Italy Tour Itinerary
The following provides a rough overview of areas that we will visit to give you an idea of our tour. It is preliminary and based upon our 2007 tour we will make changes to improve our tour of Italy for 2008!
Day 1
Sunday, 31st August
Transfer from Florence to Pienza:
Pienza displays a stunning unity of style, especially in its main square, and is a perfect example of Renaissance town planning as commissioned by Pope Pious II, a humanist philosopher who wanted to build the ideal town.
Lodging: Pienza
Day 2
Monday, 1st September
Pienza loop ride:
Montepulciano An attractive Renaissance town occupying a remarkably picturesque setting on the top of a tufa hill that separates two valleys. Poets have long sung the praises of its ruby-red wine (Vino Nobile). Antonio da Sangallo the Elder of the famous family of Renaissance sculptors and architects bequeathed some of his most famous works to the town.
Bagno Vignoni This hamlet has long been renowned for its spring water which was reputed for its effectiveness in the treatment of arthritis and rheumatism as far back as Roman times. The houses cluster around an old bathing pool flanked by Saint Catherine’s Portico – the saint is reputed to have come here at the end of her life.
Montalcino This hillside town, which still has part of its 13th century walls and its fortress, is known throughout Italy for its excellent red wine, Brunello, a high quality vintage from a restricted wine-growing area. Every autumn during the Thrush Festival, the four districts of the town recall the past with a parade in medieval costume and an archery contest.
Abbazia di Monte Oliveto Maggiore The huge pink brick buildings of this famous abbey nestle among the cypress trees in a landscape of eroded hills Mount Oliveto is the mother-house of the Olivetians, a congregation of Benedictine monks founded in the early 14th century
Lodging: Pienza |
Tour Details:
15 Days / 14 Nights
Travel Dates:
August 30 - September 14, 2008
Trip Start / End Location:
Florence, Italy
Cost:
$2995 per person / $5990 per tandem team
Average Mileage:
Approximately 50 miles per day

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Day 3
Tuesday, 2nd September
Pienza to Monte San Savino:
Lucignano This peaceful village in the Val di Chiana has an unusual shape, the main street rising in spirals before entering a picturesque maze of medieval streets.
Monte San Savino The medieval town has a thoroughfare lined with fine historic buildings that links the two gates set within the walls of the old stronghold. The sculptor and architect Sansovino (1470 – 1529) was born here.
Lodging: Monte San Savio
Day 4
Wednesday, 3rd September
Monte San Savino to Cortona:
Cortona The town (of “Under the Tuscan Sun” fame) occupies a remarkable site on the steep slope of a hill overlooking the Chiana Valley not far from Lake Trasimeno. It belonged to the league of 12 Etruscan towns before coming under the control of Rome. Cortona has retained its medieval town walls commanded by the huge citadel and the town has barely changed since the Renaissancce, with fine mansions and steep paved streets leading to irregularly shaped squares lined with arcades and impressive public buildings.
Castiglion Fiorentino small, walled city in eastern Tuscany, in the province of Arezzo, between the cities of Arezzo and Cortona. It is well known for its annual festivals and Etruscan archeological site.Castiglion Fiorentino lies at the centre of a triangle formed by important cities such as Florence, Siena and Perugia. Like many of the small towns of the Val di Chiana, Castiglion Fiorentino’s history begins in the Etruscan and Roman periods (4th - 6th century B.C.). The original name of the town was Castiglion Aretino (for Arezzo) until the Florentines seized the town and changed the name to Castiglion Fiorentino in 1384.
Lake Trasimeno (in Italian: Lago Trasimeno), is the largest lake in peninsular Italy with a surface area of 128 km/sq, just slightly less than that of Lake Como.Historically, Trasimeno was known as “the lake of Perugia” and this name makes it easy to understand the importance that the lake has always had for the whole of north-western Umbria and for the Tuscan Chiana district. A significant battle took place on the north shore of the lake in April 217 B.C. during the Second Punic War.There are three islands in the lake. The second largest, Isola Maggiore, is the only inhabited one. The small fishing village, which reached its height in the 14th century, today has only around thirty residents. Most of the buildings, including the ruins of a Franciscan monastery, date from the 1300’s.
Lodging: Cortona
Day 5
Thursday, 4th September
Cortona to Città di Castello:
Monte S. Maria Tiberina is a beautiful tiny medieval hilltop town dominating the Upper Tiber Valley.
Citta di Castello The town has a beautiful historic centre, many grand buildings and the second most important art museum in Umbria (after the National Gallery in Perugia), containing most notably works by Raphael, Vasari and Signorelli. The Collezione Burri houses the main collection of Alberto Burri’s work – the town’s favorite son began his art career in 1946 after he returned from being held as a prisoner of war in Texas.
Lodging: Città di Castello
Day 6
Friday, 5th September
Città di Castello loop ride:
Sansepolcro The town is best known as the birthplace of Piero dell Francesca. The Museo Civico has some of his works, the most famous being the Resurrezione (Ressurection) The town has a cathedral founded in the 11th century,. There is also the Aboca museum, housing displays dedicated to the history of pharmacy and herbal medicine, and a re-creation oif a 17th century laboratory. The Palio della Balestra is a crossbow contest between the men of Sansepolcro and the men of Gubbio, held on the second Sunday in September - participants dress in medieval costumes and use antique weapons.
Lodging: Città di Castello
Day 7
Saturday, 6th September
Città di Castello to S.Angelo in Vado :
Sant’Angelo in Vado is one of the towns richest in history and art of Le Marche region, it has a well preserved medieval historic center surrounded by its walls and the streams of Metauro river. The area of Sant’Angelo is also known for the “Tartufi” the truffles, a local delicacy known all over Italy.
Lodging: Sant’Angelo in Vado
Day 8
Sunday, 7th September
S. Angelo in Vado loop ride:
Urbino, wonderful Renaissance pearl in the heart of Le Marche. Its Ducal Palace, built for the grand duke Federico da Montefeltro, with its stately rooms, towers and magnificent courtyard forms a perfect example of the architecture of the time. Today, the building still houses the Galleria Nazionale delle Marche (The Marche region National Gallery) with precious paintings by Piero della Francesca, Laurana and Raphael, whose house has been transformed into a museum.
Lodging: Sant’Angelo in Vado
Day 9
Monday, 8th September
S. Angelo in Vado to Gubbio:
Gubbio, one of the most ancient towns of Umbria, is a medieval town of white limestone very well preserved in the centuries and a true masterpiece of the 13th-14th century architecture rich in monuments and buildings that acknowledge its glorious past.
Lodging: Gubbio
Day 10
Tuesday, 9th September
Gubbio to Assisi:
Assisi: There is perhaps no other place on earth that is as tied to its famous son as Assisi is with Saint Francis, who was born here in 1182. Founder of the Franciscans, he became the patron Saint of Italy in 1939.Possibly the quintessentially perfect Italian hill town, The history, architecture and art of Assisi are among the best to be found in Umbria. Perched on the slopes of Monte Subasio, its buildings shimmer in the sunlight. The Basilica di Francesco is the town’s main draw.
Lodging: Assisi
Day 11
Wednesday, 10th September
Assisi loop ride:
Torgiano The Tower of Janus, that where the name Tor-Giano comes from even if in this tiny town there is another roman god that is now ruling, he is Bacchus! Torgiano is a very well known red wine area.
Deruta A beautiful small medieval town, the Italy’s capital of majolica ceramics
Lodging: Assisi
Day 12
Thursday, 11th September
Assisi to Spoleto:
Eremo delle Carceri This is the hermitage to which St Francis retreated to after hearing the word of God. Apart from a few fences and paths, everything remains as it was when Francis lived there.
Spello is an enchanting and very beautiful little town in the foothills of Monte Subasio. The narrow cobblestone streets provide a fascinating. The colorful L’Infiorata del Corpus Domini is the most beautiful festival and carpets of flowers decorate the streets.
Bevagna This quiet town began as an Umbrian settlement, became Etruscan and finally became a Roman Municipium on the Via Flaminia. The Roman Mosaic Museum of Antiquities has a well preserved tile floor from ancient Roman baths – there are also the remains of an old Roman theatre. At the end of June, The Festival of the Gaite takes the town back to medieval rimes – you can buy all kinds of medieval inspired handicrafts and food. The Sagra della Lumaca (Festival of the Snail) takes place in August.
Trevi This town calls itself the “Slow City” – it has largely avoided the hustle and bustle of the growing Umbrian tourist industry. Trevi spawned the world’s first pawn shop and the first press association. The olive oils produced in the hillsides around Trevi are amongst the best in Italy.
Montefalco The excellent and highly acclaimed Sangrantino wine is produced here. The Museo Civico has a moving fresco cycle about the life and works of St Francis.
Lodging: Spoleto
Day 13
Friday, 12th September
Spoleto loop ride:
Todi A favourite weekend destination, the charm of Todi continues unabated. Perched on its impregnable rocky hill, the Medieval flavour of this town rich in monuments and things to see continues to attract quality tourism from Italy and abroad.
Appenine Mts challenging ride towards the remote mountains that surround the Spoleto valley
Umbra Vale relaxing ride on the minor roads of the valley
Lodging: Spoleto
Day 14
Saturday, 13th September
Transfer from Spoleto to Florence:
Our transfer back to Florence will take approximately ½ a day, giving us an afternoon free to explore the city.
Lodging: Florence
Day 15
Sunday, 14th September
Depart for home or other desitnations.
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