Umbria private tour
Every itinerary that I propose can be changed to accommodate your desires.The day trip start in general at 8.00 am and it is about 8 hours long:

Assisi

Although Umbran in origin, Assisi was influenced by the nearby Etruscan settlements. Under the name Asisium, it became a flourishing Roman municipality. At the beginning of the 3rd century A.D., the martyr Rufino, the first bishop of Assisi, introduced the Christian faith.
After the fall of the Roman Empire, Assisi was razed by Totila and the Goths (545 A.D.), recaptured by the Byzantines, conquered by the Lombards. Subject for a considerable period to the Duchy of Spoleto, it flourished again during the 11th and 12th centuries with the first experiments as an independent township, but soon it was troubled by wars. Subdued by Barbarossa, it was here that Federico II was educated. St. Francis and St. Claire were born here during this period (the former in 1181 or 1182, the latter in 1193 or 1194).
Besides imperial and papal dominion, Assisi was subject at various times to the Perugians, the Viscontis, the Montefeltros, the condottiere Braccio Fortebraccio, and the Sforzas. It was torn by feuds between the Upper and Lower parts of the town (Parte de Sopra and Parte de Sotto). From the 16th century to 1860, except for the brief Napoleonic period, it was part of the Papal States.

Orvieto

The city of Orvieto exists in symbiosis with the tuff cliff on which it stands, an extraordinary example of the integration of nature by the work of man. An example of the fact that our ancestors were aware of this relationship between architecture and nature is the inscription on the famous well of San Patrizio which reads: quod natura munimento inviderat industria adiecit (What nature denied for defence - in this case water - was added by the work of man).
Visiting this town means journeying through history, for traces of each and every period of the almost three thousand years of its existence crop up everywhere in this preconstituted physical entity. The two statues of Boniface Vlll set in the city gates at the opposite ends of the town suggest an ideal itinerary for the tourist of today, for the Pope entered the town through the Porta Soliana, known later, after the "Rocca" or Fortezza dell'Albornoz was built, as Porta Rocca, and he left through the Porta Maggiore.
Boniface Vlll was anything but a tourist and had even been Capitano del Popolo in Orvieto, yet somehow these two statues, which earned him no less than a charge of idolatry, can serve as symbols both of the attention the city of Orvieto so truly merits, and the traditional hospitality of its inhabitants. Nowadays one no longer has to reach the top of the cliff on a mule, for a modern system of "alternative mobility" provides an access to the town that is both easy to use and fascinating with the funicular (run by water in the nineteenth century and now completely modernised) at one end and a lift and an escalator are at the other, signs that the old historical centre, built on a human scale, has been returned to citizens and tourists alike and is once more the realm of the pedestrian.

Spoleto

An important Umbrian centre, in the 3th century it began to come in the Roman orbit, until it became a colony, called Spoletium, in 241 B.C.. The town remained always loyal to Rome, especially during the war between Hannibal and the Romans, when it repelled the enemy. In about 100 B.C. it was, according to what Cicerone says, one of the richest and most beautiful colonies in Central Italy, and in 90 B.C. it became Municipio optime jure, belonging to the Horatia tribe; it was also Caio Melisso's native city.
Then the town followed the vicissitudes of the Roman Empire: it was converted to Christianity, and was invaded by barbarian tribes – passed there Teodorico, Belisario, Totila and Narsete. Later Spoleto was occupied by the Longobards and became the capital of the important Duchy of Spoleto, which began in 569 with Faroaldo I. On the fall of the Longobard dominion the Duchy passed under the rule of the Franks, and when their empire was dismembered, the dukes of Spoleto aspired to the imperial crown itself: the plan could not be realised because of the German intervention led by Frederick Barbarossa who, come to Italy to meet the Pope, destroyed the town in 1155. Contended between Empire and Papal State, Spoleto was finally subjected to the latter from 1247. .
After long years of struggles between Guelphs and Ghibellines the town was pacified by Cardinal Albornoz and became a very important centre: among its governors there was also the famous Lucrezia Borgia, in 1499. Spoleto passed through centuries of history in the ultra-conservatism of the Papal State, alternating periods of greater or lesser splendour, without any shocks until the French occupation: in that period the town became chief town of the Trasimeno District, surpassing in importance Perugia itself. After the Restoration Spoleto was a seat of the Papal Delegation: the papal rule lasted until 17 September 1860, when the town was incorporated in the Kingdom of Italy. Spoleto is a splendid town: characteristic corners and historical suggestions; a place where one can understand the importance of the relation between man and nature, and between history and landscape; a magic, harmonious place, perfect scenery to represent the marvels and the enchantments of the Festival of Two Worlds.

Gubbio

Gubbio was a very ancient Umbrian settlement, testified by the famous EUGUBINE TABLETS: they are seven bronze sheets, now visible at the Civic Museum, discovered in the 15th century, written in Umbrian language using the Latin and the Etruscan alphabets, fundamental epigraphic document of the Umbrian civilization; dating to the end of the 2nd century BC, they report religious prescriptions, information about places and about the government system of the town. Allied with the Romans in the beginning of the 3rd century BC, Gubbio in 90 BC became Municipium belonging to the Crustumina tribe; it was an important centre during the Empire, and was later destroyed by Totila.
Gubbio recovered and by the 11th century it had become an independent and important Commune, first Ghibellin, then Guelph. In 1350 the town became a seigniory ruled by the Gabrielli, and after various events – rebellions, armed intervention by the Papal State, popular government – the town submitted itself to the Montefeltro's rule, enjoying a long period of peace and prosperity. In 1508 the Montefeltro were succeeded by the Della Rovere and the last member of this family ceded the town to the Pope in 1624. Later there was the annexation to the Kingdom of Italy.
Gubbio is surely one of the most picturesque and characteristic towns, not only in Umbria but in Italy, thanks to its nearly intact medieval aspect: set in the higher part of a plateau at the foot of Mount Ingino, it has a rather simple plan, that is five parallel streets running at different levels on the slopes of the hill and connected each other by alleys. The buildings are mainly Romanesque in shape, with ogival arches inserted; typical of the town is the so-called door of the dead, a narrow pointed arch door placed above street level, which, according to tradition, was reserved for the passage of coffins. Much more reliable the other interpretation explaining it as the main entrance to the house, placed above shops or warehouses: by retracting, in the evening, the wooden steeps, the house was more protected and safe even in the dark of the Middle Ages.

Perugia

The history Perugia dominates the Tiber Valley from a high, irregular and rough hill: the particular feature of the land has generated a wide variety of urbanistic situations, giving the town a very special aspect. The rich artistic and cultural patrimony and the natural environment make Perugia an unique city of major importance, and this from the beginning of its history. Perugia lies on a hill inhabited ever since the prehistoric times; it was first a settlement of the Umbrians, then it passed under the rule of the Etruscans, becoming one of the most important cities in the High Tiber Valley.
Conquered by the Romans, Perugia was deeply involved in the civil war between Antonio and Ottaviano; this latter took possession of the town in 40 B.C. and this, after being heavily destroyed, was given the name of "Augusta". After the fall of the Roman Empire Perugia was destroyed again by Totila in 547; then it belonged to the Byzantine dominions, and finally it became a powerful independent city-state allied to the Papal State. The 14th century was characterised by violent struggles between Nobles (Beccherini) and Populars (Raspanti) and by the war against the Pope who wanted the Umbrian cities to be under his rule; the war finished with the Peace of Bologna in 1370, when Perugia was forced to recognise the Papal authority.
Also in the following centuries the town continued to be divided into various rival factions fighting to come to power: the Popular government leaded by Biordo Michelotti was replaced by the sway of the soldier of fortune Braccio Fortebraccio; the leading families were always making conspiracies and massacres, causing a grave moral and political decline. In 1540 Perugia was placed under the direct control of the Papal State and pope Paolo III ordered to Antonio da Sangallo the erection of the Rocca Paolina, symbol of the papal power over the city. The papal rule continued – brief breaks excepted during the French occupation and the Roman Republic – until the formation of the Kingdom of Italy in 1861. Perugia today is a modern and cosmopolitan city known all over the world because of its cultural events and the University for Foreigners. Proud of its historical traditions and the beautiful buildings of the past, Perugia let itself be admired in its thousand picturesque corners where present and past integrate one another and create an unforgettable atmosphere.

Todi

We don't know the exact year when the town of Todi was founded - some chroniclers indicate 1955 B.C. - but we know without doubt that it was first inhabited by Umbrian tribes, later by the Etruscans. The name derives from the term "tular", "border": the town marked for a long time the border between the Etruscan and the Umbrian territories. In the 3rd century B.C. the Romans conquered Umbria and since the 4th century Christianity spread all over the region: the new doctrine arrived in Todi with S.Terenziano, first bishop of the town and martyr under the Emperor Adrian. Very important was also the figure of the bishop Fortunato, who led the citizenry in the struggle against the Goths.

In the Middle Ages Todi assumed the feature of a medieval castle and it was ruled by feudal barons such as the Arnolfi, the Montemarte, the Atti. After 1000 A.D. the town expanded: commerce and handicraft return to flourish, the heads of the arts and craft associations - the Priors - began to be very important, and Todi was a free commune since the first years of the 12th century. In 1236 came into the world, in Todi, Jacopo dei Benedetti, called Jacopone, one of the most important figures of Franciscanism. Later Todi belonged to various dominions, and after this period the town was placed directly under the central power of the Papal State, which finished in 1860, with the Unification of Italy. The 20th century has made Todi famous all over the world: for its historic monuments, the fascination of its medieval atmosphere and the unique beauty of its countryside.

Cortona

From the ETRUSCAN ORIGINS UNTIL the RENAISSANCE the city of Cortona has a richer and far more important history: as all the small centres also ours do not escape to that custom, it had noble and famous origins, to give fame to itself. It is said that Cortona had been founded from the Dardano hero, which must be also the foundation of Troy. The simplest one is that the foundation of Cortona was due to the splendour of the Etruscan civilization, inside a precise function in their civil context, military and religious. According to Livio, Cortona was quite one of the twelve Lucumonìe of the Etruscan state: and the importance it had is confirmed by testimony walls and the tombe of the outskirtses, beyond the objects of refined and good handicraft in bronze and pottery recovered in the within of the city.
Later under the roman dominion, the history of Cortona identifies with that one of other small centre, far away from the imperial magnificence and with dark and absolutely impersonal vicissitudes. We only know that in the 450 b.C. it endured the destiny of Rome: the Goti occupied it and they made of it one city even more anonymous. Only in the ' 200, with prevailing of the Common ones, the city of Cortona revives to new splendour; the dominion is increased, begins the fights with the near centres for the control of near by territories, until 1258, when the city was occupied from Aretini and the inhabitants were forced to the exile. It begins to this point the rise of the family Casali, than for approximately two centuries it will have the lordship of the city. After having the Cortonesi back in native land, in means to fights, intrigues and periods of tranquillity, the wealth Casali gave to Cortona one prosperity never enjoyed until then.
To the beginning of XV the century, in 1411, Ladislao, King of Naples, who had occupied the city, started a market with the republic of Florence. From this moment Cortona loses its autonomy and it returns to being a subject territory, is pure remaining adherent to its noble traditions and customs. Its history does not have greater moments, even if illustrious personages bring themselves to the light especially in the artistic field: Luca Signorelli, Francesco Laparelli, Pietro Berrettini. After the unity of Italy, Cortona, that has lived without troubles the passage from the Grand-duchy of Tuscany to Italy, finally rejoined, continues living calmly, from the traditions of the past, more than trying to set off towards the future. Therefore, the impression it gives, is of a calm city , far from the troubles and changes more intentional, from the modern civilization.