Classic Tuscany Itinerary 2019

A 8 day trip to Italy 
4.92 out of 5 stars
12 reviews

Classic is another word for quality and charm, words that describe the splendor around you. Cafes set out tables alongside streets offering you a moment to yourself surrounded by indescribable history. Standing in front of Michelangelo’s David teaches you how to treasure a moment. Listening to the quiet passing of the Arno River provides a soundtrack to unforgettable memories. Your custom tailored 2018 Tuscan tour offers you the true meaning of classic, where no single image creates the wonders of the region. Instead, you find a unique combination of Tuscan experiences that shows why the word “classic” is synonymous with timelessness. 

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General Information

Detailed Itinerary

Places Visited 

Florence, Lucca, San Gimignano, Siena, Asciano, Monte Oliveto Maggiore, Pienza, Montepulciano Monteriggioni 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Light from the Shadows 

Florence is home to dazzling art and superb culture, emanating from the cobblestone streets and classic architecture. Cafes line the banks of the Arno River. Palaces hide behind stunning gates at the heart of the city. Your private transfer greets you at the airport and escorts you into the historic city center. The splendor of the city is almost overwhelming.

The dome of the Duomo adds shape and dimension to the antique skyline of bell towers. In Santa Croce Church, the aroma of frankincense continues to waft up and down the nave. Giotto’s frescoes dating back to the 14th-century decorate the walls, depicting the life of St. Francis. Funerary monuments of Leon Battista Alberti, Galileo, and Machiavelli decorate the interior, including the tomb of Michelangelo, casting a long and inspiring reach on the arts of the city.

The laidback culture of the city brings to light the ideals of truth and beauty in art. The Accademia houses Michelangelo’s David, and Bargello Museum houses Donatello’s David. Both works of art are a testament to their time, marked with indescribable detail, and sensational in their size, able to tell an entire story in a single pose.

The scent of café con latte, or coffee with milk, fills the afternoon air. Bakeries display dwindling pieces of cake and cookies. It is easy to settle into the luxuries of the city cast in the preserved antiquity.

What’s Included: transfer, accommodation

Day 2: Enlightened Beginnings

The morning begins with the scent of espresso drifting out of gilded cafes. You can sit and enjoy a morning cappuccino, letting the foam add a pillow-like softness to the texture of your drink. Your guide meets you at the hotel after breakfast ready to show you the city, known as the Birthplace of the Renaissance. Consider learning more about your luxury Italy tour companies who strive to provide you with the highest quality and meticulously personalized itinerary. The white and green marble of the Cathedral glints in the sunlight. The replica-gilded doors of Giotto’s Gate’s of Paradise situated on the Baptistery illuminate the stories of the Old Testament. The actual golden doors stand in the Museo dell’Opera del Duomo in the Piazza located behind the cathedral.

The city has an undeniable energy ready to sweep you up and convince you to stay. The scent of the morning filled with baked brioches and coffee fades to freshly made pasta and simmering sauces. The Uffizi is an absolute must see when in the city, highlighting the vibrancy of the Renaissance in the representation of people and objects. Cosimo de Medici funded the building in the 16th-century to use as offices for the city’s magistrate. Today, the marble floors and open windows create an opulent space to house works invented by some of the greatest artists the Western World has ever known.

The building itself is emblematic of its holdings, where every step offers insight into the past inside an opulent space with classic style. The air is cool inside, and the sunlight reaches every corner of the interior. Your guide brings you to the painting, Dukes of Urbino, painted by Piero della Francesca in the 15th-century. The painting depicts the Duchess and Duke facing one another and commemorates the Duke’s ability to turn the city of Urbino into a refined and renowned cultural center. Your guide explains the reason for the profile depiction, due to the fact the Duke had lost his left eye during a tournament.

What’s Included: breakfast, tour, accommodation

Day 3: Against the Apuan Alps

In the morning, you can see the greenery of Tuscany cast in the hills around the city. Cypress trees stand along the landscape standing out against the bright blue sky. After breakfast, your private transfer sweeps you away from the city and into the charming foothills of the Apuan Alps in the town of Lucca. The city is known for its ramparts constructed in the 16th-century, which still enclose the city today. In the background, you can see the snowcapped peaks of the mountain range. The red-tiled roofs of the historic center shine against the lushness of the walls, now inhabiting a public park. Romanesque churches line the cobbled streets.

Residents ride bicycles and jog around the historic and impressive walls. San Michele in Foro has a tiered façade resembling a wedding cake, complete with sham arches and pillars. The church stands atop the old Roman Forum and was erected between the 12th and 14th-centuries. A statue of the Archangel Michael adorns the tiers looking down on the square. The original pavement continues to decorate the interior in gray and white, along with the marble pillars and Corinthian toppers. The beauty of the city goes beyond the encompassing walls and fits into the preserved wonders of Lucca, including the embracing culture.

After a morning of exploring, you will make your way to a class designed to teach conversational Italian skills. The qualified native Italian speakers of Lucca Italian School will teach you everything you need to know to confidently travel through Italy. Learn how to order your favorite Italian meal and introduce yourself to impress the locals. A wonderful Lucchese style lunch is served at a local restaurant to showcase traditional Tuscan heritage. Afterwords recollect on the Italian you have learned and set out to practice your new skills for the rest of your journey through Italy

What’s Included: breakfast, transfer, accommodation, conversational Italian course with Lucca Italian School

Day 4: Twin Towns

In the morning, the image of the undulating peaks of the Apuan Alps fades. The walls disappear. Your private transfer escorts you away from the medieval town of Lucca and into a city that once controlled the most powerful navy on the Mediterranean coast, Pisa. The sun casts the Piazza dei Miracoli in light, highlighting the pristine marble of the Cathedral, Baptistery, and acclaimed Leaning Tower. The tower stands 183 feet tall and lists almost four degrees, decorated with quintessential Pisan architectural design. Outside of the square, the city is often overlooked. However, there is more to the city than the Leaning Tower.

The National Museum is a former Benedictine Convent of San Matteo and features Tuscan images dating between the 12th and 15th centuries. The unassuming edifice contains sculptural masterworks by Pisano and Donatello, along with antique paintings by Berlinghiero and Volterrano. The museum is located near the Palazzo Medici along the banks of the Arno River. You can hear the current brushing the water against the subterranean walkways.

You have found that the best moments in Italy come when you take the time to notice your surroundings. In the calm cityscape, outside of the Piazza dei Miracoli, you can’t help but notice the historic majesty of Pisa.

What’s Included: breakfast, transfer, accommodation

Day 5: Pristine Past

In the morning, the sunlight highlights the strength and height of the San Gimignano’s 13 remaining towers. The wealthy 14th-century families of the city built the towers as a symbol of their wealth and prestige, once numbering 72 separate towers climbing along the hilltop. The city has an unparalleled enchantment set in the meandering cobblestone streets, climbing towers, and panorama of the Tuscan countryside. You climb to the top of Torre Grossa, standing at a height of more than 177 feet. The view is outstanding.

The red rooftops slope into the rugged sandstone facades of the old city. You can still hear the sounds of people walking along the streets. The antique ambiance of the historic city opens to the valley floor. A breeze brings cool and refreshing air. You can see as far as the Apuan Mountains in the distance. When you descend the tower, you venture into Palazzo del Pòpolo, a 14th-century building connected to the tower. Inside the connected Municipal Art Gallery, you can find a room dedicated to the 13th-century poet Dante Alighieri, author of the Divine Comedy. The poet once visited the town and stayed in the room now decorated with an elaborate collection of medieval frescoes.    

What’s Included: breakfast, transfer, accommodation

Day 6: Into the Palaces

Siena has a golden sheen in the morning, cast by the historic red brick buildings topped by Palazzo Pubblico, which now stands as the city’s town hall. The day is yours to explore the city, taking in the wonders of the staggering Torre del Mangia, the 334-foot tower overlooking the Piazza del Campo, and the Cathedral of Santa Maria Assunta, home to numerous mosaics etched into the marble floor.

The cool breeze brushes over the hillsides, and you come to Piazza Salimbeni, surrounded on three sides by the facades of threes separate palaces. The 14th-century Gothic Palazzo Salimbeni stands at the center. The square once acted as the palace’s garden until the mid 18th-century. The palace itself now houses the offices of Monte dei Paschi di Siena, a bank founded in the 15th-century. The original decoration has been preserved, showcasing unique busts adorning the ledge above the entryway. The uniqueness of the building and its preserved nature immerses you deeper into the culture of the city and its vibrant hold of its history. 

What’s Included: breakfast, tour, accommodation

Day 7: Slowly Finding Tuscany

In the morning, you leave behind the hills of Siena making your way towards the charming town of Montepulciano. En route, you notice a sensational abbey standing perched on a cliff. The structure is the 15th-century Oliveto Maggiore Abbey, known as a type of territorial abbey. The creamy stones of the building stand out against the greenery of the Tuscany countryside. You access the monastery over a drawbridge, which encapsulates the brilliance of Tuscany. So much history can be preserved in the rush of perpetual progress. A terracotta of the Madonna and Child adorns the entrance arch.

The large and graceful structure opens into cavernous halls that absorb the echo of your footsteps. The oldest side of the cloister, erected between the 1420s and 1440s, contains various frescoes, one specifically painted by ll Sodoma, situated underneath the vaults and representing the masterworks of the Italian Renaissance. The work shows an account of St. Benedict’s life with marvelous detail paid to the architecture and cherubic faces of the characters. The continuous marvels of the countryside are no longer surprising but always enriching and captivating. You continue to Pienza and eventually find yourself near the palaces and the Renaissance church of Montepulciano.

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

Day 8: Renaissance Once More

Vines and cypress trees drape the tall hills of Tuscany, producing some of the most treasured wine and landscape in all of Italy. After breakfast, your guide meets you at the hotel to take you on a brief tour of the city, known for its cool wine cellars overtaking Etruscan tombs. Wine shops line the meandering streets. The walls surrounding the 16th-century town have helped preserve the historic ambiance and detail, with touches of Baroque architecture and noble familiarity perched on the hills.

The church of San Biagio stands atop a cypress-lined avenue. The golden color of travertine shines in the afternoon light at the center of Tuscan lushness. The high dome ceiling encompasses a floor plan of an equal length Greek cross. The image of the building itself is striking, and you admire the focus it took to design and create the interior. After your tour, your private transfer meets you at the hotel and escorts you to Florence International Airport for your flight home.

What’s Included: breakfast, tour, 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.