Multi-Day Tuscany Trips Based in Siena
Multi-day trips from Siena
Siena works as a base for southern Tuscany because three landscapes meet here: Chianti Classico to the north, the pale clay hills of the Crete Senesi to the east and the Val d’Orcia to the south. The city is compact and has good evening dining, and the roads out of it lead to each area. A four-day plan with a car is described below; without a car, stick to Siena, San Gimignano and Monteriggioni by bus and add a small-group tour for the south.
Cars, parking and the traffic zone
Everything inside the walls is a camera-controlled traffic zone, and the fine amount is not confirmed, so do not drive in. Park outside the walls and use the free escalators. The Il Campo, Il Duomo, San Francesco and Santa Caterina car parks charge about EUR 2 an hour and EUR 35 a day, and many hotels offer a guest rate of EUR 25 a day via a code. A hotel parking discount does not give permission to enter the traffic zone. The station car park is cheaper, at about EUR 2 a day, but sits 62 m below the walls, so you walk or use the free escalator up to the Antiporto at Porta Camollia.
Day 1: Siena itself
Spend the morning on the Duomo complex with the three-day OPA SI PASS, at EUR 14 for adults or EUR 16 while the floor is uncovered, and the afternoon in the Museo Civico and the Torre del Mangia, which together cost EUR 15. Finish with a drink on the Campo.
Day 2: Monteriggioni, San Gimignano and Chianti
Drive northwest to the walled circle of Monteriggioni, then on to San Gimignano for the tower houses and the Collegiata frescoes. In the afternoon, cross the Chianti hills through Castellina and Radda in Chianti and book a cellar tasting in advance. Return for dinner in Siena.
Day 3: Pienza, Bagno Vignoni and Montalcino
Take the road through the Crete Senesi to Pienza, with its pecorino shops, and lunch in San Quirico d’Orcia near the Horti Leonini garden. At Bagno Vignoni you can look at the thermal basin in the square but not bathe in it. Montalcino and the Sant’Antimo abbey are further south. This is a very long day by car, so choose two of the stops, not all four, and check opening hours.
Day 4: San Galgano and Monte Oliveto Maggiore
Head southwest to the roofless abbey of San Galgano and the Sword in the Stone chapel on the hill above, which is free. In the afternoon, go east to Monte Oliveto Maggiore, an active Benedictine monastery in the Crete Senesi with a cloister painted with scenes from the life of Saint Benedict by Signorelli and Sodoma. Return to Siena for dinner.
Where to eat
Lunch pici with wild boar sauce at Osteria degli Svitati on Via della Galluzza in Siena, and look for farmhouse lunches on the road in Chianti. Book in advance, as small places fill in high season.
If you stay longer
Add the Bottini tunnel tour if you are travelling outside June to August, and use the Wednesday market as a morning stop. Nights in Siena work better than moving hotels each day.
Read more: day trips from Siena and the 4 day itinerary .
Official information: Duomo passes and Bottini visits . Stays to compare: Siena hotels on Booking.com .