Aerial view of Castello di Casole and its pools in the Tuscan countryside

Tuscany

Florence, Siena and the estate stays of Chianti and the Val d'Orcia

Tuscany

Tuscany is Florence and Siena, the hill towns, and the countryside between them: cypress roads, vineyards and the estates that are the reason to stay. It is not a hotel market so much as an estate market, and the right stay is a working farm, a wine estate or a restored borgo that becomes the destination.

Four to five nights at one estate beats two-and-two splits. Our Tuscany shortlist is the where-to-stay page; this one is the overview of where to go and when.

Researched profile: this page is written from our planning research and partner knowledge rather than a Wild Atlas stay — when that changes, this line comes off.

What and Where It Is

Tuscany is the region of central Italy between Rome and the north, with Florence as its capital on the Arno, Siena an hour south, and Pisa on the coast. The countryside people picture is Chianti, between Florence and Siena, and the Val d'Orcia south of Siena around Montalcino and Pienza, UNESCO-listed for its landscape. The hill towns (San Gimignano, Volterra, Montepulciano, Cortona) are scattered through it, and the Maremma coast and Monte Argentario to the south-west are the Tuscany most visitors never reach.

What You Do Here

Florence is a one- or two-day visit from an estate or a stop of its own: the Uffizi and the Accademia with timed tickets, the Duomo and Brunelleschi's dome, the Oltrarno workshops across the river. Siena is the medieval city around the Piazza del Campo, where the Palio is run in July and August. The rest of the trip is the countryside: wine tastings at the Chianti Classico and Brunello di Montalcino estates, a hill town in the morning and lunch on a terrace, a cooking lesson at the estate, and the drive itself through the Val d'Orcia, which is the landscape on every Tuscany poster and better in person.

Best Time to Go

May, June, September and October are Tuscany's months: warm, green in spring, golden at harvest, and busy without being impossible. September adds the vendemmia, the grape harvest, and October the olive harvest and the truffles. July is hot; August is hot, crowded, and the month Italy itself goes on holiday. Winter is quiet and often beautiful in the cities, but the estates are mostly seasonal and the countryside is for fireplaces rather than pools. Our shoulder-season guide covers the estate opening dates.

For May–June and September–October, book by January; harvest-season weeks at the wine estates go first.

Month by month

  • January: Mixed.
  • February: Mixed.
  • March: Good.
  • April: Very good.
  • May: Excellent.
  • June: Excellent.
  • July: Good.
  • August: Mixed.
  • September: Excellent.
  • October: Excellent.
  • November: Good.
  • December: Mixed.

Getting There and How Long to Stay

Florence is about an hour and a half from Rome and under two hours from Milan by fast train; Pisa and Florence airports have European connections. An estate stay works better with a driver than a rental car for the wine days and the town days, and we arrange one. Four to five nights at one estate is the right length; add two or three in Florence if the city is a priority, or make it the first stop after Rome.

Where to Stay

The five estates we would build a trip around, each anchored to a different part of the region, are on our Tuscany hotels shortlist: Rosewood Castiglion del Bosco, Borgo Pignano, Castello di Casole, Borgo Santo Pietro and Il Pellicano on the coast. In Florence itself, The St. Regis Florence on the Arno is the classic base. Read the shortlist for the book-it-if and skip-it-if on each.

Pairs with: Rome as the bookend, Emilia-Romagna over the Apennines for a food trip, the Riviera up the coast, and the Italy guide.

Plan this trip with us. $250 planning fee, credited in full toward your trip.

Culture & Sights

  • Florence — the Uffizi, the Accademia's David, the Duomo and Brunelleschi's dome, and the Oltrarno workshops.
  • Siena — the Piazza del Campo and the Palio, run on July 2 and August 16.
  • The Val d'Orcia — the UNESCO-listed landscape of cypress roads and hill towns south of Siena: Pienza, Montalcino, Montepulciano.
  • Chianti — the wine road between Florence and Siena, and the Chianti Classico estates.
  • San Gimignano and Volterra — the tower town and the Etruscan hill town west of Siena.
  • The Maremma and Monte Argentario — the quieter coast to the south-west, about 90 minutes from Rome.

Ready to plan your trip?

Every itinerary begins with a 20-minute planning call. From there, a $250 planning fee, credited in full toward your booked trip and non-refundable if you don’t book. I brief the property before you arrive — that's what the fee funds.

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