Tuscany in autumn: four hotels for the harvest, the olives and the first fires
When summer leaves, Tuscany changes pace: grapes and olives come in, fires are lit in the evenings, and the woods above the hills turn copper. Four places for the season.
By The Unlisted Editorial Team · 14 September 2026 · 7 min read
For a table fed by its own farm, Borgo Santo Pietro, 22 rooms on a 300-acre organic estate near Siena. For a family-run castle among vines and olives, Castello di Vicarello in the Maremma. For a thermal spa over the Val d'Orcia, Castello di Velona near Montalcino. For Florence at your feet, Villa San Michele in Fiesole, open this season until 3 January.
Tuscany is at its most beautiful when the summer crowds have gone. The grapes come in from September, the olive harvest begins as autumn goes on, fires are lit in the evenings and the woods above the hills turn copper.
These four hotels suit the season: a farm estate near Siena, a castle in the Maremma, a fortress over the Val d'Orcia and a former monastery above Florence.
The four hotels at a glance
Several Tuscan country hotels close for the winter in late autumn, so check dates before planning November.
| Hotel | Where | Why in autumn | Keep in mind |
|---|---|---|---|
| Borgo Santo Pietro | Chiusdino, near Siena | A 300-acre organic estate that feeds its own kitchen | Inland and green rather than panoramic |
| Castello di Vicarello | Maremma | A 12th-century castle among organic vines and olives | Around seven suites; seasonal |
| Castello di Velona | Montalcino | A thermal spring over the Val d'Orcia | 45 suites and a busy events calendar |
| Villa San Michele | Fiesole, Florence | Florence below and open until 3 January | Up the hill: you drive or take the shuttle |
Borgo Santo Pietro: a table fed by the farm
Borgo Santo Pietro keeps 22 rooms in a 13th-century villa on a 300-acre organic estate near Chiusdino, with market gardens, orchards, vineyards, a dairy and woods that feed its own kitchen. In autumn the fires are lit in the sitting rooms, and the gardens are still producing.
Eat at Saporium, the estate restaurant, and ask to see the gardens its ingredients come from. Siena is about 40 minutes away.
Castello di Vicarello: a castle for the harvest
The Baccheschi Berti family spent 18 years restoring Castello di Vicarello, a 12th-century castle in the Maremma, southern Tuscany's wilder and emptier corner. It stands among organic vineyards and old olive groves, and makes its own wine and oil.
With around seven suites it feels like a private house. It is open roughly from April to October, so autumn means the last weeks of its season: confirm dates before you plan.
Castello di Velona: a thermal spring over the Val d'Orcia
Castello di Velona is a thousand-year-old fortress on a ridge near Montalcino, looking over the Val d'Orcia. A natural thermal spring of its own feeds the spa and its panoramic pools, and the estate is surrounded by Brunello vineyards.
It has 45 suites and hosts weddings and events. Book a room on the valley side, and time the thermal pool for sunset.
Villa San Michele: Florence, into the winter
What was once a 15th-century monastery on the hillside of Fiesole is now Villa San Michele, a Belmond hotel of 39 rooms with Florence spread out below. Dinner is served in the old loggia, and the gardens climb to a pool with the same view.
This season it stays open until 3 January, which makes it the one to keep in mind after the country hotels close. The hotel runs a shuttle down to the centre of Florence.
When to go, and how to plan
Late September and October bring the grape harvest and mild days; the olive harvest usually runs from late October into November and December, depending on the year. November is quiet and often wet, and many country hotels close until spring.
You need a car for the three country estates. Florence is the exception: Villa San Michele is 20 minutes from the centre, with a shuttle, so it works well as the last stop of a trip before flying home.
How we selected these hotels
This selection comes from our Tuscan Autumn series on Instagram. Every hotel is scored on the public Unlisted Index, and the facts were checked against each hotel's own website on 14 September 2026; opening dates change every season, so confirm them when you book. For more hotels, see our Tuscany guide.
Availability buttons may use affiliate links and can earn The Unlisted a commission without changing your price. Commercial links do not decide inclusion.
Frequently asked questions
Is autumn a good time to visit Tuscany?
Yes, one of the best. The summer crowds have gone, the vineyards are harvesting, the light is softer and the evenings are cool enough for a fire. November is quieter and wetter, and some country hotels close.
When is the olive harvest in Tuscany?
Usually from late October into November and December, depending on the year and the estate. New oil is one of the pleasures of a late-autumn trip; ask estates such as Castello di Vicarello about their harvest weeks.
Which Tuscan hotels stay open in winter?
Of these four, Villa San Michele stays open this season until 3 January. Many country hotels close from November to spring, so check opening dates before booking late in the year.
Do you need a car in Tuscany in autumn?
For Borgo Santo Pietro, Castello di Vicarello and Castello di Velona, yes: they sit on their own estates, down country roads. Villa San Michele, above Florence, runs a shuttle into the city.
