Founded between 4th and 3rd Century B.C., Montepulciano sits nearly 2,000 feet in elevation and is located in the province of Siena in the southeastern Tuscany. As one of the steepest hill towns in Italy, Montepulciano offers breathtaking views over the beautiful countryside that surrounds it including the Val di Chiana. Cars are not permitted in the town center, making it an inviting and truly exhilarating walking town with its enchanting palaces, churches, fortresses, and towers. Montepulciano is famous for its wine with many vineyards situated nearby. Renowned for its pork, cured meats, cheese, hand-rolled “pici” pasta, lentils, and honey, it is perhaps best known for its remarkable wines. In the Piazza Grande, there are several shops that offer wine tasting from local vineyards. Just outside the walls of the town, the renaissance Tempio di San Biagio beckons travelers to walk or drive and take in its lovely Greek cross style architecture and bucolic setting. Montepulciano presents itself as a destination rich in every sense, and beckons the adventurous traveler to stop and partake in its many delights.
Truly an ancient town dating back in written historical records to the 9th Century B.C. Set within a full circle of fortified walls and watched over by a mighty castle of medieval perfection, the town has scarcely changed in appearance since the 16th century. Montalcino, is a beautiful village immersed in the breathtaking Val d’Orcia Natural Park. The town takes its name from a variety of oak tree that once blanketed the terrain. The dizzying heights of the town offer stunning views over the Asso, Ombrone and Arbia valleys of Tuscany, dotted with silvery olive orchards, vineyards, fields and villages.
Expansive vineyards and olive groves dominate the lower slopes of Montalcino hill itself. Renowned worldwide for the production of its precious Brunello red wine, this fairytale village is a feast for the eyes, the senses, and the taste-buds.
Pienza is a compact hill town of great beauty, and one of the few that are actually “flat” once you get to the center. Located between the towns of Montepulciano and Montalcino, Pienza is in the midst of the unforgettable Val’ d’Orcia with a picture-postcard view that stretches for miles in many directions. Pienza is also renowned for its Pecorino cheese which can be sampled in the many shops that line the main street. It is a restful and peaceful place to enjoy the bounty that Tuscany offers.
The town of Pienza is possibly the first planned urban ‘utopia,’ this charming village is widely known as the “ideal city of the Renaissance,” and is the creation of the great humanist Enea Silvio Piccolomini who later became Pope Pius II. Piccolomini had the money and influence to transform his birthplace village, the humble Corsignano, into what he considered the Utopian city should be, exemplifying the principles and philosophy of classical times and of the great Italian Renaissance. Thus, Pienza became the realization of a dream! Orderly, beautiful, and well planned, there is a symmetry in the grouping of the harmonious buildings all defining the edges of the town piazza. Whether enjoying leisurely walks along the easy rambling streets, or out beyond the walls through the rolling countryside, Pienza is a hill town to treasure.
Cortona is an ancient hilltop town in the province of Arezzo, in Tuscany, Italy. It sits on the border with Umbria and there have been many battles over the eons to lay claim to this highly valued town. It is iconic as the setting for the celebrated book “Under the Tuscan Sun.” Many travelers have been inspired by the beauty of the setting in the subsequent movie and seek that uniquely Italian experience. The elevation varies from a height of 1,600 to 2,000 feet, with narrow steep streets surrounded by medieval architecture making for dramatic cityscapes. Dating back as far as the 7th Century B.C. there are many influences represented in the artistic and architectural features. Inside the Palazzo Casali is the Museo dell’Accademia Etrusca, items from Etruscan, Roman, and Egyptian civilizations are on display, as well as art and artifacts from the Medieval and Renaissance eras. A walk out of town along the Roman road provides a shaded route to drink in the sprawling vistas of the valley floor stretching away to the west.
Pitigliano is a walled town in the Maremma region of the province of Grosseto in Tuscany. Not very “touristy” it sits 1,026 feet above sea level. This tiny medieval village in Tuscany called Pitigliano (known as La Piccola Gerusalemme or Little Jerusalem) and has an old world ambiance of ceramic roof tiles, parapets, and multi-tiered buildings. It was once a Jewish settlement, which is why it might have that Jerusalem feel to it. So much of Italy’s history involves the Roman’s and Papal dynasty that it is refreshing to find this gem that still offers the history of its long ago Jewish root.
As you walk through the medieval gate into the old city, you see a wonderful 14th Century fortress called Orsini Palace which is now a museum. Pitigliano has a population is only about 4,000 residents, almost none of them of the Jewish tradition. Passed down over centuries by controlling families, it takes its name from the last great family to possess it as a private estate. The food, the people, and summer temperatures are warm and inviting. It sits at the southern end of Tuscany and is a gem unlike most others in the region.
Volterra, known to the ancient Etruscans as Velathri, and to the Romans as Volaterrae, is a town in the western-central area of the Tuscany region of Italy. It is believed to have been continuously inhabited as a city since the 8th Century B.C., although the controlling powers have varied widely. Influences of these many and varied cultures appear throughout the city. It is a Bronze Age settlement of the Villanovan culture, and an important Etruscan center – one of the twelve cities of the Etruscan League. It was later ruled by the Romans, became a bishop’s residence in the 5th Century, an Episcopal center in the 12th Century, and later captured by the Florentines.
There are some interesting sights here, including the Volterra Duomo. It was enlarged in the 13th century after an earthquake and has significant art and religious features. Be sure to visit the Guarnacci Etruscan Museum with thousands of funeral urns dating back to the Hellenistic and Archaic periods. There is also the Roman Theatre of Volterra which dates back to the 1st Century B.C. that was excavated in the 1950’s. The Town Hall, located on Piazza dei Priori, dates back to the early 13th Century, taking nearly 50 years to complete between 1208 and 1257. There are also excavations of the Etruscan tombs in the Valle Bona area. Make sure you also have time to visit the traditional Alabaster workshops of Volterra, a craft that has been in existence since Etruscan times. The history of Volterra is outdone only by the breathtaking vistas of the town.
This central Tuscan city is distinguished by its medieval brick structures and Gothic churches. It has a fairytale quality, displaying centuries of craftsmanship and fine art. The Palazzo Pubblico dominates the fan-shaped Piazza del Campo, and the buildings surround the piazza in a fascinating circular fashion. The Gothic town hall is impressive, and Torre del Mangia, a slender 14th-century tower with sweeping views from its distinctive white crown dominates the skyline. Siena sits in the heart of Tuscany and is famous for its cuisine, art, museums, medieval cityscape and the Palio, the renowned horse race. The Palio is the most important event in Siena, taking place on July 2 and August 16 every year. In the Palio the various Sienese contrade, or areas in which the city is divided, challenge one another in a passionate horse race in the heart of the city in the Piazza del Campo. The excitement is palpable as the entire city participates and the streets become the racecourse. Each jockey represents his contrade and each has a color and coat of arms with a representative icon, such as a turtle, unicorn, dragon, or giraffe. If you are fortunate enough to be in Siena during the Palio, you must witness this unique tradition.
San Gimignano is known as the Manhattan of Tuscany for its skyline of remaining defensive towers. At one time as many as 72 towers loomed above the valley surrounding this hill town. Residents knew the value of vertical space and surrounding the triangular town square are town houses of four and five stories. Encircled by 13th-century walls, this town was a stopping place and reference point for anyone traveling along the Via Francigena road and pilgrimage route leading to Rome, serving as a protected place of respite. One can stroll the narrow streets to find chapels, fountains, frescoes, and beautiful detail in the stonework. If you happen to be in the area in June, be sure to attend the Ferie delle Messi or Medieval Harvest Festival. Step back in time into a fertility festival, which dates back to 1255. Contests between four distinct neighborhoods compete to win favor of the fertility gods. Archery, tug of wars, exhibitions, entertaining shows, and tests of skill between knights lead to the most awaited moment of the festival: the Corteo delle Messi or Grand Procession, where over 500 people in medieval costumes parade through the streets. The weekend festival culminates with the blessing of the horses that will carry their knights in a final battle of skill and bravery.
The city of the Italian Renaissance and the regional capital of Tuscany, is also considered by some to be one of the most beautiful cities in the world. This is a metropolis not to be missed on any tour of Italy. From ancient times until current day, Florence has been a center of banking and finance, high fashion, fine arts, and religious influence. Masterpieces of art abound. The Galleria dell’Accademia displays Michelangelo’s “David,” while the Uffizi Gallery exhibits preeminent works such as Botticelli’s “The Birth of Venus” and da Vinci’s “Annunciation.” One of the most popular and iconic sites is the Florence Cathedral with the rich architecture of its tiled arches and spectacular bell tower, as well as an abundance of artwork.
A center of finance through the ages, Florentine money has financed Kings, Popes, and Industry alike. The language spoken in the city during the 14th century was, and still is, accepted as the Italian language. Much of Italian Literature of the ‘golden age’ is associated with Florence, leading ultimately to the adoption of the Florentine dialect as a literary language of choice. Through two millennia artists, poets, architects, financiers, political and religious leaders have been inspired here whether passing through on major Trade Routes, or just by the immense beauty of the city and surrounding countryside. Whether you come to enjoy the arts, watch the latest in fashion on the runways of designers, or take in the energy that seems to flow and buzz through this place, it is one to be sure to place on your itinerary.
Greve in Chianti is a village famous the world over for its wine. Since early medieval times, Greve evolved as the principal market town at the center of an (The Chianti region supports a variety of agricultural activities, especially the grapes that comprise the world-famous Chianti and “Super Tuscan” wines. Each September there is a festival called the Chianti Classico Wine Festival, a four-day affair in which local merchants display their products, and wine tasting is free. Olive oil served on fresh sliced Italian bread is also available for tasting along with the delectable local cheeses. About a mile from the center of Greve is the castle of Verrazzano that sits atop a prominent hill. The surrounding land is bountiful and provides an array of products that make this town special. Extra virgin Tuscan olive oil is highly prized for its delicate flavor. Black and white truffle harvesting is a distinguishing feature of local food production. The region is also noted for its meat, including the Cinta Senese pig unique to this region, which produces pork of superlative quality. Wild game is a common feature on local menus, including rabbit, pigeon, venison, and especially, cinghiale (wild boar). Greve is home to one of Italy’s oldest and most renowned butcher shops, the Macelleria Falorni.