Five days is the minimum time to do Tuscany properly. It’s enough to see the essential without feeling rushed, Siena, San Gimignano, the Chianti wine country, the Val d’Orcia and Florence, all from a single base.
This itinerary uses Poggibonsi as a fixed base, no moving bags between hotels, no wasted time on logistics.
Siena, Florence, the Chianti, the Val d’Orcia - all within an hour of Poggibonsi. Unpack once. Sleep well. Head out each morning in a different direction. This is the most efficient way to see Tuscany.
Why Poggibonsi is the perfect base for a Tuscany itinerary
Poggibonsi sits at the geographical centre of central Tuscany. From Hotel Alcide, you can reach:
- San Gimignano: 12 km, 15 minutes by car
- Siena: 25 km, 30 minutes by car or train
- Florence: 50 km, 55 minutes by train
- Chianti Classico: 15 km east
- Val d’Orcia: 60-90 km south
A fixed base saves time and energy. You unpack once, sleep well, and head out each morning in a different direction.
Hotel Alcide has been operating at this same location since 1849, the Ancillotti family knows the territory.
Day 1: Siena, the city of the Palio
The first day is for Siena, 30 minutes by car or train.
Morning: Piazza del Campo, arrive before 9am for the best experience, before the crowds. The shell-shaped piazza, divided into nine segments representing the medieval Council of Nine, is one of Europe’s great public spaces. Walk around it, sit on the brick, watch how it functions as a living room for the city.
Mid-morning: the Duomo. The marble interior, the intarsia floor (partially covered to protect it), the Piccolomini Library with Pinturicchio frescoes, the Crypt with 13th-century frescoes. Budget at least 90 minutes.
Afternoon: the Palazzo Pubblico and its Civic Museum. The Simone Martini frescos (the Maestà and the equestrian portrait of Guidoriccio da Fogliano) and Ambrogio Lorenzetti’s Allegory of Good and Bad Government are among the most important medieval paintings in Italy.
Evening: return to Poggibonsi, dinner at Ristorante Alcide.
Day 2: San Gimignano and the Val d’Elsa
The second day explores the valley around Poggibonsi.
Morning: San Gimignano (12 km). Arrive early, the towers are most beautiful in morning light, before the tour groups. The Collegiata church with its medieval frescoes, the Torre Grossa (climb it for the view), and Dondoli’s gelateria are the essentials.
Afternoon: Colle Val d’Elsa (8 km from Poggibonsi). The red-brick medieval upper town, Colle Alta, is little visited by foreign tourists, which is precisely its charm. The Crystal Museum tells the story of a town that produces 15% of the world’s crystal.
Optional extension: Certaldo (15 km), Boccaccio’s home town, red brick, medieval walls, the Palazzo Pretorio.
Day 3: Chianti, wineries and hilltop villages
The third day goes into the Chianti Classico wine country.
Morning: Castellina in Chianti (15 km), walk the Via delle Volte (the covered medieval street inside the town walls), then continue to Radda in Chianti.
Midday: winery visit with tasting (pre-booked). A Chianti Classico tasting in the producer’s own cellar, with a view of the vineyard outside, is one of the most memorable food experiences in Italy.
Afternoon: Panzano in Chianti, the panorama over the Conca d’Oro valley, and a stop at the Macelleria Cecchini if it’s open.
Evening: back to Poggibonsi for dinner.
Day 4: Val d’Orcia, Pienza, Montalcino and Bagno Vignoni
The fourth day covers the UNESCO Val d’Orcia landscape, the most visually dramatic day of the itinerary.
Early morning: drive south on the Via Cassia, through the Siena crete (the white clay hills). First stop: Bagno Vignoni. The medieval village with a thermal pool instead of a piazza square, steam rising from the water in the cool morning air.
Mid-morning: Pienza (12 km from Bagno Vignoni). The Renaissance ideal city of Pope Pius II, Piazza Pio II, the Duomo with its Gothic windows, the Piccolomini Palace with its garden overlooking the valley. And the Pecorino cheese shops: buy something.
Lunch: Pienza or a local agriturismo in the hills.
Afternoon: Montalcino (22 km). The medieval Fortress with the Brunello wine bar inside the walls. The views from the ramparts across the Val d’Orcia are extraordinary.
Evening: return to Poggibonsi (1 hour).
Day 5: Florence by train
The final day uses the train, 55 minutes from Poggibonsi station to Florence Santa Maria Novella.
Morning: the Duomo complex, the Baptistery, the external architecture of the Cathedral, and either the climb to Brunelleschi’s dome (pre-booked, essential) or the Giotto campanile.
Mid-morning: the Uffizi. With a pre-booked ticket, you avoid the worst queues. Focus on the rooms you actually want to see: the Botticelli rooms, the Titian rooms, the Leonardo and Raphael. Two hours is enough for a focused visit.
Afternoon: cross the Arno at Ponte Vecchio and explore the Oltrarno, the less touristy south bank, with artisan workshops, local cafes and the quieter neighbourhood feeling.
Late afternoon: Piazzale Michelangelo for the panorama over Florence at golden hour.
Evening: train back to Poggibonsi. Final dinner at Ristorante Alcide.
Practical tips: budget, transport and booking
Transport: rent a car for days 1-4 (essential for Chianti and Val d’Orcia). Use the train for day 5 to Florence.
Booking in advance: Uffizi and Duomo dome need advance tickets, especially in spring and summer. Winery tastings need at least 3-5 days notice.
Budget per person (excluding flights): €120-200/day covering hotel, meals, petrol and entrance fees.
Best season: April-May or September-October for the best weather and manageable crowds.
Planning a trip to Tuscany?
Hotel Alcide is in Poggibonsi, in the heart of the Val d’Elsa.
25 km from Siena, 12 from San Gimignano, in the heart of Chianti.
The Ancillotti family has welcomed guests here since 1849.
