Medieval Tuscany 8-day tour
Florence (1 night), Siena (4 nights), Montepulciano (2 nights)
This is a sample itinerary which is completely customizable, ask us how.
Highlights of the trip
- Village hop all over Chianti: Castellina, Ponzara, Montefioralle, Greve, Gaiola
- Visit medieval fortress villages: Siena, San Gamignano, Monteriggioni
- Sample Chianti Classico at the source paired with local dishes
- Cruise around the hills of Chianti stopping in quaint villages
Daily Itinerary
Day 1: Florence with a guided tour
Explore the iconic landmarks of Florence, including the Florence Cathedral (Duomo), Giotto’s Bell Tower, and the historic center with attractions like Piazza della Signoria and Palazzo Vecchio accompanies by an expert guide.
Overnight: Florence
Day 2: Siena with a stop in San Gimignano
En route from Florence to Siena you will stop to visit the medieval hill town of San Gimignano, known for its well-preserved towers and historic architecture.
Explore key landmarks such as Piazza della Cisterna, Piazza del Duomo, and the Cathedral of Santa Maria Assunta.
Overnight: Siena
Day 3: Siena guided tour
Spend the morning in Siena exploring Piazza del Campo, the Cathedral of Santa Maria Assunta, and the surrounding medieval streets with an expert guide with a leisurely lunch in one of Siena’s traditional trattorias.
In the afternoon, delve deeper into Siena’s history with visits to the Museo dell’Opera del Duomo and the Palazzo Salimbeni.
Overnight: Siena
Day 4: Monteriggioni day trip
Start the day with a guided tour of the Contrada museums, learning about the unique traditions and rivalries of Siena’s neighborhoods.
After lunch, take a short trip to Monteriggioni to explore the medieval fortress town and its circular walls. Return to Siena for dinner at a local osteria, enjoying traditional Tuscan cuisine.
Overnight: Siena
Day 5: Chianti wine region
Spend the day exploring the picturesque Chianti region, known for its vineyards and olive groves.
Visit a local winery for a wine tasting and tour, learning about the production of Chianti Classico.
Enjoy a drive through the rolling hills of Chianti, stopping in charming villages such as Greve and Castellina.
Overnight: Siena
Day 6: Montepulciano stopping in Pienza
Explore the UNESCO World Heritage Site of Pienza, known for its Renaissance architecture and panoramic views of the Val d’Orcia. Our guide will take you to visit key landmarks such as Piazza Pio II, the Cathedral of the Assumption, and Palazzo Piccolomini.
Continue to Montepulciano, a medieval town famous for its Vino Nobile wine. Explore the historic center and enjoy wine tasting at local cantinas.
Overnight: Montepulciano
Day 7: Day trip to Cortona
Spend the day exploring Cortona, a hill town with Etruscan history and medieval charm. Visit key attractions such as the Etruscan Museum, the Diocesan Museum, and the Church of Santa Maria delle Grazie al Calcinaio.
We recommend an evening stroll through the narrow streets of Cortona, admiring the panoramic views of the surrounding countryside.
Overnight: Montepulciano
Day 8: Departure from Florence
Return to Florence for departure, with optional visits to any missed attractions or leisure time for souvenir shopping.
Why Travel with Bellarome
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