Best of Montepulciano

Top itineraries and travel advice in and around Montepulciano
The hilltop village of Montepulciano in Tuscany is among the best options for travelers looking for a taste of small-town Italian life. Famous for its Vino Nobile di Montepulciano wine, the village is comprised of beautiful Renaissance architecture and peaceful narrow lanes, and surrounded by scenic landscapes of cypress, vineyards, and olive groves. Montepulciano also makes a great base to explore the UNESCO World Heritage-listed Val d'Orcia (along with nearby Montalcino, where some travelers opt to stay while visiting this region).

Beyond joining the evening passeggiata along Il Corso, enjoying Tuscan culinary delights, and admiring the panoramic views over the surrounding landscape, kimkim travelers often choose to spend their time here day tripping to other nearby villages including Montalcino and Pienza. Opportunities for wine tasting also abound, including visits to small family-run vineyards specializing in Vino Nobile as well as Montalcino’s rich Brunello. Or, for a taste of nobility, savor a private dinner under the stars in a 1,000-year-old castle tucked away deep in the Tuscan countryside.
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Main square of Cortona
Map of Tuscany Road Trip: Florence, Siena, & Montepulciano - 8 Days
Tuscany Road Trip: Florence, Siena, & Montepulciano - 8 Days

This road trip around Tuscany is perfect for those looking to delve into Italian wine culture. Start in Florence, the birthplace of the Renaissance, stroll around its medieval plazas and cathedrals and see for yourself the history that permeates the city. Visit picturesque Tuscan villages and local wineries, getting a taste for local life and in some incredible surroundings.

Side street of Cortona
Map of Tuscany Road Trip: Florence, Siena, & Montepulciano - 9 Days
Tuscany Road Trip: Florence, Siena, & Montepulciano - 9 Days

This road trip around Tuscany is perfect for those looking to delve into Italian wine culture. Start in Florence, the birthplace of the Renaissance, stroll around its medieval plazas and cathedrals, and see for yourself the history that permeates the city. Visit picturesque Tuscan villages and local wineries, getting a taste for local life and in some incredible surroundings.

Chianti vineyards
Map of Tuscany Road Trip: Florence, Siena, & Montepulciano - 7 Days
Tuscany Road Trip: Florence, Siena, & Montepulciano - 7 Days

This self-drive tour around Tuscany is perfect for those looking to delve into Italian wine culture. Start in Florence, the birthplace of the Renaissance, stroll around its medieval plazas and cathedrals and see for yourself the history that permeates the city. Visit picturesque Tuscan villages and local wineries, getting a taste for local life and in some incredible surroundings.

Hillside of Montepulciano
Map of Explore Tuscany: Florence, Siena, & Montepulciano - 10 Days
Explore Tuscany: Florence, Siena, & Montepulciano - 10 Days

This road trip around Tuscany is perfect for those looking to delve into Italian wine culture. Start in Florence, the birthplace of the Renaissance, stroll around its medieval plazas and cathedrals and see for yourself the history that permeates the city. Visit picturesque Tuscan villages and local wineries, getting a taste for local life and in some incredible surroundings.

Tuscany, Italy
Map of Hiking the Hill Towns of Tuscany in Val d'Orcia: Montepulciano, Pienza, and Siena - 8 Days
Hiking the Hill Towns of Tuscany in Val d'Orcia: Montepulciano, Pienza, and Siena - 8 Days

Explore the magnificent natural beauty of the Val d'Orcia region in Tuscany, walking through cypress-lined hills and vineyards, with time for tasting the wine, cheese, honey, and other culinary delights that the area is known for. Your adventure will take you through the wine-growing town of Montepulciano, then to Pienza where you can taste its distinctive Pecorino cheese, and finally to the medieval Tuscan powerhouse of Siena.

Other popular travel destinations in Italy
Tuscany · Rome · Florence · Venice · Naples · Amalfi Coast · Sicily · Milan · Siena · Lakes District · Palermo · Capri · San Gimignano · Lake Garda · Verona · Cinque Terre · Lake Como · Taormina · Syracuse · Chianti · Italian Riviera · Emilia Romagna · Sorrento · Piedmont · Agrigento · Bologna · Turin · Umbria · Puglia · Catania · Lecce · Alberobello · Dolomites · Bari · Aeolian Islands · Ragusa · Sardinia · The Langhe