Old homes in Montepulciano

Val D’ Orcia Wine Tasting in Tuscany


Enjoy a wine-tasting tour in the Tuscan countryside, vising the picturesque hilltop town of Montalcino. You’ll also taste local Nobile wines in historical cellars in Montepulciano and savor a full farm-to-table lunch near Pienza.

You’ll start by touring the cellars and tasting the wines at a Brunello winery. Then pass through the stunning landscapes of the UNESCO-protected Val d’Orcia territory as you make your way toward Montalcino. You’ll explore the world-famous wine-producing area of Brunello, also known for its countryside dotted with hilltop towns and fortresses. Stop to visit a castle where the brave soldiers of the Republic of Siena made their last stand to Florence and the Medici. Next, spend time visiting the Montalcino’s shops to taste the local honey or Brunello wines, or simply wander around the city walls. Enjoy the incredible views overlooking an endless stretch of valleys and vineyards. 

Next, head to a local farm near Pienza for lunch. While you dine, you’ll enjoy stunning views over the Val d'Orcia. The farm produces wine and extra virgin olive oil and hosts a cheese laboratory to make pecorino sheep and goat cheese. Kids love to see the animals, and adults enjoy the memorable farm-to-table lunch on a panoramic terrace! 

In the afternoon, you’ll visit the proud old town of Montepulciano, built at the top of a high hill. Your guide will lead you to elegant churches, palaces, piazzas, and imposing walls designed by famous Renaissance artists. Montepulciano is also among Tuscany’s oldest wine regions, and some of its Nobile di Montepulciano wine is still made and aged in centuries-old underground cellars. Spend some free time enjoying the sites and perusing the wine and crafts shops. 

Your last stop is a wine cellar with a truly impressive selection of local wines. Enjoy a tasting from a wide variety of vintage and estate wines.

Read more about unique and interesting activities in Tuscany and culinary experiences in Italy.

Traveler reviews

David E.
Fort Leonard Wood, MO | Reviewed on May 06, 2022

Danny was an excellent guide. We truly enjoyed this experience. read more

Danny was an excellent guide. We truly enjoyed this experience.

Quality of Experience
Guides, Drivers and Staff

Itineraries with Val D’ Orcia Wine Tasting in Tuscany

Explore Tuscany: Florence, Siena, Pisa, & Lucca - 9 Days

If spending 9 days seeing top works of art and eating chocolate Foccacia sounds good, then this trip is perfect for you.  Start in Florence to see Michelangelo's 'David', tour the Uffizi Gallery, and go shopping on the medieval Pontevecchio Bridge. See the Tuscan countryside from the top of Pisa's leaning tower, then see soaring cathedrals and ancient Piazzas in medieval Siena. Explore food and wine in the Val d’Orcia before ending in romantic Lucca, where quiet courtyards, 12th-century chapels, and the perfect cup of afternoon coffee await.

Explore Liguria & Tuscany: Cinque Terre, Florence, Pisa & Val D'Orcia - 13 Days

Explore Mediterranean beaches, Renaissance capitals, and medieval hill towns on this delightful 13-day tour through the Italian regions of Liguria and Tuscany. Start your adventure on the west coast, where you'll discover the quaint villages, rugged shorelines, and breathtaking scenery of the Cinque Terre. Head inland to spend a day wandering through history in Pisa, before journeying west to soak up the Renaissance splendor of Florence. The final five days take you deep into the Tuscan countryside, where you'll stay at a rural agriturismo villa and immerse yourself in the culture and landscape of the Val d'Orcia—wine tasting and truffle hunting around picturesque hill towns.

Exploring Italian Wines in Tuscany and Cinque Terre - 5 Days

Indulge your taste buds on this Tuscan tour, visiting beautiful vineyards and medieval towns like Siena, Volterra, and San Gimignano, where you'll enjoy the flavors of the region with wine tastings and traditional, locally-sourced cuisine. Explore ancient cobblestone streets and monuments, enjoy the old Cypress trees of Bolgheri, and sleep soundly in your cozy farmhouse accommodation. End your trip on the rocky coast of Cinque Terre where you'll enjoy more wine and regional foods, plus one last stop at the Leaning Tower of Pisa.