Best overall
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
Highest Outty Ranking in the city right now.
Outty Ranking 95 · from $190
Things to do in Siena, compared
We rank 120 experiences in Siena, Italy, and compare the top 20 on ranking, price, length, and traveler rating. The strongest overall is Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena at 95 out of 100, the lowest entry price is $3 per person, and 2 experiences sit in the Outty 90+ Club. Traveler ratings shown here are provided by Viator and Tripadvisor.
Which one should you book?
Best value
Skip the Line: Siena Duomo and City Walking Tour
The lowest price we rank above 70, so cheap without being a compromise.
Outty Ranking 92 · from $3
Best with kids
A Brunello Cooking Class with Vineyards View Winery
Top ranked experience the operator lists as family friendly.
Outty Ranking 84 · from $259
Best short trip
Exclusive Wine Tasting in the Historic Center of Siena
The quickest strong option when you only have a spare morning.
Outty Ranking 76 · from $35
Full comparison
| Experience | Outty Ranking | Verdict | From | Duration | Traveler rating | Cancellation |
|---|---|---|---|---|---|---|
| Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena | 95 | Peak Performance | $190 | 9h | 4.9/5 (1,017) | Free to 24h before |
| Skip the Line: Siena Duomo and City Walking Tour | 92 | 90+ Club | $3 | 2h | 4.8/5 (780) | Free to 24h before |
| Siena: A Wine Tour and Tasting Experience | 89 | Exceptional | $85 | 3h | 5.0/5 (391) | Free to 24h before |
| Small-Group Montepulciano and Pienza Day Trip from Siena | 88 | Exceptional | $190 | 8h | 4.9/5 (322) | Free to 24h before |
| Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better | 87 | Exceptional | $59 | 3h | 4.9/5 (239) | Free to 24h before |
| Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner | 85 | Exceptional | $130 | 4h | 4.8/5 (353) | Free to 24h before |
| A Brunello Cooking Class with Vineyards View Winery | 84 | Exceptional | $259 | 4h | 5.0/5 (314) | Free to 24h before |
| Small-Group Chianti Trip with Wine Tasting from Siena | 82 | Exceptional | $190 | 8h | 5.0/5 (82) | Free to 24h before |
| Classic Wine Tasting with Traditional Tuscan Products | 82 | Exceptional | $12 | 1.5h | 4.9/5 (78) | Free to 24h before |
| Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch | 82 | Exceptional | $229 | 8h | 4.9/5 (108) | Free to 24h before |
| Small-Group Tuscan Cooking Class with Wine & Lunch from Siena | 81 | Exceptional | $64 | 4h | 4.8/5 (176) | Free to 24h before |
| Guided Winery Tour and Wine Tasting in Siena | 80 | Exceptional | $75 | 2.5h | 5.0/5 (75) | Free to 24h before |
| Tuscany Hiking Tour from Siena Including Wine Tasting | 80 | Strongly Recommended | $60 | 4h | 4.9/5 (122) | Free to 24h before |
| Wine Class - Tuscan Classics | 80 | Strongly Recommended | $60 | 2h | 4.9/5 (266) | Free to 24h before |
| Small-Group San Gimignano and Volterra Day Trip from Siena | 79 | Strongly Recommended | $190 | 8h | 4.9/5 (200) | Free to 24h before |
| Discover the Medieval Charm of Siena on a Private Walking Tour | 78 | Strongly Recommended | $31 | 2h | 4.8/5 (263) | Free to 24h before |
| Siena: Chianti Sunset Tour with Dinner & Wine Tasting | 77 | Strongly Recommended | $95 | 3h | 5.0/5 (50) | Free to 24h before |
| San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting | 77 | Strongly Recommended | $84 | 11h | 4.5/5 (192) | Free to 24h before |
| Small-Group Chianti and San Gimignano Sunset Trip from Siena | 77 | Strongly Recommended | $190 | 8h | 4.8/5 (65) | Free to 24h before |
| Hidden Castles & Chianti Wine Experience– Small Group | 77 | Strongly Recommended | $25 | 5h | 4.5/5 (181) | Free to 24h before |
Traveler ratings and review counts are provided by Viator and Tripadvisor. The Outty Ranking is our own evaluation and is calculated independently of them.