Wonders of Italian Renaissance Tour: Past & Present

A 8 day trip to Italy 
4.75 out of 5 stars
16 reviews

When imagining Tuscany, you can easily conjure up medieval towers and historic walls, undulating hills and vibrant sunflowers. Cities radiate historic artwork and the countryside bursts with vineyards. Step beyond the imagined, venturing past the veil of your imagination and into the true grandeur of history. Your custom tailored tour immerses you in the splendor of Tuscany and lets you experience the beatitudes of alpine foothills, overlooked Renaissance towns, and even poetic vendors, allowing you the chance to discover the character of life in every day Tuscany. 

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General Information

Detailed Itinerary

Places Visited 

Florence, Prato, Pistoia, Lucca, Garfagnana, Pisa, Volterra, San Gimignano, Siena, Chianti 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Beginning with the Renaissance

The signs of the past are written all over Florence, from the architecture beautifying the historic city-center to the statues in the public squares symbolizing an enlightenment of art and knowledge. The aroma of espresso beans and marzipan emanates from gilded cafes; their doors flank enticing display cases lining Via del Corso. The image of Palazzo Vecchio stands to watch over Piazza Signoria and was erected at the beginning of the 14th century. The Romanesque building continues to house the seat of Florentine government, and casts an imposing shadow over the square, stemming from its adorning tower standing more than 308 feet tall. When you arrive at Florence International Airport, your private transfer is there to greet you, ready to escort you to the city center.

You notice the historic city walls lining the outside of the city center, near Fortress da Basso, dating back to the 13th century, with the outline of the original walls surrounding the central square at Piazza del Duomo, constructed by the Romans. The city is unlike any other you have ever visited, bustling with youthful energy and vigor and brimming with history. Art and architecture students study Florence Cathedral. Sculptures examine the statue of Perseus holding the head of Medusa. Chefs taste the simple flavors of the cityscape, each paying tribute to the traditional tastes of Tuscany. You have just arrived and already feel the wave of the city’s wonders washing over you. Consider reading some of our travelers' Italy tour reviews to gain additional ideas 

What’s Included: transfer, accommodation

Day 2: Inside the City Walls

Inside the walls of the historic city center is the preserved world of the Renaissance. An image of the wall’s full power stands against the backdrop of the Fortress of Belvedere, where an old tower still stands. Near the Boboli Gardens, the walls look to separate the rolling cypress-clad hills of the countryside from the cobblestone streets of Florence. After breakfast, your guide meets you in the lobby of your lavish hotel, eager to lead you on a private tour of the city.

The Uffizi Gallery and the Accademia contain some of the most iconic images of Medieval and Renaissance art, from Michelangelo’s David to The Birth of Venus by Botticelli. Your guide leads you through the dazzling array of artistry, eventually bringing you through the vibrant neighborhood of San Lorenzo. The outdoor marketplace lines the streets near the Central market. Scarves, hats, and leather goods decorate the stalls. Behind the melee of commerce is the inconspicuous Basilica de San Lorenzo, the parish of the Medici Family designed by acclaimed architect Filippo Brunelleschi in the 15th century.

Inside the stone structure, the cloister provides a private arcade encircling a lush courtyard. The library has a collection of historical manuscripts collected by Cosimo the Elder that continued to expand throughout the years, including holding an 8th-century Bible and a Roman encyclopedia. A copper gridded ceiling decorates the reading room. Marble floors line the walkway. Natural light pours through the numerous open windows, providing stunning illumination and captivating warmth.

What’s Included: breakfast, tour, accommodation

Day 3: Deserved Attention 

The morning stretches over Tuscany, and you can see the hillsides around Florence brighten with an emerald green hue. At breakfast, you sit and savor the strong flavor of a fresh espresso, nibbling on a sweet almond brioche. Your private transfer meets you at your hotel and leads you away from Florence, and into the charms of lesser known, and often overlooked, Pistoia. The city is an amalgamation of influences from Pisa and Florence, prevalent in the medieval churches, artistic accouterment, and even inspiring contemporary architecture. The Museo Capitolare, Cathedral Treasury, was erected in the 12th century, mentioned by Dante in the Divine Comedy, and always thought to be overflowing with riches. Red brick nudges against white and black marble, creating a unique exterior.

The bell tower next to the treasury stands almost 219 feet tall. Once inside the museum, you can find the priceless work of the Cross of St. Atto, designed in a Venetian workshop in the 13th century. You can also find 40 separate works by the famous Ferrara painter Giovanni Boldini, which are considered some of the most important preserved pieces providing insight into the study of 17th-century Florentine paintings. The mastery of the city is undeniable. The beauty of the city is in part due to its tranquility, feeling to you more like a lovely secret.

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

Day 4: More than a Tower

Wake up in Lucca, a delightful Tuscan town surrounded by preserved medieval walls. In the morning, the city begins to liven with the aroma of espresso dripping out of countless cafes and shops. The display windows of the nearby bakeries shine out to the cobblestone avenues. Your guide leads you along the path of the city showcasing the old stone of the walls and how today they also act as a park for locals to visit. Many people jog along the pathways lining the ramparts. After your exploration of Lucca, you travel to the celebrated city of Pisa, known most ardently for the Leaning Tower.

The piazza that holds the tower is as enchanting as the tower itself, filled with the Pisan architectural style of marble work, with small columns adorning the cathedral and baptistery. The tower casts a shadow over the grass, much like a sundial. The architecture is impressive in its scale and beauty, with 294 steps leading to the top of the 14th-century construct that lists nearly four-degrees. One of the main sights of the city overshadowed by the Piazza dei Miracoli is the Palazzo dei Cavalieri.

The palace was enlarged in the 1500s and remains the most ornate building outside of the Piazza dei Miracoli. You find the façade adorned with the coats of arms and busts of six Grand Dukes of Tuscany, all from the Medici Family. A double staircase leads to the entrance underneath a projecting roof. To this day, the palace houses the Scuola Normale Superiore, an elite college of higher education founded by Napoleon in the early 19th century.

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

Day 5: Searching the Hilltops

In the morning, you leave behind the pristine marble of Pisa and make your way through the treasured Tuscan hills, showcasing the unparalleled greenery sprawling along the rolling landscape, quickly reaching the town of Volterra. The town emanates the picturesque beauty of the region’s famous medieval history. The stone streets wind along the city’s prevalent past, along with touching its ancient history in the form of Etruscan walls and arches dating back to the 3rd century BC. In the 18th century, the city became known for mining and shaping alabaster. The earthen aroma reminds you of glazed clay. Red-tiled roofs top the cream colored stones of the city.

There is a local charm to the streets, filled with gelaterias selling refreshing fruit flavors like strawberry, and indulgent flavors like chocolate chip. In Piazza dei Priori, Volterra’s central square, you find the Palazzo dei Priori. The palace was erected in the 13th century and contains the coat of arms decorating an austere façade. The building housed the chief magistrate and later the Florentine Priori, highlighted by the heraldic lions of Florence embossed on the columns flanking the exterior. On the main floor of the Council Chamber, you find frescoes decorating the walls, telling the detailed history of the city in 19th-century bravura.

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

Day 6: Unexpected Siena

The city of Siena climbs along the hilltops like a crown. The 17 neighborhoods, known as the Contrade, have had a prideful rivalry for centuries, culminating in the Palio horseraces two times a year. During the rest of the year, the city walks the tightrope between energetic and sleepy, spread along the medieval cobblestone streets and decorative churches of the historic city center. The Municipal Palace stands at the edge of the main square topped with a large tower with a marble crown, standing 334 feet above the piazza.

Water fountains erected in the Middle Ages feed on underground aqueducts and continue to trickle throughout the city. Walking down the typical alleys, you notice the lanes wind underneath storied buildings and stone buttresses supporting the historic structures. Locals add lushness to the streets with plants and hanging pottery outside their green shuttered windows. For a unique view of the city’s splendor, you venture into the Gates of Heaven, which takes you under the roof of the Siena’s Cathedral.

The gothic structure was erected in the 13th century. The black and white striped marble catches your eye before you see the glimmer of the gilded portico. The cathedral is known for its stunning beauty, which includes the one of a kind marble etching in the floor, containing 56 panels showcasing tales of the Old Testament. You climb the hidden travertine staircase to the roof, where the Gate of Heaven opens to the entire cathedral, providing a view to the star-studded vaulted ceiling, down the narrow nave, and over the magnificent details, including the indoor pipelines used to carry rainwater from the roof to the courtyard.

What’s Included: breakfast, tour, accommodation

Day 7: More than Vibrant Hills

The landscape around Siena evokes an immaculate beauty stretching out from under the Tuscan sunshine. After breakfast, your private transfer meets you at the hotel and escorts you into the hillsides, passing under the shade of cypress trees, and alongside the far-reaching vines of boutique wineries. Inside the province of Tuscany is the region of Chianti, known for the wine it produces and the fascination it evokes. The main town of Greve has a market-town ambiance with a charming main piazza. Cafes and restaurants encompass the stone square. Enoteche, wine shops, offer samples of the regional favorites. The restaurants and enoteche complement one another nicely, blending the best flavors and traditions of Tuscany.

The triangular shaped Piazza Matteotti contains 500 years of history, with arched colonnades supporting the bordering buildings and adding a flair of the past. The aroma of freshly made Pici, a Tuscan pasta, emanates from the cuisines set in street-side cafes. The shingled rooftops guide your eyes to a view of the encompassing hills rolling across the horizon. The simple pleasures of Italy shine in Tuscany. A castle near Greve has you out on the terrace with a view of the lush countryside, sipping on a glass of wine in the shade, tasting the magnificence of the province all around you. You could even visit the “Poet butcher” of Panzano, who recounts memorized lines from Dante’s Divine Comedy when slicing pieces of prosciutto to take with you.

What’s Included: breakfast, transfer, accommodation

Day 8: Carrying the Renaissance Home

In the morning, you wake up to the sounds of the past echoing off of the stone buildings and cobblestone streets. When in Florence, you can’t help but think of the marvelous artistry decorating the museums and inspiring students, baristas, architects, artists, business people, and others from around the world. In the morning, you can sip a foamy cappuccino, a treat to accompany you among the statues of the Loggia. You take in a final breakfast surrounded by the Renaissance art sitting in the open for everyone to experience.

You nibble on a brioche filled with chocolate and look up to see the infinitesimal details of the dangling strands of hair of Hercules as he battles Nessus. Soon your private transfer will meet you at the hotel to escort you to Florence International Airport, but you could always extend your stay, continuing your immersion into history with a visit to classical Rome or charming Venice.

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.