A Perfect Private Tour of Tuscany in 2 Weeks

Tuscany is a province in Italy unlike any other. Countless stories have been told over the centuries than exude the essence of lush rolling hills and streets lined with cypress trees. Dante Alighieri penned the world famous Divine Comedy, encapsulating the nature of the landscape and inspiring poets across the globe for almost a millennium. Botticelli captured the beauty of the trees and coastline in his paintings without ever referencing his natural muses in the work itself.

You arrive at Florence International Airport eager to experience the depths of Tuscany. Your private transfer greets you at the airport and escorts you to the historic center of Florence, a city that has preserved its Renaissance flair and acts a symbol of the lavish artists of the past. The cobblestone streets lead through narrow alleys winding around 13th-century buildings and open up into wide avenues lined with historically luxurious palaces. Elegant statues stand beneath the Loggia on the southeast corner of Piazza della Signoria, creating a museum-like ambiance in the open air of the city. The aroma of freshly baked brioche combines with the scent of creamy gelato drifting out of the hidden, delectable shops. Walk through San Lorenzo Market and enjoy the jovial atmosphere of the leather merchants continuing a trade that has lasted hundreds of years and continues to thrive with artisans graduating from the Scuola del Cuoio, the Leather School.

In the morning, you find a city awakening with an espresso-fueled pep in its step. The scent of freshly ground coffee beans emanates from the doors of the city’s countless cafes. Office workers sip their espressos at the counter. Locals with more time in their morning sit at street-side tables and watch the youthful energy return to the city.

Your guide meets you in the lobby after breakfast with an eagerness to show you the fair city of Florence in its entire splendor. Before the city has had a chance to awaken fully, your guide leads you to the Piazzale Michelangelo to take in the panorama, sweeping across Florence with the dome of the Cathedral and the bell tower of Palazzo Vecchio creating the impressive antique skyline. The red-tiled shingles on the roofs have a particular glow in the expanding light.

The cathedral was built in the 15th-century, and the dome stands at a height of 376 feet. The brick dome remains the largest ever constructed and was designed by Brunelleschi. The exterior of the cathedral is as magnificent as the dome, with green and white striped marble encircling the structure, encompassing more than 89,300 square feet. When you walk through the center of the church, the faint aroma of frankincense lingers. Candles flicker in the quiet, natural light pouring through the upper windows. A large painting of Dante standing before 15th-century Florence decorates the nave.

At breakfast, you enjoy the flaky texture of a fresh chocolate brioche before your private transfer from Guido’s Tours meets you at the hotel. Soon you are outside of the city’s antique walls separating the rolling hills of the countryside from architectural splendor. The greenery of Tuscany rolls along the hills and rises in the bushel of oak trees. The farther south you travel, the more olive groves you see. Gracefully segmented vineyards traverse the landscape.

When you reach the region of Chianti, you find numerous wineries situated in classic villas. The image creates a romantic ideal, where you can imagine tending to your private vines in a refurbished building that acts as a testament to the culture as much as a testament to the surrounding landscape. The country roads wind through the wild forests and medieval pilgrim trails. When you reach a 12th-century castle, you find a charming winery with a terrace providing a view of the hillside.

Your guide leads you through the vines, showing you the sugar content of the grapes, explaining how the particular soil from this particular hill enhances the specific flavors of the wine. The aroma of olive groves comes from the nearby trees. During your tasting, your guide explains the color of the wine and mentions a variety of notes you may find on the nose, from dark berries to leather. The tranquility of the vineyard and the landscape allows you to be present in the moment.

When you wake up in a small town like Greve in Chianti, you have the best view. The streets are quiet in the morning. The cobblestone lanes lead to the edges of the medieval hilltop town, opening up to a view of the sunbathed hills and dew-soaked grass. After breakfast, your private transfer leads you to the quaint town of Arezzo, one of the loveliest Tuscan cities, but it also tends to be overlooked. The main piazza was a focal scenic point in Roberto Benigni’s Oscar-winning film “Life is Beautiful.” The city was once an Etruscan trading post but gained prominence as a free republic in the 10th-century.

The Piazza Grande slopes gracefully downhill, flanked on three sides by antique palaces. In the Cappella Bacci, the 14th-century Basilica di San Francesco houses the work of Piero della Francesca. The fresco depicts the cyclical legend of the True Cross and was painted in the 15th-century. With only 25 people allowed in the room every half-hour, you have an intimate setting to enjoy the simple techniques of the master painter. One of the most notable scenes depicts the Queen of Sheba and King Solomon together. The large, arched window at the front of the nave helps the colors of the church shine brighter.

The Tuscan landscape continues to captivate you every day you travel along the country roads. Today you continue your discovery of small towns across the hills and valleys of Tuscany, eventually leading you to Volterra. En route, you stop at the exquisite town of Massa Marittima. The medieval streets are quiet and calm. An eccentric collection of museums speckles the town. The large piazza has a handsome allure. The city dates back to the 11th-century and is dissected into three districts, that of Old Town, New Town, and the Borough.

The cathedral stands atop a platform in Piazza Garibaldi and stands as the central point of the town. The 13th-century Romanesque-Gothic style has a number of small loggias and arches leading upwards into tripartite pinnacle. The bell tower stands 242 feet tall overlooking the main square. A carved marble urn decorates the interior of the cathedral situated behind the high altar. The city has serene charm, deriving from its ancient beginnings, preserved Middle Ages, and welcoming present.

In the morning, the slight breeze in Volterra carries the scent of the surrounding oak and chestnut trees. After breakfast, your private transfer escorts you away from the preserved Etruscan walls and into a city housing a series of Romanesque churches and an unforgettable open-air market. Piazza della Sala fills with lively locals meandering through a sea of blue awnings enjoying the scent of seasonal fruits and vegetables. On Saturdays and Wednesdays, a marketplace blossoms underneath the alluring façade of the city’s cathedral in Piazza del Duomo. The historic center is strikingly well-preserved and tranquil.

The Church of Sant’Andrea was consecrated in the 8th-century but was unfinished for centuries. Green and white marble shapes the arcade. Two lions flank the main doorway. The interior nave has a tall and narrow design with a timber roof. The city is a radiant surprise on your exploration of Tuscany, filled with unforgettable towns, architecture, and people.

When the daylight washes over Pistoia, you find the medieval streets comforting; they are a reminder of your private, personalized journey through the wonders of Tuscany. This morning you sip on a frothy cappuccino and enjoy the layers of flavor amongst the zip from the coffee. You notice you are starting to pay attention to the little pleasures of life, taking note of the culture around you.

After breakfast, you journey to the famous city of Pisa to visit the tremendous Piazza dei Miracoli. You stroll along the Arno River before you visit the square, noticing the relative calm and stunning architecture around the city. When you reach the Piazza, you find three sensational architectural structures in the form of the cathedral, baptistery, and the Leaning Tower, each constructed with elements specific to historic Pisan design. The tower stands at nearly 200 feet tall and once listed at an angle of almost 10 degrees. The city broke ground for the tower in the 12th-century to commemorate a series of naval battles. The circular tiers are decorated with archways and columns.

In the background, you can see the Apuan Mountains undulating across the horizon. The lushness of the square adds an organic quality to the beautiful marbled structures. You can’t hide your excitement over viewing a symbol of Tuscany and an image you have wanted to witness in person for so long.

When you return to Florence, you find a city that feels familiar and inviting. The aroma of marzipan from the bakeries on Via del Corso is a reminder of all the beauty you have already observed in the city, and yet there is always so much more to experience. Strolling along the palazzos in the middle of the historic center, and noticing the blue and white colors shining on the façade of Santa Croce, can’t help but bring a smile to your face.

The Bargello Museum is often passed over by visitors of the city. The Bargello contains breathtaking work housed in the Palazzo del Popolo, a former prison. The palace was erected in the 13th-century and was once the oldest public building in Florence. When you enter the museum, you immediately step into the inner-lower courtyard. Plaques decorate the wall. The collection upstairs encompasses works by Michelangelo and Sansovino, showing a wide range of textiles, silver, ceramics, and tastes. One of the most exquisite works in the collection is Donatello’s David, designed in the 15th-century and cast complexly in bronze. The image shows the mythical figure with a sword in hand, sporting a lavish hat and little else. It was the first unsupported work of bronze in the Renaissance.

The Casentino Valley is an isolated area of Tuscany filled with churches, ancient forests, authentic cuisine, and brilliant castles. When you arrive in the valley, it feels more like a secret, or private property, than an area connected to the Tuscan hills. The town of Poppi, one of the numerous historic towns you will visit, stands atop the Arno plain. When you reach Poppi Alta, the upper section of town, you can look out at the drifting clouds of the Tuscan morning sweeping across the lower landscape. Green fields line the riverbanks. Vineyards cover the hills. The aroma of focaccia bread spills out of Consumo Bar.

Castelo dei Conti Guidi was built in the 13th-century under the patronage of Count Simone da Battifolle. The dungeon is dark and cold, contrasting the elegance of the brightly lit and fashionable ballroom. Original frescoes decorate the chapel. One of the highlights is the courtyard, which looks like the spitting image of a fairytale enclosure. A staircase edges the side of the castle, encircling the square and linking rooms and hallways across the edifice. The majesty of the valley continues outside of the castle and in the hidden monastery of Camaldoli.

In the morning, you leave Florence once again, setting out to the historic medieval city of Siena. The city is known for its 17 distinct districts that twice a year compete in a saddleless horserace around the magnificent and slightly sloped, Piazza del Campo. The city itself is a preserved time capsule, taking its visitors into the past just by walking along the cobbled streets. The city was once Florence’s chief competitor and housed a number of artists and engineers to match.

The city streets ramble up and down the hillside, narrowing into stunning alleys, and somehow leading into astonishing piazzas. The city is filled with Gothic churches and the aroma of creamy gelato. The largest draw of the city is the Cathedral of Santa Maria Assunta. The black and white marble façade is immaculate. The circular rose window allows light to pour into the cavernous interior. The church is known for its 56 separate marble mosaics decorating the cathedral floor.

You have the opportunity to view the church in a way most visitors are unaware. You will follow your guide into the Gates to Heaven. A stairway leads you to the ceiling above the altar where you have a view of the vaulted ceilings decorated to match the Tuscan starlight. The panels on the floor tell different tales from the Old Testament cast in remarkable color and detail. Although it is the same church, a change in perspective can make all the difference.

Farmland stretches from the gates of the old city to the horizon. The vines of boutique vineyards ripen with juicy grapes. After breakfast, your guide leads you into the countryside once more to visit a number of unforgettable abbeys dotting the landscape. The Abbey of San Galgano was erected in the 13th-century and stood for many years as Italy’s finest Gothic structure. Today, the Abbey stands more in ruin than preservation, empty of windows and a roof. However, the brick and open archways, where the windows once stood, adds a touch of drama to the countryside.

The remaining pieces of the cloister have a tint of red and gold from the stone. You can continue to Pieve di Montesiepi, a local and renowned parish church. The church has a round outline referred to as a rotunda overlooking the sweeping greenery of the countryside. The archways offer a view of the rolling hills and cypress trees waving in the breeze. This church commemorates the legend of Saint Galgano who stuck his sword into the rock on the hilltop where it could never be removed.

The country roads outside of Tuscany can lead you to mountains and valleys, including to a small town with a panorama of Florence. The town of Fiesole is an easy and fast venture. The town is nestled in the hilly valleys separating the Arno River from the Mugnone River. The air is crisp and fresh. The breeze rustles against oak trees and the collection of cypress trees rising along the hills. The Etruscans settled in the hillside around the 9th to 8th-centuries BC.

The Cathedral was erected in the 11th-century and contains a shrine to St. Romulus inside the golden-stone exterior. The tranquil ambiance of the city is welcoming. Famous writers from Boccaccio to Gertrude Stein enjoyed the solitude and natural beauty of the town, including the atmospheric winding streets that lead to the Zona Archeologica, housing a collection of 1st-century BC Roman ruins. The Roman Theater was constructed on a natural slope, able to accommodate thousands of spectators. Its well-preserved condition allows the town to use it for concerts in the summer for a perfect blend of different cultures. When you look out to the view of Florence, you can see the city where your trip began, embodied in the wondrous dome of the Florence Cathedral.

In the morning, you find comfort in the familiar streets of Florence. You can walk down the same avenues you have strolled past before, taking in the sweet aromas of marzipan and freshly baked cakes. Secret bakeries deliver their delicious confections to local cafes. People linger at tables lining the sidewalk and sip their morning espressos. You spend time reveling in the daylight, wandering down alleys you had never noticed before. Signs on certain buildings connote the passages in the Divine Comedy.

Soon, your private transfer will meet you in your hotel lobby and escort you to Florence International Airport. For now, you can continue you personalized exploration of Tuscany with each new step you take on the charming streets of Florence.