Tuscany Tour of Medieval Cities & Renaissance Preserves

View of Pitigliano town at sunset. Picturesque and unusual - built on tuff, tufaceous volcanic rock.
A 8 day trip to Italy 
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When you think of Tuscany, you can already imagine the green hills and practically taste the lingering pleasures of Chianti wine. Your custom tailored Tuscany tour of Medieval cities shows you the celebrated Italian province by taking you deeper into the cities you already know, and into the countryside towns protected from the toils of time like a secret. Let your private guide lead you to Renaissance artwork and down preserved streets of medieval villages holding close to heritage and tradition. Taste award-winning local cheese and revel in a perfect view of Tuscany from atop a medieval tower. 

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General Information

Detailed Itinerary

Places Visited 

Florence, Pisa, Lucca, Cortona, Arezzo, Siena, Monteriggioni, Crete Senesi, Volterra, Montepulciano, Montalcino

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Familiar Florence 

The city of Florence is at once newly exciting and wholly familiar. When your private transfer greets you at the airport, you can feel your heart racing, eager to set your eyes on a city known for art, architecture, and legendary leaders. The old city walls layer various districts of the city, culminating with the 13th-century walls that continue to encircle the historic center. In the heart of the city, you can see the towering red brick dome of the Florence Cathedral, the largest brick dome in the world, set behind the pink and white marble façade. Renaissance and medieval palaces continue to line the streets, now filled with boutique shops and apartment complexes. The city’s officials fill the halls and rooms of the Old Palace located in Piazza della Signoria. Statues vibrant with detail decorate the large plaza, each telling a story of its Renaissance designer and ancient content.

After your settle into your centrally located hotel, your guide meets you in the lobby, enthusiastic to lead you on a private tour of Florence’s luxurious sites. The scent of freshly made gelato drifts out of elegant gelaterias. You can see the influence of the Medici’s in much of the city, including inside the family’s church, the Basilica of San Lorenzo. The church was erected in the 15th-century and has maintained a graceful interior. The polished marble floors lead to the high altar, flanked by tall-pillared archways. The design is unique and fits the elaborate tales of the historic wealth and exuberance of the family that helped shape much of Tuscany.

What’s Included: transfer, accommodation

Day 2: Essence of the Pisan Republic

In the morning, the scent of fresh espresso adds an undeniable energy to the air around the city. Locals linger in the cafes and sip their rich and bitter drink before continuing to work for the day. After breakfast, your guide meets you at the hotel and escorts you to the famous city of Pisa. The city once had a navy to rival that of Genoa. The renowned structure of the Leaning Tower was built to commemorate the Republic’s important naval battles.

The city around the Piazza dei Miracoli quietly sits on the banks of the Arno River. The Church of Santa Maria della Spina sits on the left bank with charming Gothic spires, which leads to the church’s name, meaning “thorn.” Inside the Piazza del Miracoli, you find marvelous marble structures in the Baptistery, the Cathedral, and the Leaning Tower. The grass around the piazza looks brighter set against the pristine facades of the buildings. Cypress trees create a fragrant air. The tower leans at a four-degree angle and stands over 183 feet.

The Republic broke ground for the tower in the 12th-century, adding more layers to the statue as the centuries passed, making the structure look similar to tiers of an intricate wedding cake. The Cathedral has a grandeur of its own, erected in the 11th-century, with a marble Pisan Romanesque façade. You are immediately drawn to the marble inlay around the three portals filled with bronze doors. The intrigue of the city goes beyond the tower and brims from the striking history of the Republic.   

What’s Included: breakfast, tour, accommodation

Day 3: Leisurely Lucca

After breakfast, you travel through the Tuscany hills en route to Lucca. Oak and chestnut trees grow along the valleys. Cypress trees line country roads that lead to hidden medieval villages. Olive groves provide a succulent aroma to the landscape. When you arrive in Lucca, the well-preserved historic walls surrounding the old city center are striking. Today, a public park encompasses the walls, lined with pathways where locals walk, job, and cycle. The greenery lends itself to the powerful stone ambiance cast by the ramparts. Inside the walls is a city filled with a creamy and rustic hues.

Guinigi Tower is a massive edifice at the center of the city topped with holm oaks. The lush trees sprawl from atop the red brick building, which are two connecting mansions constructed between the 14th and 15th-centuries. The tower stands 145 feet tall overlooking the encompassing cityscape. It takes 230 stairs to climb to the top of the tower and enjoy the shade of the hanging garden. The view of the outlining three concentric city walls and Roman center of town offers you the uniqueness of Lucca and the exquisite landscape of Tuscany in one sweeping panorama, including the image of the 14th-century clock tower across town.  

What’s Included: breakfast, tour, accommodation

Day 4: Over the Etruscans

The antique world of Tuscany shines brightly throughout the day, whether in one of Florence’s many museums or strolling along an ancient street in a hilltop town outside of the province’s capital city. If you'd like more time in Florence, consider extending your time in the remarkable city. You may want to browse the reviews for our Florence tour operators.

After breakfast, your private transfer leads you to the town of Arezzo, considered one of the oldest cities in Tuscany, dating back to its Etruscan roots as far back as the 6th-century BC. The medieval atmosphere rushes along the cobblestone streets and around Piazza Grande. An elegant colonnade lines the north edge of the square, with three separate palaces helping border the public space. The city itself has an undeniable charm. Construction began on the cathedral in the 13th-century but was not completed until the 20th-century. Three doorways adorn the façade beneath a large rose window. The entire church stands on Arezzo’s highest point. The interior holds a fresco by Renaissance master painter Piero della Francesca. The painting depicts Mary Magdalene as a saint, with an abundance of brown hair striking a vibrant contrast to the bright colors of her clothing. Your day continues on the enchanting streets of Cortona, the medieval town where numerous scenes from “Under the Tuscan Sun” were filmed. 

What’s Included: breakfast, tour, accommodation

Day 5: Medieval Towns and Lunar Landscape

The diverse setting of Tuscany is endless, filled with splendor in the hilltop towns and wonder in the landscape itself. In the morning, the lush countryside is blanketed in a light mist. The sunrise burns away the moisture, leaving the greenery shimmering in dew, from the grass to the cypress trees. You leave Florence for the day making your way to Siena. On the way, you find the incredible countryside of Crete Senesi, known for its lunar-like landscape separating it from the iconic Tuscan scenery. Barren, gentle hills run against solitary cypress trees and sporadic oak trees. Old farmhouses point to small, wooded areas that lead to the edges of hidden villages.

A clay formation adds a vibrant whiteness to the semi-arid foothills around the Desert of Accona. Monte Oliveto Maggiore Abbey stands on an isolated hill resplendent in cypress trees at the heart of the Desert of Accona, encircled by steep ravines. The abbey was erected in the 14th-century and has amassed a vast collection of ancient books and parchments. To access the monastery, you have to cross a drawbridge that immediately takes you back to a different era of Italian life. The palace is constructed of red brickwork with a quadrangular tower. A botanical garden stands behind the bordering cypress trees. The ambiance is unparalleled and perfectly sets the tone of historic wonderment to come throughout the day.  

What’s Included: breakfast, tour, accommodation

Day 6: Slice of Life

In the morning, locals set out on the Arno River and paddle against the current near the Ponte Vecchio. In the early hours, people jog alongside the riverbanks taking in the beauty of the historic city center. After breakfast, your guide leads you to the hilltop city of Volterra. The city projects a medieval ambiance with such effortlessness that the city was cast as the principal setting for certain characters in Stephanie Meyer’s best-selling Twilight book series.

Volterra’s roots date back to the Etruscans and fell to the Romans in the 3rd-century BC. The ancient walls continue to encircle the vibrant, Renaissance city center. The Cathedral of Santa Maria Assunta was built between the 12th and 13th-centuries but remodeled in the 16th-century. The chapel has a small fresco depicting the Procession of the Magi. The bright colors and detailed characters create an absorbing atmosphere.

You venture into the Tuscan countryside following your exploration of the hilltop city. A farm encompassing 6,177 acres has approximately 1,000 sheep grazing freely across the landscape that helps ensure the high-quality diary that adds to the taste of the superior Pecorino cheese. Your guide leads you through the production, taking in the different stages, including showing you the aging process. At the end of your tour, you can taste the variety of flavors set in the traditional hard texture of the sheep’s cheese.

What’s Included: breakfast, lunch, tour, accommodation

Day 7: The Maremma

Extensive forests pave the countryside of Maremma leading to the coastline. Salt marshes and estuaries contain blossoming flowers bordering country roads, and charming villages with unique customs separate from Tuscany’s most notable cultures. When passing through the unpaved roads, you can find cowboys herding Maremmana, a type of cattle unique to the region with long horns and white pelts. Your guide leads you through the upper and lower regions of Maremma, each known for different types of splendor, from hilltop towns to treasured wines. At the base of Pitigliano, you find a town sitting atop rugged cliffs. The town had a large Jewish population for more than seven centuries.

An unusual road connects Pitigliano, Soran, and Sovana by way of Etruscan necropolises excavated from the vertical walls of the cliffs. Stairways twist around the ascending city. Cobbled alleys bend beneath elegant archways lining charming stone houses. La Piccola Gerusalemme, means “Little Jerusalem” and stands near a kosher butcher, bakery, wine cellar, and the small but lavish synagogue erected near the end of the 16th-century. Natural light spreads across the marbled floors and central dais. Eight chandeliers hang from the lofted ceiling. The grace of the sanctuary encompasses the entire history of the town and its ability to endure.

What’s Included: breakfast, tour, accommodation

Day 8: Preserving Memory

The gilded plated doors of the Gates of Paradise glisten in the morning light. The streets are tranquil and filled with the aroma of freshly baked pastries. Shops open their doors for the day, setting out their displays in the windows open to the historic walkways. You can sit and enjoy your last morning, sipping espresso and watching the locals start their day.

Your private transfer meets you at the hotel ready to escort you to Florence International Airport. Now that you have experienced the unending treasures of Tuscany, you could always extend your stay, or even venture south to Rome to spend time in the Eternal City.

What’s Included: breakfast, transfer


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.