This 8-day itinerary takes you on a gastronomic adventure through two of Italy’s most spectacular landscapes and cuisines. Starting in the Piedmont hill town of La Morra, you’ll work your way south to Tuscany, ending in the medieval city of Montalcino. In between, you’ll explore picturesque villages, sample local dishes, and visit historic wineries. 


  • Walk along medieval pilgrimage routes
  • Savor the regional cuisines of Piedmont and Tuscany
  • Learn the art of truffle hunting 
  • Visit the wine meccas of Barolo, Montalcino, and Montepulciano
  • Explore historic hill towns, wineries, and abbeys

Brief Itinerary

Day Highlights Overnight
Day 1 La Morra, Alba & Santo Stefano Belbo Santo Stefano Belbo
Day 2 Monforte, Roddino & Barolo Santo Stefano Belbo
Day 3 Barbaresco & Canelli Santo Stefano Belbo
Day 4 Pietrasanta & Pienza Pienza
Day 5 Monticchiello & Montepulciano Pienza
Day 6 San Quirico d'Orcia, Vignoni & Bagno Vignoni Montalcino
Day 7 Sant'Antimo & Montalcino Montalcino
Day 8 Arrividerci Tuscany  

Detailed Itinerary

Day 1: La Morra, Alba & Santo Stefano Belbo

View of La Morra, Piedmont.
View of La Morra, Piedmont.

Your trip begins in La Morra. Framed by rows of vines and guarded by the Alps, this beguiling hilltop village is a picture-perfect example of the Piedmont landscape. Stretch your legs with an easy first walk through vineyards and peaceful country roads to the castle of Grinzane Cavour. Tour the medieval rooms of this imposing 11th-century fortress, home to the first regional winery of Piedmont as well as a Michelin-starred restaurant. 

After lunch, hop on a short transfer to Alba—considered the capital of the Langhe region due to its gastronomic reputation and modern charm. Here the truffle is sacred, celebrated with a much-awaited yearly fair. To learn what the ardor is all about, take part in a sensory workshop: a truffle connoisseur will guide you through an olfactory journey where you’ll learn to tell a good truffle from an excellent one. 

Finish your evening by settling into the quiet nearby town of Santo Stefano Belbo, which will serve as your base for the next three nights.

Walking distance: 5 miles (8 km)

Day 2: Monforte, Roddino & Barolo

View across vineyards to the town of Barolo.
View across vineyards to the town of Barolo.

Today’s walk starts in the medieval hamlet of Monforte. The first section brings you to Serralunga d’Alba, offering stunning views of rolling countryside covered in orderly vineyards. Continue to Roddino, where you can recover your energy in a local trattoria.

After lunch, head to nearby Barolo, a vinicultural hub that charms wine-lovers and teetotalers alike. Enjoy a sip (or many) of the best Barolos in the regional winery—take a glass and choose from among 32 varieties. Afterward, stroll among the ancient streets of the city center, enjoying the rich scent of “brasato” stew escaping the restaurant doors. 

Walking distance: 7 miles (12 km)

Day 3: Barbaresco & Canelli

Red rooftops in Barbaresco.
Red rooftops in Barbaresco.

Day three takes you to the tiny village of Barbaresco, where you’ll climb its 12th-century tower for one of the best views in the region. Let your eyes wander through red-roofed towns and a green sea of vineyards, before coming down to earth for a taste of the local vintage. If you feel energetic, you can also reach Barbaresco with a scenic e-bike ride—you may even spot the local truffle hunters (men & dogs) setting off for their daily hunt.

Your next stop is Canelli, in the Monferrato area, well-known for its “underground cathedrals”: vaulted cellars which enshrine a treasure of Metodo Classico (Italian Champagne) bottles. Learn how this precious wine is still produced following century-old traditions and enjoy a taste of the winery’s best varieties, paired with fragrant grissini and hazelnuts.

In the afternoon, head back to Santo Stefano Belbo to relax, or arrange a cooking lesson to learn how to recreate the best of regional Piedmont cuisine at home.

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Day 4: Pietrasanta & Pienza

The village of Pienza in the Val d'Orcia.
The village of Pienza in the Val d'Orcia.

Today you say “arrivederci” to Piedmont and travel to Tuscany, your base for the next four days. 

Make a stop in Pietrasanta for lunch. Located in the seaside Versilia region of Tuscany, this jewel of a town is beloved by artists and creative souls. Stretch your legs with a stroll through the streets of the enchanting city center, browsing vintage bookshops, organic cafes, and local marble workshops.

End your day in Pienza, in the heart of the Val d’Orcia. A Unesco Heritage Site, this quintessential Tuscan town of cobbled streets, magnificent palaces, and tiny shops is also famous for its Pecorino cheese, whose sweet and salty taste pairs perfectly with home-made jams and honeys.

Day 5: Monticchiello & Montepulciano

Markets at Montepulciano's Piazza Grande.
Markets at Montepulciano's Piazza Grande.

Set off for your first walk in the Tuscan countryside, traveling along a picturesque road to the pretty stone hamlet of Monticchiello.  On your way, you’ll pass an iconic landscape of rolling hills dotted with cypresses and farmhouses.

A short transfer takes you to Montepulciano, the heart of the local wine region. Explore its steep medieval streets, gothic piazzas, and renaissance palaces, then relax with a glass of its famed Vino Nobile. 

Head back to Pienza in time for dinner, watching the sunset on the terrace of one of the many excellent local restaurants.

Walking distance: 4 miles (6.5 km)

Day 6: San Quirico d'Orcia, Vignoni & Bagno Vignoni

Thermal baths in the town square of Bagno Vignoni.
Thermal baths in the town square of Bagno Vignoni.

Today you’ll walk a section of the Via Francigena, a medieval pilgrimage route leading from northern France to Rome. Start in San Quirico d’Orcia, a peaceful hamlet nestled amidst gentle hills, known for its fortress, Romanesque parish church, and hidden 15th-century gardens. Continue along the quiet strade bianche (gravel roads) to the hilltop village of Vignoni, then descend through vineyards and olive groves to Bagno Vignoni.

This remarkable town its famous for its ancient thermal bath in the middle of the main square, said to be beloved by ancient Romans and water nymphs. Follow the small canals that lead out of town to reach the secluded Parco Naturale dei Mulini, where you can soak tired feet or take a refreshing dip in the natural springs before returning to Montalcino for the evening.

Walking distance: 4 miles (6 km)

Day 7: Sant'Antimo & Montalcino

View across vineyards to the Sant'Antimo Abbey near Montalcino.
View across vineyards to the Sant'Antimo Abbey near Montalcino.

Your last day takes you on a remarkable final walk to the serenely beautiful abbey of Sant’Antimo. Find the fantastical animals hidden in its Romanesque exterior before stepping inside, where you can browse 12th and 13th-century paintings, a peaceful garden, and a pharmacy selling honey, herbal teas, and other products made by the local monks.

After enjoying glorious views across the Orcia Valley and Ripa d’Orcia Castle, head back Montalcino for a laid-back afternoon. Enjoy a late lunch in a local trattoria before savoring the last wine-tasting of your trip: a celebration of the dense and delicious Brunello di Montalcino. 

Walking distance: 8.5 miles (14 km)

Day 8: Arrividerci Tuscany

View across olive groves to Montalcino.
View across olive groves to Montalcino.

Bid a fond farewell to the hills of Tuscany as you depart for your flight home.


Map of A Wine-Lover’s Walking Tour: Piedmont & Tuscany - 8 Days
Map of A Wine-Lover’s Walking Tour: Piedmont & Tuscany - 8 Days