Some of the best wines and food in the world will fuel you on this 8-day cycling adventure through rolling hills and quaint villages in Tuscany. Begin your active trip with a truffle workshop in Alba before cycling through Piedmont and on to Tuscany. Along the way, you'll wander through medieval villages of golden sandstone and limestone, dine in Michelin-starred restaurants, sample world-class wines and cheeses, and learn how to make pasta.


  • Learn how to identify and pick truffles in Alba
  • Tour an underground wine cathedral in Barbaresco
  • Dine at a Michelin-starred restaurant in Monferrato
  • Tour a vineyard and wine cellar in Montepulciano
  • Visit the UNESCO World Heritage Site of Val d'Orcia

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Alba - Ride to Località Manera Località Manera
Day 2 Ride to Santo Stefano Belbo Santo Stefano Belbo
Day 3 Ride to Asti - Transfer to Cioccaro Cioccaro
Day 4 Transfer to Pienza - Walking Tour Pienza
Day 5 Montepulciano Loop Ride Pienza
Day 6 Bagno Vignoni Loop Ride Montalcino
Day 7 Ride to Montalcino Montalcino
Day 8 Depart Italy  

Detailed Itinerary

Day 1: Arrive in Alba - Ride to Località Manera

Alba is a foodie paradise
An array of cheeses at a market in Alba

Welcome to Italy! When your plane lands in Cuneo International Airport (CUF), a driver will be waiting to drive you about 28 miles (46 km) to Alba. After you take in the views iconic vineyards along the way, you'll be dropped off with your guide for a bike fitting and your first ride into the vine-covered hills of Alba. 

Alba, in the Langhe area of Piedmont, is known for its delicious food, including truffles, and its truffle fair each year in October and November. Your first activity will be a truffle workshop where you will learn how to distinguish a good truffle from an excellent one. If you'd like, you can also choose to go on a food tour across the city and try local specialties like hazelnut cake, dark chocolate, and the area's world-class wines.

You might enjoy lunch at Michelin-starred Piazza Duomo, or La Piola Bistrot, both located in Alba’s main square.
If you'd like to take another short gastronomic tour, you can stop by a local sheep farm housed in a wooden building known as a ciabot. Silvio, the head of the farm, is happy to share his cheese-making and truffle-hunting secrets as well as answer your questions about life on the farm. Before you leave, make sure you sample the sheep's cheese known as Tuma di Langa.

After you finish exploring Alba, you'll hop on your bike and ride 7 miles (12 km) to Localitá Manera. Once you arrive, you will check in at your hotel. You can have dinner at one of the hotel's excellent restaurants, the Michelin-starred Damiano Nigro or the hip DaMà.

Day 2: Ride to Santo Stefano Belbo

Barbaresco vineyards
Barbaresco vineyards

In the morning, you'll set off on your bike for a panorama-packed ride that will take you 27 miles (45 km) into Barbaresco—a wine-growing region for Barbaresco grapes. Along the way, you'll see acres of geometrically-planted vines among the hills.

Once you arrive in Barbaresco, you can climb the 12th-century tower known as Torre di Barbaresco for incredible views of the surrounding red-roofed villages and green vineyards.

Your next stop will be Canelli, in the Monferrato area, which is known for its underground cathedrals. These cathedrals aren't for religious purposes, but instead for storing Metodo Classico—bottles of Italian sparkling wine. You'll learn how this precious wine is produced following centuries-old traditions and enjoy a guided tasting of the winery’s best varieties paired with fragrant grissini (breadsticks) and hazelnuts.

You'll arrive in Santo Stefano Belbo in time for lunch, and after you check in at your hotel, you'll dine at Ristorante San Marco, a Michelin-starred restaurant with a comfortable, refined atmosphere. In the afternoon, you can book a pasta-making class and learn how to make the region's most popular pasta, tajarin.

If you'd like a more restful break from cycling, you can book a wine-themed spa experience that includes a massage with grapeseed oil and time in a sauna made out of an original wine barrel from the early 20th century.

Day 3: Ride to Asti - Transfer to Cioccaro

Asti, a city of many towers
Asti, a city of many towers

After breakfast, a driver will pick you up and take you 32 miles (53 km) northeast to the region of Monferrato. From there, you will get on your bike and begin your 31 miles (50 km) ride for the day. Your destination will be Asti, known as a city of 100 towers and the home of the eponymous sparkling white wine.

On your route, you'll cycle through the rolling hills of Barbera, passing picturesque villages like Fubine, Montemagno (with an imposing fortress guarding red-roofed houses), and Portacomaro. You may wish to make a stop in any of these destinations for a drink, lunch, or to snap photos.

You'll continue on to Casale Monferrato, the area's historical capital. Your guide will then load up your bikes and take you to Piazza Castello, which is named after a hexagonal-shaped castle that still stands guard over the city. In the piazza, you can enjoy a cappuccino or a glass of the local wine, Grignolino del Monferrato, possibly with a slice of muletta, a local pork delicacy.

You'll spend the night at a 16th-century estate in the heart of Monferrato, where you'll be able to have dinner in its Michelin-starred restaurant.

Day 4: Transfer to Pienza - Walking Tour

A scenic view in Pienza

Today, your guide will pick you up at your hotel and drive you to the city of Pienza in Tuscany, about 313 miles (505 km) south. 

On the way to Pienza, you'll make a stop in the artist's seaside town of Pietrasanta for lunch. After your meal, you can stroll through the streets of the enchanting city center, browse boutiques, stop in art galleries, and grab a drink at a cafe before getting back on the road.

If you'd like, you can make another stop in Carrara, where Michelangelo sourced marble, and visit a local marble workshop. 

When you arrive in Pienza you'll be in the heart of Val d’Orcia, a breathtaking valley that has been recognized as a UNESCO World Heritage site.

After you check in at your hotel, you'll meet back up with your guide for an evening tour of Pienza, where you'll see the town's cobbled streets, palaces, and small shops filled with local Pecorino cheese. After the tour ends, you can choose a restaurant and enjoy an authentic Tuscan dinner.

Day 5: Montepulciano Loop Ride

A church in Montepulciano

You'll set off into the Tuscan countryside today for a 21-mile (35-km) loop ride around Montepulciano.

Your route will take you along a panoramic road dotted with cypress trees, farmhouses, and hilltop villages. You can stop and explore the medieval stone-built hamlet of Monticchiello before continuing your ride into Montepulciano, where you'll be able to visit a cellar and learn about Vino Nobile.

On your way back to Pienza, you can also take a floral-arranging class on an enchanting flower farm a few miles outside of Montepulciano.

When you arrive back at your hotel in Pienza, you can enjoy a delicious dinner on the terrace of an ancient convent that has been turned into a Michelin-starred restaurant. You won't want to miss the view of the sunset behind the hills as you sip local wines.

Day 6: Bagno Vignoni Loop Ride

Bagno Vignoni
Ancient thermal bath in Bagno Vignoni

Today will be a more relaxed day, and you'll have an easy 17-mile (28-km) loop ride south along smooth country roads through vineyards and olive groves to reach Bagno Vignoni, which is famous for the ancient thermal bath in the middle of the main square that was popular with ancient Romans.

You'll have time to explore Bagno Vignoni on your own and enjoy one of the cafes that overlook the thermal bath.

If you'd like to extend your ride, you can ride further to the hilltop hamlet of Castiglion d’Orcia and have lunch at Michelin-starred restaurant Osteria Perillà.

Your ride back to Pienza will take you through the gently undulating hills and unspoiled countryside that make Tuscany famous, so be sure to stop to take a few photos along the way. When you arrive back in Pienza, you can enjoy a leisurely evening at a countryside estate that will be your accommodation for the night.

Day 7: Ride to Montalcino


Today, you'll set off on a 14-mile (23-km) ride to Montalcino. You'll pedal through vibrant fields of sunflowers, past Buonconvento—where you may wish to stop and explore—and into the heart of the Brunello wine-growing region.

As the Monte Amiata comes into view, the surrounding countryside will transform into endless olive groves and vineyards. When you arrive in the fortified city of Montalcino, you can check in at your hotel and leave your luggage before going out fo a late lunch. 

In the afternoon, you may want to stroll around town, book a wine tasting, head to the Museo Civico e Diocesano d'Arte Sacra to see some religious art, or tour the Fortress of Montalcino. As it's your last evening in Italy, you may want to have a special dinner or book a visit to the spa as a reward for all of the miles you logged.

Day 8: Depart Italy

The Tuscan countryside
View of the Tuscan countryside

It's time to say goodbye to Italy! A driver will pick you up at your hotel and take you to the airport for your flight home or to your next destination.


Map of Cycling and Food Tour of Tuscany: Alba, Asti, Pienza, & Montepulciano - 8 Days
Map of Cycling and Food Tour of Tuscany: Alba, Asti, Pienza, & Montepulciano - 8 Days