What are the Best Places to Stay in Tuscany?
Where to stay in Tuscany depends on what the trip is for, and for most first visits the answer is Chianti, the hills between Florence and Siena, where both cities are a day trip and the vineyards start at the garden wall. Stay in the hills around Florence if the city is the reason for the trip, near Siena for the Palio and the hill towns, in the Val d’Orcia for the landscape and its wines, near Lucca for a quieter north close to Pisa airport, and in the Maremma for the sea. Below are the six areas, what each one suits and how far it sits from the cities, with one house in each from our Tuscany villa rentals, every one of them visited by our team.
The six areas at a glance
| Area | Best for | Distances, from our houses there |
|---|---|---|
| Chianti | A first stay, wine estates, village dinners | Radda: the village 1.5 km away; Florence and Siena both day trips |
| Hills around Florence | Days in Florence without sleeping in the city; large groups | San Casciano: 9 miles to Florence, 13 to Florence airport |
| Siena and its countryside | The Palio, Siena, San Gimignano and Monteriggioni | Near Sovicille: 14 km to Siena, about an hour to Florence |
| Val d’Orcia and Montepulciano | The landscape, Brunello and Vino Nobile, hot springs, slow days | Near Montepulciano: about an hour to Siena, 95 minutes to Florence |
| Lucca | A quieter north, flights into Pisa, a day at the beach | 4 miles to Lucca, 11 to Pisa airport |
| The Maremma | The sea, Monte Argentario, the springs of Saturnia | South of Grosseto: a path to the beach, 1 h 40 to Rome airport |
Chianti: the first choice for a first stay
Chianti fills the hills between Florence and Siena, crossed by the Chiantigiana road that links the two cities. Its historic heart is Gaiole, Radda and Castellina, the three towns of the medieval Lega del Chianti, whose black rooster is now the symbol of Chianti Classico; Greve, with its triangular piazza, and Panzano lie closer to Florence. It suits a first stay because it asks for no compromise: Florence and Siena are both day trips, the wine estates are minutes from the house, and the villages have their shops and trattorias for an evening out. See our Chianti villas; Visit Tuscany’s guide to Chianti maps the villages.
Palladia
Radda in Chianti · 6 bedrooms · sleeps 12
A medieval lookout above Radda, with the Carleone vineyard at the edge of the garden and a panoramic pool. A breakfast buffet is included, served indoors or outside, and Radda’s shops, restaurants and pharmacy are about a mile away.
The hills around Florence: for days in the city
The hills south of Florence put the city within easy reach without sleeping in it. San Casciano in Val di Pesa, at the northern edge of Chianti, is nine miles from the centre and thirteen from Florence airport: a driver takes you in for the Uffizi in the morning and brings you back for dinner by the pool, and no one has to drive into the historic centre, which is closed to most traffic. With ten bedrooms or more, houses like Villa Matteo make the area a natural base for a family reunion, or for a group that wants Florence every other day. See our villas in and around Florence, or our guide to villas near Florence.
Villa Matteo
San Casciano in Val di Pesa · 10 bedrooms · sleeps 22
Brunelleschi’s dome is in view from the top terrace. Inside are an indoor heated pool, a sauna and a steam room; outside, a helipad. A villa manager, daily housekeeping and a buffet breakfast are included.
Siena and its countryside: for the Palio and the hill towns
Siena’s countryside suits those who want the city on the doorstep and the hill towns around it: Monteriggioni inside its ring of walls, San Gimignano and its towers, the woods of the Montagnola to the west. The Palio is run twice a year in Piazza del Campo, on 2 July and 16 August, the climax of four days of celebrations in the city; if the race is the reason for the trip, ask for those dates nine to twelve months ahead. Our Siena villas include houses less than half an hour from the city.
Villa Cetinale
Near Sovicille, Siena · 13 bedrooms · sleeps 27
A Baroque villa from 1680, fourteen kilometres from Siena and fifteen from Monteriggioni. It is fully staffed, with a private chef for every meal (the food is extra), waiters and a porter; cooking lessons and riding nearby can be added.
Val d’Orcia and Montepulciano: for the landscape
The Val d’Orcia, south of Siena, is the Tuscany of the photographs: the cypresses of San Quirico d’Orcia, Pienza, rebuilt by Pope Pius II as an ideal Renaissance town, Montalcino and its Brunello, and the thermal pool in the square of Bagno Vignoni. UNESCO listed the valley as a World Heritage cultural landscape in 2004. Montepulciano, home of Vino Nobile, stands on the ridge between the Val d’Orcia and the Val di Chiana. Florence is about an hour and a half away by car, so the area suits a week of slow days more than a week of city trips. See our Val d’Orcia villas.
Villa Teresa
Montepulciano · 6 bedrooms · sleeps 12
Three kilometres from Montepulciano, with a 25-metre infinity pool facing the Val di Chiana and a hammam. Breakfast and housekeeping are daily, and a visit to the neighbouring park of Villa Trecci is included.
Lucca: for a quieter north
Lucca is the quiet north of Tuscany: a city inside its Renaissance walls, wide enough to walk or cycle around on top, with Pisa airport about half an hour away and the beaches of the Versilia coast close enough for a day by the sea. The villas stand in the hills around the city, among olive groves and old country estates, and Florence is a little over an hour away by car or train. See our Lucca villas.
Villa Contrada
Near Lucca · 12 bedrooms · sleeps 24
An eighteenth-century country house four miles from Lucca and eleven from Pisa airport. It is fully staffed: a chef cooks breakfast and one other meal six days a week, with maid service six mornings a week and a concierge.
The Maremma: for the sea
The Maremma is the southern coast of Tuscany and the country behind it: Monte Argentario with the harbours of Porto Ercole and Porto Santo Stefano, the hot springs of Saturnia, the hill towns of Pitigliano and Capalbio, and the Maremma Regional Park, where the woods run down to unspoilt beaches. It is the area to choose when the sea matters as much as the countryside. Rome’s airport is closer than Florence’s, and Siena is about an hour and a quarter by car. See our Maremma villas.
Via del Mare
South of Grosseto · 10 bedrooms · sleeps 22
An eighteenth-century house on the sea, in four hectares of olive trees, palms and woodland sixteen miles south of Grosseto, towards Monte Argentario. It is fully staffed, with a cook and table service for lunch and dinner (the food is extra); a path through the garden leads down to a pebble beach.
How to choose
- A first visit, with Florence and Siena: Chianti.
- Florence is the point of the trip: the hills south of the city, with a driver for the days in town.
- The Palio in July or August: Siena’s countryside, booked early.
- Landscape, wine and hot springs: the Val d’Orcia and Montepulciano.
- Flying into Pisa, or a family that wants beach days: Lucca.
- The sea every day: the Maremma.
For twenty or more guests, our large villas in Tuscany sleep the whole group under one roof, and for a house with a chef and staff, see our fully staffed villas in Tuscany. If you would rather choose a town than an area, our guide to the best towns to stay in Tuscany compares them one by one.
When to go, and when to book
Spring and autumn are the easiest seasons for the cities and the drives between the hill towns; July and August are hot inland, which is when a house on the coast or a pool with a view earns its place. For June to September and the holidays, ask nine to twelve months ahead; for spring and autumn, six to nine months is usually enough. Our guide to the best time to visit Tuscany goes month by month, and if Tuscany is one of several options, we compare it with the Amalfi Coast and Lake Como.
Our concierge, included with every stay, arranges what sits around the house: the airport transfer, the driver for Florence, tastings at the wine estates, a cook for the nights in.
Where to stay in Tuscany: your questions
Where is the best place to stay in Tuscany for a first visit?
Chianti, in the hills between Florence and Siena. Both cities are day trips, the wine estates are close, and villages such as Radda, Greve and Castellina have restaurants for the evenings.
Is it better to stay in Florence or in the Tuscan countryside?
For a villa stay, the countryside. From the hills south of the city, Florence is about nine miles away, close enough for a driver to take you in for the day, and you come back to a pool and a garden instead of the traffic of the historic centre.
Where should I stay to visit both Florence and Siena?
In Chianti or in the hills around San Casciano in Val di Pesa. From San Casciano, Florence is nine miles away and Siena thirty-six; from Radda, in the heart of Chianti, both cities are within a day trip.
Where should I stay in Tuscany to be near the sea?
In the Maremma, on the southern coast, near Monte Argentario, Porto Ercole and the Maremma Regional Park. In the north, the villas around Lucca are within reach of the beaches of the Versilia coast.
Where should I stay in the Val d’Orcia?
Near Pienza, Montalcino or Montepulciano, where the villas look over the valley. Siena is about an hour away by car and Florence about an hour and a half, so it suits a slower week.
How far ahead should I book a villa in Tuscany?
For June to September and the holidays, nine to twelve months ahead; for spring and autumn, six to nine months. For the Palio in Siena, on 2 July and 16 August, ask as early as you can.
Plan your stay in Tuscany
Tell us your dates, how many of you are travelling and what the trip is for. A specialist replies with the area that suits it and a short list of villas there, each one visited by our team.
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