Tuscany
Florence · Siena · Val d'Orcia
Estimated budget
£18k
2 travellers · full trip
Nine days moving through the three registers of Tuscany. Begin in Florence: three nights in a palazzo on the Arno, private access to the Uffizi before it opens, dinner at Buca Mario where the Florentines eat. Then south to Siena: three nights in a wine estate above the city, truffle hunting with a third-generation tartufaio, the Palio field at dusk when the tourists have gone. Finally the Val d'Orcia: three nights in a converted medieval village where the cypress avenues and the light are exactly what the painters saw, where the breakfast bread is baked on the premises and the wine comes from the estate. Tuscany is not a discovery — it is a confirmation.
Estimated budget
Estimated budget
From
£17,800
Estimates in GBP for two people. Final pricing depends on dates, availability, and preferences.
Florence
3 nights in Florence · Italy
Florence is the most concentrated museum in the world and a genuinely excellent food city. The combination is not obvious but it works — an afternoon with Botticelli followed by a bistecca at Buca Mario is a Florentine day perfectly executed.
Where you're staying
Day 1
Arrival — Arno & first Florentine dinner
Arrive, walk the Arno at dusk, eat Florentine steak. The city announces itself without effort.
Florence Peretola Airport
AdAstra, Lungarno Torrigiani
Florence has been the same city since the 15th century — the same skyline, the same stone, the same argument between the Arno and the hills that Brunelleschi and Alberti resolved and no one has revised since. The approach along the south bank gives you the Ponte Vecchio and the Uffizi facade from across the water as your first view, which is the right introduction to a city built for exactly this kind of arrival.
Ponte Vecchio & Arno at dusk
The Ponte Vecchio at sunset in October, when the tourists have started to leave and the goldsmiths close their shutters.
Lungarno, Florence
Dinner — Buca Mario
Buca Mario is the oldest restaurant in Florence (founded 1886) and serves the definitive bistecca alla Fiorentina — Chianina beef, wood-fire cooked, 1.2kg for two.
Piazza degli Ottaviani, Florence
Day 2
Uffizi at dawn & artisan leather
The Uffizi before it opens, with no one else in the room with Botticelli. In the afternoon, the leather school where Florentine artisans have been trained since 1950.
Uffizi Gallery — private pre-opening access
The Uffizi holds the greatest collection of Renaissance painting in the world.
Piazza della Signoria, Florence
Scuola del Cuoio — leather workshop visit
The Scuola del Cuoio has been teaching Florentine leather craft since 1950, in the former dormitory of Santa Croce monastery.
Santa Croce, Florence
Onward to Siena
Florence
AdAstra Florence
Siena
Castello di Casole
The Chiantigiana road south through the Chianti vineyards takes 90 minutes and is one of the great drives in Italy — cypress avenues, hilltop villages, the vendemmia (harvest) visible in the vineyards in October.
Florence
3 nights in Florence · Italy
Florence is the most concentrated museum in the world and a genuinely excellent food city. The combination is not obvious but it works — an afternoon with Botticelli followed by a bistecca at Buca Mario is a Florentine day perfectly executed.
Where you're staying
Day 1
Arrival — Arno & first Florentine dinner
Arrive, walk the Arno at dusk, eat Florentine steak. The city announces itself without effort.
Florence Peretola Airport
AdAstra, Lungarno Torrigiani
Florence has been the same city since the 15th century — the same skyline, the same stone, the same argument between the Arno and the hills that Brunelleschi and Alberti resolved and no one has revised since. The approach along the south bank gives you the Ponte Vecchio and the Uffizi facade from across the water as your first view, which is the right introduction to a city built for exactly this kind of arrival.
Ponte Vecchio & Arno at dusk
The Ponte Vecchio at sunset in October, when the tourists have started to leave and the goldsmiths close their shutters.
Lungarno, Florence
Dinner — Buca Mario
Buca Mario is the oldest restaurant in Florence (founded 1886) and serves the definitive bistecca alla Fiorentina — Chianina beef, wood-fire cooked, 1.2kg for two.
Piazza degli Ottaviani, Florence
Day 2
Uffizi at dawn & artisan leather
The Uffizi before it opens, with no one else in the room with Botticelli. In the afternoon, the leather school where Florentine artisans have been trained since 1950.
Uffizi Gallery — private pre-opening access
The Uffizi holds the greatest collection of Renaissance painting in the world.
Piazza della Signoria, Florence
Scuola del Cuoio — leather workshop visit
The Scuola del Cuoio has been teaching Florentine leather craft since 1950, in the former dormitory of Santa Croce monastery.
Santa Croce, Florence
Onward to Siena
Florence
AdAstra Florence
Siena
Castello di Casole
The Chiantigiana road south through the Chianti vineyards takes 90 minutes and is one of the great drives in Italy — cypress avenues, hilltop villages, the vendemmia (harvest) visible in the vineyards in October.
Siena
3 nights in Siena · Italy
Siena is medieval Tuscany with the volume turned up — terracotta towers, the Piazza del Campo tilted like a stage, and the Palio field still marked in the stone. Three nights in a wine estate above the city gives you access to the truffle season, the harvest, and the best chianti in the world.
Where you're staying
Day 4
Chianti drive & estate arrival
The Chiantigiana through the October harvest vineyards. Arrive at the castello in time for lunch.
AdAstra Florence
Castello di Casole, Casole d'Elsa
The scenic Chiantigiana road south through the Chianti vineyards. In October the vendemmia is underway — grapes being harvested by hand on both sides of the road.
Piazza del Campo at dusk — without the crowds
The Piazza del Campo is the finest medieval square in Europe — brick, shell-shaped, tilted 11 degrees toward the Palazzo Pubblico.
Piazza del Campo, Siena
Day 5
Truffle hunt & cellar dinner
A morning in the estate forest with Sergio and Turbo the dog. In the evening, a private wine dinner in the castle cellar.
White truffle hunt — Sergio and Turbo
October is white truffle season in Tuscany.
Castello di Casole estate
Private cellar dinner — estate wine pairing
A private dinner in the 11th-century castle cellar, with a five-course Tuscan menu and six estate wines personally poured by the winemaker.
Castello di Casole wine cellar
Onward to Val d'Orcia
Siena
Castello di Casole
Val d'Orcia
Rosewood Castiglion del Bosco
The road south from Siena into the Val d'Orcia passes through the landscape that Ambrogio Lorenzetti painted in 1338 in his fresco of good government. It has not changed.
Siena
3 nights in Siena · Italy
Siena is medieval Tuscany with the volume turned up — terracotta towers, the Piazza del Campo tilted like a stage, and the Palio field still marked in the stone. Three nights in a wine estate above the city gives you access to the truffle season, the harvest, and the best chianti in the world.
Where you're staying
Day 4
Chianti drive & estate arrival
The Chiantigiana through the October harvest vineyards. Arrive at the castello in time for lunch.
AdAstra Florence
Castello di Casole, Casole d'Elsa
The scenic Chiantigiana road south through the Chianti vineyards. In October the vendemmia is underway — grapes being harvested by hand on both sides of the road.
Piazza del Campo at dusk — without the crowds
The Piazza del Campo is the finest medieval square in Europe — brick, shell-shaped, tilted 11 degrees toward the Palazzo Pubblico.
Piazza del Campo, Siena
Day 5
Truffle hunt & cellar dinner
A morning in the estate forest with Sergio and Turbo the dog. In the evening, a private wine dinner in the castle cellar.
White truffle hunt — Sergio and Turbo
October is white truffle season in Tuscany.
Castello di Casole estate
Private cellar dinner — estate wine pairing
A private dinner in the 11th-century castle cellar, with a five-course Tuscan menu and six estate wines personally poured by the winemaker.
Castello di Casole wine cellar
Onward to Val d'Orcia
Siena
Castello di Casole
Val d'Orcia
Rosewood Castiglion del Bosco
The road south from Siena into the Val d'Orcia passes through the landscape that Ambrogio Lorenzetti painted in 1338 in his fresco of good government. It has not changed.
Val d'Orcia
3 nights in Val d'Orcia · Italy
The Val d'Orcia is a UNESCO World Heritage landscape and the subject of every painting of Tuscany you have ever seen: the rolling hills, the cypress lines, the isolated farmhouse on a ridge. Three nights at Rosewood Castiglion del Bosco — a converted medieval village in the middle of the valley — is the end of Tuscany done correctly.
Where you're staying
Day 7
Val d'Orcia arrival & Brunello cellar
Arrive in the valley, walk the cypress avenues, taste the Brunello.
Castello di Casole
Rosewood Castiglion del Bosco, Montalcino
The road south from Siena into the Val d'Orcia — through Buonconvento and toward Montalcino — passes through the landscape painting. The cypress avenues and the rolling ridges are the real thing.
Private Brunello tasting — estate cantina
Castiglion del Bosco produces some of the finest Brunello di Montalcino in the DOCG appellation.
Rosewood estate cantina, Montalcino
Day 8
Cypress avenues & hilltop villages
The slowest day. A morning walk through the cypress avenues, a long lunch, the afternoon doing nothing in particular.
Val d'Orcia cypress avenue walk
The avenue of cypresses running from the borgo to the horizon is the most photographed view in Tuscany.
Castiglion del Bosco estate, Montalcino
Pienza — the Renaissance ideal city
Pienza was built in 1459 on the orders of Pope Pius II as the first purpose-designed Renaissance town.
Pienza, Val d'Orcia
Dinner — Campo del Drago Osteria
The estate osteria uses ingredients from the estate kitchen garden and the valley farms.
Rosewood Castiglion del Bosco
Val d'Orcia
3 nights in Val d'Orcia · Italy
The Val d'Orcia is a UNESCO World Heritage landscape and the subject of every painting of Tuscany you have ever seen: the rolling hills, the cypress lines, the isolated farmhouse on a ridge. Three nights at Rosewood Castiglion del Bosco — a converted medieval village in the middle of the valley — is the end of Tuscany done correctly.
Where you're staying
Day 7
Val d'Orcia arrival & Brunello cellar
Arrive in the valley, walk the cypress avenues, taste the Brunello.
Castello di Casole
Rosewood Castiglion del Bosco, Montalcino
The road south from Siena into the Val d'Orcia — through Buonconvento and toward Montalcino — passes through the landscape painting. The cypress avenues and the rolling ridges are the real thing.
Private Brunello tasting — estate cantina
Castiglion del Bosco produces some of the finest Brunello di Montalcino in the DOCG appellation.
Rosewood estate cantina, Montalcino
Day 8
Cypress avenues & hilltop villages
The slowest day. A morning walk through the cypress avenues, a long lunch, the afternoon doing nothing in particular.
Val d'Orcia cypress avenue walk
The avenue of cypresses running from the borgo to the horizon is the most photographed view in Tuscany.
Castiglion del Bosco estate, Montalcino
Pienza — the Renaissance ideal city
Pienza was built in 1459 on the orders of Pope Pius II as the first purpose-designed Renaissance town.
Pienza, Val d'Orcia
Dinner — Campo del Drago Osteria
The estate osteria uses ingredients from the estate kitchen garden and the valley farms.
Rosewood Castiglion del Bosco
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