Siena

Siena's old-world charm surpasses that of any European city, and it should be on the top of every Italian itinerary. This Tuscan paradise exudes a fusion of Medieval and early Renaissance characteristics, which is well complemented by its delicious food and wine. There may not be a more authentically Tuscan town in Tuscany, so it's no surprise that restaurant franchises like Olive Garden have attempted to replicate Siena's enchantment.

Two of the most impressive buildings from the Middles Ages are also in Siena. The first is Palazzo Pubblico (Town Hall) which sits on the main square and houses some of the best Medieval frescos in Europe. The town hall also has the Tower of the Eater (Torre del Mangia) which you can climb and was the tallest in Italy when it was completed in 1348 at 289 feet tall. The other major structure is the famous Cathedral of Siena (Duomo) which was built over an Etruscan Acropolis and consecrated in 1215. The interior of the stunning cathedral is our favorite in Italy as it is filled with zebra-striped columns, amazing mosaic floors, plus artwork from masters like Michelangelo and Donatello. Next to the Cathedral is a true gem from the Middle Ages called the Santa Maria Della Scala which is a former hospital turned into a wonder Medieval museum.

In addition to the wonderful city of Siena, there are numerous great Medieval castles to visit, such as Castello di Celsa and the Castello Meleto Castle Winery. The magnificent Castello di Barone Ricasoli, where Chianti wine was developed, is our favorite local castle to visit. This farm was founded in 1141, and both the castle and its family have been among Tuscany's most famous wine producers.