Combine historic hill towns, fine wines, and the Tuscan countryside for an Italian eight-day road trip to remember. Get your bearings amid the Renaissance splendor of Florence, then set out into the surrounding landscapes—basing yourself first in Siena and then in Montepulciano. Along the way, you'll experience wine tastings and workshops focused on local Chianti vintages and set off on day trips to hilltop villages like San Gimignano, Monteriggioni, and Cortona.
Best of Montepulciano
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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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.
Wind your way through the hill towns and vineyards of the Tuscan countryside on this weeklong exploration of Italy's most famous wine country. Arrive in Florence and kick things off with a guided walking tour in the birthplace of the Renaissance. Then it's time to hit the road to Siena, San Gimignano, and Montepulciano, where medieval architecture and plenty of wine-tasting experiences await.
This sophisticated 10-day trip is ideal for travelers looking to experience art, culture, food, and wine—all things that make Tuscany one of Italy's most sought-after regions. Start in Florence, the birthplace of Renaissance art and architecture, to experience the city's rich history and walkable center. Then begin a self-guided road trip around Tuscany, visiting UNESCO-listed monuments, picturesque hill towns, and notable vineyards, including a memorable sit-down lunch and wine pairing in Montepulciano.
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.
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