These itineraries for fantastic day trips between Florence and Rome are inspired by the famous pilgrimage route called the Via Francigena. From Rome there are so many amazing stops you can make on your way to Florence, so don’t waste a day of your vacation, book a transfer tour with us based on your interests. Here are a few detailed itineraries to get you excited about all there is to see in Italy, including Viterbo, Montefiascone, Lake Bolsena, Acquapendente, Radicofani,  Val d’Orcia, Bagni San Filippo, Montepulciano, Pienza, Montalcino, Siena, San Gimignano and San Donato.

What is the Via Francigena pilgrim route?

The Via Francigena is a series of trails and roads that follow in the footsteps of the pilgrim Sigeric, Archbishop of Canterbury, who traveled this route in 990 from Canterbury, England all the way to Rome. The route then became popular among Christian pilgrims and was named “Via Francigena” because it went across France.

When traveling by car, we can loosely follow this route by driving along the SR2 or Via Cassia that lies on the ancient Roman road that was built to connect Rome to Siena and Florence. It is a unique route with only sporadic traffic and provides a relaxing and enjoyable journey filled with beautiful and dramatic landscapes and sights and historical stops that is perfect for exploring on a day trip from Rome to Florence.

Sutri

As you leave Rome comfortably seated in a luxury vehicle with your luggage stored conveniently in the trunk, we will head north towards Viterbo and in no time at all we will be in the town of Sutri, built on a tuff rock. In the 4^th century BC, Sutri was initially a Latin colony before becoming Roman. The town is remarkable for its Roman Theater and a Mithraeum cave-like structure located in the crypt of the Madonna del Parto church. A stop, no matter how short, is worth it to see this amazing place.

Viterbo

After Sutri, we will continue heading north and in a little over half an hour arrive to the city of Viterbo. Due to the frequent presence of popes over the centuries, Viterbo was nicknamed the City of Popes. A Gothic papal palace was even built in 1255-67, whose elegant Loggia is the main attraction. The Papal seat became famous for witnessing a conclave held in 1271 for the election of Pope Gregory X.

The conclave, in fact, seemed that it would never end so the local citizens took matters into their own hands and locked all the participants inside to speed up the election of the new Pope. The Papal Palace is still one of the most important sites in the city today.

In the same square as the Papal Palace, designed over an ancient acropolis, is the Cathedral of Viterbo named San Lorenzo (St. Lawrence). In the 12^th century, the church was built over another small church dating to the 7^th century dedicated to the same St. Lawrence. In 1570, the present façade was added and the interior was later restored in Romanesque form. Notable as well is the 12^th century bell tower. The most picturesque quarter of Viterbo is the nearby San Pellegrino. It shows a typical medieval settlement with elegant houses provided with profferlo, which are  external staircases that were standard in the Middle Ages. Viterbo is one of the only places you can still see this type of architecture today.

And lastly, don’t miss enjoying the wonderful Viterbo fountains that embellish the city center, such as Piazza Della Rocca, Piazza Fontana Grande, Piazza delle Erbe, and Piazza Della Morte. If you are staying for longer in Viterbo, you can even enjoy one of the local thermal baths made of volcanic pools with hot sulfurous thermal waters and mud. These thermal baths have been in use since the Etruscan age and all the populations that came after including the ancient Romans and the medieval period (including plenty of popes) up to the present day. One of them is even named the Pope’s bath.

Montefiascone and Bolsena Lake

Continuing north along the Cassia Road, our next stop will be Bolsena Lake, the largest volcanic lake in Europe, formed by the collapse of the volcanic apparatus Vulsinio. The area emptied and collapsed following the volcanic eruptions, creating a vast caldera filled with water. Montefiascone is situated in a panoramic position on the top of a hill, crowned by a cathedral, overlooking Bolsena Lake. The Church of San Flaviano, dating back to the 12^th Century, consisting of two overlapping buildings, is the most interesting site to visit. This area is an important agricultural center that is famous for its wines, including the wine Est!Est!Est!, which means East!East!East! in English, the stuff of legends.

In 1111 AC, Enrico V from Germany went to Rome to be crowned the Holy Roman Emperor, traveling with Johannes Defuk, a bishop and wine expert. Both men were always looking for great wines to taste and so their servant, Martino, was commissioned to visit the places before their arrival to discover the best wines. Martino was told to write “Est” on the door, which translates to “there is,” a signal to his masters traveling behind him that there was good wine in this establishment. He was apparently so impressed with one wine that he wrote “Est!Est!Est!” and that is how the wine Est!Est!Est! got its name.

Bolsena

Proceeding along the lake, the next city worth visiting is Bolsena. At first glance, Bolsena appears like a typical medieval city, with the castle on the hilltop facing the lake. But Bolsena has a big story to tell…

Bolsena is known for being the city of the Eucharistic miracle in 1263. Transubstantiation is the Roman Catholic belief that during Mass the bread and wine are transformed into Christ’s body and blood. The story of the Eucharist miracle says that a priest, Peter, from Prague had significant doubts about transubstantiation while celebrating the Mass in the Basilica of St. Christina. Suddenly, the host bled on the corporal, a cloth covering the chalice. On August 11, 1264, Pope Urban IV issued the festivity of Corpus Domini. The Corporal of Bolsena was eventually moved to Orvieto where it is displayed in a rich reliquary.

Bolsena has a castle just like all other medieval cities, a towering fortress built-in 1156 by Pope Adrian IV that was later passed to the Monaldeschi family. There is a legend regarding the castle as well, reporting the presence of a ghost that is often felt by visitors, especially in the living room, known as the “ghost’s room.” Many people have reported feeling like they were being watched while admiring the room’s frescoes.

San Lorenzo Nuovo

In 1157, Adrian IV, after building fortresses in the Papal States, built a castle along the nothern Bolsena lakeside. Unfortunately, the area was very swampy and often got flooded. Therefore, in 1794, Pope Clement XIV moved the previous town to San Lorenzo Nuovo. This name means the new San Lorenzo, located 3 km above the hill, overlooking the lake by the modern Cassia Road. Only some of the castle’s ruins remain in the place of the old site. The construction of the new city took 5 years and the architect assigned to the job was Francesco Navone, who designed the town with an octagonal perimeter. The Parish church of San Lorenzo Martire has a few significant masterpieces such as two Vasari paintings, a splendid wooden cross from the 12^th century and a marble bust representing Pope Pius IV attributed to the Canova pupils.

An old gastronomic tradition in San Lorenzo Nuovo is cultivating a local kind of bean named the “fagiolo secondo.” The name means “second beans given” and they are called this because the seeding is only after the wheat harvest in late June and they are not harvested themselves until August.

Acquapendente and Radicofani

The next two cities on this fantastic route are Acquapendente and Radicofani.

Acquapendente is the last city of the Lazio region, and Radicofani represents the first town across the border into Tuscany. In the past, they were border cities of the Papal State and the Gran Duchy of Tuscany.

Acquapendente is a tiny medieval city between the Paglia River’s right bank and the Cassia Road. It has Etruscan origins and later became a Roman town before the Lombard people occupied and destroyed it. In the 10^th century, the town was reborn due to the Francigena road, which brought sudden growth. The Cathedral of the Holy Sepulcher is a Romanesque church, which is the most interesting site due to holy relics, such as stones stained with Christ’s blood. Due to the surrounding natural environment, which is incredibly green, Acqaupendente has also been nicknamed the Green Jerusalem.

Radicofani is the highest city along the Cassia Road. It’s fortress holds a dominating position over the most famous Tuscan Valley: the Val d’Orcia. In this area of Tuscany the scenery becomes dramatic and full of incredible colors that change with the seasons. Radicofani’s main attraction is “La Rocca,” also known as the Ghino di Tacco Castle. Its construction dates back to 978 by the Carolingians. Radicofani has a tiny population, just a bit more than 1000 inhabitants. San Pietro is the name of its Romanesque Church, which houses important works by Andrea Della Robbia.

Tuscany Itinerary Number 2-  Val D’Orcia, Montepulciano, Pienza, Bagni San Filippo, Bagno Vignoni and Montalcino

This itinerary goes through some of the most beautiful and stunning landscape in all of Tuscany on your private transfer from Rome to Florence or vice versa. If you are a red wine lover, then visiting the land of Brunello di Montalcino or Nobile di Montepulciano is surely high up on your list of priorities. We can take you to the best wineries for a tour and tasting and then show you the magic of charming villages like Montalcino or the thermal baths of Bagno Vignoni. Join us for a customizable private transfer on your next trip to Italy. Keep reading to learn what special places you can visit.

Val D’Orcia

From Rome, we will make our way north to Tuscany and arrive to the Val d’Orcia, a stunning valley that is one of the most celebrated landscapes in all of Italy.  This beautiful landscape appears in countless works of art from Renaissance painting to modern photography. In 2004, the Val d’Orcia became a UNESCO World Heritage Site. We will take you to stunning lookouts so you can create your own memories taking photographs and enjoying the rolling hills covered in wheat fields, vineyards and olive orchards.

Montepulciano

Montepulciano appears perched on a hill at 605 meters above sea level and dominatis the vast Val d’Orcia. Montepulciano has Etruscan origins, and is filled with shops and museums. One of the most famous places to shop is a tiny coppersmith workshop because the owner became famous after the guidebook writer Rick Steves shopped there several times and included him in his guidebook.

Piazza Grande is the main square, it hosts a 17^th century cathedral with an unfinished facade. Palazzo Comunale is similar in style to the Palazzo Vecchio in Florence. Other palaces that are located in the main square were once owned by nobility and now house museums or hotels.

One of the best aspects of Montepulciano is the excellent wine produced in the surrounding countryside, the famous Nobile di Montepulciano. Nobile wine is considered to be one of the three best red wines in Italy. The wine is prized for its unique qualities that come from the terroir and unique microclimate generated by the big hill. Nobile wine is made with Sangiovese grapes and requires years of aging.

The hilltop of Montepulciano has other precious secrets; below the imposing palaces are ancient caves that are perfect for aging wine, among other things. In fact, two of the most important local wineries have their cellars in this type of cave. Montepulciano’s soil is made of tuff stone, therefore it is very soft and easy to shape and excavate.

Because of this unique soil, it is not surprising that we will encounter typical Etruscan chamber tombs with primitive frescos in the area. Moreover, you can easily see fish fossils in the walls of the tuff vault. But why are there fish fossils at an altitude of 605 meters? The answer might surprise you: in the primitive ages Montepulciano was under the sea!

Pienza

Just a few minutes from Montepulciano is the second gem of this fabulous area: Pienza. This small city was created at the behest of Enea Silvio Piccolomini, who later became Pope Pius II. He was born in Corsignano, a tiny village with a few houses right next to Pienza. Upon becoming Pope, he decided to build a brand new city in 1462, including the new humanist features. He commissioned Bernardo Rossellino, a Florentine architect influenced by Giovan Battista Alberti, one of the greatest humanist architects. He designed the city which became known as the flagstone of the humanist philosophy: the ideal renaissance city.

But Pienza is not just about beautiful architecture, it is famous around the world for its delicious Pecorino cheese. Since ancient times, this extraordinary cheese has been made in the surrounding countryside. Pecorino is a cheese made from sheep milk and you will see lots of flocks of sheep grazing in the open fields as you drive along the country roads. Walking down the main street of Pienza you can smell the Pecorino cheese everywhere and if you pop into one of the pecorino cheese shops you can try a free taste and even have them ship the cheese home directly to your house.

Bagni San Filippo & Bagno Vignoni

In the Val d’Orcia area, you will be in close proximity to several hot spring locations, including Bagni San Filippo and Bagno Vignoni. Located at the bottom of the medieval hilltop city of Castiglion D’Orcia, Bagni San Filippo has unique hot spring waters filled with calcium carbonate, which forms white deposits and waterfalls.

Bagni Vignoni has more extensive hot springs and is renowned among tourists because of hotels featuring deluxe spas. Bagno Vignoni is also nicknamed “the bath of the Medici family,” for its famous visitors including Lorenzo the Magnificent, Pope Pius II, Santa Caterina di Siena, and many artists. The hot springs have been used since the Etruscan period and through ancient Roman times. At the entrance of the small city, there are Roman bath ruins as well as a large rectangular basin in the middle of the village, which is a hot spring water source. It has been used since the 16^th century to collect the waters from below.

Montalcino

As you head towards Montalcino, we will pull over so you can admire and take pictures of the stunning Val d’Orcia landscape below. This spot is famous because it appears in the film Gladiator in the scene when General Maximo returns home. Once you reach Cassia Road, another photo stop is a must at the famous circular group of cypresses trees in the middle of a field.

Now we will leave the main road and take the secondary road that winds its way up to Montalcino. Driving up the hill you will see that the farming activities in this area  are 99% grape production. Vineyards surround you on all sides!

Brunello di Montalcino wine

We could fill a book with interesting facts and praise for Brunello di Montalcino wine. Someone once described Brunello as the “Nectar of the Gods” and perhaps no better definition can be found to describe this top wine that is aged to perfection.

Brunello di Montalcino is known worldwide as the top Italian wine made from Sangiovese Grosso grapes. The unique terroir and microclimate of this area determine the powerful flavors that exist only here, and are impossible to recreate in other areas. To make Brunello di Montalcino wine, the winemakers select only the best grapes (1/4 of the total production). All the other grapes are left for other types of wines, such as Rosso di Montalcino. The most essential rule for making Brunello di Montalcino is aging it in oak barrels and then in the bottle. The wine is aged in oak Slavonian casks or French oak barrels after the first fermentation process. After this process, the bottle can be labeled with a DOCG certification. The label includes the farm’s name (vigna), the vintage year, and the serial number of each bottle. DOCG stands for Denominazione di Origine Controllato e Garantita or Controlled and Guaranteed Denomination of Origin.

If you are a wine lover, let us know ahead of time and we will book you for a tour and tasting at one of the top Brunello di Montalcino wineries in the area. Many wineries offer wonderful tours, a chance to try their wines and often their extra virgin olive oil, and sometimes even enjoy a lunch while on the property. If you have a favorite, let us know – if not, we will take you to one of our favorites you are sure to love.

Montalcino

As we arrive to Montalcino, you will see a medieval castle from the 14^th century, a sort of gate or entry point for the town of Montalcino. From this fortress in the highest part of the hill, at 567 meters above sea level, you will have a dominating view over the entire area. To reach the upper part of the castle, you need an entrance ticket which can be purchased at the Enoteca (wine shop) just inside the main courtyard. Upon entering, you will walk along a walkway up in the fortress walls and you can snap stunning pictures of the valley below.

Montalcino was built by the Etruscans and later became a Roman colony. Walking in the streets you will notice the symbol of Rome: A she-wolf statue with the twin brothers. This is the sign left by the ancient Romans everywhere they established their control to remind people of their rule. During the Middle Ages, the Montalcino economy was booming due to Via Francigena’s vicinity. At the beginning of the 14^th century, Montalcino entered the orbit of Siena, becoming a Vicarship in 1310. Finally, in 1555, Florence dominated Siena and Montalcino was added to the Grand Duchy of Tuscany until 1861 when the Grand Duchy was integrated into the new Italian Kingdom.

When you are in Montalcino, be sure to head to the Piazza del Popolo main square. The most prominent buildings are located here, such as the 13^th century Palazzo Dei Priori city hall of Montalcino. Next to it, you can admire a very high bell tower used to warn people in case of danger. For some amazing views, check out one of the many enoteca (wine shops) or cafes with outside seating with views of the valley below.

Tuscany Itinerary Number 3 – Siena, Palio di Siena, San Galgano, Monteriggioni, Colle di Val D’Elsa, San Gimignano, Chianti wine region

We love Siena, and if you have time during your Italian vacation, we highly recommend planning an overnight stop in this stunning medieval city. But, if you don’t have time for an overnight stay, then doing a day trip to Siena while transferring between Florence and Rome is a fantastic idea. If you are a history or art buff or just want to delve deeper, let us know and we can arrange for an English-speaking guide to take you to see the city’s highlights and give you the insider’s scoop of this Tuscan gem.

Siena

About two thirds of the way from Rome to Florence is the medieval gem of a city and one of our favorite places in Tuscany, the city of Siena. Siena was settled by the Etruscans in the 2^nd century BC and later it became a Roman colony named Saena Julia. In medieval times, the Via Francigena road passed through the city, helping Siena become one of the wealthiest trading centers during the Middle Ages. Siena was a prosperous city-state due to the trading and banking supported by its political structure. In fact, the Republic of Siena, especially in the 13^th century, became one of the most important democracies in Europe.

Siena competed with Florence from an early age, especially for banking activities. The Medici’s’ were already famous bankers throughout Europe, lending money to many royal families and Popes. In 1472, the Republic of Siena founded the Monte dei Paschi di Siena bank, which is said to be the first public bank in the world. Still today, Monte dei Paschi bank is one of the largest in Italy, but for Siena it’s the most crucial institution of the entire city.

As an early democracy, Siena developed its economy and remained independent from the Florentine state until 1555. During that year, the Grand Duchy of Tuscany Cosimo I was backed by the Spanish Emperor Charles V after a war ended with a prolonged attack on the city. In previous centuries, Siena was the invincible enemy of Florence, renowned for several battles with its rival Florence. The rivalry between these two cities still runs deep in the heart of local citizens. There is great civic pride found in being from Siena and even more emphasis is given to the precise “contrade,” or neighborhood where one is born. The city, in fact, is made of 17 ancient neighborhoods who participate against each other in the famous Siena Palio horse race. Keep reading to learn more about this exciting event.

The Palio of Siena

Since medieval times, the palio horserace has been run in Siena, but it has changed throughout the centuries. The race was originally run in a line and not in a circuit such as the current race, which takes place around the periphery of the Piazza del Campo main square. That primitive race started from outside the walls of the Duomo. The Palio of Siena is a historical horserace done with jockeys riding bareback and consisting in three laps around the Piazza del Campo. Each of the Palio races is run between 10 of the 17 neighborhoods. Palio actually means prize and represents a special painted banner that is given to the winning neighborhood after the race and is kept in the private neighborhood museum.

The race is held twice a year on July 2^nd and August 16^th. The winner of this unique competition is the horse and not the jockey; with jockeys regularly falling off during the race. The track race is in the beautiful Campo square, which is shell-shaped. The pavement is made out of “pietra serena” slabs, which would be too dangerous to race on, so the slabs are packed with yellow sandstone powder to create a more ideal racing surface.

The city also attracts many Italian and foreign students to study here, with both a renowned Italian University and one for foreigners. The medieval soul of Siena is still very visible everywhere you go. The main buildings of Siena are in the Piazza del Campo, such as the Mangia tower, at 102 meters high, next to the Palazzo Pubblico, which dominates the entire city.

Another incredible place is the Duomo of Siena, the city’s main cathedral whose construction began in the 12^th century over a pre-existing medieval church. The church’s walls are made of alternating stripes of white marble of Carrara and black marble from Verano (a local quarry) to mimic the coat of arms of Siena. In 1313, the bell tower was completed. In 1339, Siena reached the pinnacle of its greatness and to compete with its rival, Florence, the city planned to make the Duomo even larger. The project began, but in 1348 they had to suspend the work on the new building because the black plague affected Siena badly, killing many of its residents and bringing a period of decline to the city.

The Duomo interior is rich in masterpieces such as the floor in-lay work (a particular type of mosaic) and the Pulpit by Nicola and Giovanni Pisano. Unfortunately, the floor is usually covered throughout the year and it is only fully uncovered during a short period in September. There are so many notable artists to see here, including Donatello, Bernini, Michelangelo, and Duccio di Buoninsegna. About the latter, his most significant masterpiece is visible in the adjacent Opera del Duomo Museum.

San Galgano

If you are in the Siena area and have a little extra time to spend, there is a legendary site we highly recommend visiting, the Gothic San Galgano Abbey that was built in the 13^th century by the Cistercian monks outside the city of Chiusdino. Today the church is completely without a roof, but the majesty remains. About 200 meters away is another small church called the Rotonda di Montesiepi where St. Galgano stuck his sword in a stone as a sign of peace. Since that time, nobody has been able to remove the sword from the stone. This sword reminds us of another sword, the one from the legend of the King Arthur. The San Galgano sword can be viewed by visitors and is protected by a glass structure to avoid any damage.

Monteriggioni

Once we leave Siena, we will take the main highway north about 20 minutes to Monteriggioni, a tiny village known in the past as the garrison fort of Siena. Monteriggioni is a walled town with two gates and numerous towers to watch all directions and send a message to the army of Siena in case of danger. The city, when viewed from a distance, is so impressive that even the most famous Italian writer and poet, father of the Italian language, Dante Alighieri, mentioned Monteriggioni in his masterpiece the “Divine Comedy.” The town has an adorable town square, lots of little shops selling everything from souvenirs to handmade shoes and is a great place to grab a gelato as you stroll and relax.

Colle di Val D’Elsa and San Gimignano

From Monteriggioni, we will drive through the backroads of the famous Tuscan rolling hills along a scenic road and past the walled city of Colle di Val d’Elsa, known for its incredible crystal production and unique blue waters of the Elsa River that runs below the town.

Soon after going through Colle di Val d’Elsa, you will start getting glimpses of the San Gimignano skyline, the city of the towers. The city was first settled by the Etruscans. In the 10^th century, Sigeric, on his return trip to Canterbury, made his 19th “mansio” a stop along the Via Francigena itinerary, which he named after “Sancte Geminiane,” a holy bishop of Modena. Beginning in medieval times, San Gimignano benefitted greatly from its proximity to the pilgrimage route, growing richer and more powerful. The city is known for its historically important production of saffron, which is worth more than its weight in gold, and the white wine, Vernaccia di San Gimignano, produced in the countryside surrounding the city.

The most important feature of this walled city are the high towers that are visible even from a long distance away. At one point, there were 72 towers, but only 14 remain today. The presence of so many towers in a small city such as San Gimignano was a normal occurrence during the Middle Ages. People built these tall houses mainly for security. During that age, wars and fighting among differing factions, such as the Guelfi and Ghibellini, or simply among the wealthy families occurred very often.

The town of San Gimignano sits on a hill and has several main city gates, the two most important being San Giovanni and San Matteo. The city center is crossed by the main street. Halfway through the town you’ll come to Piazza Della Cisterna, which is famous for the big well right in the center of the square. Then you will come to the main Duomo square, ringed by the most important buildings such as the city’s main cathedral, a 14^th century Romanesque-Tuscan church, and the Palazzo del Podesta, the city hall, plus two of the best-preserved towers.

Chianti region

On the other side of the valley from San Gimignano is the Chianti wine region, one of Italy’s most famous wine regions. There are many different Chianti areas and a vast amount of land is included, but this is specifically the Chianti Classico region comprised of the areas of Castellina in Chianti, Radda in Chianti, Gaiole in Chianti, and Greve in Chianti.

This region is called “Classico,” which means classic or original, because it is the oldest area and the very core of this famous wine region. It is sometimes called Gallo Nero because of the image of a Black rooster on the round label you find on each bottle’s neck. Gallo Nero, or Black rooster, was chosen as the Chianti League symbol in 1384.

In 1872, Baron Bettino Ricasoli, established a specific recipe for Chianti wine, setting the precise proportions of the main grape: 70% Sangiovese, and then Cannaiolo, Malvasia, and Trebbiano as the remaining 30%.

 Ricasoli was the first to realize the potential in producing wine on a large scale as a business. The Chianti wine is top-rated and includes so many great winemakers in the Chianti consortium. The other Chianti subzones besides Chianti Classico are: Colli Fiorentini near Florence, Chianti Colli Senesi on the southern side of Siena, Chianti Montalbano to the west of Florence, Chianti Rufina to the east of Florence, Chianti Colli Aretini south and east of Florence, and Chianti Colli Pisane in the hills of Pisa.

The Chianti countryside is popular today, but in the second half of the 1900s, many local farmers decided to move away what was a poor farming region at the time, looking for a better life in the big cities. Many foreigners, especially from Great Britain and other northern European countries came to buy those abandoned farms. There were so many Brits and other expats that it was nicknamed Chiantishire. Many became involved in the winemaking business, and others began using the typical Tuscan farmhouses in the new wave of tourism tied to agriturismi, farm stays, with this area having the highest concentration in Italy and perhaps the world.

The Chiantigiana road

Time permitting, if you would like to see as much of the Chianti as possible, the best idea is to get off the main highway and take the secondary road called the #222 or Chiantigiana. This road winds through endless farms, vineyards, olive groves and charming medieval villages and towns.

The first of these cities you’ll meet along this itinerary is Castellina in Chianti, which is also at the highest elevation of all the towns. The Rocca is the most remarkable building in the small city; it is the local fortress with a tower dominating the entire valley below and dates back to the 14^th century. It hosts an archeological museum with items from the Bronze Age through the Etruscans. If you are a history buff interested in the Etruscan culture, just outside Castellina, you can visit an Etruscan tomb. Castellina is also the place where the Chianti League was born. After that, the drive goes downhill towards Panzano, Greve in Chianti, and finally to Florence.

Greve in Chianti

Greve in Chianti is the unofficial capital of the Chianti area. This area has many castles and hamlets, the most famous is the Verrazzano Castle. Giovanni Da Verrazzano was born there and is celebrated as the important citizen. In fact, probably someone might make the connection between this famous last name and one of New York’s main bridges: Verrazzano Bridge. Giovanni da Verrazzano was a great navigator and like Christopher Columbus, he explored the new continent sailing along the northeastern coast and discovering the Hudson Bay.

The main square of Greve in Chianti is therefore dedicated to Verazzano with a statue erected on one side. In the same square, you can smell the delicious aroma of the prosciutto from Antica Macelleria Falorni, famous for its cold cuts, such as hams, sausages, bacon, salami, and the celebrated Florentine steaks, plus other local specialties. If you want to enjoy a glass of the local wine, you can go to one of the numerous wine shops or the amazing local Enoteca, where you can enjoy a tasting of the famous red wine.

Leaving Greve heading toward Florence, you have two possibilities: one is to continue driving along the Chiantigiana road. The other possibility is to drive on a provincial road, which leads to Florence but follows the Greve River. After joining the main Cassia Road near San Casciano, you can stop at the Falciani cemetery for a quick but significant stop. This is an important American War World II cemetery, the second largest in Italy. It was built by the Americans to lay to rest 4000 American soldiers fallen in the WWII Italian campaign, for those who died in the northern part of the country. This site is a unique place for remembrance and for letting people feel peace in the silence of the Tuscan countryside. It has the same typical architecture of the other American war cemeteries spread around the world.

From here, you are just a few miles outside of Florence and you will arrive to your destination shortly. We will take you directly to your hotel for check in after your fantastic day exploring the hidden gems of Tuscany.

Tuscany Itinerary Number 4 – The Tuscan coastal route – Tarquinia, Tuscania, Pitigliano, Porto Ercole, Grosseto, Bolgheri Wine Region

As you can see from the number of stops we listed, the road that goes from Rome to Florence along the coast is full of incredible sights to see. There are charming seaside villages, Etruscan tombs and sites to explore, and plenty of seafood, fine Italian wines and so much more to see. If you are transferring from Rome to Florence, or vice versa, take advantage of this precious day of your vacation by spending your time relaxing and exploring the stunning Italian coastline, you will not regret it.

After being collected at your Rome hotel with your luggage, your English-speaking driver with luxury vehicle will take you toward the coast instead of heading to the main highway. You will be traveling on a secondary road that runs along the beautiful Mediterranean coast (this part of the sea is actually called the Tyrrhenian Sea). If you love archeology (especially the Etruscan period), fine Italian wine and are interested in spending time in a more natural and wild Italian countryside, such as the Natural Park of Maremma Parco dell’Uccellina, or the Capalbio beaches, then this itinerary is perfect for you! Remember that we can fully customize any itinerary to match your group’s timeline, needs and pace.

The Aurelia Road and the Etruscan sites

Leaving Rome toward the northwest, you’ll drive on the Aurelia Road, also known as the Italian national road #1. The ancient Romans laid this road 2000 years ago to connect Rome to France by going along the Italian coast, and they eventually kept building to connect all the way to Spain.

After passing, Civitavecchia, the city that features Rome’s main port built in the 2^nd century AD to replace the ancient Roman port of Ostia, you’ll reach Cerveteri and nearby Tarquinia. These two cities are famous for the Etruscan ruins, mainly the tomb and burial chamber sites found in the area. These archeological sites were very significant to the study of the Etruscan civilization, revealing much about their way of life and burial rites. The Tyrrhenian Coast and the area immediately inland were all part of the Etruscan state called Etruria.

The Etruscans were quite advanced, even coming into contact with Greece due to their commercial activities by sea. Therefore, their customs were ahead of their age. Their social system was quite democratic and offered equality between men and women, contrary to the Romans. Moreover, the Etruscan religion considered women as holy because they could give birth to a new life. The Etruscans were also the first farmers to use irrigation in agriculture to transform land cultivation into an economic activity. In fact, by producing large crops beyond what their families’ needed, they could sell the excess and attain other goods.

Cerveteri and Tarquinia

Both Ceveteri and Tarquinia are located in northern Lazio, so not yet in the Tuscan region. They are both very famous for the burial chamber archeological sites left by the Etruscans. The site in Cerveteri, called Banditaccia, is laid out like a city and the types of tombs differ. Some are like burial mounds while others are more monumental. The Tarquinia Etruscan necropolis is called Monterozzi. It has about 6000 graves dug in the rock of which 200 have painted rooms. Both sites are fascinating to visit if you are interested in archeology.

Vulci

Continuing up towards Tuscany along the Aurela road, you can stop to visit another wonderful Etruscan site: Vulci. Near the modern City of Montalto di Castro lies the ancient Etruscan town of Vulci, just a bit inland. It is an enormous archeological park that is rich with immense treasures of antiquity. You can choose several itineraries to discover this park, all immersed in the natural landscape.

Pitigliano

Arriving from Lazio into the Tuscany region you will arrive to an area known as the Maremma. A few minutes inland is a fantastic city perched on the tuff hill: Pitigliano. This city was built in the same way as Sovana, Sorano, and Orvieto and like them has Etruscan origins. Pitigliano offers notable sites such as the Orsini Palace and its museum, an aqueduct, and many unique fountains.

One very interesting aspect of Pitigliano is the Jewish ghetto that formed in the 16^th century when the Pope in 1555 and again in 1569 issued harsh restrictions on the Jewish community living in Rome. Consequently, some of them left Rome looking for a different place to live in peace. But even in Pitigliano, the Medici family (rulers of the Grand Duchy of Tuscany started a campaign against Jews in 1570, siding with the Pope’s politics. They ordered all Jewish people in Pitigliano into a ghetto, following the example of Rome. Today the district is named Little Jerusalem. It is preserved and open to visitors to show them the Synagogue, and the underground workshops dug in the tuff stone where the people used to work and live. Don’t miss out on tasting the famous local pastries at the Jewish Bakery.

Monte Argentario peninsula

Next you can visit the stunning natural area with exclusive beach real estate called the Monte Argentario peninsula, which is connected to the mainland by two stretches of land that create two lagoons. In fact, in the old ages, Monte Argentario was an island. The only way to reach it is to drive through the town of Orbetello, famous for its very vibrant fishing activities. The whole area is considered a sort of natural park. In fact, you won’t see tall buildings, but rather beautiful and luxurious villas immersed in the lush Mediterranean vegetation. Moreover, small fishing villages are characterized by their docks used mainly by sailing boats and yachts.

Porto Ercole and Porto Santo Stefano are the two main cities. From the latter, you can reach the Tuscan islands such as Giglio or Giannutri. The highest peak of Monte Argentario is Mount Telegrafo, 635 mt above sea level, where the Fortress of Santa Caterina sits, dominating the whole area.

Grosseto and Roselle

Taking the Aurelia Road still, we will cross the Ombrone River and be in the proximity of Grosseto, a large city in southern Tuscany. Grosseto was founded in the 9^th century and ruled by the Aldobrandeschi family until the 13^th century. The city is surrounded by impressive walls built by the Medici in 1564.

Once inside the city walls, you can admire the Romanesque Cathedral of St. Lawrence in white and black marble. Its most important piece of artwork is a carved baptismal font dating from the 15^th century and a Madonna delle Grazie painted by Matteo di Giovanni from the same period. Another remarkable religious building is St. Peter’s Church. You can also see many palaces, such as the Aldobrandeschi palace, once a leading family of Grosseto. This palace was rebuilt in the early 19^th century and hosts the Grosseto province government offices, the Grosseto city hall is next to the Cathedral built in the early 19^th century, and there are many others…

Near Grosseto, staying in or Etruscan theme, we can’t avoid mentioning another impressive archeological site: Roselle. Originally named, Rusellae, this is an ancient Etruscan settlement that became a Roman colony in 3^rd century BC. The most impressive ruins are the Roman theatre, the Austustales house, the mosaics house, and the thermal baths.

Gavorrano and Baratti

We will continue north until we reach Gavorrano, a medieval hilltop city. Gavorrano is set in an area known as the metal hills because there were many metal mines that are now closed and converted into a Naturalistic Mining Park.

After Gavorrano you reach Piombino, a bustling port city that offers the most convenient ferry service to Elba Island and the rest of the Tuscan archipelago. Elba is the largest Tuscan Island in the Tuscan Archipelago National Park and is famous for hosting Napoleon during his first imprisonment from 1814-15. It has beautiful beaches and a busy summer season filled with visitors from all over Italy and the world enjoying the beautiful beaches, hiking, wine and activities.

From Piombino, proceeding along the coast, you will come to an interesting Etruscan site called Baratti-Populonia and a beach named after it called Baratti, known as the best Tuscan beach. In the Etruscan archeological site there are more Etruscan tombs and burial sites. These tombs demonstrate just how important this area of Tuscany, the Maremma, was to the Etruscan civilization. This settlement is almost directly on the sea and was the center of trading for the Etruscans with the Greeks.

Bolgheri

While Bolgheri might not be a household name like Chianti or Brunello, it is actually one of Tuscany and Italy’s best kept wine secrets. This wine region, producing Super Tuscan wines, gets hot in the summer and has a special microclimate that creates excellent wines. In 1974, the wine label Sassicaia won an award competing against more famous Bourdeaux wines in a competition organized by Decanter, an important fine wine magazine.

Bolgheri is both the wine region as well as a very charming medieval town. Driving up to the town, you go along an iconic straight road flanked by the famous Tuscan cypresses trees on both sides. The town is also home to Giosue Carducci, an important Italian poet.

 From here we will head on to Florence or your final destination in Tuscany. Your driver will take you and your luggage directly to the front door of your hotel, where you can check in happy, knowing that you made the absolute most of your transfer day between Rome and Florence and saw some wild and unexpected sites along the way.

Tuscany Itinerary Number 5 – Livorno, Pisa and Lucca

If you love cities and want to see as many of the most iconic sites of Italy as possible during your trip, you surely have the Leaning Tower of Pisa on your list of must-see attractions. While Lucca and Pisa can be done as a day trip from Florence, why not take advantage of your transfer day from Rome to Florence and visit one or more of these charming, unique cities with so much to offer. This itinerary includes Livorno, Pisa, Lucca and the charming villas outside of Lucca.

In Rome, your driver will come to your hotel and safely store your luggage in the back of the car or van and then you can relax and enjoy the ride north on the main highway or along the coast, depending on your preferences.

Livorno

After a few hours you will arrive in Livorno, the third biggest city in Tuscany and its largest port. As you can understand, most activities are related to the commercial port and the tourism generated by the thousands of cruise ships docking here annually.

Livorno is a city of ancient Roman origin but it only really gained importance during the 16^th century. In fact, only after the Medici family created a fortress did Livorno became a thriving city because of the port and its international trading activities.

The most famous sites in Livorno are the Terrazza Mascagni, a chessboard-shaped belvedere facing the sea. The Fortezza Vecchia and the Fortezza Nuova date back to the 16^th century. The main square of Livorno is Piazza Grande, which was rebuilt after WWII and is where the cathedral and Palazzo Grande are located. Livorno is also very well known for its fish restaurants specializing in “cacciucco,” a delicious fish soup.

Pisa

From Livorno, taking the Aurelia Road, there is a natural canopy made by endless pine trees flanking the road. You will reach the city of Pisa in a little less than half an hour. About half way there, you’ll notice a large military base named Camp Darby. This is one of the largest American bases in Italy, with around 1400 US soldiers stationed here. This base was used to ship most of the material needed in the Gulf wars, both from the nearby airport and the Livorno port, where there is also a navy base. Outside Pisa, there is a big airport split into two sections. The civilian section is named Galileo Galilei Airport in honor of this famous citizen.

Approaching the city of Pisa, you will cross a bridge over a wide river, the Arno! This is the same river that flows through Florence. Pisa is one of the last places it goes through on its way to the delta a few kilometers west that reaches the Tyrrhenian Sea. The Arno River played a big role in the city’s history and has been important to Pisa’s economic development since ancient Roman times. As a result, a fluvial port was built just outside the city walls.

As you enter the city you will see the city walls that were built in the 12^th century and reinforced later. My favorite route for reaching the most famous monument of Pisa, the Leaning Tower, is by entering through the St. Ranierino Gate. As you enter the gate, if you look right you will be amazed by a stunning view of the Leaning Tower suddenly appearing from behind the walls.

The most asked question I get about the Leaning Tower of Pisa is: “Why did they build the Leaning Tower?” The answer is easy. At the time it was built, in the 11^th century, Pisa was one of the four Italian Maritime Republics. But in 1284, after a defeat against Genoa, one of their biggest rivals, the Republic of Pisa was in decline. Pisa needed a significant monument to show their prestige and economic power and so they commissioned the tower.

The second most common question is: “Why does the Leaning Tower of Pisa lean?“

The tower is leaning because of a mistake in evaluating the soil under the tower. The engineers did not realize that the ground they chose to build on was not solid enough to support the enormous weight of the tower. Therefore, immediately after construction was completed the tower started to lean. Every year it leaned more, until 1990 when the tower had reached a truly critical point in which it could fall at any time. At that point, the tower was closed and the government launched an international contest among the worlds’ scientists and engineers to find a solution to save it. Soon they formed a team of engineers from all over the world. Unfortunately, the first attempt in which they pumped water underneath the building failed. They tried again and luckily, the next solution worked. This solution was to drill 40 holes in the soil only on the higher side of the tower and remove the ground to create an empty cavity. the weight of the building then automatically balanced, and little by little it returned to a more vertical position, just enough to avoid collapse.

In 2001, the Tower of Pisa was reopened to the public. Today you can also tour the inside and climb to the top. As only 30 people are allowed for each 30-minute window so you need a reservation ahead of time to do the climb, which is possible to do online. Please do let us know if you would like us to get tickets for you to any of the sites, as having a reservation will save you a lot of time and hassle.

The Tower of Pisa is located in the Miracle Square, with several other beautiful religious sites worth visiting. As of 1987, this location has been listed as a UNESCO World Heritage Site. The Duomo, Baptistery, and Camposanto were all built at the same time as the tower to complete the square, and it was later renamed the Miracle Square for the many masterpieces in such a small area.

There is more to Pisa that just Miracle Square, we happen to also love the beautiful Piazza Dei Cavalieri, built during the period in which Pisa was at the height of its importance. It was remodeled by Vasari, who gave a new name to the square in honor of the Medici family, the rulers of Pisa beginning in the 16^th century. In the same court, the most prestigious building is the Palazzo de Cavalieri, the site of the Scuola Normale di Pisa considered to be one of the top Italian universities. It should be noted that even Galileo Galilei taught there for three years before moving to Padova.

Lucca

Pisa is very close to another charming and fun city to visit, Lucca. Over a mountain, past the olive groves and through the “Il Foro” tunnel and you will be in Lucca in around 20 minutes. Lucca is very unique because it is completely surrounded by a medieval wall which rings the city for 5 km.

Lucca was settled in the Roman age and developed mainly during the Middle Ages. Huge churches, squares, and palaces embellish the town. The most interesting peculiarity here is the peacefulness of the streets and alleys. In fact, the city has a relaxing musical vibe most likely because of its most famous citizen, Giacomo Puccini, one of the greatest music composers of all time. Giacomo Puccini was born in Lucca in 1858, in a house in downtown Lucca that is open to visitors today. Near Lucca, in Torre del Lago by Massacciucoli Lake, there is a Puccini Museum housed in another dwelling he lived in.

Another significant historical figure who has ties to Lucca is Napoleon Bonaparte. In 1805, the French Emperor gained the Principato of Lucca and Piombino. He entrusted his sister, Elisa Bonaparte, who was later appointed as Grand Duchess of Tuscany, and her husband, Felice Baiocchi, to govern the Principato and the whole of Tuscany. Elisa Bonaparte did great things for the city, starting big urbanization plans such as the Napoleon square and even constructing an aqueduct to bring water to the town from the nearby hills.

The Villas outside Lucca

Ville Lucchesi is just a few minutes drive outside the city of Lucca and is a wonderful villa with sprawling grounds to explore, often considered the best example of a Renaissance garden. Villa Reale is probably the most famous of the villas, bought in 1806 by the Princess of Lucca, Elisa Baciocchi, and later given to the Italian royal family. Villa Mansi, near Capannori, is a fantastic property bought in 1675 by Ottavio Mansi and refurbished in the 18^th century. The villa is rich in green areas, small lakes, fountains, and statues to offer great spots for fantastic pictures.  Villa Torriggiani is very close to Villa Mansi, and located in Camigliano. This villa is especially famous for its English garden. However, the interior is also worth seeing because of the original furniture. The villa dates back to the middle of the 16^th century. Later in the 17^th century, Nicolao Santini bought it and created a fantastic garden with swimming pools in the style of Versailles.

By now you will have seen so much art and so many monuments of historic importance that you will be ready to head to your hotel in Florence. Your driver will deliver you and your luggage safely to your hotel for a good night’s sleep before you begin your exploration of the fascinating Renaissance wonders of Florence.