Flavors of Italy: From Private Truffle Hunting to Cooking Class Itinerary

Black truffles mushrooms on rustic wooden table.
A 10 day trip to Italy & Vatican City 
4.75 out of 5 stars
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In Italy, good food is as important as breathing, so each bite is meant to be an indulgence. Your personalized tour of Italy will immerse you in the luxury of gastronomic excellence. Follow an experienced hunter through the hills of Umbria in search of black truffles, explore the depths of a cave where local purveyors age their celebrated prosciutto and then enjoy the comforting aromas of an exceptional glass of Brunello in Tuscany before savoring an unforgettable Roman gnocchi made by your own hands. From the sweet life to ancient tradition, you can experience the artistic pleasures of an unparalleled Italian tour in culinary style.  Read more here to explore itineraries throughout Italy and extend your culinary journey.

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General Information

A chef ladles on fresh tomato sauce onto a pizza base.
Morning sun rise on the Colosseum in Rome.
View of Tuscany from the restaurant.
Tables and chairs outside a cafe in Pienza, Italy.
Lush green fields of the Tuscan landscape.
The cobbled streets and fortress of Montalcino in Tuscany, Italy.
Looking across to the medieval fortress of Montalcino in Tuscany.
A beautiful street in Pienza, Italy.
The Abbey of Sant'Antimo in the comune of Montalcino, Tuscany.
The Colosseum in Rome, Italy.
Green and black olives on a branch.
Looking out onto the surrounding fields of Montalcino in Italy.
Spaghetti with parmesan cheese and a glass of white wine.
The Abbey of Sant'Antimo in Montalcino, Tuscany.
A gondola carries tourists along the Venice canals, Italy.
A row of gondolas in Venice, Italy.
Castel Sant'Angelo and the river Tiber in Rome, Italy.
Italian risotto with mushrooms.
Piazza Navona in Rome, Italy.
The Palazzo Vecchio is the town hall of Florence, Italy.
Pienza square of the Cathedral in Tuscany.
Detailed Itinerary

Places Visited 

Venice, Rome, Florence, Pienza, Siena, San Gimignano, Montalcino, Pettino, San Miniato, Vatican City 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Venice – Arrive in Venice for a Grand Canal Tour of the Famous Republic

Venice floats along canals, and the eponymous lagoon with grace and distinction as grand palaces shimmer with Istrian marble and elegant gondolas drift along the water. Bridges arch over the narrow waterways that connect the nearly 120 islands that create the fascinating city, and your flight will land at Marco Polo Airport on the shores of the Grand Canal.  You will step aboard a private boat ready for your marvelous exploration of the two-mile long highway of water that runs through the city.

You can see the tower of St. Mark’s Campanile as you ride across and it will add dimension to the charming skyline as it reaches a height of more than 320 feet. The scent of grilled fish dressed with lemon juice blends with the aroma of freshwater as you arrive at the wooden plinths that are used to support the surrounding structures as they rise out of the canal. Barges and speeding vaporettos cast rippling wakes as you glide past the Rialto Bridge. The marble feature was created in the 16th century to replace the collapsed wooden bridge, and the figure now stands as one of the iconic images of Venice as the renowned gondoliers row beneath the archway. Click here for reviews from our other travelers as you look forward to your own arrival to Italy.

What’s Included: airport transfer, accommodation, tour

Day 2: Venice – Relish a Half-Day Tour of Venice and a Delicious Culinary Excursion

The aromas of persimmons and eggplant float around the Rialto Market in the returning morning as vendors call to passersby with fish, fruit and all sorts of food to enjoy. Your guide will greet you in your hotel lobby to take you on a private tour of the grandeur of the former Republic, beginning in the famous square of Piazza San Marco. The bulbous domes of the Basilica reach a height of more than 140 feet tall as the sunlight washes over the façade to reveal the golden Byzantine mosaics. Your guide will point to the two griffins on the first arch near the glistening reliefs that cover the 6th-century marble pilasters.

The interior contains the herbaceous spices of frankincense and myrrh and the brilliant light pours through the windows to cause the nearly 45,650 square feet of golden mosaics to shine with an ethereal luminosity. In the evening, your guide will lead you through the hidden neighborhoods of Venice to cross the walking bridges and cobblestone lanes set beside the bustling Cicchetti, the Venetian wine bars. Locals enjoy the cool night air and the delicate aromas of salted cod or pork meatballs dressed in rich tomato sauce. You will join them in the comforts of watching the city pass you by as you sip a refreshingly crisp white wine accompanied by squares of grilled polenta, fried olives, and cheese dipped in olive oil.

What’s Included: accommodation, tour, breakfast

Day 3: Florence – Visit a Celebrated Prosciutto Farm and Enjoy a Tour of Florence

You will take to the Grand Canal in the morning as you use the private dock of your luxurious hotel to pass the impressive façade of the Santa Maria della Salute. The structure was built in thanks after the end of the plague in the 17th century, and the calm waters ripple beneath the magnificent dome. You will arrive on the opposite bank and step into a private car bound south for remarkable Florence, and the meadows and floodplains around the Veneto region turn to the foothills and forests of Emilia Romagna as you drive.

You will stop at a private prosciutto farm to meet with the masters that craft the delicious flavors of the cured meat that is enjoyed across Italy and around the globe. The lesser-known area of Culatello provides more flavor than the better-known Parma ham due to the condensation of the Po River and early morning fog. The cows and sheep graze on the lush meadows around the farm leading to the pens while the villa overlooks the verdant farmland that leads to the nearby trees. The scent of pine fills the air and castles rise along the mountains around the region.

Your guide will introduce you to the process of crafting the perfect prosciutto, and you will watch as they roll the pork leg in salt and pepper, wrapping it in a clean net to dangle from the rafters of a cave. You will find the aroma in the grotto familiar as it fills with the scent of the aging, seasoned meat. At the end of the tour, your guide will slice away a freshly taken prosciutto for you to taste the flavor of the classic, regional dish.

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

Day 4: Florence – Explore the Art Museums and Legendary Culture of Florence

The scent of freshly baked brioche will drift over the cobblestones of Florence in the morning and emanate from the bakeries that are hidden around the historical city center. The vendors along the San Lorenzo Market open their doors and stalls to showcase the fine leather goods and silk products that are crafted by hand in the heart of Florence. The decadent scent of fresh espresso will fade beneath the earthy fragrance of the leather purses and belts and surround you. Your guide will greet you after a small breakfast and lead you through the aisles of the 19th-century wrought iron structure of the Central Market as vibrant fresh fruit creates pyramids of color beside the delicious carrots, artichokes, and zucchini flowers.

Local vendors present olive oils and beautiful cheeses crafted on mills and farms in the Tuscan countryside. Sandwich makers create unforgettable panini beneath the lofty rooftop crafted by the famous Italian architect Giuseppe Mengoni. You can sample some of the soft and hard cheeses, enjoy the savory flavor of the salami, and continue to the Uffizi Gallery to view the renowned artworks on display crafted by the artists such as Michelangelo, Botticelli, and da Vinci.

What’s Included: accommodation, tour, breakfast

Day 5: Tuscany – Discover White Truffles, Olives, and Medieval Towns in Tuscany

The cafes in Florence’s city center return their tables and chairs to the cobblestone streets and piazzas as locals visit the corner bars for a quick espresso before work. The sunlight will wash over the bronze replica of Michelangelo’s David that adorns the Piazza Michelangelo with its tremendous view over the city skyline. Your private transfer will escort you away from the Renaissance city to traverse the beauty of Tuscany, beginning in the town of San Miniato. Cypress and oak trees decorate the country lanes as pale pink towers rise above the surrounding vineyards and rolling verdant hills.

Local traditions abound through the continued efforts of leather works and truffle hunters, as the town gained prominence in the 13th century due to its connection to Via Francigena, the road connected France to Rome. The medieval square of Piazza della Repubblica has curved protective walls that were built during the medieval period leading to craftsmen workshops that date back to the 14th century. Outside of town, you will follow your guide through the trees on a hunt for the white truffle, often referred to as the “Golden Mushroom.” The will dogs will dig their noses into the grasses to help you search through the vast landscape of picturesque hills with the aromas of oak and chestnut as they overlook the banks of the Sieve River. The dogs will begin to bark, and your heart will pound with excitement as you unearth the round and slightly golden mushroom, whipping away the remnants of soil and eager to sample the seductive, pungent flavor.

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

Day 6: Tuscany – Delight in a Wine Tasting Tour in Montalcino and Pienza

The emerald hue of the Tuscan hills returns with the sunlight as freshly brewed espresso offers a vibrant aroma that lingers in the dining room of your luxurious accommodation. Idyllic wineries spread across the foothills, valleys, and knolls and after breakfast, you will venture to the first of a selection of celebrated wineries near Montalcino to sample the excellent flavors of Brunello, a wine made from a distinctive Sangiovese grape. You will arrive at a winery that has been decorated with vines and olive orchards as a historical villa crowns the hill.

During the harvest, farmers take to the vines with large bins to collect the grape bushels by hand. You will walk along the aisles and touch your fingers to the smooth, deep purple skin of the grapes and notice the plump texture. You will pull a grape from the vine and pop it into your mouth, and the juice will burst and offer a slightly sweet and sour flavor. The cellar will overtake 5,500 square feet and resembles a church as it rises out of the vines. The cool, unchanging climate protects the wine throughout the aging process beneath cedar slats that undulate along the rooftop. You will sample your first Brunello and find aromas of dark fruit, chocolate, and leather drifting from the glass. You will continue to the town of Pienza for an immersive look at the preserved architecture of the Renaissance.

What’s Included: accommodation, tour, breakfast

Day 7: Rome – Enjoy a Black Truffle Hunt in Umbria and Explore Baroque Rome

The beauty of the medieval alleyways of Montalcino and the Renaissance piazzas of Pienza will replay through your mind at breakfast. You will set out for the day after your meal to explore the fascinating history of Rome with a stop in Pettino, Umbria along the way. The old village carries the traditions of its culture through its preserved architecture, rich forests, and continued customs. The 15th-century narrow lanes and sporadic towers stand atop a plateau at over 3,600 feet above sea level, surrounded by the peaks of the Apennines. Farmers grow farro and lentils while keeping sheep, cattle, and goats.

The moisture in the woodlands allows truffles and porcini mushrooms to thrive, so your guide will meet you in the village before leading you through the beech and oak trees in search of the black truffle. The decadent ingredient grows along the valleys beneath the soaring mountain peaks. You will have a sensational view across the Spoleto Valley, with glimpses of the Assisi and Perugia in the distance. You can scour the hills and lowlands with the energetic dogs while following the traditions of the truffle that date back more than 200 years. You will discover the round, dark brown and black truffles peeking out of the soil. Your guide will tell you to inhale, and you will find familiar hints of strawberries and cocoa emanating from the truffle. You will then return to Pettino to sample the robust flavor of the amazing ingredient with a multi-course lunch designed to highlight the variety of culinary uses for the delectable truffle.    

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

Day 8: Rome – Experience Ancient Rome and Enjoy a Delicious Cooking Class

Ancient Rome continues to inspire and enchant visitors from around Italy and across the world thanks to the masterful architecture that has been well preserved. The culture has spread and evolved over the more than two millennia, which is reflected in the way the morning market brims in Campo dei Fiori. Calla lilies blossom against roses and sunflowers on the flower stalls as the square fills with the aroma of blooming daisies. Your guide will lead you on an early tour through the vibrant market to find the perfect ingredients to craft a traditional Lazio lunch. Tomatoes shimmer with ruby skin as oranges offer a vibrant, zesty aroma to the air. You will enjoy the aromas of the marketplace before retreating to a private kitchen to learn about the importance of simplicity for the food.

Your guide will turn now to chef and detail the intricate movements involved to turn semolina into delectable gnocchi, differing from the Northern Italian tradition of using potatoes. After forming the dough into a thin, long roll, you will cut nearly identical pieces away. You can taste the savory pecorino Romano cheese and sausage spiced with red pepper. After completing the meal, you can dive into the indulgent flavors of a Roman artichoke dressed with black and white olives. After lunch, continue into the depths of Ancient Rome to stand in the shade cast by the nearly 160-foot tall outer wall of the Colosseum.

What’s Included: accommodation, tour, breakfast

Day 9: Rome – Traverse the Vatican Museum, Villa Borghese, and Trastevere

The scent of truffles will fade beneath the sweet aroma of honey in the daily market beside Circo Massimo. Artisans from around the Lazio region offer splendid arrays of cheese, olive oil, cured meats, and wine, and honey, along with the celebrated truffles discovered at the base of the hills. Your guide will escort you to St. Peter’s Square after breakfast to see the magnificent oval-shaped piazza that crowns the dome of the Basilica. You will enter the museum to discover the various tastes of the successive popes that date back to the early 16th century when Pope Julius II opened the galleries to the public.

The halls glisten with marble floors, antique pillars, and gilded frames, and you can follow the grand paths into the former papal apartments as decorated by the master artist Raphael. The work culminates in the piece School of Athens, which depicts masters of the Renaissance as Greek philosophers, including Leonardo da Vinci as Socrates. The depiction of each character embodies the Renaissance in their humanistic elegance. After exploring the gardens of the Borghese Villa, your guide will lead you on a private tour of the cuisine of Rome inside the working neighborhood of Trastevere. Ivy coats the facades and dangles down to the cobblestone streets as the night fills with music and the ambiance of artists sipping espresso in the cafes. The aroma of classic Italian dishes, such as pizza and pasta, drift through the doors of the hidden trattorias. 

What’s Included: accommodation, tour, breakfast

Day 10: Rome – Depart for Home

The morning light will spill through the large circular hole at the center of the Pantheon’s gigantic dome. The architecture inspired Michelangelo’s work on St. Peter’s Basilica and Brunelleschi’s dome on Florence’s cathedral. The bustling flower market in Campo dei Fiori returns with the aromas morning glories and jasmine while nearby the marble stairs of the Spanish Steps glint beneath the Trinita dei Monti. The scent of coffee emanates from a popular cafe that opened in the late 1930s. Their secret blend brings Romans from around the city to enjoy the unique specialty flavors crafted by the mid-20th-century wood-roasting machine. After one last morning to enjoy it all, your private transfer will greet you at your hotel and escort you to Rome’s Fiumicino Airport for your flight home.  

What’s Included: airport transfer, breakfast


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.