Three and Four Day Trips Around Southern Tuscany
Using Siena as a base for several days
Staying put in Siena for three or four nights and radiating out is easier than changing hotels. The city lies where Chianti Classico, the bare clay hills of the Crete Senesi and the Val d’Orcia come together, and its roads lead out in each direction. This page offers a three-day plan, with a fourth day if you have a car.
Before you start
Within the old walls, cameras enforce a limited-traffic zone around the clock. The fine amount is not confirmed, and a hotel parking discount does not allow you through the gates. Use a car park outside the walls: Il Campo, Il Duomo, San Francesco and Santa Caterina charge about EUR 2 an hour up to EUR 35 a day, with a hotel guest rate of EUR 25 a day arranged through your hotel. Free escalators link the car parks and station to the centre.
Arriving from Florence, the 131R coach takes about 75 minutes and costs about EUR 10.90. It arrives at Via Tozzi, outside the northern edge of the old centre. The slower Regionale train takes about 1 hour 30 minutes.
Day one: the city
Spend the morning in the Duomo complex on the three-day OPA SI PASS (EUR 14, or EUR 16 when the floor is on show). In the afternoon take the Museo Civico and tower ticket (EUR 15) and sit on the Campo at dusk. A second evening can include a Bottini tour if you travel outside June to August and have booked through the Comune.
Day two: the northern hills
Take the bus or drive to Monteriggioni and San Gimignano. By bus, line 130 serves San Gimignano with a change at Poggibonsi and costs about EUR 8.10 booked in advance. By car, add the Chianti road through Castellina and Radda for a cellar tasting booked in advance, and be back in Siena for dinner.
Day three: the southern valley
A car or small-group tour makes this day work. Drive through the Crete Senesi to Pienza, lunch at San Quirico d’Orcia near the Horti Leonini garden, and stop at Bagno Vignoni to look at the thermal square, where bathing is not allowed. Montalcino for Brunello and Sant’Antimo abbey lie further on, so choose one or the other and check hours.
Optional day four: abbeys
Drive southwest to San Galgano, where the abbey church has no roof and a small round chapel above holds the Sword in the Stone. In the afternoon go east to Monte Oliveto Maggiore, a working Benedictine monastery whose Great Cloister carries 36 frescoes about Saint Benedict by Luca Signorelli and Il Sodoma.
If you have no car
Concentrate on Siena, San Gimignano and Monteriggioni by bus, and book one small-group tour for the Val d’Orcia. Do not expect to string several Val d’Orcia villages together on line 112, which makes only a few journeys a day.
Choosing where to sleep
The centre is walkable end to end, so a base near the Campo or the Duomo avoids hauling bags up hills. Ask whether breakfast and luggage help are included.
Read more: day trips from Siena and the 3 day itinerary .
Official information: Duomo pass details and Museo Civico and tower tickets . Stays to compare: Siena accommodation on Booking.com .