Autumn in Tuscany, villas for the harvest
Autumn is the season when Tuscans work hardest and eat best. The grape harvest draws to a close, the woods fill with porcini and chestnuts, and from late October the olives are picked and pressed, producing the peppery green new oil poured over toasted bread at every table. In November the hills around San Miniato are known for their white truffles, sought out with trained dogs.
The villas below make fine bases for the season. Among them are a 19th century hilltop farmhouse on 35 hectares in the Bolgheri wine country, a castle near the coast with 10th century walls, a chapel, a watchtower and full staff, and a villa at Castiglioncello set in a walled garden of nearly 40 palm trees.
At a glance
- 232 private villas
- From 1 to 22 bedrooms
- Up to 41 guests in one villa
- 224 with a private pool
- 25 with sea views
- 75 with a cook or staff
- Availability and price on request, reply within one working day
Visit a local frantoio in November to taste oil straight from the press, bright green and peppery, on grilled bread.
The wine estates of Bolgheri are busy but welcoming in autumn. Book tastings ahead and try the reds with wild boar.
October on the Tuscan coast can still bring warm afternoons, and the empty beaches make for long, peaceful walks.
Choose your villa
Add up to five villas to your list and send one request with your dates: we confirm availability and price with each owner.
























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Positions are approximate: the exact address is shared once your stay is confirmed.
Questions before you choose
When is the best time for truffles?
White truffles are gathered from autumn into winter, with November the classic month. Many Tuscan towns hold truffle markets in the season, so ask locally once you arrive.
Are villa pools open in October?
Most pools stay open until the end of October, though the water may feel cool without heating. By November they are usually closed; ask us about heated pools.
Do autumn stays need to be a full week?
Not always. After the summer, many owners accept shorter stays and flexible arrival days. Choose up to five villas for one enquiry and we reply within one working day.
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