From Siena: Tuscany Day Trip with Wine Tasting & Snacks
Visit Pienza and Montepulciano and sip legendary wines where vineyards meet volcanic soil
Sip renowned Chianti and Nobile di Montepulciano at two traditional wineries while learning how ancient olive groves and volcanic soil shape every vintage. This full-day tour from Siena whisks you through rolling countryside to taste wines paired with local snacks and oil, then sets you loose in Pienza and Montepulciano to explore Renaissance architecture and medieval charm. It's the best way to experience Tuscany's wine culture without driving narrow hillside roads yourself.
What You Get With This Tour
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Unwind into Italy’s wine heart
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Expert English-speaking tour leader
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Round-trip transport from Siena
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Chianti wine tasting with snacks
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Nobile di Montepulciano wine tasting
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Olive oil sampling
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Free time in Pienza and Montepulciano
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Guide tips
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Lunch
Tour Itinerary
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1
Meet at Siena Train Station for your Tuscan adventure
You'll meet your guide at Stazione di Siena and board a comfortable, air-conditioned coach or minivan. Settle in as you head toward the rolling Chianti hills, where centuries-old vineyards stretch across sun-drenched slopes. -
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Taste Chianti wines at a family-run winery
Your first stop brings you to a traditional Chianti winery. You'll sample three distinct wines while learning about local winemaking techniques. Pair your tasting with home-produced olive oil and fresh Tuscan bread as your guide shares stories. -
3
Explore Pienza's Renaissance streets and panoramic views
Next, you'll arrive in Pienza, a hilltop town where Renaissance architecture frames sweeping Val d'Orcia landscapes. Wander narrow lanes at your own pace, grab lunch at a local trattoria, and soak in views that have inspired artists for centuries. -
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Discover Montepulciano's medieval charm and wine culture
Continue to Montepulciano, where grand palaces and historic churches line steep cobblestone streets. You'll have free time to explore this wine-famous town, admire breathtaking valley views, and perhaps sample a glass of the celebrated Nobile di Montepulciano. -
5
Savor Nobile di Montepulciano at a second winery
Your second winery visit focuses on the renowned Nobile di Montepulciano. Taste this elegant red wine paired with traditional Tuscan snacks. Your guide explains the differences between the wines you've sampled and the region's unique terroir. -
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Return to Siena with Tuscan memories
Board your coach for the scenic drive back to Siena. Relax as the countryside rolls past and the sun sets over the hills. You'll arrive back at Siena Train Station with photos, stories, and a deeper appreciation for Tuscany's wine heritage.
Additional Information
Good to know:
Lunch: Please note that lunch is not included on this tour. You'll have free time in Pienza to purchase lunch at your own pace at one of the local restaurants or cafes.
Accessibility: Unfortunately, this tour is not wheelchair accessible. The tour involves moderate walking on cobblestone streets and uneven terrain in the hilltop towns of Pienza and Montepulciano. If you have concerns about your mobility, please contact us in advance to discuss your needs.
Minimum Group Requirement: The tour requires a minimum of four participants to operate. If the minimum is not met, the tour may be cancelled or rescheduled, and you will be notified as soon as possible.
Check-in: Arrive 15 minutes early for check-in at the meeting point so the group can depart on time.
Your 10-hour tour includes:
Expert English tour leader
Round-trip transportation by air-conditioned bus or minivan
Wine tasting at a Chianti winery (three wines)
Wine tasting at a Nobile di Montepulciano winery
Traditional Tuscan snacks and olive oil at both wineries
Free time to explore Pienza and Montepulciano
Maximum group size of 50
What to bring:
Comfortable walking shoes
Water bottle
Camera
Money for lunch
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Frequently Asked Questions
Is this tour family friendly?
Yes, this tour is family friendly with no age restrictions.
What if I have concerns about my mobility on this tour?
Unfortunately, this tour is not wheelchair accessible. The tour involves moderate walking on cobblestone streets and uneven terrain in the hilltop towns of Pienza and Montepulciano. If you have concerns about your mobility, please contact us in advance to discuss your needs.
How much walking is involved on this tour?
This tour involves moderate walking through the hilltop towns of Pienza and Montepulciano, where you'll navigate cobblestone streets and gentle inclines. Comfortable walking shoes are essential for enjoying the medieval villages and winery visits.
Is lunch included in the tour price?
Lunch is not included on this tour. You'll have free time in Pienza to purchase lunch at your own pace at one of the charming local trattorias or cafes in the town center.
