probably not on the first trip to Tuscany

Best village to stay in Tuscany

This is a short list of the most interesting villages to stay in Tuscany.

All of them are in the South East area, probably the most scenic part of the region. If you are asking yourself where to stay in Tuscany for a romantic stay than one of the below destinations surely will provide the answer.

They all have lots of character and they are all somehow different

  • Cortona: I start from the village made famous by the book, and film, “Under the Tuscan sun”. It’s as beautiful as you have seen it in the cinema, although it can be really crowded with buses of tourists that drive in/out on a daily basis. The best experience is early in the morning and late in the afternoon when the village becomes more livable

  • Montepulciano: famous for its magnificent wine, the Nobile di Montepulciano. A lovely small medieval village that has not changed in the last 500 years. Reachable by bus or train. This is probably the best village to stay in Tuscany if you are after a boutique wine and food experience.
  • Montalcino: as medieval as Montepulciano and with a well-known wine (Brunello di Montalcino). If you are considering to visit one of the two, keep in mind that Montalcino does not have a train station and public buses are rare and far between
  • San Gimignano: just outside Siena, it can be easily reached by bus or train. This village stands out for its medieval architecture and unique towers, erected by the wealthiest families of that era. It’s a popular village to visit, however, it can also be quite busy, especially in July and August
  • Pienza: seating in the famous Val D’Orcia, between the incredible rolling hills that have made Tuscany world famous. It should be in the bucket list
  • Pitigliano: one of the most characteristic villages in Tuscany, also called the little Jerusalem, seating on a huge tufa rock surface. Once you approach town you will literally be open mouth
View when approaching Pitigliano

View when approaching Pitigliano

Tuscany farmhouses vs agriturismo vs hotels

If you are already looking for an accommodation you may have come across “Tuscany farmhouses” and “Tuscany agriturismo”.

They look the same but they are actually not. And let me explain why:

  • the agriturismo is a farm that rents a few rooms, cabins, units or just part of the main house to tourists. However, this is not the main income of the farm. By law, agriculture or wine production has to be. They have to serve breakfast and dinner (where available) only with products locally made. You may, however, experience the noise from the working environment (tractors or animals). The agriturismo is a fantastic option, but double check the accommodation to avoid disappointments.
  • the farmhouse is a farm, with a similar business concept as the agriturismo, however, it may live just of tourism, without any form of agriculture. In fact, in most of the cases, you will not have animals or tractors around. The trick is that there is no obligation to serve local food (most do it anyway) and they usually pay more tax (rooms are more expensive). The farmhouse is more of a hotel/motel accommodation but in the countryside

And then come the hotels, which usually are in the city/town/villages. They are super practical because you can visit all the attraction without the need of a car or any public transportation.

You can also opt for an AirBnb style. I would, however, suggest having lunch and dinner at the restaurant or agriturismo, to have the real Tuscany experience.

In the following two chapters, I will suggest a few itineraries of Tuscany, with a rented car or without.

Here are a couple of valuable quick tips you may want to keep in mind:

  • if you don’t want to rent a car then book your stay in towns, main villages or Florence itself. If you book an agriturismo you will be most probably stuck there. And if you are looking just for a romantic stay it may be actually a great option. From every town, you can always organise a day trip to the countryside and the wine regions.
  • if you rent a car, you have more options. I would only suggest avoiding Florence by car. You will have a headache driving around. There are other towns with ZTL (the centre is limited only to the locals). However, once you book the hotel, you can contact them and they will send you a special permit that you can use for your stay. Usually, the traffic in Siena, Pisa or Lucca is not that mad but keep in mind the streets can be quite narrow (especially in Lucca).

It’s now time to see a few possible options either by car or without. Do not hesitate to leave a comment if you need more information.

San Gimignano - Piazza Pecori

San Gimignano – Piazza Pecori

Best places to stay in Tuscany without a car

This region can be absolutely visited without a private or rented car.

It may take more time, it may require to plan it more carefully however you will be more relaxed along the trip, either on a train or a bus.

Here below I list a few possibilities for a short stay in Tuscany (7 to 10 days).

If you are planning two weeks or more, keep reading till the next chapter. I will add a few ideas based on a car/no-car decision. You can also mix the two.

Base in Florence and day trips

If you are planning a cultural trip then Florence is the best place to stay in Tuscany. From there you can easily organise day trips.

In this respect, I consider Florence as the best place to stay in Tuscany without a car.

I personally suggest to budget at least 2-3 days for Florence itself. This will allow you to get a good overview.

The remaining part of your trip can be spent on short excursions.

A corner of Tuscany

A corner of Tuscany

Keep in mind that moving between towns or villages in Tuscany is actually quite easy.

If you plan also to visit the countryside then you better book an organised trip.

As an example, moving around the Chianti area by public transportation is almost impossible or it would require way too much time.

Moreover, with an organised tour, you will have easy access to wineries and local trattorie (family-run restaurants usually using only local products)

Here is a list of activities and trips I would suggest from Florence:

  • Day trip to Siena. This can be easily done on your own. You need to take a direct train from the main station (1.5hours). There is a handy one at around 8am that will give you most of the day to explore Siena.
  • Day trip to Pisa: the Leaning Tower is a unique attraction in the world. Also, in this case, there is a direct train (1 hour)
  • (Half)Day trip to Lucca: my beloved destination. There is a train from Firenze, stopping in Pisa where you need to catch another one. I would give a full day to Lucca, however, if you do not have much time then you could organise it on a day trip together with Pisa
  • Organised tour in the Chianti region. There are a few leaving from Firenze. You can check here a great one that will give a fantastic overview of the area beside some wine tasting along the way

Check Tour of the Chianti Region

  • Organised tour to San Gimignano or any other village I listed above. All of the villages are not well served to Florence with public transportation. You would need hours to get there. In this case, I suggest either to rent a car or, even better, join an organised tour.
  • Day trip to Bologna. We are not anymore in Tuscany here however there is a really tempting super-fast train (40 minutes) that connects these two cities
  • Rome (1:20) and Venice (2 hours). Obviously, both cities deserve more than just one day, however, if you do not have much time left keep in mind that you could possibly see both cities on a long day trip
Siena - Palazzo Pubblico & Torre del Mangia

Siena – Palazzo Pubblico & Torre del Mangia

Florence and Siena, to visit the south at your own pace

Staying in Florence for the whole stay is a great option, however, it makes things challenging if you want to explore a few of the villages in the south at your own pace or you want to see Siena without the crowd (at sunrise and night).

My suggestion here is to split your stay between Florence and Siena.

In Florence beside visiting the city, you can also organise some of the day trips I described above.

Than you move to Siena, your next base, where you can organize other day trips:

  • San Gimignano: grab the bus 130 from Siena-V.Le V.Emanuele. The trip takes around 1 hour and you will experience a bit of the typical Tuscany countryside along the route
  • Montepulciano: look for the direct train with destination Chiusi-Chianciano Terme. It takes around 1 hour. It’s a very easy trip
  • Montalcino: it’s a trip which is more complicated to organise on your own as you would need to take a train to Buonconvento (30 minutes) and from there a taxi. Buonconvento is actually a nice old village with a medieval wall all around, so it may be an option for a full day combined trip if you can budget in the taxi
  • Wineries around: if you prefer the freedom to check the wineries that you want then I suggest to rent a car for the day. There is not much traffic once out of Siena. Otherwise, join a tour, it will make things for you easier and you will have no worries to drink more than expected (this does happen with that fantastic wine)
  • Pienza and Val D’Orcia: this is a must trip, Val D’Orcia is probably the most characteristic countryside of Tuscany with its rolling hills. A tour would help you to experience in a day the most magnificent spots. If you are keen to drive on your own then you will have the freedom to experience the area at your own pace, probably the best solution if you are after some great photos. This is a map with a possible itinerary.
Beautiful rolling hills of Tuscany

Beautiful rolling hills of Tuscany

Florence, Siena and Arezzo – the perfect triangle

In the previous two itineraries, I missed two important towns: Arezzo and Cortona.

Both of them could be visited from Siena, or Florence, on a day trip, however, you would spend more time travelling than actually enjoying the destination.

My third option of the best places to stay in Tuscany without a car is what I call the “perfect triangle“.

Start the trip in Florence, move to Siena, continue on Arezzo and back to Florence. Check the map below to have a better picture.

Best places to stay in Tuscany without a car

Best places to stay in Tuscany without a car, the “perfect triangle”

Arezzo is absolutely as beautiful as underrated. It’s a great town to spend at least a couple of days.

From Arezzo, you can easily organise a day trip by train to Cortona (less than an hour)

As a reference:

  • The trip from Florence to Siena takes around 1.5 hours
  • Similar time from Siena to Arezzo by bus (#138)
  • There are many direct trains from Arezzo to Florence (just 30 minutes)

Tuscany itineraries with car

The best places to stay in Tuscany with a car are the farmhouse or the agriturismo, in my opinion. They can be really romantic, they provide local products and they are usually cheaper than the hotels in the city.

If you are dreaming of that beautiful rolling green hills, the typical Tuscany postcard view, then you should plan your trip in the south, possibly with a car.

The car will make a huge difference in your trip in Tuscany. 


Because it will add a local pace, made of no timeline and breaks in villages that the organised trip usually skips.

As an example, the trip from Montalcino to Montepulciano can be done in 1 hour with a bus or in 1 day with a car, visiting the few villages between, driving through the beautiful hills and stopping for a few photos, making an excursion in a “Riserva Naturale” (National Park), having lunch in a local “trattoria” and so much more.

San Quirico D'Orcia

San Quirico D’Orcia

The trip to a place becomes the experience itself and not just a way to reach the destination.

There are so many itineraries through Tuscany that is hard to suggest any in particular. 

Here is just a brief list of 3:

  • The unusual itinerary: you will find only a few famous villages and towns. This itinerary (around 300km) is though for the adventure people, looking for the alternative route, to discover and enjoy in a lazy way.
  • The Etruscan drive: from Arezzo to Chianciano (100km)
  • From Florence to Siena, through San Gimignano (130km)

My suggestion here is to rent the car, use Google map and wander around through the secondary roads. It will take much more time, however, it will be the best way to experience the countryside of Tuscany.

As I previously said, do not venture with the car inside Florence, unless you are looking for a headache which will start with the impossibility to park (unless you fork 30 euros, or more, for a day).

If you have the car and you want to visit Florence then I suggest parking it just outside the city at one of these two places:

  • Villa Costanza, this is the newest and best spot in my opinion. You don’t even need to leave the “Autostrada” (highway). The tram #1 will take you directly to the city centre. The parking is less than 10 euro/day. Absolutely a bargain
  • Piazza Don Pietro Puliti in the town of Galluzzo. It’s free parking, which is great. Walk to the next square, Piazza Acciaiuoli, and catch the tram 36 or 37 to the city centre.

TIP: Don’t leave any bag in the car that people can see, even if there nothing inside. 

The tram tickets can be bought in a convenience store (“Tabaccheria”) or at the newsstand. Remember to validate it once on board.

Other cities like, for example, Siena have a ZTL and you cannot drive inside the old centre. If your hotel is in the ZTL area then ask them, once you have booked your room, to provide the special pass.

If you are visiting the city on a day trip, consider parking the car outside the centre and get a tram or bus to go in. It’s cheaper and easier. Some of the streets can be quite narrow too, once in the medieval part of town.

Siena - Piazza del Duomo

Siena – Piazza del Duomo

Travel Photography Stefano FerroStef Ferro is the founder and editor of MEL365, a travel & photography website made to enhance the travelling experience and improve the photography work.

Stef is a professional travel photographer with past experience in the cycling and film industry. 

Stef runs travel photography workshops in Melbourne and around the world. 


Stefano Ferro
Stef Ferro is the founder and editor of MEL365, a travel & photography website made to enhance the travelling experience and improve the photography work.
Stef is a professional travel photographer with past experience in the cycling and film industry. 

Stef runs travel photography workshops in Melbourne and around the world.

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