Tuscany Countryside
Florence β San Gimignano β Siena β Pienza
San GimignanoβSienaβPienza
5 daysAutumnEasyLuxury3 segments7 stops
A slow drive through rolling hills, cypress-lined roads, medieval hill towns, and vineyards β the essence of la dolce vita in central Italy.
π AutumnEasyLuxury5 days
3 segments 7 landmarks 2h 45mπ 160 km
Day-by-Day Plan
1 / 5
Florence: Renaissance Heart
Day 1 Activities
- Duomo di Firenze climb
- Uffizi Gallery highlights
- Ponte Vecchio at sunset
- Gelato at Vivoli
StayPortrait Firenze
MealsBreakfast: Caffè Gilli, Lunch: All'Antico Vinaio, Dinner: Trattoria Sostanza
β swipe between days β
Route Segments
1
Florence β San Gimignano
π 1hπ 55 km
2
San Gimignano β Siena
π 45mπ 45 km
3
Siena β Pienza
π 1hπ 60 km
landmarks
πΊοΈ
Plan This Trip
Affiliate links β we may earn a commissionπ Duomo di Firenze
π Ponte Vecchio
π San Gimignano
π Piazza del Campo
π Siena Duomo
π Pienza
π§‘
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Tuscany Countryside
Florence β San Gimignano β Siena β Pienza
Segments3
Landmarks7
Distance160 km
Duration2h 45m
Day-by-Day Plan
1
Florence: Renaissance Heart
- Duomo di Firenze climb
- Uffizi Gallery highlights
- Ponte Vecchio at sunset
- Gelato at Vivoli
Stay
Portrait Firenze
Meals
Breakfast: Caffè Gilli, Lunch: All'Antico Vinaio, Dinner: Trattoria Sostanza
2
Chianti Wine Road β San Gimignano
- Chianti vineyard tour & tasting
- Certaldo old town
- San Gimignano medieval towers
- World Champion gelato at Dondoli
Stay
Hotel La Cisterna
Meals
Breakfast: Florence, Lunch: vineyard picnic, Dinner: Cum Quibus
3
Monteriggioni β Siena
- Monteriggioni fortress walk
- Piazza del Campo
- Siena Duomo striped marble
- Torre del Mangia climb
Stay
Grand Hotel Continental Siena
Meals
Breakfast: San Gimignano, Lunch: Osteria Le Logge, Dinner: Taverna di San Giuseppe
4
Crete Senesi β Val d'Orcia
- Crete Senesi lunar landscapes
- Abbey of Sant'Antimo Gregorian chants
- Bagno Vignoni thermal square
- Cypress-lined photo stops
Stay
La Bandita Townhouse
Meals
Breakfast: Siena, Lunch: Daria in Monticchiello, Dinner: La Terrazza del Chiostro
5
Pienza & Pecorino Farewell
- Pienza Renaissance piazza
- Pecorino cheese tasting
- Val d'Orcia panoramic drive
- Montepulciano wine cellars
Stay
La Bandita Townhouse
Meals
Breakfast: Pienza bakery, Lunch: Latte di Luna, Dinner: Osteria Acquacheta
Route Segments
| # | From | To | Transport | Duration | Distance |
|---|---|---|---|---|---|
| 1 | Florence | San Gimignano | car | 1h | 55 km |
| 2 | San Gimignano | Siena | car | 45m | 45 km |
| 3 | Siena | Pienza | car | 1h | 60 km |