An Italian Wine Tasting Journey: From Piedmont to Tuscany Wine Tour

Rolling hills in Piedmont to Tuscany during fall.
A 9 day trip to Italy 
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Italy should be devoured! Piedmont with its mountains and Tuscany with its hills: fill your senses with tastes from award-winning vintners, wines that range from robust to comforting, old to young, and food that sings and melts in your mouth, all with medieval towns at your fingertips. Italy allows you to slow down, smell the grass, smell the food, smell the wine, see the land, touch history, and devour it all. 

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General Information

Lake Maggiore, Italy.
House with vibrant flowers hanging on its wall in Tuscany.
Wheels of parmesan cheese in Tuscany.
Detailed Itinerary

Places Visited 

Barolo, Barbaresco, Alba, Greve in Chianti, Radda in Chianti, Montalcino

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1 – Brace Yourself for the Feast

Arrive at the Milan airport, meet the driver and prepare to be transported to a world where taking the time to enjoy yourself isn’t an indulgence: it’s a way of life. Enjoy the ride from Milan to La Morra as you pass the green mountains and high hills into the Piedmont region. Take time to notice the hillsides covered in grapevines from top to bottom, with the remnants of a medieval town looming over it all. Check into your intimate home away from home nestled in the Nebbiolo vineyards. Enjoy the heartwarming and welcoming aperitif that will not only kick-start your appetite, but also the insatiable need to know, taste, and touch all that Italy has to offer.

Your private guide will ensure that your tastes in Piedmont, whether with food, wine, history, or culture, are satisfied. That satisfaction begins with meeting Elio Altare, acknowledged globally as one of the world’s greatest wine makers. He is also a leader of the revolution in cellar and vineyard technique in the Barolo area. He is a sweet and humble person that might remind you of your favorite uncle. You will be guided through his small family cellar where you will have an exclusive tasting session, full of wines that can range from full bodied and smelling of roses to tannic and tasting of blackberries. Enjoy typical Piedmontese fare: the pungent delicacy of Grana Padano cheese and gnocchi alla bava, velvety and supple potato dumplings garnished with melted cheese and butter. 

What's Included: transfer, winery visit, accommodation

Day 2 – A Burst of Flavor 

Stroll through the narrow and concentric streets of the La Morra commune, where you can see and touch the history of this charming medieval town. Buildings and towers made of stone stretch above the vine-covered hills, where the scent of growing grapes is never far away. Explore La Morra until your tour of the Benedictine Abbey of S. Martino di Marcenasco— an abbey so famous for its wines that Pope Pius VII requested it for his personal consumption. Today, instead of monks, you’ll find the Ratti Museum located deep in the cellars of this Roman Baroque building. The Ratti is a museum dedicated to the history of wine and the vine. The contents of the museum range from wine bottles that date back to the early 1700s—some are hand-blown—to antiquated vintner tools. 

Pay a visit to the Wine Estate Fratelli Oddero, founded in 1878, in the Langhe hills, and positioned like an island in a sea of vines. Determined to keep their wine flavorful and traditional, they only use grapes from family-owned vineyards to make their wine, the Barolo, also known as “The King of Wines.” You will smell violets and licorice,  and its taste is dry, full bodied, and strong. Delight in the wine as the Italian lifestyle allows you to do.

In the village Barolo you can see the Castello Falletti di Barolo—where the legend of the “King of Wines,” was born—looming large above the village. Finish the day with a tasting at the Giacomo Borgogno & Figli Winery, where you will enjoy Barolo Classico, made according to tradition with proper oak barrels and aging techniques. Satisfy your hunger with a quick food demonstration on Piedmontese cuisine about foods like fiori di zucca ripieni, fluffy, lightly fried stuffed squash blossoms, and crocchette, crisp rice or potato croquettes that are stuffed with cheese. 

What's Included: breakfast, accommodation

Day 3: Wake Up and Smell the Vineyards

Today you’ll spend time in Alba and Barbaresco. Pass through the deep purple of the Nebbiolo grapes and past estates into the quaint village of Barbaresco, where you can sit in the shadow of a 10th-century tower that was built for battle and has been fought over for supremacy. Its height and construction still inspire awe. In a deconsecrated Baroque church where the glimmer of gold is still visible, the Enoteca Regionale is devoted to present the efforts and contributions of the Barbaresco region to the ingenuity of the vineyard and the cellar. You can see bottles from 130 different wineries and 250 labels. Venture into I Produttori del Barbaresco, where you will taste the Barbaresco, see the brilliant ruby red fade to maroon with age. Taste the dry, warm, tannic flavor, and smell the hints of vanilla. You can learn about the “terroir” and how the area of Barbaresco affects the grapes—in particular, how the soil, climate, sun, and air can shape different flavors on the same hill—along with the history of the beautiful wine. 

Stroll through the center of medieval Alba, the White Truffle Capital of the World. Alba can satisfy all tastes, whether for culture, food, or shopping, with classic architecture, chic clothing, deliciously strong espresso, and the smell of fresh pastries permanently in the air. If visiting Alba in the autumn, do not miss the White Truffle Fair, usually between the end of October and beginning of November. It is a chance to enjoy the white truffle in its earthy scent and strong taste in various forms, from shavings in everything such as delicate pasta and creamy risotto to dark chocolate and silky ice cream. The end of the day brings a visit to the historical cellar of Pio Cesare, where a tasting of Barolo and Barbaresco await. Take this opportunity to assert the knowledge you’ve gained so far about the atmosphere and flavors of the delicious wines you are experiencing.

What's Included: breakfast, wine tasting, accommodation

Day 4: A Hunt Can Be Satisfying

Casa del Trifulau means “Truffle Home,” and it will be more than just a home for you while you scour through the green of trees, large vines, and guarded earth. Join in the excitement of the hunting party, the bark of the dogs, the jokes of the crowd, the heart-pounding exhilaration of finding an illusive white truffle, and feel your mouth water in the knowledge that soon you will be able to taste its powerful yet delicate flavor.

Lunch brings a beautiful tasting menu and wine pairing at Castello di Grinzane, with a faded brick interior and the smell of fresh pasta and bread filling the dining room. Afterwards, a tour of the Cerreto vineyard will indulge more than just the palate but will be a feast for the eyes, as well. 

Sitting between the villages of Barolo and La Morra is the colorful, quadrangular creation of Cappella delle Brunate, also known as the Brunate Chapel. Enjoy a guided tour of the chapel, whose squares of blue, red, and yellow make it look as if the structure was made from a deconstructed rainbow instead of a dilapidated church. With a visit to the cellar of Bricco Rocche Winery and to the glass cube amongst the vines, you’ll absorb and indulge in the taste of divine Ceretto wines. The sweet smell of the Piedmont air, the beauty of the modern art, and the diversity of the culture ensure your final evening in the region is an unforgettable one.  

What's Included: breakfast, truffle hunting, lunch, guided tour, accommodation

Day 5: A Different World of Flavor

Depart for Tuscany where—even though it may be geographically close—a different world of wine and food await you. Watch the mountains of Piedmont give way to the rolling hills of Tuscany as you make your way to Greve in Chianti. Have lunch at La Scuderia in Badia a Passignano, a beautiful restaurant located at the top of a hill in a medieval castle. Enjoy the tart earthiness of porcini mushrooms and artichoke on crostini, or have your first taste of the decadent bistecca alla Fiorentina, a luscious Florentine t-bone steak that’s seasoned with olive oil and salt. 

Meet Valentina Lami, your guide through Tuscany, a sommelier with a Masters in Aesthetics. She will escort you through the best of Tuscany, beginning in Greve at a charming piazza surrounded by buildings of pink, white, and yellow. In the mornings here you can smell the pastries, and in the evenings, you can smell the candle smoke and salumi. Stroll through the piazza, and visit the local butcher to grab some panini. Top off your afternoon with a visit to Casaloste, a small winery with international recognition, where they concentrate on quality (not quantity) through intense supervision of the grapes during harvest and a continuous monitoring of fermentation. Their concern for their product, and for sustainability, mixes tradition with creativity. The outcome is a harmonious wine with an intensity that everyone can enjoy. 

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

Day 6: Here You Taste Innovation

Today you break from the traditional ruby and tannic Chiantis. Treat your palate to Super Tuscans in the Chianti Classico area. Venture to Castelnuovo Berardenga where you will find the Felsina Winery near Siena, the sleepy medieval town that explodes twice a year in the summer for Il Palio. This bareback horse race encompasses the entire main piazza and was the background festivities for the beginning chase scene in the 2008 James Bond movie, Quantum of Solace. Felsina Winery is in an area the Romans thought to be blessed by nature, and you will see why: in the bright blue sky, the green and gold hills covered with vines, the air that smells of grapes, and the richness of the earth. Felsina wines will refresh your senses with a variety of dark berry and peppery scents. See if you can smell the barrels, their potency infused into each wine. 

At the vineyard of Montevertine you can revisit your knowledge of terrior and its affect on the various grapes on this nearly 45-acre property, like the Montevertine, made with Sangioveto and aged in Slavonian oak. Enjoy your lunch at Le Panzanelle in Radda, Chianti. The Pici all'aglione is a traditional Tuscan pasta, made of tender and firm, fat spaghetti that’s often tossed in a refreshing, citrus tomato sauce with a zip of garlic. Settle into the scent of fresh tomato sauce, simmering all morning for you to savor.

Next, you will visit Fontodi, south of the town of Panzano, called “the Golden Shell” because of its amphitheater-like shape. Fontodi is known for the plush and herbaceous Case Via Syrah and their famous Flaccianello della Pieve, a classy red with cherry and raspberry accents and a vibrant finish. Have a guided tour of Radda in Chianti. The city’s been enclosed in defensive walls since the Middle Ages and is located high up on a hill between the valleys of Arbia and Pesa. Walk through the cobblestone streets. Duck into local stores that sell handmade and well crafted clothing, or incredible panini. Do as the Italians do, and sit in the piazza with a caffe, a robust shot of espresso with a side of bottled water to round out the flavor of the dark coffee. 

What's Included: breakfast, transfer, wine tasting, lunch, guided tour, accommodation

Day 7: Here You Taste Tradition

High quality—as a tradition of Tuscan wine—originated in Burnello, notably at the Biondi Santi Winery. Known for its aroma of blackcurrant and a full bodied, sapid taste, Biondi Santi is a cathedral of Brunello, with vines that run over the tasting room, letting the façade blend in with the hills. At Cerbaiona Winery, you will relish the traditional flavors of a Brunello di Montalgino, with layers of smoke, menthol and licorice; it is elegant and graceful. At Enoteca Osticcio, you will be treated to a special tasting menu full of Montalcino and Chianti Classico, and the variety of aromas and flavors that come with them. 

Next stop is Talenti Winery. Named after the proprietor, Talenti is a young and passionate winemaker whose innovation is matched with tradition to produce the best possible taste in every grape. Complete your day with a visit to the Abbey of Sant’Antimo, a beautiful brick structure that stands against the vibrant green Tuscan hills that surround it. The Canons, an order of priests, have called the abbey home since 1992 and are also known as the White Canons because of their dress robes. Enjoy the beauty and grace of the abbey and its surrounding landscape, with the sound of rushing water from the River Starcia and the smell of olive trees nearby. 

What's Included: breakfast, winery visits, accommodation

Day 8: Another Day to Relish

Your last day in Tuscany brings with it a taste of Bordeaux along the Tuscan coast. Marchese Incisa della Rocchetta is located in Tenuto San Guido and known for its Sassicaia, a wine that’s full-bodied, with dried berry and coco bean and hints of wood. Like your journey through Piedmont and Tuscany, it’s luxurious. Not just for those who love wine, Tenuta San Guido is also an oasis for wildlife, and is the first WWF Wildlife Refuge in Italy. Don’t forget to look skyward for the variety of birds that soar through the area. 

Ornellaia and Masseto Wineries are situated in Tenuta dell’Ornellaia, which overlooks the calm of the Tuscan coast. Not only is the tart scent of grapes in the air, but also the salt of the ocean. Take a moment to feel the sand between your toes. Feel the cool, saltwater on your feet. Let the breeze of the coast rush through your hair. Take a moment to yourself and remember where you are.

Pay a visit to Enoteca Tognoni, a delicious and quaint wine purveyor inside the Castello di Bolgheri. With its large spires and cropped windows, it will make you feel like royalty coming home at the end of a journey, with a tasting menu of local wines.  

What's Included: breakfast, wine tasting, accommodation

Day 9: Full of Life and Full of Experience

Take the morning to explore the Tuscan countryside one last time, with a strong caffe in the piazza and a sweet brioche. Bask in the memories of the trip and let the flavors, smells, and adventures fill you. Depart for either the Florence or Pisa airport. Or if you, like so many others, have been seduced by the majesty of Italy and haven’t devoured enough, extend your trip and get ready for another helping of Italy’s limitless offerings.

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.