Travel · Italy
Where to Stay in Tuscany
wine, oil, and the long lunch
Vineyards, olive groves, and hilltop towns — the most delicious corner of Italy, and where to base yourself to taste it properly.
Tuscany is the corner of Italy you taste before you see it: olive oil pressed down the road, a glass of Chianti poured without ceremony, pecorino and warm bread, a lunch that starts at one and forgets to end. For the traveler who plans the trip around the table, there is nowhere better.
Base yourself in Florence for the art and the markets, in Chianti for the wine, or in the Val d'Orcia for the slow gold of the countryside — then let the eating, drinking, and lingering set the pace.
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Where to Stay
Hand-picked Hotels
A frescoed townhouse in the Oltrarno
€€Florence
Across the river from the crowds, steps from the artisan workshops, trattorie, and the morning market.
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A wine estate with rooms among the vines
€€€Chianti
Sleep on a working estate between Florence and Siena — tastings at the cellar, dinner under the pergola.
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A restored farmhouse (agriturismo)
€€Val d’Orcia
Cypress avenues, a pool over the hills, and a kitchen that cooks what the garden grew.
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A stone palazzo in the old town
€€San Gimignano
Towers, Vernaccia wine, and the countryside a short drive in every direction.
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What to See & Do
Florence & the Uffizi
The Renaissance city — and the Mercato Centrale and Sant’Ambrogio markets for the appetite.
The Chianti wine road
Greve, Castellina, and Radda — cellar doors, sangiovese, and long views between the vines.
Siena & the Val d’Orcia
A medieval city and the most photographed countryside in Italy: Pienza, Montalcino, cypress hills.
A cooking class or olive-oil tasting
Roll pasta with a nonna, or taste new-harvest oil at the frantoio — the heart of an Epicurean trip.
Questions, Answered
When should I visit Tuscany?
May–June and September–October are ideal: warm days, the vines green or in harvest, and far fewer crowds than high summer.
How many days do you need?
Five to seven to base in one area and day-trip; ten to pair Florence with a stretch in the countryside.
Do I need a car?
For the wine estates and hill towns, yes. Florence itself is walkable — pick up the car as you leave the city.
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