Culture of Tuscan Wine & Cuisine Tour

A 9 day trip to Italy 
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The red hue of a perfect bottle of wine shines like a ruby. The scent of freshly made pasta emanates from a restaurant located in a historic cellar. Chestnut trees and olive groves fill the open Tuscan valleys, leading you to far-reaching vineyards and medieval hilltop towns. Your custom tailored food and wine tour of Tuscany takes you on a unique blend of wine and culinary experiences set in the world-renowned countryside of Tuscany. Tuscany is where the cuisine is as artful as the region’s Renaissance paintings, the wine is as important as the medieval architecture, and the culture is rooted in the landscape.

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General Information

Detailed Itinerary

Places Visited 

Florence, Carmignano, Chianti, San Gimignano, Volterra, Bolgheri, Elba, Siena, Montalcino, Montepulciano

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: A Tuscan Introduction

Florence is the capital of Tuscany, brimming with artistry from the architecture to the cuisine. The fame of Michelangelo, Galileo, and Dante Alighieri precede the glory of the city. The aroma of creamy gelato drifts out of the award-winning gelateria, “Perche No!” The scent of freshly made pasta wafts upwards from the succulent sauces showcased on a street-side café table.

One of our Italy tour operators will arrange for a transfer to greet you at Florence International Airport. As you are driving to your hotel, you feel like the imagined flavors of the city have already captivated you. You have thought about sitting alongside the Arno River savoring espresso with the sound of the current lapping against the riverbanks.

In the evenings, the low hum of Gregorian chants fills the have of San Miniato al Monte, overlooking the skyline of Florence. The small and historic artisan shops on the Otrarno, the opposite side of the river, fill with handmade jewelry and leather goods. The city is exactly how you imagined it: contemporary energy inside a Renaissance shell.

For dinner, you venture into a typical 14th-century building to find a delectable restaurant highlighting the succulent cuisine of Tuscany, including sliced tender beef with regional Pecorino cheese. To accentuate each dish, you have a paired wine chosen directly from the antique family cellar.

What’s Included: transfer, dinner, accommodation

Day 2: Absorbing Tradition

The morning light glints off of the top of Florence Cathedral’s famous brick dome, which glows a golden red. You enjoy a foamy cappuccino and flaky brioche at breakfast before venturing outside of Florence to the charming town of Carmignano. The village is located inside one of the smallest wine regions in Italy, totaling 279 acres with only 13 wineries. The art of winemaking in the region dates back hundreds of years and was officially recognized by the Grand Duke of Tuscany in the 18th-century. The iconic vision of Tuscany encompasses the town, filled with creamy stone buildings surrounded by lush green hills rolling across the landscape.

The climate is slightly cooler than in Florence, which affects the grapes grown on the east-facing slopes, changing the flavors of the wine entirely. You can see the 16th-century Medici villa with grass terraces and distinguished chimneys in the distance. Your guide leads you through a local vineyard and pulls a grape from the rows of vines. The earth is soft, and the grapes are ripening. Your guide explains the difference in the growing process, from Chianti in the south to the climate around Florence, and how the Sangiovese grapes, along with Cabernet Franc brighten in the cooler climate. In the tasting room, you sip at a blend of Cabernet-Sangiovese and find an aroma of dark berry fruits and forest herbs.

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

Day 3: Touch of the Enthusiast

When the sun rises over the countryside, you can see the bell tower of the 12th-century Romanesque church of San Leonardo rising in front of the hills. After breakfast, your private transfer escorts you southbound to the Chianti region for a deeper understanding of the variety of grapes across Tuscany, sampling the most favored wine of the region, Chianti. The town of Greve in Chianti is a medieval hilltop village whose main streets are lined with wine shops, each specializing in unique terroir. The cobblestone streets provide unparalleled ambiance, and the surrounding lushness of Tuscany reminds you of the relaxing countryside of which you can enjoy.

You arrive at a villa located on the hills overlooking the Greve River. The reddish hue of the building stands out from the emerald hue of the cypress trees and trimmed garden hedges. A stone dog and lion guard the entrance looking out to the southbound hills. Chestnut trees and oak surround the small terraces and shade galloping horses at the farm. Wheat fields and vines lead to olive groves. The aroma of dried timber blends into the fragrant air. The villa was originally constructed in the 14th-century and continues to produce notable Tuscan wines. 

Your local chef shows you through the kitchen, where you find baskets of fresh ingredients harvested from the farm. A plate of extra virgin olive oil entices you to taste the locally sourced and produced dressing. Your chef leads you through each ingredient, where it came from, and its importance to the meal. You follow your guide, tasting each piece of the puzzle until a fresh, beautiful coursed meal stands before you, filled with traditional earthen flavors, such as cannellini beans with red onion and brightened with lemon juice.

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

Day 4: Towers and Cellars

The succulent aroma of the olive grove adds to the reminiscent citrus of yesterday’s unforgettable lunch. The splendor of the villa stays with you as you remain in Chianti but venture southeast towards San Gimignano, a town known for its splendid white wine and invigorating medieval towers. The towers stood as a sign of wealth to the noble families of the area, once totaling 72. The tallest tower, Torre Grossa, was erected in the 14th-century and stands 177 feet tall offering a stunning panorama to the encircling countryside. It is easy to stroll around the meandering cobblestone streets, which rise and fall with the hillside, absorbing the harmonious and historic ambiance.

Many different enoteche, wine stores, offer samples of the Vernaccia, a Tuscan white wine with an aroma of white flowers and dried apricots. You find a silky and layered flavor that unfolds on your palate, much like the city itself. In the afternoon, you visit the sister city of Volterra, once an Etruscan stronghold, and delight in a charming restaurant situated inside an ancient Etruscan cellar. The historic gates of the city are made of stone and continue to protect Volterra from outsiders. The Etruscan arch dates back to the 4th and 3rd-centuries BC, combining heritage, tradition, and delicacy. 

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

Day 5: Between History and Essence

In the morning, you can see the towers of San Gimignano rising over the surrounding mountains. The beautiful scenery around Tuscany never fades, and instead, continues to surprise you. After breakfast, you venture west towards the Etruscan Coast, known for sensational beaches and crystal clear waters. A little more than six miles from the shore is the town of Bolgheri, a few miles north of the principal coastal city of Livorno. Lush cypress trees line the road into town ending at Bolgheri Castle. The red brick of the castle initially hides the charming town. A coat of arms adorns the main gateway welcoming you into the city and dates back to the 13th-century.

The preserved historic center showcases the brick and stone of the past and offers insight into the rich cuisine and enticing wines engrained in the local culture. The vineyards beyond the hamlet reach to the foothills. The area is known to produce more than one lavish wine, including the Bordeaux trio, combining Cabernet Sauvignon, Cabernet Franc, and Merlot, along with the celebrated Super Tuscan Sassicaia, one of the finest Italian red wines. The Tenuta San Guido Winery has produced the coveted wine since the 1940s. The elegant notes contain an aroma of chocolate and light smoke with a silky texture and slightly fruity flavor on your palate, taking in the elements of the landscape.

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

Day 6: A Different View of Tuscany

In the morning, your private transfer leads you farther west, taking in the view of the azure waters on the Tuscan coast. You board a ferry at Piombino. The ocean breeze has a semi-sweet aroma that is cool against your skin. The salty air has a seducing quality. You arrive on the shores of the Island of Elba, in the town of Portoferraio. The island was once home to Napoleon after his exile from France. The historic qualities of Elba are prevalent along the cobblestone streets leading away from the harbor and along the rugged mountains climbing to a height of 3,343 feet on the summit of Mount Capanne.

A small group of people populates the beaches all around the island, soaking in the Mediterranean sunlight and dipping their toes into the refreshing waters. The hills glimmer with green beryl and purple amethyst when the light hits the island slopes. At the Villa dei Mulini, you can enter the home of Napoleon, who was brought to the island in 1814. The villa was once two homes joined together. The barn was converted into a ballroom. The location provided a commanding position over the island’s capital and a view to the water. The interior contains the Imperial style furniture bringing the past back to stylish life. In the evening, you can indulge in the daily catch accompanied by a glass of Aleatico, a locally produced sweet, red wine, with flavors of roses, plum, and strawberry.

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

Day 7: Sunlight to Sunflowers

The morning light washes over the beaches and shines along the crystal azure Mediterranean. The golden hues of Portoferraio imitate the color of the water where the sun is reflected. The aroma of espresso is unmistakable and inescapable around Italy. It is refreshing and inviting. You can hear the water lapping on the shores of Elba and are a bit sad to leave the island behind.

When you return to mainland Tuscany, your private transfer greets you at the ferry terminal and escorts you through the lush landscape. Behind you, the tranquil shores of Italy fade, replaced by rolling hills lined with oak and cypress trees. The country roads meander around fields of vibrant yellow sunflowers. The closer you move to Siena, the brighter the sunflowers. You can see the medieval city before you reach, its historic center crowning the hill. Olive groves and vineyards climb up and down the landscape. The verdant aroma is pleasant and relaxing. The city itself has a quiet power encased in the cobbled streets, romantic alleyways, and black and white marbled cathedral. The cathedral was erected in the 13th-century with a façade spire reaching a height of 252 feet. The interior floor is as decorated as the frescoed walls, with 56 mosaics etched into the marble.

After your exploration of the city, you can sit down for an indulgent meal in a tuff-stone restaurant with a crisscrossing vaulted ceiling. Enjoy the typical dishes of Tuscany in a secluded niche where each dish uses seasonal, locally sourced produce, paired with an exquisite wine.

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

Day 8: Nobles of the Tuscany

In the morning, the cafes of Piazza del Campo set out their tables and open the umbrellas for an extra area of shade underneath the Tuscan sun. After breakfast, your private transfer guides you away from the sensational city of Siena and towards the quaint and regal towns of Montalcino and Montepulciano. Each town is known for its production of Brunello di Montalcino and Vino Nobile di Montepulciano respectively.

A historic fortress guards the hilltop town of Montalcino. It resembles a storybook village huddled inside of the ramparts overlooking the Ombrone and Asso Rivers. The current walls were erected in the 14th-century, but Etruscans settled on the hill over 2,000 years ago. When you walk around the city, you can press your fingers against the hard stone of the preserved walls. Six gates and towers remain standing, now adding ambiance to the historic atmosphere.

Inside the fortress is a charming wine shop specializing in the local splendor of Brunello di Montalcino. Your guide explains the process of the wine and what makes this particular varietal so special. Exposed brick lines the cellar. A window lets in natural light. A small table holds your glasses. You listen to the sound the wine makes as your guide pours it into the glass, explaining that the wine first gained prominence in the 14th-century and celebrated the world over for its merits. When the Brunello is darker and richer in color, the fruity, leathery aromas are accentuated. When the velvety, complex flavors fade on your palate, you understand the reason people celebrate Brunello di Montalcino.

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

Day 9: Always More than Average

The morning in Florence has a particular song-like quality. The shops open along Via Tornabuoni. Steam rushes out of espresso machines. Locals stand at café counters nibbling on fresh brioche before heading into work. You have tasted your way through Tuscany, venturing to towns and enjoying the cuisine. You can sip your morning frothy cappuccino and know that you have immersed yourself in the true flavors of Tuscany, taking the splendor of each city, town, and village with you.

Soon your private transfer will meet you in the lobby and escort you to the Florence International Airport, but for now, you sit and recall the simple memories of your travels across the countryside.

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.