Italian Vineyards, Cuisine & Culture Trip: Tuscany, Umbria & Piedmont - 14 Days

Highlights

• Learn about traditional food, local wine, and seasonal eating in Florence
• Visit the chocolate factory where Baci kisses are made in Umbria
• Taste wines and olive oils at an estate near the fabled town of Assisi
• Go hiking in the Langhe and visit a hazelnut farm
• Go on a private truffle hunt in search of prized white truffles

Brief Itinerary

Detailed Itinerary

Day 1: Arrive in Florence, Florentine Food Tour & Dinner

Ciao, and welcome to Italy! You've landed in Florence, a jewel of the Renaissance and the capital of Tuscany. This historic city is filled with architectural beauties, such as the Duomo, and is home to world-famous art by Michelangelo and da Vinci. Upon arrival, a driver will meet you and take you to your accommodation. Drop your bags and refresh ahead of tonight's delicious adventure, which will set the tone for the next two weeks. This evening you'll experience the real Florence through food, learning about local ingredients and the importance of seasonality from a local guide.

The fun begins in the Oltrarno neighborhood, off the well-worn tourist path. Here, you'll stop at various places to try local charcuterie meats, cheeses, truffles, and the city's answer to focaccia. Stroll through Piazza Santo Spirito for a predinner aperitivo. Visit a local enoteca (wine bar) to tour the cellar, then pass artisan shops and local bakeries along Via Santo Spirito on the way to an authentic dinner spot. Sit down for a traditional four-course meal, starting with a Tuscan soup. End, as the Florentines do, with a digestif and gelato invented here in Florence!

Day 2: Art Lovers Tour, Florence Market Tour & Gelato Making Class

Serious art lovers know that Florence is more than just the Uffizi and the Accademia Galleries. This Renaissance city is a true open-air museum. Put on comfortable walking shoes and set out to explore a hand-picked list of the most interesting and notable palaces, cathedrals, architecture, and masterpieces. There are four museums in one building at the Palazzo Pitti, while the Basilica di Santa Maria Novella and Basilica di Santa Spirito churches house religious art with frescos adorning their interiors. You can take the morning at your pace and choose where to stop.

Day 3: Drive to Perugia, Perugina Chocolate Tour & Umbrian Food Tasting

This morning, pair your Italian espresso with something sweet, then collect a rental car and hit the road for a two-hour drive to Perugia, capital of the Umbria region. On arrival, take an orientation tour, starting at the Piazza IV Novembre, where you'll find the stunning Fontana Maggiore, a 13th-century fountain. Nearby, admire the Cattedrale di San Lorenzo, a Gothic-style cathedral with beautiful frescoes. Stop at a local trattoria for a leisurely lunch of Umbrian cuisine. Try dishes such as truffle pasta, porchetta (roast pork), or a hearty plate of wild boar stew. 

This afternoon's food adventure takes you to the Perugina Chocolate Factory, famous for its Baci chocolates. Join a local guide for a tour of the chocolate laboratory to see the production process in full swing. Then, you'll get to taste various chocolates and products made on-site. Afterward, you'll visit a traditional food shop for a light meal. Here, Signore Lucio Tabarrini will share his Umbrian food secrets, and you'll sample a range of local products.

Day 4: Palazzo Sorbello & Etruscan Well Tour with Aperitif

Day 5: Assisi Walking Tour, Umbria Wine Tasting & Olive Oil Tour

Located on a gentle slope beneath the peak of Monte Subasio, the Umbrian town of Assisi has become legendary as Italy's most famous pilgrimage site. Today, you'll join a local guide for a three-hour walking tour combining history, architecture, art, and religion. Saint Francis was born in this village of warm pink stone in 1182. He founded the mendicant Franciscan order, which he gave his name in 1210. The church where his consecrated remains lie is said to have the best art collection, including frescoes and paintings by Cimabue, Giotto, Lorenzetti, and more.

In the afternoon, you'll discover the two main staples in the Italian culture and diet: wine and olive oil. Your half-day experience includes visits to a winery and olive grove, so you can delve deeper into the process and history of both while soaking up stunning vistas of the region. Discover the winemaking tradition and learn how to pair local varietals with regional products, then visit an oil mill to observe the milling process firsthand. Then, you'll taste the farm's top-tier extra virgin olive oils before returning to Perugia for the evening. 

Day 6: Day Trip to Gubbio & Spello

Today, you'll venture through the glorious Umbrian countryside on a self-guided trip to two charming towns. In the morning, make tracks for the medieval hill town of Gubbio, famous for its massive cathedral. Start at the panoramic Piazza Grande, home to the Gothic-style Consul's Palace. Inside is the Municipal Museum, home to the seven "Eububine Tables," ancient bronze tablets dating to the third and fourth centuries BCE. In front of the cathedral is the 15th-century Ducal Palace, and don't miss St. Ubaldo's House, an ancient tower house once home to Gubbio's patron saint.

In the afternoon, switch to the postcard-perfect village of Spello. This little gem is home to a yearly flower festival, earning it the nickname of Umbria's most colorful town. Beyond the festival, proud locals fill the streets with flower boxes—so bring your camera! Spello's historic center is surrounded by medieval walls with ancient city gates. Be sure to visit Villa dei Mosaici di Spello, a sizable Roman complex with beautiful mosaic floors.

Day 7: Drive to Montalcino via Montepulciano

After breakfast, drive an hour through beautiful Umbrian and Tuscan landscapes to Montepulciano. This hilltop medieval town is filled with elegant Renaissance palaces, historic churches, and charming squares, and it enjoys panoramic views over the Val d'Orcia and Val di Chiana valleys. Venture into Piazza Grande, the heart of Montepulciano. Visit the Cathedral and admire the Palazzo Comunale and its beautiful clock tower, then get lost in the cobblestone streets. Stop for a coffee to watch Vespas buzz by, then visit artisan shops for souvenirs.

Continue 40 minutes on the road to Montalcino, a gem of history and art in the hills of the Val d'Orcia. Discover the city's old medieval layout and its 1361-built citadel, then seek out the world-famous wine Brunello di Montalcino. In the mid-nineteenth century, local winemakers experimented with the local Sangiovese grape, crafting a wine that could withstand aging and improve over time. Once the last line of defense against Medici expansion, this storied city in the Chianti region will be your base for the next two nights.

Day 8: Chianti Cellars Visit, Discover San Gimignano

After a leisurely breakfast, jump in the car and drive 80 minutes north to the cellar door of Antinori nel Chianti Classico. The innovative space combines architecture, wine, and the landscape into an in-depth two-hour tour. You'll discover Marchesi Antinori's passion for winemaking and family history, which stretches back six centuries, and visit the barrel rooms. Then, enter the striking suspended tasting room to taste at least three delicious wines.

Afterward, drop into the nearby town of San Gimignano, Italy's "Manhattan of the Middle Ages." This charming medieval hill town is encircled by 13 medieval towers—both architectural marvels and symbols of power and wealth. Prominent merchant families constructed these towering structures to show off their riches, creating a medieval skyline like no other. In between sightseeing, you should stop by a wine shop in the UNESCO World Heritage Site to try the local white wine, Vernaccia di San Gimignano.

Day 9: Drive to Siena, Afternoon Walking Tour

This morning, you'll drive from Chianti to Siena, an easy one-hour journey along rural Tuscan roads. Give yourself plenty of time to soak in the beautiful landscape, hilltop towns, charming villages, and, of course, the vineyards en route. Siena is considered an open-air museum of medieval monuments, museums, palaces, and churches. Park outside the pedestrian-only city center and venture in. The ancient city is set on a hill, so wear walking shoes and expect to get your steps up! Find a local trattoria for lunch and try pici, a rustic homemade spaghetti often paired with wild boar ragù.

This afternoon, you'll explore the medieval gem on foot with a local guide. Begin at the renowned Basilica of San Domenico, a 13th-century masterpiece home to Renaissance art. Continue through narrow cobbled streets, delving into the past with stops outside stunning palaces and charming historic shops. History will unfold before you with stories of conquests and culture. Enter the iconic Piazza del Campo, a central square pinned by the grand Palazzo Pubblico or town hall. Continue to the 12th-century Cathedral of Siena and savor its grandeur before parting ways.

Day 10: Drive to the Monferrato/Langhe Hills, Afternoon Hike

Today starts with a five-hour drive from Siena to the gentle hills of Monferrato and Langhe, an area of Piedmont squeezed between the Alps and the Riviera. This northwest Italian corner offers a lush and verdant change from Tuscany. En route, you'll skirt around Florence and cruise close to the coast. Feel free to stop in a small seaside village for lunch before turning inland at Genoa.

Spend the rest of the afternoon hiking through the Monferrato hills, passing by rolling landscapes of vineyards, olive trees, stone villages, and wildflowers. Here, rows of grapevines stretch as far as the eye can see, and little towns offer a step back in time. Whether you're a casual walker or a seasoned hiker, there are trails to match your fitness level. After, reward your efforts with a glass of local Barbera or moscato wine and a truffle-infused delicacy.

Day 11: Visit a Hazelnut Farm, Contemporary Art Tour

This morning, you'll visit a family-run sustainable hazelnut farm in Alta Langa. Discover how the family uses sheep to keep the grass short and skips using any pesticides. You'll tour the farm, then enter the shelling plant and pastry lab to see how the nuts are toasted at low temperatures for a long time to keep their aroma and nutritional elements intact and not burn their oils. The best-looking hazelnuts are sold whole, while others are used in creams, cakes, biscuits, and chocolates. Afterward, sit down for a multicourse lunch around the IGP Piedmontese hazelnut.

Castles, contemporary art, and cuisine define Piedmont's Langhe and Roero territory. This area is home to some of the most prestigious and beloved wines, such as Barolo, Brunello, and dolcetto d'Alba, and is famous for its fresh truffles. This morning, you'll tour the countryside with a driver and guide, looking at site-specific art installations by world-famous artists. As you seek out contemporary art, you'll see plenty of fairy-tale villages and castles and learn about the region's history, local food, and wines. 

Day 12: Wine Tasting in Castle, Explore Alba

How can you make a wine taste better? By aging it in a castle. This morning, you'll visit an exceptional winery set within the walls of an ancient castle. You'll soak up magnificent views in every direction while touring the grounds, visiting wine cellars where huge barrels are aging beneath the Baroque orangery, old stables, and near the historic kitchens. After, you'll pause to taste a few low-intervention, high-quality wines that best represent the winery.

Then, it's time to visit Alba. This small city may be rich with Roman history and great Baroque art, but now it's better known as the gourmet capital of Piedmont, famous for its white truffles, wine, and chocolates. It's where Ferrero Rocher and Nutella come from! Start at the Cattedrale di San Lorenzo, a mishmash of architectural styles, and admire the skyline of medieval towers. Then, venture out to Grinzane Cavour, one of the most renowned landmarks of Langhe. Seek out a trattoria in town, or visit the charming villages of Roddino and Castiglione Falletto for dinner.

Day 13: Countryside Truffle & Wine Experience

On your last full day in Italy, you'll dive deep into the essence of Langhe with a private guided truffle tour. On today's sensory adventure, you'll meet your local truffle hunter and their dog, and enter the woods in search of the prized white truffle of Alba. See firsthand the magic of finding truffles and get to know the special training techniques and the relationship of trust between the hunter and their dog.

You'll learn about the trees under which white truffles grow and discover various flavors and aromas. After a walk in the woods, it's time for a tasty truffle lunch at the Trifolau farmhouse. A seasonal menu of traditional Piedmontese dishes will land on the table, pinned by black and white truffles and local wines. After, you'll visit a prestigious historical winery where you'll taste the wines of their production, including the local Barolo.

Day 14: Drive to Milan, Depart

It's your final morning in Italy. After breakfast, make the two-hour drive to Milan's airport for your departing flight home or onward. Make sure you leave enough time to refuel and return the rental car. Safe travels!

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