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Day Trips from Siena: Compare 56 Options (October 2026)

Independent comparison Prices checked October 4, 2026 Prices shown in EUR 56 options compared

Our top pick is Small-Group Montepulciano and Pienza Day Trip from Siena (8 h, ★ 4.9 (335)). Well-rated options start at €49 from, per person, and 50 of 56 options offer free cancellation.

Our picks

Small-Group Montepulciano and Pienza Day Trip from Siena
Best overall

Small-Group Montepulciano and Pienza Day Trip from Siena

8 h · ★ 4.9 (335) €190 from, per person
Free cancellation
Highest weighted rating of 8 options with 50+ reviews. Check availability
Hidden Castles & Chianti Wine Experience– Small Group
Lowest price

Hidden Castles & Chianti Wine Experience– Small Group

5 h · ★ 4.5 (183) €49 from, per person
Free cancellation
Lowest starting price among the well-rated options. Check availability
Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch
Shortest

Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch

6 h–8 h · ★ 4.8 (81) €249 from, per person
Free cancellation Likely to sell out
Shortest well-rated option, if you are short on time. Check availability

Compare the options

Option Duration Rating Price Book
Small-Group Montepulciano and Pienza Day Trip from Siena
Free cancellation
8 h ★ 4.9 (335) €190
from, per person		 Check
Small-Group San Gimignano and Volterra Day Trip from Siena
Free cancellation
8 h ★ 4.9 (203) €190
from, per person		 Check
Small-Group Chianti Trip with Wine Tasting from Siena
Free cancellation Likely to sell out
8 h ★ 5.0 (82) €190
from, per person		 Check
Small-Group Chianti and San Gimignano Sunset Trip from Siena
Free cancellation
8 h–9 h ★ 4.8 (67) €190
from, per person		 Check
San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
Free cancellation
11 h ★ 4.5 (195) €79
from, per person		 Check
Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch
Free cancellation Likely to sell out
6 h–8 h ★ 4.8 (81) €249
from, per person		 Check
Hidden Castles & Chianti Wine Experience– Small Group
Free cancellation
5 h ★ 4.5 (183) €49
from, per person		 Check
San Gimignano, Chianti, and Montalcino Day Trip from Siena
Free cancellation Likely to sell out
11 h ★ 4.3 (153) €155
from, per person		 Check
Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour
Free cancellation Private
8 h ★ 5.0 (42) €700
from, per person		 Check
Small group Chianti Classico & Brunello wine region from Siena
Free cancellation Likely to sell out
5.5 h ★ 4.9 (33) €180
from, per person		 Check

Explore all 56 options

  1. Small-Group Montepulciano and Pienza Day Trip from Siena
    Small-Group Montepulciano and Pienza Day Trip from Siena 8 h · ★ 4.9 (335)
    Free cancellation
    €190 from, per person Check availability
  2. Small-Group San Gimignano and Volterra Day Trip from Siena
    Small-Group San Gimignano and Volterra Day Trip from Siena 8 h · ★ 4.9 (203)
    Free cancellation
    €190 from, per person Check availability
  3. Small-Group Chianti Trip with Wine Tasting from Siena
    Small-Group Chianti Trip with Wine Tasting from Siena 8 h · ★ 5.0 (82)
    Free cancellation Likely to sell out
    €190 from, per person Check availability
  4. Small-Group Chianti and San Gimignano Sunset Trip from Siena
    Small-Group Chianti and San Gimignano Sunset Trip from Siena 8 h–9 h · ★ 4.8 (67)
    Free cancellation
    €190 from, per person Check availability
  5. San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
    San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting 11 h · ★ 4.5 (195)
    Free cancellation
    €79 from, per person Check availability
  6. Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch
    Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch 6 h–8 h · ★ 4.8 (81)
    Free cancellation Likely to sell out
    €249 from, per person Check availability
  7. Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour
    Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour 8 h · ★ 5.0 (42)
    Free cancellation Private
    €700 from, per person Check availability
  8. Hidden Castles & Chianti Wine Experience– Small Group
    Hidden Castles & Chianti Wine Experience– Small Group 5 h · ★ 4.5 (183)
    Free cancellation
    €49 from, per person Check availability
  9. Small group Chianti Classico & Brunello wine region from Siena
    Small group Chianti Classico & Brunello wine region from Siena 5.5 h · ★ 4.9 (33)
    Free cancellation Likely to sell out
    €180 from, per person Check availability
  10. VIP Chianti, Brunello wine & Pienza with lunch From Siena
    VIP Chianti, Brunello wine & Pienza with lunch From Siena 8 h–9 h · ★ 5.0 (28)
    Free cancellation Likely to sell out
    €235 from, per person Check availability
  11. Small Group E-Bike Chianti Tour with farm lunch from Siena
    Small Group E-Bike Chianti Tour with farm lunch from Siena 6 h · ★ 4.8 (40)
    Free cancellation Likely to sell out
    €190 from, per person Check availability
  12. Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano
    Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano 10 h–11 h · ★ 4.7 (7)
    Free cancellation
    €229 from, per person Check availability
  13. Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA
    Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA 8 h · ★ 5.0 (37)
    Private
    €550 from, per person Check availability
  14. San Gimignano, Chianti and Montalcino Tour through Tuscan wine
    San Gimignano, Chianti and Montalcino Tour through Tuscan wine 11 h · ★ 4.8 (8)
    Free cancellation
    €140 from, per person Check availability
  15. Chianti Classico E-Bike Tour
    Chianti Classico E-Bike Tour 5 h–6 h · ★ 5.0 (25)
    Free cancellation Private
    €260 from, per person Check availability
  16. Pisa, San Gimignano & Chianti Day Trip with Lunch & Wine Tasting
    Pisa, San Gimignano & Chianti Day Trip with Lunch & Wine Tasting 11 h · ★ 4.5 (6)
    Free cancellation Likely to sell out
    €79 from, per person Check availability
  17. Small-Group Arezzo and Cortona Day Trip from Siena
    Small-Group Arezzo and Cortona Day Trip from Siena 8 h · ★ 5.0 (6)
    Free cancellation Likely to sell out
    €190 from, per person Check availability
  18. Private Montalcino and Montepulciano Tour from Siena
    Private Montalcino and Montepulciano Tour from Siena 7 h–8 h · ★ 5.0 (2)
    Free cancellation Private
    €520 from, per person Check availability
  19. Private Off Road Wine Tour in Chianti from Siena
    Private Off Road Wine Tour in Chianti from Siena 6 h · ★ 5.0 (2)
    Free cancellation Private
    €401 from, per person Check availability
  20. San Gimignano, Chianti, and Montalcino Day Trip from Siena
    San Gimignano, Chianti, and Montalcino Day Trip from Siena 11 h · ★ 4.3 (153)
    Free cancellation Likely to sell out
    €155 from, per person Check availability
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Best overall · €190 Check availability