Where you sleep in Tuscany shapes the whole trip, more than almost anywhere I know. Base yourself well and the region unfolds around you in easy day trips, with long golden evenings on a terrace; base yourself badly and you spend the holiday in the car. The good news is that the choice is a pleasure, because Tuscany’s signature way to stay, the agriturismo, is one of the loveliest forms of travel there is. Here is how to decide where to put down your bags.
First, the Agriturismo
If you take one piece of advice from me, stay at least a few nights on a farm. An agriturismo is a working agricultural estate, a vineyard, an olive grove, a farm, that also takes guests, and staying at one is the essential Tuscan experience. You wake to vines outside the window, breakfast on eggs and honey and jam made a few metres away, swim in a pool with a view over the hills, and often eat dinner made from the estate’s own produce. They range from simple and rustic to genuinely luxurious, and prices span accordingly, but even the smart ones tend to cost less than a comparable hotel, and they give you something a hotel never can: the feeling of living in the landscape rather than visiting it.
Choosing Your Base by Region
Tuscany is bigger than it looks, and the drives add up, so the trick is to base yourself in the middle of what you most want to see rather than trying to see everything from one spot.
The Val d’Orcia is where to base yourself for the classic Tuscany: the cypress-hill landscapes, the wine towns, the photography. The most central choice is San Quirico d’Orcia, a charming small town sitting neatly between Montalcino and Pienza with the whole valley on its doorstep. Pienza itself is a beautiful, if busier, base, and Montalcino suits wine lovers. From anywhere in the Val d’Orcia you can reach Montepulciano, Bagno Vignoni and the great photo spots within half an hour. This is my favourite part of Tuscany to stay in.
Chianti is the smart base if you want to combine the countryside with the cities. The Chianti hills sit right between Florence and Siena, so a farmhouse near Greve, Radda, Panzano or Castellina puts both great cities within an hour’s drive, along with the wine roads on your doorstep. It is greener and more wooded than the Val d’Orcia, and wonderful for a first Tuscany trip that wants a bit of everything.
Near the cities makes sense only if your trip is mostly urban. If you are really here for Florence, Siena and the museums, stay in the cities themselves, car-free, and treat the countryside as a day trip or a guided tour. But if the hills are why you came, do not base yourself in Florence and drive out each day; you will spend hours in traffic and ZTL anxiety. Sleep in the country and drive into the cities instead.
A Few Places I Would Look At
Around Pienza and the Val d’Orcia there are some lovely options at different levels. La Bandita Townhouse is the chic little design hotel in the centre of Pienza itself, stylish and intimate. Just outside town, Fonte Bertusi offers charming apartments in cottages around an estate, with a farm breakfast, and Agriturismo Terrapille is a beautifully restored farmhouse in the hills with sweeping suites. Over toward Montepulciano, Villa Cicolina is a former noble villa turned agriturismo, all antique character and modern comfort. In Chianti, the choice of farm stays and small country hotels is enormous, so pick one with a pool and a view and you will not go far wrong.
Practical Points
Book early for spring and autumn, which are the best and busiest seasons; the good agriturismi go months ahead. Almost all of them are down country lanes and often require a car, so confirm exactly how to reach yours without crossing a town’s ZTL. Ask whether dinner is available on site, as many farms cook a set menu a few nights a week that is worth planning around. And if you are staying a week, consider splitting your time, a few nights in Chianti for the cities and the wine roads, then a few in the Val d’Orcia for the landscapes, which gives you two very different sides of Tuscany without a single long drive.
My Advice
For most people on a first proper Tuscany trip, I would do this: a night or two in Florence with no car, then pick up the car and settle into an agriturismo in the Val d’Orcia near San Quirico for the rest, driving out each day to the towns, the vineyards and the photo spots and coming home each evening to a terrace and a glass of the local red. It is, quite simply, one of the great ways to spend a week anywhere.
Frequently Asked Questions
What is an agriturismo and should I stay in one?
An agriturismo is a working farm or wine estate, an olive grove, vineyard or farm, that also hosts guests, usually with a pool, a view and a farm breakfast, and often dinner made from its own produce. It is the classic and most rewarding way to stay in the Tuscan countryside, and I would recommend at least a few nights in one over a conventional hotel.
Where is the best area to base yourself in Tuscany?
For the classic cypress-hill scenery and wine towns, base yourself in the Val d’Orcia, ideally around San Quirico d’Orcia, which sits centrally between Montalcino and Pienza. For a first trip combining the countryside with Florence and Siena, base yourself in Chianti, between the two cities. Choose the middle of what you most want to see.
Should I stay in Florence and day trip, or stay in the countryside?
If your trip is mostly about the cities and museums, stay in Florence car-free. If the hills are the reason you came, base yourself in the countryside and drive into the cities as day trips, rather than the other way around, because driving out of Florence each day means traffic and ZTL headaches.
How far in advance should I book accommodation in Tuscany?
For spring (April to June) and autumn (September to October), the best and busiest seasons, book several months ahead, as the good agriturismi and country hotels fill up early. Summer is also busy. You have more flexibility and lower prices in winter, when many farm stays drop their rates significantly.
Do I need a car if I stay at an agriturismo?
Almost always, yes. Agriturismi sit down country lanes with no public transport, and the whole point of a rural base is driving out to the towns and vineyards. Confirm with your host exactly how to reach the property and where to park in nearby towns without crossing a ZTL.
Read also: Getting Around Tuscany | The Perfect Tuscany Itinerary | The Complete Guide to Tuscany
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