Journey · 10 days · 3 homes
Florence, Chianti & Siena
in ten days
Three nights in a Renaissance palazzo in Florence, four in a medieval hamlet in the Chianti hills, three among the vineyards south of Siena.
The idea
The classic Tuscany trip, from three historic homes
Ten days is the right length for a first Tuscany: Florence and its museums, the vineyards and villages of Chianti, then the open country of the Val d'Orcia, where cypress lanes and hill towns look exactly as they do in the paintings. Three homes, three very different ways of living the region: a city palazzo, a medieval hamlet, a villa on a Brunello estate.
- 1Florence 3 nights
- 2Chianti 4 nights
- 3Val d'Orcia 3 nights
Day by day
10 days, 3 homes
For every stop: what to see and where to go, the dishes to try and where to eat them. Below, two or three of our homes in the area, with live rates for your nights.
Stop 1 · 3 nightsDays 1 – 3
Florence, on foot
The Renaissance city is best seen early in the morning and late in the evening, when the day visitors have gone. Stay in the centre and let the streets do the rest.
What to see & where to go
- The Uffizi and Michelangelo's David at the Accademia, booked ahead
- Brunelleschi's dome: climb it at opening time
- The Brancacci Chapel frescoes in the Oltrarno, without a queue
- Sunset from San Miniato al Monte, above Piazzale Michelangelo
- The artisan workshops of Santo Spirito and via Maggio
- Fiesole on the hill, for the Roman theatre and the view back over the city
What to eat
- Bistecca alla fiorentina, a thick T-bone grilled rare over embers
- Ribollita and pappa al pomodoro, the bread soups of the Florentine kitchen
- Lampredotto, the tripe sandwich sold from street carts
- Schiacciata with finocchiona, the fennel-scented salami
Where to eat
- Trattoria Mario, near San Lorenzo: lunch only, shared tables, ribollita
- Cibrèo Trattoria, Sant'Ambrogio: Florentine cooking without the frills
- Gelato at Vivoli, the city's oldest gelateria
Where you sleep
Loggiato dei ServitiPiazza SS. Annunziata
15th-century building, 150 m from the Accademia.Why stay hereYou wake up on Florence's most harmonious Renaissance square, 150 m from Michelangelo's David, in rooms furnished with period pieces.See the home
15th-century building, 150 m from the Accademia.Why stay hereYou wake up on Florence's most harmonious Renaissance square, 150 m from Michelangelo's David, in rooms furnished with period pieces.See the home
Hotel Torre Guelfa100 m from Ponte Vecchio
13th-century palazzo with a tower terrace over the city.Why stay hereA 13th-century tower 100 m from Ponte Vecchio: its terrace is one of the finest views over the rooftops of Florence.See the home
13th-century palazzo with a tower terrace over the city.Why stay hereA 13th-century tower 100 m from Ponte Vecchio: its terrace is one of the finest views over the rooftops of Florence.See the home
Palazzo dal BorgoCentral Florence
15th-century building with an internal courtyard.Why stay hereA 15th-century palazzo with an inner courtyard: quiet at night, and everything is within walking distance.See the home
15th-century building with an internal courtyard.Why stay hereA 15th-century palazzo with an inner courtyard: quiet at night, and everything is within walking distance.See the home
Stop 2 · 4 nightsDays 4 – 7
Chianti, from a medieval hamlet
Between Florence and Siena the hills are lined with vines, olive groves and castles that have made wine for centuries. Four nights leave room for two wine days, one day in Siena and one by the pool.
What to see & where to go
- Castello di Brolio, home of the Ricasoli family and of the Chianti formula
- Badia a Coltibuono, an 11th-century abbey among the woods
- Siena: the Campo, the Duomo and the Piccolomini Library
- Radda, Volpaia and Castellina, the villages of Chianti Classico
- The Saturday morning market in Greve in Chianti
- Monteriggioni and its ring of towers
What to eat
- Pappardelle with wild boar ragù
- Crostini neri, toasted bread with chicken-liver pâté
- Chianti Classico, the wine of the black rooster
- New-season olive oil and aged pecorino from the estates
Where to eat
- Antica Macelleria Cecchini in Panzano: Dario Cecchini's butcher shop and tables
- Osteria di Passignano, a starred table next to the Badia a Passignano cellars
- Osteria Le Logge in Siena, a few steps from the Campo
Where you sleep
Borgo VescineRadda in Chianti
Medieval hamlet, heated pool among the vines.Why stay hereA whole medieval village in the heart of Chianti Classico, with a heated pool among vineyards and olive groves.See the home
Medieval hamlet, heated pool among the vines.Why stay hereA whole medieval village in the heart of Chianti Classico, with a heated pool among vineyards and olive groves.See the home
Castello di FonterutoliFonterutoli
The Mazzei family hamlet, cellar tours on site.Why stay hereYou sleep in the hamlet of the Mazzei family, winemakers here for centuries, with the cellar tour a few steps away.See the home
The Mazzei family hamlet, cellar tours on site.Why stay hereYou sleep in the hamlet of the Mazzei family, winemakers here for centuries, with the cellar tour a few steps away.See the home
Palazzo LeopoldoRadda in Chianti
14th-century villa, heated indoor pool and spa.Why stay hereA patrician villa from 1310 in the centre of Radda, with a heated indoor pool and spa for the evenings after tastings.See the home
14th-century villa, heated indoor pool and spa.Why stay hereA patrician villa from 1310 in the centre of Radda, with a heated indoor pool and spa for the evenings after tastings.See the home
Stop 3 · 3 nightsDays 8 – 10
Val d'Orcia and Montalcino
South of Siena the landscape opens up into the Val d'Orcia, a UNESCO site of cypress lanes, wheat fields and small Renaissance towns. This is also the land of Brunello and Vino Nobile.
What to see & where to go
- Pienza, the ideal Renaissance town of Pope Pius II
- Montepulciano and its underground cellars
- The Abbey of Sant'Antimo at the hour of Gregorian chant
- Bagno Vignoni and its thermal pool in the village square
- The Cappella della Madonna di Vitaleta and the cypresses of San Quirico
- A Brunello tasting in Montalcino
What to eat
- Pici all'aglione, hand-rolled pasta with garlic and tomato
- Pecorino di Pienza, fresh or aged in walnut leaves
- Brunello di Montalcino and Vino Nobile di Montepulciano
- Cinta senese, the native Sienese pork, as salumi or roasted
Where to eat
- Osteria La Porta in Monticchiello, with a terrace over the valley
- Trattoria Latte di Luna in Pienza, for pici and roast pork
- Osteria Acquacheta in Montepulciano, famous for its steak
Where you sleep
Villa Le PrataMontalcino
18th-century villa on a Brunello estate, pool and restaurant.Why stay hereAn 18th-century bishop's villa on a Brunello estate near Montalcino, with pool, restaurant and tastings on the grounds.See the home
18th-century villa on a Brunello estate, pool and restaurant.Why stay hereAn 18th-century bishop's villa on a Brunello estate near Montalcino, with pool, restaurant and tastings on the grounds.See the home
Palazzo Pio IIISarteano
Historic palazzo with spa, the Val d'Orcia at the door.Why stay hereA historic palazzo with a small spa, perfectly placed between the Val d'Orcia and the thermal springs of southern Tuscany.See the home
Historic palazzo with spa, the Val d'Orcia at the door.Why stay hereA historic palazzo with a small spa, perfectly placed between the Val d'Orcia and the thermal springs of southern Tuscany.See the home
Villa Di SottoVilla a Sesta
Infinity pool, spa, restaurant; between Chianti and Siena.Why stay hereAn infinity pool looking over the hills between Chianti and Siena, with spa and restaurant on site.See the home
Infinity pool, spa, restaurant; between Chianti and Siena.Why stay hereAn infinity pool looking over the hills between Chianti and Siena, with spa and restaurant on site.See the home
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.
