Suggested Itinerary
Two Weeks Exploring Siena and Authentic Tuscany at a Relaxed Pace
This 15-day itinerary is designed for travellers who want to discover Siena and its province at a slower pace. The days combine art cities, medieval villages, abbeys, scenic roads, food and wine experiences, thermal heritage, countryside walks and time to rest, using San Giusto as a convenient base for daily excursions.
Day 1 · First Impressions of Siena
Begin your holiday in Siena's historic centre, a UNESCO World Heritage Site and the cultural heart of the area. Start in Piazza del Campo, admire Palazzo Pubblico and consider climbing Torre del Mangia for views over the city and the surrounding countryside. Continue to Siena Cathedral, renowned for its black-and-white marble, decorated floor and important works of art. In the afternoon, wander at a relaxed pace through the medieval streets, cross some of the historic contrade and stop at the artisan shops in the centre. End your first day with a dinner featuring traditional Sienese dishes.
Day 2 · Siena’s Museums, Churches and Contrade
Spend a second day in Siena exploring places that deserve more time. Visit the Santa Maria della Scala museum complex, a former medieval hospital that is now an important cultural centre, or enter the Civic Museum inside Palazzo Pubblico. Continue to the Basilica of San Domenico and the quieter areas of the historic centre, discovering fountains, oratories and places connected with the life of the contrade. In the late afternoon, reach the Medici Fortress for a panoramic walk. Dividing Siena across two days allows you to experience the city more calmly instead of fitting all its major sights into only a few hours.
Day 3 · Monteriggioni and the Via Francigena
Travel to Monteriggioni, a small medieval village enclosed by an almost perfectly preserved ring of walls. Enter through the main gate, visit Piazza Roma and walk along the accessible sections of the fortifications for views over the surrounding landscape. The village stands on the Via Francigena, so you can add a short walk along part of this historic pilgrimage route, choosing the distance and difficulty according to the season. In the afternoon, stop at a village or panoramic viewpoint between Monteriggioni and Siena. Keeping this day intentionally light leaves time to relax when you return to the agriturismo.
Day 4 · Colle di Val d’Elsa and the Villages of the Valley
Visit Colle di Val d'Elsa, known for its crystal craftsmanship and hilltop historic centre. Walk through lanes, arches, old buildings and panoramic terraces, then discover the workshops and traditions associated with local craftsmanship. Depending on the time available, you can add a short stop in another town in Val d'Elsa or follow a scenic road through hills, vineyards and small rural settlements. Avoid making the programme too busy. A 15-day holiday gives you the opportunity to devote more attention to each place and stop for lunch or a walk without rushing.
Day 5 · San Gimignano
Spend a full day in San Gimignano, famous for its medieval towers and UNESCO-listed historic centre. Walk between Piazza della Cisterna and Piazza del Duomo, visit the Collegiate Church and climb to one of the panoramic viewpoints overlooking Val d'Elsa. During your visit, you can taste Vernaccia di San Gimignano, the area's historic white wine, or stop at one of the gelaterias in the centre. In the afternoon, explore the quieter streets and viewpoints along the town walls. Return along a scenic road, allowing time for a few stops among vineyards and olive groves.
Day 6 · Castellina and Radda in Chianti
Begin exploring the Siena side of Chianti with Castellina in Chianti and Radda in Chianti. Walk through their historic centres, visit fortresses, churches and small museums, then travel slowly along roads crossing vineyards, olive groves and woodland. Book a Chianti Classico tasting at a local winery or choose lunch at a traditional restaurant to discover the area's produce. Limiting the day to two villages gives you time for panoramic viewpoints and spontaneous detours without turning the excursion into a succession of short stops and long drives.
Day 7 · Gaiole, Castles and Chianti Landscapes
Spend a second day in Chianti travelling to Gaiole in Chianti and exploring an area known for its castles and agricultural estates. Choose one or two visits according to their opening hours and book winery experiences in advance. Between stops, follow the quieter roads and pause at panoramic viewpoints and small villages. If you prefer a more active programme, replace one visit with a short walk or bicycle ride. Always organise tastings and travel responsibly, ensuring that the designated driver does not drink alcohol before the return journey.
Day 8 · Crete Senesi and Asciano
Explore the landscapes of the Crete Senesi, shaped by rolling hills, clay gullies, isolated farmhouses and rows of cypress trees. Begin in Asciano, where you can walk through the historic centre and visit one of the museums dedicated to local art and culture. Continue along the scenic roads, stopping at the most attractive viewpoints. Morning and late-afternoon light are particularly effective at revealing the shapes and colours of the landscape. Allow time for a stop in a village or restaurant, choosing produce and dishes connected with the traditions of the Sienese countryside.
Day 9 · Monte Oliveto Maggiore and Buonconvento
Travel to the Abbey of Monte Oliveto Maggiore, a monastic complex surrounded by woodland and the landscapes of the Crete Senesi. Spend time in the cloister and admire its important Renaissance frescoes while respecting the opening hours and peaceful atmosphere of the site. Continue to Buonconvento, a village on the Via Francigena with a compact historic centre of medieval origin. Walk through its streets, visit a church or one of the small museums and stop for lunch. This day combines spirituality, art and village life, with manageable distances and a pace suited to a longer holiday.
Day 10 · Montalcino and Brunello Wine
Visit Montalcino, a hill town surrounded by the vineyards used to produce Brunello. Walk through the historic centre, reach the fortress and admire views across the countryside. If you are interested in wine, book a winery visit and tasting, choosing an experience that explains both the local landscape and production methods. Spend the rest of the day in the town and along the nearby scenic roads without adding too many destinations. End with a food stop or return slowly towards San Giusto. If you are travelling by car, make sure that the driver does not consume alcohol.
Day 11 · Pienza and San Quirico d’Orcia
Devote the day to two of the central villages of Val d'Orcia. Begin in Pienza, a Renaissance town overlooking one of Tuscany's best-known landscapes. Visit Piazza Pio II, walk through the historic centre and taste the pecorino cheese produced in the surrounding area. Continue to San Quirico d'Orcia, with its Collegiate Church, historic streets and Horti Leonini gardens. Stop at panoramic viewpoints along the route, parking only in permitted areas and respecting private property. The programme leaves enough time for walking, photography and an unhurried lunch.
Day 12 · Bagno Vignoni, Thermal Heritage and Relaxation
Plan a slower day in Bagno Vignoni, a small thermal village built around the large pool of water occupying its main square. Walk through the centre, observe the historic water system and follow one of the nearby paths, choosing a route suited to the season. If you would like a spa experience, check facilities, access arrangements, reservations and available services in advance. Do not bathe in areas where access to the water is prohibited. You can combine the visit with a short panoramic stop in Val d'Orcia or return to the agriturismo earlier and continue relaxing in the countryside.
Day 13 · Sant’Antimo and the Landscapes of Val d’Orcia
Travel to the Abbey of Sant'Antimo, an elegant Romanesque church surrounded by countryside near Montalcino. Visit the abbey while respecting the times of religious services and spend a few moments enjoying the surrounding landscape. Continue along the roads of Val d'Orcia, choosing only a few stops among farmhouses, cypress trees and small rural settlements. The day can be completed with lunch at a farm estate or a short walk, without repeating the more intensive programme of previous days. This excursion reveals the spiritual and rural character of the area at a peaceful pace.
Day 14 · Val di Merse and San Galgano
Discover Val di Merse, beginning at the Abbey of San Galgano, famous for its large roofless Gothic church. Continue to the nearby Hermitage of Montesiepi, home to the sword in the stone associated with Saint Galgano. If time allows, visit Chiusdino or reach the picturesque Ponte della Pia, surrounded by the valley's greenery. You can complete the day with a short walk through woodland and beside streams, choosing a route suited to the condition of the ground. The area offers a particularly memorable combination of history, legend and nature.
Day 15 · Sovicille, the Montagnola Senese and Relaxation
End your holiday close to Agriturismo San Giusto. Visit Sovicille, the parish church of Ponte allo Spino or one of the small villages in the Montagnola Senese, then choose a short walk through woodland and along quiet country roads. Alternatively, return to Siena to purchase local products or revisit a favourite place. In the afternoon, return to the agriturismo and enjoy a few hours in the garden or by the seasonal swimming pool. A day without long journeys allows you to finish the stay calmly, organise your photographs and enjoy the colours and scents of the Tuscan countryside one last time.