Pienza Wine Tours 7 options
Chianti & Brunello wine tour from Siena: Small group, 2 wineriesVisit Siena with a licensed guide, taste Chianti Classico at an organic winery with Tuscan lunch, sample Brunello di Montalcino at a family estate.Next departure: 19 Mar 2027 · Ages 18–75★ 5.00 (28)8h–9hEN · IT✓ Free cancellationfrom€ 235per person
Pienza & Montepulciano wine tour from Siena: Nobile tastingsDay trip from Siena through Valdorcia valley to taste Nobile di Montepulciano and Super Tuscan wines in historic cellars, enjoy cheese farm lunch.Every day · 09:00 · Hotel pickup · From age 12★ 4.89 (27)6h–8hEN✓ Free cancellationfrom€ 499per person
Private Cheese and Wine Tour from Siena: Pienza, MontalcinoPrivate guided tour from Siena through Val d'Orcia to Pienza and Montalcino with organic cheese tasting, winery visit and Brunello wine tasting included.Every day · 09:30 · Pickup optional★ 4.98 (44)8hEN · DE · ZH · IT +2✓ Free cancellationfrom€ 700per group
Val d'Orcia tour from Siena: Montalcino, Pienza, MontepulcianoDay trip from Siena through Val d'Orcia with stops in Montalcino for Brunello wine tasting, Pienza for a three-course lunch.Every day · 08:30 · All ages★ 4.75 (8)10h–11hEN✓ Free cancellationfrom€ 229per person
Montepulciano Pienza Montalcino Tour: Medieval TownsDrive from Siena into the Orcia Valley to visit three medieval wine towns in one day (Montepulciano, Pienza and Montalcino) with hotel pickup.Every day · 09:00 · Hotel pickup★ 5.00 (5)8h–9hEN✓ Free cancellationfrom€ 988per group
Private Montalcino and Pienza Tour from Siena: Val d'OrciaPrivate tour from Siena through Val d'Orcia to Montalcino and Pienza, sampling local cheese and wine while enjoying Tuscan lunch in the rolling countryside.Every day · 09:30 · Pickup optional · From age 3★ 4.00 (3)6hEN · IT · ES✓ Free cancellationfrom€ 467per person
Montalcino vineyard trek with wine and cheese tastingTrek through Brunello vineyards in Montalcino with a sommelier, taste Pecorino di Pienza at the dairy, and enjoy lunch in the cellar paired with local wines.Every day · 09:00 · Pickup optional · From age 18★ 5.00 (1)6h–8hEN · DE · IT · ES✓ Free cancellationfrom€ 197per person
All 7 options, side by side
✓ 2026-10-29| Option | Price | Duration | Rating | Days and times | Guide languages |
|---|---|---|---|---|---|
| Chianti & Brunello wine tour from Siena: Small group, 2 wineriesOur pick | € 235 per person | 8h–9h | 5.00★ · 28 | Next departure: 19 Mar 2027 | English, Italian |
| Val d'Orcia tour from Siena: Montalcino, Pienza, MontepulcianoBest value | € 229 per person | 10h–11h | 4.75★ only 8 reviews | Every day · 08:30 | English |
| Montalcino vineyard trek with wine and cheese tastingLowest price | € 197 per person | 6h–8h | 5.00★ only 1 review | Every day · 09:00 | English, German, Spanish +1 |
| Pienza & Montepulciano wine tour from Siena: Nobile tastings | € 499 per person | 6h–8h | 4.89★ · 27 | Every day · 09:00 | English |
| Private Cheese and Wine Tour from Siena: Pienza, Montalcino | € 117 per person€ 700 per group (split 6 ways) | 8h | 4.98★ · 44 | Every day · 09:30 | English, German, Spanish +3 |
| Montepulciano Pienza Montalcino Tour: Medieval Towns | € 141 per person€ 988 per group (split 7 ways) | 8h–9h | 5.00★ only 5 reviews | Every day · 09:00 | English |
| Private Montalcino and Pienza Tour from Siena: Val d'Orcia | € 467 per person | 6h | 4.00★ only 3 reviews | Every day · 09:30 | English, Spanish, Italian |
Pienza Wine Tours at a glance
- Our pick: Chianti & Brunello wine tour from Siena: Small group, 2 wineries, € 235 (8h–9h, 5.00★ · 28).
- Best value: Val d'Orcia tour from Siena: Montalcino, Pienza, Montepulciano, € 229 (10h–11h, 4.75★ · only 8 reviews).
- Lowest price: Montalcino vineyard trek with wine and cheese tasting, € 197 (6h–8h, 5.00★ · only 1 review).
Real price per person across the 7 options: € 117–€ 499 (median € 229).
Of the 7 options: 7 with free cancellation, 6 with instant confirmation, 5 with hotel pickup, 2 kid-friendly, 3 private and 5 bookable last-minute.
How we rank: quality, number of reviews and relevance to the topic. In the comparison table, our top 3 comes first. Real price per person: the group price divided by the seats it includes.