From Florence: Private Pienza, Montepulciano, and Moltancino Day Trip
- Instant confirmation
- Guided tour in English
About this experience
Discover the beauty and flavors of southern Tuscany on a private full-day Val d’Orcia tour. Visit Montalcino, home of Brunello wine, stop for photos along the famous cypress-lined road, and enjoy a farm tasting near Pienza with artisan cheese, craft beer, and local products. Explore the Renaissance charm of Pienza before heading to Montepulciano for a guided wine tasting in historic underground cellars. An unforgettable Tuscany experience combining culture, wine, food, and iconic landscapes.
Next available dates
What’s included
- Private minivan transportation through the scenic Val d’Orcia with an informative local tour leader.
- Photo stop at the iconic Gladiator Road in the Tuscan countryside.
- Visit Pienza, a UNESCO World Heritage Site, with free time to explore.
- Enjoy a Val d’Orcia farm experience with Pecorino cheese, jams, honey, and craft beer tasting.
- Discover Montepulciano with a guided wine tasting in a historic underground cellar.
- Visit Montalcino, home of the famous Brunello di Montalcino wine.
Not included
- Lunch (aside from the generous cheese tasting at the farm — additional meals are at your leisure during town visits)
- Additional wine or product purchases (available at your own expense)
- Gratuities (optional, but appreciated for guides and hosts)
- Entrance tickets to museums or monuments (if guests wish to visit sites independently during free time)
- Hotel pickup/drop-off
Itinerary
- 1
Ready to Depart
Set off in the morning aboard your private minivan, relaxing as the city fades into gentle hills and olive groves.
- 2
Scenic drive passing by Val D'Orcia
Your local driver-guide will share insights along the way, preparing you for the day’s rich discoveries, through the heart of Val d'Orcia, a UNESCO-listed region known for its postcard landscapes, world-class wines, and artisanal flavors.
- 3
Montalcino – The Home of Brunello
Arrive in the medieval town of Montalcino, famous worldwide for its prestigious Brunello wine. Enjoy some free time to wander its charming streets, visit the fortress, or savor a coffee while admiring sweeping views of the surrounding vineyards. Iconic Cypress Road Stop Pause at one of Tuscany’s most famous and photographed locations: a peaceful country road lined with towering cypress trees, set against the backdrop of golden hills. Perfect for stunning photos and a moment to breathe in the quintessential Tuscan landscape.
- 4
Artisan Cheese & Beer Tasting at a Local Farm
Visit a charming, family-run sheep farm near Pienza, where you’ll meet Elia, the passionate cheesemaker lovingly known as the “Shepherd of Val d’Orcia.” This is a truly authentic Tuscan experience, watch and learn the traditional, hands-on process of crafting Pecorino cheese exactly as it’s been done for generations. Elia’s warm hospitality makes you feel like part of the family as you savor a generous tasting of his handcrafted cheeses, paired with homemade jams, local honey, and his one-of-a-kind craft beer. All of this unfolds against the breathtaking, unspoiled backdrop of the Tuscan countryside, offering a rare glimpse into rural life and genuine artisan traditions.
- 5
Pienza
Spend time in Pienza, a UNESCO World Heritage Site famed for its harmonious Renaissance architecture and artisan shops. Stroll through its quaint streets, sample local delicacies, or simply soak up the peaceful atmosphere of this hilltop town.
- 6
Montepulciano
Head to Montepulciano and descend into centuries-old underground cellars for a guided tasting of the renowned Vino Nobile di Montepulciano & Brunello di Montalcino. Complement the wines with samples of extra virgin olive oil and aged balsamic vinegar, experiencing the true flavors of the region.
- 7
Return back to the starting point
Relax and enjoy the scenic drive back in the early evening. Departure Points available for this tour: Florence: Address: Parcheggio Oltrarno , in front of the blue “ P” sign by Porta Romana , Piazza della Calza 1, Florence. Take me here Tuscany on Wheels: Address: Tuscany on Wheels office, Strada di Sant’ Appiano 9/i, Barberino Tavarnelle ( FI ). Take me here San Gimignano : Address:Bivio Volterra, at the Bus Stop, in Via S. Gimignano, San Gimignano. Take me here
Good to know
- Duration
- 12 hours
- How you meet
- Meet on location
- Confirmation
- Instant confirmation
- Cancellation policy
- This booking is non-refundable once confirmed.
- Difficulty
- Easy
- Minimum age
- 13+ years
- Guide
- Guided tour in English
- Start times
- 08:00
Know before you go
- This tour may not be suitable for people with mobility impairments
- This tour involves walking on uneven surfaces
Cancellation policy
This booking is non-refundable once confirmed.
24h Cancellation Policy
Meeting point
View on map
Florence
- Address
- Florence: Parking Oltrarno, Piazza della Calza 1, right in front Porta Romana at the blue P (parking) sign, Firenze, 50125, IT
- How you meet
- Meet on location
- Coordinates
- 43.76093, 11.24184
Illustrative map. Open it in Maps for the exact spot and live directions.
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Frequently asked questions
How long does this experience last?
It lasts 12 hours.
Can I cancel this booking?
This booking is non-refundable once confirmed.
Is this experience guided, and in what language?
Guided tour in English
Is hotel pickup included?
No — you make your own way to the meeting point.
Where does this experience start?
It starts at Florence, Florence: Parking Oltrarno, Piazza della Calza 1, right in front Porta Romana at the blue P (parking) sign, Firenze, 50125, IT.
Is there a minimum age?
Travellers must be 13 or older.
Still have a question?
Message our team on WhatsApp — we can help with dates, group bookings and anything else before you book.
From AED 926 per person (7–8 travelers)
