Journey · 10 days · 3 homes

Florence, Chianti & Siena
in ten days

Three nights in a Renaissance palazzo, four in a Chianti castle village, three in the hills south of Siena. One rental car, picked up on day four.

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The idea

The classic Tuscany trip, done from three historic homes

Ten days is the right length for a first Tuscany: enough for Florence's museums, for the vineyards between Florence and Siena, and for the quieter country south of Siena where the postcards are taken. Three bases keep the driving short (nothing here is more than an hour) and give you three very different houses: a city palazzo, a medieval hamlet, a villa on a wine estate.

Day by day

10 days, 3 homes, one car

Every stop lists two or three of our homes; the widget under each checks live rates for those nights.

Stop 1 · 3 nightsDays 1 – 3

Florence, on foot

Land in Florence or Pisa. No car yet: the city is walkable and parking is a punishment. Sleep in the centre and do the museums early, before the tour groups.

  • Uffizi and the Accademia, booked ahead; Brancacci Chapel if you want frescoes without a queue
  • A morning at Mercato Centrale, an evening walk to Piazzale Michelangelo
  • Day trip by train to Lucca (80 minutes) or Fiesole by bus
Where you sleep
Loggiato dei ServitiPiazza SS. Annunziata
15th-century building, 150 m from the Accademia.
Hotel Torre Guelfa100 m from Ponte Vecchio
13th-century palazzo with a tower terrace over the city.
Palazzo dal BorgoCentral Florence
15th-century building with an internal courtyard.
Stop 2 · 4 nightsDays 4 – 7

Chianti, from a castle village

Pick up the car and drive the Chiantigiana (SR 222) south: 45 minutes to Radda. Four nights here means two wine days, one Siena day and one day of doing nothing by the pool.

  • Tastings at the estate you sleep in, then Fonterutoli, Castello di Brolio or Badia a Coltibuono
  • Siena for a day (40 minutes): the Campo, the Duomo, dinner back in the hills
  • Greve market on Saturday morning; Panzano for the butcher everyone talks about
Where you sleep
Borgo VescineRadda in Chianti
Medieval hamlet, heated pool among the vines.
Castello di FonterutoliFonterutoli
The Mazzei family hamlet, cellar tours on site.
Palazzo LeopoldoRadda in Chianti
14th-century villa, heated indoor pool and spa.
Stop 3 · 3 nightsDays 8 – 10

South of Siena: Val d'Orcia and Montalcino

An hour south, the landscape opens up: cypress lanes, Pienza, Montalcino and its Brunello, hot springs at Bagno Vignoni. Sleep on a wine estate or in a villa, and fly home from Florence or Rome (both about two hours).

  • Pienza and Montepulciano in one day, lunch in between
  • Brunello tasting at the estate, sunset at Bagno Vignoni's thermal pools
  • Last morning: the abbey of Sant'Antimo, then the drive to the airport
Where you sleep
Villa Le PrataMontalcino
18th-century villa on a Brunello estate, pool and restaurant.
Palazzo Pio IIISarteano
Historic palazzo with spa, the Val d'Orcia at the door.
Villa Di SottoVilla a Sesta
Infinity pool, spa, restaurant; between Chianti and Siena.
Plan it yourself, with help

Ask our assistant

This itinerary is a starting point. Tell the assistant your dates and constraints and it re-plans the stops on our homes, then checks the rooms.

  • We only have 7 days: which stop do we cut?
  • Same route but with two children under 10: which homes work?
  • Can you check the three homes for arrival on May 4?
It answers in English, knows every home in our collection and can check live rates and book for you, in the chat. It does not know your budget or dates until you tell it.
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