Vito (Billy) and Cristina’s “Hit the Road and Go” Italy Trip 2026 – 24 Places in 8 Days!

The trip began at Fiumicino, where we rented the car, a Citroën C3, and we chose to head north with the intention to ideally reach Ivrea, where Vito used to work for Olivetti, but we were willing to settle on getting to Genova if that were not possible… needless to say, we never made it that far north, but we did get close.

Even though we did not visit Fiumicino, here are a few words on this coastal town, where we go fairly often. It is just southwest of Rome, best known today as the site of Leonardo da Vinci–Fiumicino Airport. Its harbor still supports a working fishing fleet, and the seafront is lined with seafood restaurants. The beach area is actually very nice and well organized.

A small harbor town on the Monte Argentario promontory, guarded by three 16th-century Spanish fortresses built to defend the coast. The painter Caravaggio died here in 1610. Orbetello was an ancient Etruscan settlement, which in 280 BC passed under the control of the Romans, who had founded their colony of Cosa (near the modern Ansedonia).
The Roman family of the Domitii Ahenobarbi had a substantial property here, subsequently inherited by the emperor Domitian through his wife Domitia Longina. Domitian built other sumptuous villas nearby for his courtiers...…

Porto Ercole (Italian: [ˈpɔrto ˈɛrkole]) is an Italian town located in the municipality of Monte Argentario, in the Province of Grosseto, Tuscany. It is one of the two major towns that form the township, along with Porto Santo Stefano. Its name means “Port Hercules”. It is one of I Borghi più belli d’Italia (“The most beautiful villages of Italy”).

“It was an ancient and flourishing city already during the Etruscan period. It was the site of the Battle of Telamon in 225 BC between Roman and the Celtic armies.[2] After the Celts had overrun Etruria and killed 6000 Romans at Faesulae, they were advancing to Rome led by the Gaesatae kings Concolitanus and Aneroëstes. They were met by the Romans near Talamone and were defeated, 40000 Celts being killed. The decisive victory removed the Celtic threat from Rome and allowed the Romans to extend their influence over northern Italy.…”

“Siena was an important city in medieval Europe, and its historic centre is a UNESCO World Heritage Site, which contains several buildings from the 13th and 14th centuries. The city is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year in Piazza del Campo.…”

“he oldest part of the town is “Colle Alta”, with a well-preserved medieval centre. The village is entered through the ancient and monumental Porta Nova and winds its long and narrow way in a sequence of fine 16th- and 17th-century noble houses (notable are Palazzo Usimbardi, Palazzo Buoninsegni and the Town Hall) to the Palazzo Campana, which marks the entry to the Castle, the oldest part of Colle di Val d’Elsa. Here, the village is characterized by narrow paved lanes, 15th- and 16th-century noble houses (such as Palazzo Luci, Palazzo Morozzi, Palazzo Giusti, Palazzo Dini) and tower-houses, including the one where Arnolfo di Cambio was born. At the centre of the old town stands the Colle di Val d’Elsa Cathedral. Overlooking the valley stands the Convent of San Francesco. It turns out this town has a manufacturing history and is well known for “Crystal” production.…”

“San Gimignano (Italian pronunciation: [san dʒimiɲˈɲaːno]; named after St. Geminianus) is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. Known as the Town of Five Towers, San Gimignano is famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses,[3] which, with its hilltop setting and encircling walls, form “an unforgettable skyline”.[4] Within the walls, the well-preserved buildings include notable examples of both Romanesque and Gothic architecture, with outstanding examples of secular buildings as well as churches. The Palazzo Comunale, the Collegiata and Church of Sant’Agostino contain frescos, including cycles dating from the 14th and 15th centuries.[4] The “Historic Centre of San Gimignano” is a UNESCO World Heritage Site.[4] The town is also known for saffron, its dry-aged and saffron infused Golden Ham, pecorino cheese, and local white wine—Vernaccia di San Gimignano—produced from the ancient variety of Vernaccia grape grown on the sandstone hillsides of the area.…”

“Pisa is a city and comune (municipality) in Tuscany, Central Italy, straddling the Arno just before it empties into the Ligurian Sea. It is the capital city of the Province of Pisa. Although Pisa is known worldwide for the Leaning Tower of Pisa, the city contains more than twenty other historic churches, and several medieval and Renaissance palaces, mostly facing each other on the avenues along the Arno (“Lungarno”). Much of the city’s architecture was financed from its history as one of the Italian maritime republics.…”

“The first mention of Viareggio dates back to 1169 when a wooden tower guarding the coast was built. A little over two years later, in (1172) a military building named Turris de Via Regia was erected, taking its name from the road that linked it to Lucca (known today as via Montramito). In the following years the area around Viareggio, was involved in the hostilities between Pisa and Lucca, in their attempt to gain control over the coastal area. The conflict was spurred by the desire of the Lucchesi to finally gain access to the sea, and to the Pisane fear of the economic competition of its rival city. It is during these years that the feudal Lords of Versilia were forced to abdicate in favour of Castruccio Castracani. In the following years the area upon which Viareggio would eventually be built was marked by a number of minor battles, invasions and pillages. In addition, the area was also affected by the pestilence which, recounted by Giovanni Boccaccio in his masterpiece the Decameron, spread throughout the whole of Italy.…”

“Levanto first became the feudal stronghold of the Malaspina before passing to the Da Passano and then, in 1229, to the Republic of Genoa. In the Middle Ages, the village became a centre of commercial activity, benefiting from maritime and overland travel, the most important of the latter routes being the Via Francigena, the ancient pilgrims’ way that in medieval times connected Canterbury to Rome. In the post-Medieval period, the village saw major development with the construction of the Borgo Nuovo or Stagno, largely completed by the 17th century, on the plain of the small river Ghiararo. This area is characterized by painted 17th- and 18th-century houses, some built on much earlier buildings. A further phase of urban development took place at the turn of the 20th century with the opening of two new thoroughfares, the Corso Italia and Corso Roma. Beginning in 1950, the village experienced further growth, culminating during the 1970s in the present townscape.…”

“The first historical information regarding Monterosso date back to 1201, when the lords of Lagneto, owners of the castle of which today only some ruins remain, made an agreement with Genoa. In 1214 the Monterosso’s community was established, and the first fortifications were built to protect the hamlet from the invasion of the Saracens, so that this became the most majestic defense system in the Cinque Terre. The village loved by Eugenio Montale…”

“ Vernazza has a natural pier with a amphitheatre shape making it perhaps the most picturesque village of the Cinque Terre. Vernazza was a Roman installation and had a big strategical importance during the age of the Maritime Republics in Genoa. It was also famous for its carpenters. We suggest a walk in the village that is dominated by a watch tower and the “Castello” remains. In the small square, overlooking the seaside, there is the Church of Santa Margherita di Antiochia. Vernazza is the village with the safest and most convenient port in Cinque Terre. The seafaring skill of its people has been famous since the old times. Historically mentioned since 1050, it has enjoyed political importance and wealth, witnessed by the fashion of the houses, rich in balconies and arcades. Here as well the place-name comes from an old Roman family name, Vulnetia, whose slaves, after being set free, took possession of these lands. You can visit The Nostra Signora di Reggio Sanctuary, Church in the hills behind Vernazza (350 meter), dating from the 13th century. Take the Sentiero N° 8 to get there. …”

“Porto Vener was a former fishing village at the tip of a peninsula facing the Cinque Terre, with a row of tall medieval houses along the harbor and the Church of San Pietro perched on the rocks above the sea. A UNESCO World Heritage Site along with the Cinque Terre. The ancient Portus Veneris is believed to date back to at least the middle of the 1st century BC. It has been said that the name refers to a temple to the goddess Venus which was sited on the promontory where the church of Peter the Apostle now stands. The name has also been linked to that of the hermit Saint Venerius. In Roman times the city was essentially a fishing community. After the fall of the Western Roman Empire, Porto Venere became the base of the Byzantine fleet in the northern Tyrrhenian Sea, but was destroyed by the Lombards in 643 AD. Later, it was a frequent target of Saracen raids. First indications of the existence of a castle date from 1113, and in 1161 the walls were erected. Porto Venere became a fiefdom of a family from Vezzano before passing to Republic of Genoa in the early 12th century. In 1494, it suffered a devastating bombardment from the Aragonese fleet during their war with Genoa: subsequently the old part of the town declined in importance, giving way to the development of the Borgo Nuovo (“New District”), which had existed from 1139 and is centred on the church of St. Peter. On 2 December 1797, after the French established their domination in Italy, the town became part of the Department of the Gulf of Venus, with the capital in La Spezia, in the Ligurian Republic annexed to the First French Empire. From 28 April 1798 with the new French law, the territory of Portovenere fell in the seventh canton, as the capital, the Jurisdiction of the Gulf of Venus since 1803 and the main center of the third State of the Gulf of Venus in the jurisdiction of the Gulf of Venus. From 13 June 1805 to 1814 it was included in the Department of the Apennines. It was at this point which, in 1812, it became part of the coastal route called “Route Napoleon” in honor of the French general and now known as localized road 530, which still connects the marine center with La Spezia via Fezzano, Le Grazie and Terizzo…”

“A Tuscan city fully encircled by its Renaissance-era walls, which have been converted into a tree-lined promenade. Its historic center retains the oval footprint of the Roman amphitheater it was built over. he territory of present-day Lucca was certainly settled by the Etruscans, and it also has traces of a probable earlier Ligurian presence (called Luk meaning “marsh”, which was previously speculated as a possible origin of the city’s name), dating from the 3rd century BC. However, it was only with the arrival of the Romans that the area took on the appearance of a real town. It obtained the status of a Roman colony in 180 BC and of a municipality (municipium) in 89 BC.[12][13] The rectangular grid of its historical centre preserves the Roman street plan, and the Piazza San Michele occupies the site of the ancient forum. The outline of the Roman amphitheatre is still seen in the Piazza dell’Anfiteatro, and the outline of a Roman theater is visible in Piazza Sant’Agostino. Fragments of the Roman-era walls are incorporated into the church of Santa Maria della Rosa.…”

“Described by Livy as one of the Capita Etruriae (Etruscan capitals), Arezzo (Aritim in Etruscan) is believed[by whom?] to have been one of the twelve most important Etruscan cities—the so-called Dodecapolis, part of the Etruscan League. Etruscan remains establish that the acropolis of San Cornelio, a small hill next to that of San Donatus, was occupied and fortified in the Etruscan period. There is other significant Etruscan evidence: parts of walls, an Etruscan necropolis on Poggio del Sole (still named “Hill of the Sun”), and most famously, the two bronzes, the “Chimera of Arezzo” (5th century BC) and the “Minerva” (4th century BC) which were discovered in the 16th century and taken to Florence. Increasing trade connections with Greece also brought some elite goods to the Etruscan nobles of Arezzo: the krater painted by Euphronios c. 510 BC depicting a battle against Amazons (in the Museo Civico, Arezzo 1465) is unsurpassed. Roman pottery sherd from Arezzo, Latium, found at Arikamedu in India (1st century AD), an evidence of the role of the city in Roman trade with India through Persia during the Augustan period. Musée Guimet.…”

“Perugia, the historic hilltop capital of Italy’s Umbria region, began as one of the most powerful city-states in the ancient Etruscan Confederation before being absorbed by Rome in 310 BC. During the Middle Ages, it flourished as a wealthy, independent medieval commune, though it was frequently torn apart by violent feuds between rival noble families like the Baglioni. The Papacy seized direct control in 1540 following the Salt War, cementing its authority by building the massive Rocca Paolina fortress over a destroyed rebel neighborhood. Perugia bloomed artistically during this era as the cradle of the Umbrian school of painting, which included masters like Perugino. After joining the unified Kingdom of Italy in 1860, Perugia transformed into a vibrant modern city, globally celebrated today for its historic university, Perugina chocolate, and the annual Umbria Jazz Festival…”

“San Benedetto is an Adriatic resort town known for its palm-lined seafront promenade, planted with thousands of palm trees, and one of the larger fishing fleets on the central Adriatic coast.(internet). San Benedetto del Tronto was a martyr[7] and a soldier born in Cupra during the reign of Roman Emperor Diocletian. Shortly thereafter, following the edict of Constantine in 313 AD, some believers built a chapel around the tomb.[clarification needed] Since then, San Benedetto has been highly revered by locals. He later built a small church which included an apse facing the east and its entrance facing the west, in accordance with the early Christian tradition that the east, where the sun rises, and the sunrise is symbolic of Christ’s resurrection. Historians argue[who?] that archaeological findings indicate Roman origins, linking San Benedetto to the ancient city of Alba Picena on the right bank of the Albula river. …”

“A town in Abruzzo at the foot of the Gran Sasso massif, with a historic center of Roman and medieval remains, including a Roman theater and amphitheater. A settlement of the 1st millennium BC and some buildings of ancient Italic tribes were the object of archaeological excavations. The most ancient historical remains were found in the outskirts of the city, precisely in the neighborhood Madonna delle grazie, where, among many, a burial place with a dagger and a halberd were found. Allegedly, the development of the old settlement was due to the commercial center founded by the Etruscan civilization. According to the Roman author Sextus Julius Frontinus, the ancient Perut or Pretut (meaning “Hill surrounded by waters”) strongly developed in dimensions and importance until it became the capital of the Praetutii tribe.…”

“From Etruscan times Tibur, a Sabine city, was the seat of the Tiburtine Sibyl. There are two small temples above the falls, the rotunda traditionally associated with Vesta and the rectangular one with the Sibyl of Tibur, whom Varro calls Albunea, the water nymph who was worshipped on the banks of the Aniene as a tenth Sibyl added to the nine mentioned by the Greek writers. In the nearby woods, Faunus had a sacred grove. During the Roman age, Tibur maintained a certain importance, being on the way (the Via Tiburtina, extended as the Via Valeria) that Romans had to follow to cross the mountain regions of the Apennines towards the Abruzzo, the region were lived some of its fiercest enemies such as Volsci, Sabines, and Samnites… “