Tuscany Itinerary

1. ~9:30aMorning at a Chianti wine estate

   Into the cypress-lined hills for a cellar tour and tasting at a Chianti Classico estate — barrel rooms, the Gallo Nero (black rooster) seal, and the great Sangiovese reds.

   
2. ~12:00pA Chianti hill town

   A wander through Greve or Castellina in Chianti — a wine-country town of arcaded squares, enotecas, and butchers famous across Tuscany.

   
3. ~1:30pA long Tuscan lunch

   Ribollita, pici pasta, and Chianti red at a country trattoria — hearty, simple cucina povera using the region's superb ingredients.

4. ~4:00pA second tasting or an olive-oil estate

   An afternoon at another wine estate or an olive farm — tasting new-harvest oil and more Sangiovese, the golden light raking across the vines.

5. ~7:00pSunset over the vineyards

   An estate terrace or hilltop for the sunset — a glass of Chianti as the cypress-lined ridges turn gold and the valleys fill with haze.

   
6. 8:30pDinner at the estate or a country restaurantAnchor table

   A Tuscan dinner — bistecca alla Fiorentina or seasonal cooking with the estate's own wine, the day's marquee meal under the stars.

Chianti is the iconic Tuscany of cypress-lined hills and vineyards — spend the day touring wine estates and hill towns, tasting the Sangiovese reds and peppery olive oil. Use a driver for the tastings, and claim a west-facing terrace for the famous golden-hour light.

Day 1 in photos

1. ~9:30aThe Piazza del Campo

   Siena's extraordinary shell-shaped main square — a sloping medieval amphitheatre of warm brick, ringed by palazzi and home to the famous Palio horse race.

   
2. ~10:30aSiena Cathedral

   One of Italy's most spectacular Gothic cathedrals — a striped marble façade, an inlaid-marble floor of 56 panels, and a Piccolomini library glowing with frescoes.

   
3. ~1:00pLunch in Siena

   Pici pasta and a glass of local wine at a Siena trattoria, then panforte and ricciarelli — the city's famous medieval sweets.

   
4. ~3:00pA drive through the Crete Senesi or to a hill town

   Out into the surreal clay hills of the Crete Senesi, or to a perfect smaller town like Monteriggioni — walls, towers, and the rolling Sienese landscape.

   
5. ~7:30pDinner back at the estate or in a hill town

   A relaxed Tuscan dinner — seasonal cooking and Sangiovese, the medieval day winding down over a long country table.

   

Siena is the great medieval rival to Florence — the shell-shaped Piazza del Campo and the dazzling striped Duomo are the highlights, set in a beautifully preserved Gothic city. The surrounding Sienese landscape, from the lunar Crete Senesi to walled Monteriggioni, is among Tuscany's most beautiful.

Day 2 in photos

1. ~9:30aPienza, the 'ideal' Renaissance town

   A tiny hilltop town redesigned as a Renaissance utopia — a perfect humanist square, sweeping Val d'Orcia views, and the scent of its famous pecorino cheese.

   
2. ~11:30aBrunello in Montalcino

   To the hilltop wine town of Montalcino, home of Brunello — one of Italy's greatest reds — for a tasting with the Val d'Orcia rolling away below.

   
3. ~1:30pA Val d'Orcia lunch

   Pici with cheese, pecorino in many forms, and Brunello or Rosso at a country trattoria amid the postcard hills.

4. ~3:30pThe iconic Val d'Orcia views

   The postcard scenes themselves — the lone farmhouse of Podere Belvedere, the cypress avenues, the chapel of Vitaleta — the most photographed landscape in Italy.

   
5. ~5:30pBagno Vignoni's thermal square

   A unique village built around a steaming Renaissance thermal pool as its 'piazza,' with hot-spring spas to soak in the mineral waters.

   
6. ~8:00pA final Tuscan dinner

   A last country dinner — pecorino, pici, bistecca, and Brunello — closing a Tuscan journey in the landscape that defines it.

The Val d'Orcia is the Tuscany of imagination — the rolling cypress-dotted hills, the perfect Renaissance town of Pienza, and the great Brunello wine of Montalcino. It's the most photographed landscape in Italy, at its most magical in late-afternoon light.

Day 3 in photos