A roadtrip through Italy’s wine country is the perfect pairing for someone who plans to visit Italy and considers themselves a wine aficionado (or perhaps just one who enjoys the occasional glass). Located throughout Italy, from Piedmont in the north to Sicily in the south, there is a variety of family-owned, historical wineries to experience. In fact, there are over 2,000 grape varietals in Italy, which means each wine region offers something new to your palate. It’s no secret that the Italians have perfected their wines; with lower alcohol content and higher acidity, it makes for a more pleasing taste in a relaxed social setting.

Each Italian winery you visit will provide a different experience. Indeed, they vary as much as the grapes themselves. Many wineries are family-owned and operated, bringing you the most authentic and unique tastings you can have. Of course, many tastings include pairings with delectable dishes.

To truly appreciate Italian wine country, we recommend spending a week visiting one or two regions. This will allow you to fully immerse yourself while exploring at your own pace. While driving on your own offers the most flexibility, we recommend hiring a private driver for the days with wine tours to allow for the enjoyment of the tastings.


We recommend spending 2-3 days in Piedmont. Bordering France and Switzerland, this Italian wine region sits at the foot of the Alps and is best known for Barbaresco and Barolo wines.

Before starting with a winery, remember that you can’t visit Italy without sightseeing. Take a trip to the town of Canelli where you can discover Underground Cathedrals and tufa channels. Visit the Barbaresco region and stop at a family-run and well-known Barbaresco wine cellar, followed by a trip to Neive for dinner at a local restaurant.

Now that you have tasted Barbaresco, it’s time to head onward to Alba and the Barolo regions. Alba, a UNESCO Creative City for Gastronomy, is considered the capital of the precious white truffle. A diverse selection of Italian eateries will be yours to choose from, but one thing you cannot miss is the prestigious and historic Barolo winery in the town center. As a bonus, you can partake in a private panoramic tour of the region’s vineyard landscapes followed by a stop at Grinzane Cavour Castle, where you can explore their wine cellar and enjoy a tasting.


We recommend spending 3-4 days in Tuscany, just below Piedmont. This region is known for its wine, landscapes and colorful villages.

Tenon Tip: When departing for Tuscany from Piedmont, we recommend a short stop in Moderna. Here, you can visit boutique producers of prosciutto, parmesan cheese, balsamic vinegar and wine.

The wine region of Tuscany is sure to please each of your senses. In Siena, you can visit the Piazza del Campo, Piazza del Duomo and San Gimignano, a quintessential Italian hill town surrounded by 13th-century walls.

Apart from the stunning architecture is some of Italy’s finest produce. Few wine regions have the instant name recognition of Tuscany’s Chianti, first legally defined in 1716. Some of Chianti’s most acclaimed wines, however, don’t carry its name. Only reds based on the Sangiovese grape can be called Chianti. Indulge with a tasting at a local Chianti winery that welcomes connoisseurs and passionate wine lovers alike. You’ll be given a tour of the vineyards, winery and cellar as well as a thorough explanation of the various stages of production from harvest to winemaking.

When dining in Tuscany, you’ll leave wanting more. Much like its wine, dishes in Tuscany are prepared only with the high-quality ingredients that express the flavors and aromas of the Tuscan tradition. These can include handmade pasta with eggs from a local henhouse, truffles and other vegetables from an organic garden, genuine sheep’s cheese (pecorino), homemade desserts and many other local products.

Last but not certainly not least is the Orcia Valley. This encompasses the three “must-sees” during your time in Tuscany: Montalcino, Pienza and Montepulciano. These stunning medieval villages are enchanting in every season. To savor a famous red wine (just as the “King” Brunello di Montalcino) in a wine shop built with stones in a traditional Tuscan style will make you feel that you’re part of a fairytale. Enjoy a wine tasting in Montepulciano or Montalcino (or both) along with a stop at an organic farm in Pienza to experience their dairy production.

Ready to plan your own personalized trip through Italy’s wine country? View our inspirational itineraries below!

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Val d'Orcia, Tuscany, Italy. A lonely farmhouse with cypress and olive trees, rolling hills.

Italian Wine Country

8 Days | 7 Nights

Explore Italy’s regions of Piedmont, Tuscany and Orcia Valley and immerse yourself in this 7-day itinerary exploring authentic local wineries.

Starting From $3,198 per person based on double occupancy
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The Magical Lakes of Italy

13 Days | 12 Nights

Marvel at the beauty of the stunning Italian Lake District. Get away from it all with this countryside-based tour – relish spectacular views of Lake Maggiore, Lake Como and Lake Garda. Savor the tastes of the Italian food and wine, enjoy cultural activities and picturesque lakeside villages. Wrap up your tour in the metropolis of Milan, the capital of the Northern region of Lombardy.

Starting From $4,698 per person based on double occupancy
fields of blooming lavender flowers, Provence

Scents of Paris & Provence

6 Days | 5 Nights

From iconic Paris to charming Provence. Snack on croissants and sip local wine. Drive through the famous lavender fields of Luberon and explore the Roman ruins and typical Provençal markets of the Vaucluse region.

Starting From $5,669 per person based on double occupancy

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