Skip to content

Wine Tastings in Siena: Compare 132 Options (October 2026)

Independent comparison Prices checked October 4, 2026 Prices shown in EUR 132 options compared

Our top pick is Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena (9 h, ★ 4.9 (1,032)). Well-rated options start at €32.50 from, per person, and 120 of 132 options offer free cancellation.

Our picks

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
Best overall

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

9 h · ★ 4.9 (1,032) €190 from, per person
Free cancellation
Highest weighted rating of 17 options with 50+ reviews. Check availability
Montalcino: Brunello Wine Tasting Experience
Lowest price

Montalcino: Brunello Wine Tasting Experience

1.5 h · ★ 4.4 (65) €32.50 from, per person
Free cancellation
Lowest starting price among the well-rated options. Check availability
Classic Wine Tasting with Traditional Tuscan Products
Private option

Classic Wine Tasting with Traditional Tuscan Products

1.5 h · ★ 4.9 (81) €28 from, per person
Free cancellation
Highest-rated private tour: only your group. Check availability

Compare the options

Option Duration Rating Price Book
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
Free cancellation
9 h ★ 4.9 (1,032) €190
from, per person		 Check
Siena: A Wine Tour and Tasting Experience
Free cancellation
3 h ★ 5.0 (401) €85
from, per person		 Check
A Brunello Cooking Class with Vineyards View Winery
Free cancellation Likely to sell out
4 h ★ 5.0 (328) €259
from, per person		 Check
Wine Class - Tuscan Classics
Free cancellation
2 h ★ 4.9 (267) €60
from, per person		 Check
Guided Winery Tour and Wine Tasting in Siena
Free cancellation
2.5 h ★ 5.0 (77) €75
from, per person		 Check
Classic Wine Tasting with Traditional Tuscan Products
Free cancellation Private
1.5 h ★ 4.9 (81) €28
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
Siena: Chianti Sunset Tour with Dinner & Wine Tasting
Free cancellation
3 h ★ 5.0 (56) €95
from, per person		 Check
Siena Underground Wine tasting in a Medieval Cave
Free cancellation
1 h ★ 5.0 (61) €75
from, per person		 Check
Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle
Free cancellation Private
1.5 h ★ 4.7 (127) €58.90
from, per person		 Check

Explore all 132 options

  1. Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
    Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena 9 h · ★ 4.9 (1,032)
    Free cancellation
    €190 from, per person Check availability
  2. Siena: A Wine Tour and Tasting Experience
    Siena: A Wine Tour and Tasting Experience 3 h · ★ 5.0 (401)
    Free cancellation
    €85 from, per person Check availability
  3. A Brunello Cooking Class with Vineyards View Winery
    A Brunello Cooking Class with Vineyards View Winery 4 h · ★ 5.0 (328)
    Free cancellation Likely to sell out
    €259 from, per person Check availability
  4. Wine Class - Tuscan Classics
    Wine Class - Tuscan Classics 2 h · ★ 4.9 (267)
    Free cancellation
    €60 from, per person Check availability
  5. Guided Winery Tour and Wine Tasting in Siena
    Guided Winery Tour and Wine Tasting in Siena 2.5 h · ★ 5.0 (77)
    Free cancellation
    €75 from, per person Check availability
  6. Classic Wine Tasting with Traditional Tuscan Products
    Classic Wine Tasting with Traditional Tuscan Products 1.5 h · ★ 4.9 (81)
    Free cancellation Private
    €28 from, per person Check availability
  7. 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
  8. Siena: Chianti Sunset Tour with Dinner & Wine Tasting
    Siena: Chianti Sunset Tour with Dinner & Wine Tasting 3 h · ★ 5.0 (56)
    Free cancellation
    €95 from, per person Check availability
  9. Siena Underground Wine tasting in a Medieval Cave
    Siena Underground Wine tasting in a Medieval Cave 1 h · ★ 5.0 (61)
    Free cancellation
    €75 from, per person Check availability
  10. Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle
    Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle 1.5 h · ★ 4.7 (127)
    Free cancellation Private
    €58.90 from, per person Check availability
  11. Exclusive Wine Tasting in the Historic Center of Siena
    Exclusive Wine Tasting in the Historic Center of Siena 1 h · ★ 5.0 (47)
    Free cancellation
    €35 from, per person Check availability
  12. Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch
    Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch 8 h · ★ 4.9 (110)
    Free cancellation Likely to sell out
    €229 from, per person Check availability
  13. Siena walking tour with lunch & Chianti wine
    Siena walking tour with lunch & Chianti wine 2.5 h · ★ 4.8 (101)
    Free cancellation Likely to sell out
    €85 from, per person Check availability
  14. 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
  15. 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
  16. 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
  17. Savor Siena Food and Wine Tour
    Savor Siena Food and Wine Tour 2 h · ★ 4.9 (40)
    Free cancellation
    €60 from, per person Check availability
  18. Montalcino: Brunello Wine Tasting & Tuscan Lunch
    Montalcino: Brunello Wine Tasting & Tuscan Lunch 1.5 h · ★ 4.9 (15)
    Free cancellation Private
    €98 from, per person Check availability
  19. Tasting of the Best Wines in Siena in an Etruscan Crypt
    Tasting of the Best Wines in Siena in an Etruscan Crypt 1 h · ★ 5.0 (7)
    Free cancellation
    €125 from, per person Check availability
  20. 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
Prefer to browse on Viator itself? See all on Viator →

More in the same city

Food Tours in Siena Montalcino Day Trips from Siena Walking Tours in Siena Private Tours in Siena Cooking Classes in Siena Outdoor & Adventure in Siena Siena Cathedral (Duomo di Siena)
Best overall · €190 Check availability