A Foodie's Slow Tour of Tuscany

A 8 day trip to Italy 
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Cuisine runs deep in Italy, connecting families and reflecting the soul of the chef, whether cooking rustic pasta at home or preparing gourmet dishes in a restaurant. The scent of celebrated confections emanates from display windows along the main avenues. Luscious cheeses maintain complex flavors, offering insight into the care taken during their production. Ruby-tinted wines glow against the verdant hills and cypress trees. Your 8-day foodie tour of Tuscany takes you deep into local tradition by highlighting cuisines and methods of creation, from the farm and vineyard to the table, showcasing the labors of love with every sumptuous bite you take.

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General Information

Detailed Itinerary

Places Visited 

Rome, Montepulciano, Pienza, Castellina in Chianti, Greve in Chianti, Florence, Siena, San Gimignano, Montalcino

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Developing Italian Sensibilities   

Italy is known as much for its delicious cuisine as its inspiring architecture spanning millennia. When you arrive in Rome, you find more than just the Colosseum standing proud, watching over the whitewashed stones of the Roman Forum. St. Peter’s Basilica rises above the city, adding to the elegant skyline of the surrounding cupolas of the city. The aroma of freshly made pasta fades with the sweet and enticing scents of creamy gelato emanating from the countless gelaterias. Your private transfer meets you at Fiumicino Airport and escorts you to a luxurious hotel situated in the heart of the historic city center. The allure of Italy radiates around you, from the gentle splashing of the Trevi Fountain to the blossoming gardens of Villa Medici.

A true introduction to the city is saved for dinner when you enter a restaurant producing authentic dishes of Rome with innovative twists near the vast public square of Campo De’ Fiori.  The menu changes with the seasons, utilizing ingredients from local farms. The outdoor patio looks out onto Piazza della Cancelleria. Locals stroll past without a care in the world, intoxicated for a moment by the aromas drifting from the restaurant doors. When the cacio e pepe hits the table, pasta in a cheese and pepper pan sauce, you find how stunning and complex a simple dish can taste.  

What’s Included: dinner, transfer, accommodation

Day 2: Introduction to Tuscan Tastes

In the morning, you wake up to the vibrant aroma of fresh espresso wafting out of every café. Bakeries set sweet brioches in their windows, displayed to passersby. After breakfast, your guide meets you at the hotel and takes you out of the Eternal City, venturing northbound into the famous rolling greenery of Tuscany. Consider learning more about your highly experienced luxury Italy tour companies that strive to provide you with the most memorable trip of a lifetime. Cypress trees line the country roads, providing a picturesque view of the treasured hillsides. In the distance, you see the towering outcrop of Montepulciano, rising to a height of 1,984 feet above sea level on a limestone ridge. The medieval and Renaissance town has an ineffable charm emanating from the red tiled roofs and historic bell towers. Local vineyards stretch into the distance.

The main street runs for almost a mile connecting the main entrance gate to the main public square known as Piazza Grande. Wine cellars speckle the avenue offering samples of the wines grown around the cityscape. One of the most famous cellars belongs to the Cantucci family who converted the city’s antique jail into a wine cellar, optimizing the dim, cool space to protect the wines from climate and weather changes. The Cantucci family have owned vineyards and produced wine around Montepulciano for over 1,000 years.

When you enter the cellars, you find a paved brick room lined with two levels of barrels, separated by the walls and archways leftover from the building’s original design. Your guide leads you through the cellars explaining the harvesting and storing process, also pouring you a sample of the Vino Nobile di Montepulciano. The bright red color glows in the light of the cellar. You find a bouquet of cherries and violet with a balance of structure and tannins finishing your delightful sip.

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

Day 3: Road to Chianti

In the morning, a light mist settles over the lower hills of Tuscany. The sunlight spreads across the landscape, shining over the dissipating dew, and leaving behind a layer of moisture on the grass. The herbaceous scent of the countryside accompanies your creamy morning cappuccino. After breakfast, your guide leads you down the rocky ride of Montepulciano, through the harvested herbs of Castellina in Chianti and into the medieval town enchantment with an ancient history of Greve in Chianti.

At the heart of the Chianti region, you find the main triangular plaza bordered by a colonnade. The castle, from which you felt, tasted and absorbed the aromas of various herbs grown and dried in the region, watches over the city from above. The 14th-century church of Chiesa Santa Croce adorns the square. Nearby the city is a local farm that produces a variety of goat cheeses. The farmland is awash with vast greenery touching the bordering cypress trees and draping the hills. Goats roam freely around the landscape grazing on the grass.

Your guide takes you to the property, showing you the organic methods of the farmers, from the open space to the dairy. At the end of the tour, the tangy scent of goat cheese fills the tasting room, a similar aroma to the processing room where you watched the mild filtering process. A large block of cheese sits on a rustic wooden table. The crumbly cheese has bits of tarragon and chives, to create a unique and savory flavor bursting with every bite.

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

Day 4: Renaissance of Flavor in Florence

In the morning, the vineyards around Chianti look like grids across the hillside, dividing the lush landscape between the trees. After breakfast, your guide sweeps you along the road from Chianti to the fabulous city of Florence. The medieval walls continue to arch around the northern edge of the city. The Ponte Vecchio, the Old Bridge, which crosses over the Arno River, was constructed by the Romans and rebuilt in its current form in the 14th century, lined with gold purveyors and silversmiths. Images of the Renaissance continue to decorate the city, from the Palazzo Vecchio in the public square of Piazza Signoria to the marble and bronze statues adorning buildings throughout the historic center.

Santa Croce Chruch has a marbled exterior and houses the remains of Michelangelo and Galileo. After your walking tour of the exquisite city, you venture into the celebrated gelateria of “Perche No!” The store offers over 33 flavors of gelato including green tea and saffron, using ingredients sourced from around Italy, such as pistachios from Bronte, Sicily. Your guide takes you to the back of the store where they make the gelato, showcasing the care of each ingredient before churning to make a creamy, sweet, and delectable flavor, such as milk with honey and sesame seeds. 

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

Day 5: Florence Gourmet

Florence comes to life in the morning, with cafes setting out their tables along the cobbled laneways and the statues in the Loggia dei Lanzi capturing the early light with a quiet sheen. After breakfast, the day is yours to explore the city at your leisure, taking in the inspiring sites and tastes in the Renaissance ambiance. The doors of the treasured, tiny sandwich shop of I Due Fratellini opens on Via dei Cimatori, offering traditional tastes of Tuscany, including a glass of regional wine. The brilliance of the Uffizi Gallery shimmers over a long and narrow cobbled square. The gallery was commissioned by Cosimo de’Medici I to provide offices for the Florentine magistrate in the 16th century.

The prominent building now houses some of the most iconic images of the Renaissance inside the gilded rooms and polished marble floors near the Arno River, including the Birth of Venus by Sandro Botticelli. The painting was created in the 15th century and depicts the Roman goddess of love rising from the ocean as a pearl inside a shell, arriving on the shore in an adoring fashion. The wonders of the city are only enhanced by the ambiance and tastes of dinner. A Hapsburg prince who adored the flavors and cooking style of Italy created the subtle traditional ambiance and incredible dishes of La Giostra. Today his son runs the restaurant and the kitchen, producing sensational cuisine, such as the Pecorino Toscano, ravioli stuffed with pears and sheep’s cheese.

What’s Included: breakfast, dinner, accommodation

Day 6: Journey to the Middle Ages

Outside of Florence, the emerald colors of the cypress trees line the hillsides. The gilded mosaics of the San Miniato al Monte glint in the rising sunlight. After breakfast, you leave behind the Renaissance streets of Florence embarking on the medieval streets and architecture of Siena and San Gimignano. In Siena, the cobbled streets run along the hillside, paved with wide boulevards in and the sloping half-shell of Piazza del Campo, home of the famed Palio races. Siena is divided into 17 separate districts, each known as a Contrada. During the horse races, the Piazza del Campo erupts with energetic and proud locals cheering on their horses.

The tradition dates back to the Middle Ages as you see strolling through the charismatic Museo di Contrada. Different flags represent the districts of the city, each decorated with a different animal, from wolves to snails. The regal clothing connotes the colors of the each district, accentuated by the armor and weapons the standard-bearers don. The aroma of ripening grapes drifts into the city from the hillsides, taken over by the scent of panforte, an Italian pastry, from Nannini’s. The confections showcased in the windows entice passersby who prefer savory concoctions, finding ricciarellis dusted with powdered sugar.

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

Day 7: Winning Wines of Tuscany

The towers of San Gimignano watch over the encircling countryside. Once a sign of wealth, the towers now recall the opulence and pride of the families who built them. The images of the staggering edifices linger from the previous day. Settled on a hill in Tuscany is the town of Montalcino, famous for its Brunello wine and brimming with a history that dates back to the 9th century. From the top of the town, you can look over the surrounding valleys to find a mesh of meandering vines and olive orchards. The forceful ramparts of the fortress rise out of the lush trees, resembling a storybook construct. The fortress was erected in the 14th century with six gates and standing alongside the remaining towers.

Inside the fortress, you find the Enoteca la Fortezza di Montalcino, carrying a wide variety of Brunello wines. Your guide offers a brief history of wine making in the area, encompassing a millennium and providing a timeline for the encircling region, along with the enoteca lining the main boulevard of town. Your guide opens a bottle for you to gain a better understanding of the libation known as the “King of Wines.” The dark ruby liquid swirls around the glass, emanating a luscious leathery aroma blended with rich dark fruit. The velvety texture carries hints of spice before fading away on your palate.

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

Day 8: Sensory Memories

The rich aromatics of coffee scent the morning air. The slightly bitter flavor of the espresso brings the day to vibrant life. The shimmering emerald hills around Tuscany continue to inspire you. The landscape no longer just holds the lush colors of the celebrated region, but also reminds you of the flavors you have experienced, from gourmet dining to rustic farms, historic cellars to famous wines. Soon you will arrive at the Termini Train Station, where you will connect to the Fiumicino Airport for your flight home. You have discovered the true traditions of Italy, running deeper than the architecture emanating from the soulful connection and experience the people have with their food.  

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.