Enjoy a wonderful private excursion to visit three of the loveliest Tuscan towns! Your first stop today after a lovely one hour drive through the countryside is San Gimignano. A small medieval town in Tuscany, San Gimignano has a splendid skyline made up of 13 towers.

This 11th century town rises 334 meters above the Elsa Valley along the ancient “Via Francigena” on which traders and pilgrims going to Rome traveled. San Gimignano prospered considerably during this period thanks to this route and all the inns that were built along its way to accommodate the pilgrims. With prosperity, many patrons in San Gimignano were able to hire the best craftsmen and artists to magnificently decorate the churches and monasteries here. Dante Alighieri came to San Gimignano on May 8, 1300 as the Ambassador of the Guelph League in Tuscany. Today, San Gimignano’s important cultural and natural heritage have been recognized by UNESCO. As in all of Italy, the Black Plague of 1348 greatly reduced the population of San Gimignano and led the city into a grave economical depression and caused the town to submit to Florence’s rule in 1353. Later on in the centuries though, San Gimignano rediscovered its cultural importance and beauty together with its agriculture and eventually overcame its decline becoming the beautifully restored town it is today. In spite of its rather small size there is plenty to admire in San Gimignano. Besides its 13 remaining towers (there were once about 40!), you can also see the “Duomo” or Collegiate Church and its magnificent frescoes, the “Palazzo del Popolo”, the “Palazzo Nuovo del Podestà” which is now the town hall. Other interesting places to see are church dedicated to Saint Augustine with its famous fresco cycle of this Saint’s life painted by Benozzo Gozzoli, the Museum of Holy Relics, and the infamous Museum of Torture and its macabre displays of early torture instruments. You will love just wandering up and down the main street in San Gimignano and going in and out of the numerous specialty shops. The ceramics are beautiful here, but there are also places for buying leather goods and linens.

For food and wine lovers there are many shops that sell delicious local products including San Gimignano’s “Vernaccia” white wine. You will be able to taste this wine in several of the wine stores in the town.

Next stop on the way from San Gimignano to Siena is Monteriggioni. This is one of the best known and classic walled towns in Tuscany. Also on the Via Francigena, this village was built on a hill by the Sienese between 1213 and 1219 to overlook the ancient Roman road, the Via Cassia. This was a perfect position allowing for surveillance of the valleys below in the direction of the city of Florence, which was the historic enemy of Siena.

We’ll be making a lunch stop here at a typical trattoria where we’ll enjoy some mouth-watering Tuscan food before we go on our way Siena.

No trip to Tuscany is complete without a day trip to Siena, the birthplace of the beloved Italian Saint Catherine. This beautiful city made of brown Siena-colored bricks (so that’s how they named the color!), its jumble of narrow streets and delightful squares, the medieval towers that make such a spectacular skyline, its spectacular cathedral, the tall and trim Torre del Mangia, all together create an enticing atmosphere almost like stepping back in time. Siena is built on three hills and is home to one of the most authentic and important Gothic cathedrals south of the Alps. Despite the city’s architectural masterpieces, it is the unusual shell-shaped Piazza del Campo that receives the most consideration having been seen in numerous films and photographs. This brick covered square is used twice a year for the famous “Palio” horserace, an event that involves the entire population and is considered one of the most important events in the life of the Sienese people. This reckless bareback race is run on July 2nd and August 16th, has Roman origins but has first been officially recorded in 1283. A kind of happy frenzy rules over Siena during the time leading up to the Palio and visitors can get the chance to observe the locals during the many ceremonies that are involved in the “Palio” race. Almost anything will be done to win this extremely competitive race and bring home the “Palio” a silk banner that will proudly displayed in the “contrada” or neighborhood it represents.