The Sienese countryside is perhaps one the few most-photographed world wonders that wholly lives up to the hype. Folks worldwide flock to this bucolic setting expecting scenic landscapes and towns exuding the feel of centuries past – which is exactly what you’ll find. What were once hilltop fortresses are now humming centers of Tuscan culture and tradition, quaint towns that together form the charming landscape surrounding Tuscany’s larger capital cities.
Staying in Siena or a neighboring wine town? The area offers enough day trips to merit a vacation of its own. To help sort through the mix, we’ve picked a few of the best towns to fill your day trips during your weeklong holiday.
From afar, Monteriggioni emerges from the Tuscan hills like a film set, an age-old town that appears immune to the withering of time. Sky-high towers and fully intact walls bound the village to a vine-covered hill, forming a town composed of nothing more than a central square, a few homes and its impressive medieval aesthetic. It doesn’t take long to explore the small center, yet tourists head here year round, though always in bearable numbers. Besides offering authentic Tuscan dishes and a peaceful setting for a stroll, the city affords unparalleled views of the Tuscan countryside – and a chance to explore what you’ll see from above. For a more active countryside adventure, head south to trek along the world-famous Via Francigenca, the ancient route connecting Canterbury to Rome.
Abbazía di Sant’Ántimo
This abbey is located about 40 kilometers south of Siena, not far from the picturesque town of Montalcino; if top-notch Brunello wine isn’t enough to get you packing, then perhaps this incredible site will. The Benedictine abbey dates to about 813 AD and was allegedly founded by Charlemagne himself. Despite only boasting remains of the 12th and 13th-century portion of the church, the abbey remains a striking example of Romanesque architecture in Tuscany. The curious structure mixes medieval Italian flair with French-style elements, a rather unusual architectural combination for this area. And to top it off, a community of Norbertines settled here in 1992, meaning chilling Gregorian chants might be your soundtrack to exploring this stone wonder.
This UNESCO World Heritage site, otherwise known as “the city of 100 towers,” is the shining star of the Tuscan countryside. Located between Siena and Florence, the quaint town is most known for its 16 tall towers that jut against the sky, one of which you can climb for spellbinding countryside views. Given the town’s strategic location for traveling pilgrims, the center maintains traces of its historic significance, such as the 12th-century pilgrim’s shelter near the main gate. Head to piazza della Cisterna, named after a cistern in the center of the square, to witness a beautiful array of rustic façades. These structures still preserve the air of inns and taverns that once served as resting spots for weary travelers. Between the main Romanesque cathedral and wide range of Gothic art, this city is a no brainer when it comes to day trips around Siena; don’t let the crowds deter you, as the town is best visited when bustling with life.
Declared a UNESCO World Heritage Site in 1996, this dreamlike town is nothing short of a fairytale come to life. Designed by Pope Pius II, the center of town is a perfect embodiment of Renaissance architectural ideals, vaunting 15th-century buildings and a stunning cathedral. Here, you’ll dive headfirst into Renaissance history; between Piccolomini Palace and the Diocesan Museum, Pienza is full of treasures to keep history buffs fully fueled. Slip between hidden gardens and narrow alleys to discover a rather romantic surprise: names like via del Bacio (kiss) and via dell’Amore (love) crown the winding streets, making it the perfect spot to meander away with a special someone in hand. Between its dreamy air and even dreamier views, you won’t want to miss a day in Pienza, especially if pici pasta and Tuscan sausage are on your list of delicacies to savor.
Colle di Val d’Elsa
Located smack in the center of Tuscany, Colle di Val d’Elsa falls a bit off the beaten path of usual day trips from Siena. Though the lower part of town is the most populated, the upper town, Colle Alto, vaunts original 13th-century walls and a charming crisscross of medieval winding streets. The 17th-century cathedral is more airy and luminous than other churches in the area, a space that proudly vaunts a 16th-century Crucifix attributed to famed sculptor Giambologna. Colle di Val d’Elsa is perhaps most unique for its production of crystal glass; indeed, over 95% of Italian crystal is made here, which you can admire up close in the town’s Crystal Glass Museum. Together, the lower and upper parts of town fuse traditional Tuscany with modern-day life, so don’t miss strolling through the area’s artisinal shops and restaurants to get a real taste of local Tuscan life.
Located about an hour from Siena by bus, Arezzo’s non-uniform buildings reflect its centuries of history; the town dates to Etruscan times, but its most recent history involves architectural renovations following World War II bombings. From Piero della Francesca to Petrarch and Vasari, Arezzo’s roots are tied to some of the most renowned figures in Italian history. To this end, the town is teeming with medieval and Renaissance treasures, from striking frescoes to terracotta pieces, marble carvings and unparalleled stained glass windows. If you thought Cimabue was a Florentine fixture, head to Arezzo to see another crucifix by the Gothic master in the Church of San Domenico. You’ll also find an impressive Archaeological Museum, where exhibits delve into the Etruscan and Roman history of both Arezzo and its surrounding areas.