Chianti
Vineyards and hill towns between Florence and Siena.
- Suits
- Easy access to both cities
- The trade-off
- Busy roads in summer
The countryside rewards slowness: a house, a market town, and days that find their own rhythm.
Longer stays, villa living, food and wine, small towns, and the pleasure of settling into a regional rhythm.
Tuscany is a region, not a single place. Life is very different from one base to the next, so start with where to base yourself.
Sensory details you won’t experience anywhere else, and only really notice when you stay awhile.
Bars show the typical daily high; beneath each are the typical low and monthly rain. Climate figures are approximate monthly averages.
Jan–Feb, Aug
You will need a car or driver in the countryside.
The base you choose shapes the whole stay. Three we would consider for a long stay, and what you trade for each.
Vineyards and hill towns between Florence and Siena.
Cypress-lined hills around Pienza and Montalcino.
A walled city with walkable streets and a real town life.
Also consider onefinestay for Tuscany: homes with a full concierge service, from Accor’s luxury home collection.
Explore onefinestayThe right arrival airport makes the first day of a long stay easier. Private aviation is worth it for a long stay with more people and more luggage.
Plan the journey to TuscanyChecking for empty-leg flights…
What to look into for a long stay here: coastal versus inland bases, summer demand, shoulder season, airport-to-home access.
Rules depend on your passport and length of stay. Check official immigration sources before you plan.
Official travel advisories and local emergency information.
Coverage and home-internet options from official and provider sources.
Local agencies and services, chosen with care.
Places to work a little, close to your base.
Drivers, transfers and local transport, with luggage and longer stays in mind.
Official sources we check: Visit Tuscany regional tourism portal · Italian national and regional statistics · Local municipality event calendars