The Val d’Orcia region in Tuscany, Italy is known for its breathtaking landscapes, charming medieval towns, and picturesque countryside. With its rolling hills, vineyards, and cypress-lined roads, it’s no wonder that Val d’Orcia has been recognized as a UNESCO World Heritage Site. If you are planning a trip to this enchanting part of Italy, here is an itinerary to help you explore and discover the beauties of Val d’Orcia.

Day 1: Pienza

Start your journey in the town of Pienza, often referred to as the “Ideal City” due to its well-preserved Renaissance architecture. Take a stroll through the narrow streets, visit the Piazza Pio II where you can admire the Palazzo Piccolomini, and don’t forget to sample the famous pecorino cheese, a local specialty. From the town, enjoy panoramic views of the surrounding countryside, which have served as the backdrop for many films.

Day 2: Montepulciano

On day two, head to the hilltop town of Montepulciano. This medieval gem is known for its excellent wines, particularly the Vino Nobile di Montepulciano. Explore the underground cellars and taste the rich red wines produced in this region. Climb to the top of the tower of the Palazzo Comunale for a breathtaking view of the surrounding vineyards and rolling hills. Take your time to wander through the charming streets, visit churches, and enjoy a leisurely lunch in one of the many local trattorias.

Day 3: Bagno Vignoni and San Quirico d’Orcia

Day three takes you to the unique village of Bagno Vignoni. This small town is famous for its thermal waters, and its main square is filled with a rectangular pool where you can see steaming hot water bubbling up from underground. Take a relaxing dip in the thermal baths or indulge in a spa treatment. From Bagno Vignoni, continue your journey to San Quirico d’Orcia, another enchanting medieval town. Visit the Collegiata of San Quirico, a beautiful Romanesque church, and explore the town’s medieval walls and picturesque streets.

Day 4: Abbazia di Sant’Antimo and Monte Oliveto Maggiore

On day four, venture outside the towns to visit two significant religious sites. Start with a visit to the Abbazia di Sant’Antimo, a stunning Romanesque abbey surrounded by fields and vineyards. Experience the peaceful atmosphere and perhaps even catch a Gregorian chant performance. Continue your journey to Monte Oliveto Maggiore, a Benedictine abbey famous for its beautiful cloister adorned with frescoes by Luca Signorelli and Sodoma. Spend some time admiring the intricate architecture and soaking in the serene ambiance.

Day 5: La Foce and Crete Senesi

On the final day, explore the stunning countryside surrounding Val d’Orcia. Visit La Foce, a beautiful estate with a remarkable garden designed by English architect Cecil Pinsent. Take a guided tour to learn about its history and enjoy the picturesque views of the surrounding valleys. End your journey by driving through the Crete Senesi, a unique and distinctive landscape characterized by rolling clay hills. Stop at the picturesque town of Asciano, known for its charming streets and the Museo Cassioli, which houses a collection of paintings by local artist and former mayor, Telemaco Signorini.

Val d’Orcia is a region that captivates visitors with its natural beauty, charming towns, and rich cultural heritage. This itinerary will guide you through some of the most captivating spots in the area, leaving you with memories to cherish and making you fall in love with the enchanting beauty of Val d’Orcia.

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