Tuscany Countryside Tours

TUSCANY COUNTRYSIDE PRIVATE TOURS

ADVENTURE JUST A SHORT DISTANCE OUTSIDE OF FLORENCE


The landscape you will see on these Tuscany countryside tours is full of small medieval towns, winding roads, vineyards, and olive groves.

With so much to see, it can be helpful to have someone with years of experience help you with an organized tour of the countryside – including famous sites as well as special surprises that only a local could know about.

If your time in the area is limited or you simply prefer to have an expert show you around – then one of these tours should be on your itinerary. Browse the list below of Tuscany private tour ideas, including wine tasting suggestions, photo opportunities and the possibility to include tickets to major attractions.

If you don’t see what you are looking for then contact Paola and she will create your dream tour – especially for you.

Visit the beauty of the region with a full-day, private Tuscany countryside tour that explores ChiantiSiena, San Gimignano and many other towns and areas of Tuscany.

San Gimignano and Siena Guided Tour

Two of the most iconic locations outside of Florence are included in the San Gimignano and Siena guided tour.

The tour begins with a drive on a private 9 seats van with NCC license into the Tuscan countryside outside of Florence where you can admire the hills, vineyards and olive groves of Chianti.

OUR FIRST DESTINATION INCLUDES A VISIT TO THE MEDIEVAL VILLAGE SAN GIMIGNANO

San Gimignano is famous for its 13th-century towers, which symbolize the prosperity of its merchants. As we stroll the antique cobbled stone streets we admire the frescoes inside the Palazzo del Podestà patio, Duomo, and Piazza Cisterna.

There will be plenty of time for photos and shopping at both destinations for local products at the artisans’ shops which are filled with linen, leather products, pottery, olive oil and wine.

FROM SAN GIMIGNANO, WE HEAD OVER TOWARDS SIENA

This amazing city which has been designated by UNESCO as one of the World Heritage Sites.

While in Siena we will visit San Domenico, a special church restored several times due to war and earthquakes, known for the relics of Saint Catherine of Siena.

Piazza del Campo - Siena
Siena - Piazza del Campo

The tour will proceed to the unique shell-shaped Piazza del Campo where you can imagine the Palio horse race, and view the Fonte Gaia and Palazzo Pubblico, which houses the famous frescoes of the “Good and Bad Government” by Ambrogio Lorenzetti.

Siena Cathedral

Legend and mystery surround, perhaps one of the most beautiful medieval towns in Italy, Siena. History tells us that it was founded by Senius, son of Remus, one of the two legendary founders of Rome thus Siena’s emblem is the she-wolf who suckled Remus and Romulus.

The sightseeing will conclude with a visit to one of Tuscany’s most outstanding Italian Gothic cathedrals. Between the colorful facade and the inlaid marble floors, this monument to Siena’s destiny will surprise you with its serene beauty.

San Gimignano Tour
San Gimignano Skyline

San Gimignano rises on top of a hill 334m above sea level and is visible from a distance with its many still existing towers. Only 13 towers of the 72 towers from the fourteenth century still survive, and they form what has become one of the most distinctive Tuscan skylines of today.

Within the walls, well-preserved buildings include notable examples of Romanesque and Gothic architecture, secular buildings and churches. The Palazzo Comunale, the Collegiata and the Church of Sant'Agostino contain frescoes, including cycles dating back to the 14th and 15th centuries. The Historical Center has been declared a UNESCO World Heritage Site; the town is also known for its saffron, the 'golden ham', and its white wine, Vernaccia di San Gimignano, produced from the ancient variety of Vernaccia grapes grown on the sandstone hills of the area.

Cortona and Arezzo Guided Tour

The Cortona and  Arezzo guided tour is a day outside of Florence to visit two extremely engaging destinations in Tuscany: a historic journey into the past.

Arezzo Walking Tour

The tour starts with a pick-up at your accommodations in a private, air conditioned transport. The trip to Arezzo takes approximately one hour, where you will begin the walking tour of the city.

Reaching back to Etruscan origins, Arezzo is often referred to as a museum “en plein air”. The streets are lined with palazzos and churches that reflect its long and conflicting history.  As you stroll the city streets you will come in contact Etruscan and Roman ruins, including the Roman amphitheater. The narrow cobbled-stone roads are lined with medieval towers and neo-classical buildings, each with a special story attached.

The first stop includes the revolutionary frescoes of Piero della Francesca in the Basilica di San Francesco depicting The Legend of the True Cross, a story which tells of the different phases of the cross which was used in the crucification of Christ.

Arezzo - Piazza Grande

Other sites of interest in Arezzo include the Piazza Grande, the Duomo, the home of Vasari, the Roman amphitheater and the Medici fortress built on the ruins of the Etruscan temple. The tour of Arezzo will show you the local color, pointing out the passage of history, and how it shaped its story but also how it influenced the stories of nearby towns, like that of Florence, Siena and Cortona.

There will be plenty of time for photos and shopping while on the Cortona and Arezzo Guided Tour at all destinations for local products at the artisans’ shops which are filled with linen, leather products, pottery, olive oil and wine.

The tour will proceed to visit enchanting town of Cortona, made famous in the film “Under the Tuscan Sun”.

We will wander the streets, boutiques and admire the palazzos, churches and monastery which form this amazing town.

Cortona

The area between Arezzo and Cortona is famous for is wine and olive oil production, including many award winning vineyards. Upon request the lunch stop can include a wine & olive oil tasting as well as a selection of typical Tuscan specialties from the province, giving you a special insider view of the local cuisine.

Arezzo

Surrounded by memories of the Etruscans that once reigned over the area, Cortona sits perched high above dominating the landscape. Legend has it that 108 years after the Great Flood, Noah entered the  Valdichiana riding on the Tiber and Paglia rivers. The town now encompasses yesteryear and today in finely tuned harmony.

Chianti and San Gimignano Guided Tour

The Chianti and  San Gimignano guided tour combines two of the most popular destinations in Tuscany and create an adventure you will never forget.

The tour begins with a drive on my private 9 seats van with NCC license into the Tuscan countryside outside of Florence where you can admire the hills, vineyards and olive groves of Chianti.

Our first destination includes a visit to the medieval village San Gimignano, famous for its 13th-century towers, which symbolize the prosperity of its merchants. As we stroll the antique cobbled stone streets we admire the frescoes inside the Palazzo del Podestà patio, Duomo, and Piazza Cisterna.

There will be plenty of time for photos and shopping while on the Chianti and San Gimignano Guided Tour at all destinations for local products at the artisans’ shops which are filled with linen, leather products, pottery, olive oil and wine.

FROM SAN GIMIGNANO, WE DRIVE DEEPER INTO CHIANTI CLASSICO

An area whose borders are designated by Italian law and the home to the Black Rooster (Gallo Nero) labels. The landscape offers many photo opportunities with its tall cypress trees, rows, upon rows, of grape vines, and silver-green patches of olive groves.

The lunch stop will include a wine & olive oil tasting as well as a selection of typical Tuscan specialties.

The tour will proceed to visit two of the most popular towns in Chianti, just outside of Florence. 

First will be a stop at Panzano in Chianti and visit the local butcher and taste its delicatessen. 

We will proceed to Greve in Chianti positioned along the famous Chiantigiana Road, where we visit the unique square and lovely little stops. From here the Chianti and San Gimignano Guided Tour back to your accommodations in Florence.

San Gimignano (above) rises on top of a hill 334m above sea level and is visible from a distance with its many still existing towers. Only 13 towers of the 72 towers from the fourteenth century still survive, and they form what has become one of the most distinctive Tuscan skylines of today.

Surrounded by endless vineyards, Panzano in Chianti is situated in the middle of Chianti and was constantly in the mix between the feuding powers of Siena & Florence since before the 1300’s.

Standing in the shadow of the Castle of Montefioralle is the town of Greve in Chianti which served as the castle’s marketplace in the 13th century.

Lucca and Pisa Full Day Tour

This tour will be a surprise for most of you! The first stop is Lucca, a Roman town enclosed by its original massive red brick walls which were built between the 16th & 17th century.

The walls are one of the beautiful distinguishing characteristics of Lucca

This fortified enclosure makes this town totally unique because you can easily walk and cycle over it.

If you like to bike we can easily rent them and discover the city biking.

The tour proceeds with a walk or bike along via Finlungo, the main axis of the historic core, which is lined with ancient houses and towers and stops at the Roman Amphitheatre square.

Then explore the house of Puccini (one of Italy’s great opera composers), the church of San Michele and the Duomo of San Martino with its rich decoration, both typical example of Pisano Romanesque style.

With a short transfer through the mountains that separate Lucca from Pisa, the tour will give you a panoramic view of the leaning white tower.

Pisa, undeniably has one Of the most photographed monuments In Tuscany

The slant, just under 4°, gives the bellower its the name: the Leaning Tower of Pisa. But did you know there is so much more to see in Pisa?

Before we spend time exploring the Piazza dei Miracoli with the tower, baptistery, cathedral, “campo santo” and museums we will explore the inner city, the Arno River and the famous persons who once resided here, like Galileo.

⇒ Tickets to climb the Tower of Pisa will need to be purchased in advance (you can do that at this website  www.opapisa.it)  Please advise if you want to climb the almost 300 steps to the top, so we can make appropriate time allocations during the tour.

The booking for these tickets is possible 45 days in advance, the earlier the better – they run fill-up quickly. Be sure to bring photo ID if you have a ticket to climb the tower of Pisa.

The enchanting walls of Lucca, as the city grew and modernized, surrounded the old town and were maintained which was not the case for many other cities in Tuscany, including Florence. As the walls lost their military importance, the top of the walls became a pedestrian promenade, today one of Lucca’s main attractions.

Commonly referred to as the “city of one hundred churches” due to a large number of religious buildings which represent marvelous examples of architectural Italian styles.

Pisa, once served as one of the main Italian maritime republics, until the sand and sediment from the Arno river moved the shoreline towards what is now Livorno and your port of call.

From mysterious beginnings, this city is now famous worldwide for its leaning bell tower, Pisa also boasts a beautiful cathedral, one of the earliest known universities (from the 1200’s), over 20 churches and home to many special talents like that of Andrea Bocelli.

Montepulciano Pienza Montalcino Full-Day Private Tour

Discovering the three gems of Val d'Orcia in Southern Tuscany

Three of the most characteristic locations in southern Tuscany are grouped together in this full-day guided tour with a one of a kind landscape.

Leave in the morning for the characteristic town of Montepulciano, built in the 1500s on a narrow ridge of limestone.

After an explanation of the major sites, you can enjoy some free time on your own in a place well known all over the world for its imposing Renaissance palaces as well as for the very tasty Vino Nobile wine. It is perhaps one of the most appreciated Tuscan wines all over the world.

Next stop: Pienza. This is one of the most beautiful Tuscan towns, a rare example of Renaissance architecture brought to completion.

Pienza
Pienza

We have a guided tour and after that we have some free time for lunch and relax.

In the early afternoon, we’ll continue through the enchanting landscapes to reach Montalcino, famous throughout the world especially for the origin of one of the finest wines in the world: Brunello di Montalcino.

Perched on a hill on which the mighty fourteenth-century fortress rises still today.

Free time for visits, and after we’ll go to a top rated winery to taste the famous Brunello.

Montepulciano

Montepulciano

Is a medieval and Renaissance hill town in the province of Siena in southern Tuscany. According to legend, it was founded by the Etruscan King Lars Porsena of Chiusi and until the mid-16th century, lived a period of splendor with architects building luxurious palazzos.

Pienza  

has been designated by UNESCO as one of the  World Heritage Sites, and in 2004 the entire valley, the Val d’Orcia, was included on the list of UNESCO’s World Cultural Landscapes. Pope Pio II Piccolomini had the entire village of Corsignano rebuilt as an ideal Renaissance town and renamed it Pienza, which means "city of Pius". Picturesque cobbled-stone vias make this a special stop on the tour.

Montalcino 

takes its name from a variety of oak tree that once covered the terrain. The fortress, built in 1361 atop the highest point of the town, was designed with a pentagonal layout

Montalcino