Top picks for Siena Experiences

Discover 153 Experiences in Siena on Trip.com, updated 14 September 2026, with experiences lasting from 1 to 12 hours. Find the perfect adventure for your day!

From €33.14 per person, with an average total of €115.97. Choose the option that suits your plan.

This week's most popular Experiences: "San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting", with 3.983k reviews and a rating.

Now on Trip.com: "San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting", a 11-hour adventure in Siena!

The next available day tour departs on 15 September 2026. Book now to secure your spot!

Siena Experiences usually take about 11 hours — perfect for a relaxed, immersive experience!

75% of Siena Experiences now offer English-speaking guides

September is the perfect time to visit Siena! Choose from 153 available day tours, including seasonal favorites like San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting.

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

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153 results for Siena Experiences

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Reviews/Trip Moments

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Reviews: San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting
Guest User2025-10-07
Our guide (sorry can’t remember her name) was exceptional. She was firm with keeping such a big group on time and together and she was incredibly knowledgeable. You could tell she loves her job and working with people and also is extremely knowledgeable about all things from the region. The three stops were all very different but thoroughly loved each one. We would thoroughly recommend this tour to you.
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Reviews: From Florence: Tuscany Day Trip with Lunch at Chianti winery
Guest User2025-10-17
It was amazing! Victoria was our guide and she was perfect! She shares a lot of historical information and she was very kind and patient. Siena and San Gimignano were wonderful. I just didn’t enjoyed Pisa too much but it’s nice to go at least once. The others, I want to come back
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Reviews: Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence
Guest User2025-07-27
Loved it. Great guide Francesca, friendly and not overbearing; knowledgable and helpful and polite and not pushy. Good wine, olive oil and balsamic and good charcuterie and imparted knowledge at the wineries: different vibe at each place, both interesting. Easy going and not rushed. Excellent settings and San Gimigniano touristy but stunning none the less. Great advice for the gelato- try pistachio and hazelnut. Well driven too. Lovely day and only two small groups so you didn’t get overlooked.
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Reviews: Siena: Small group Cooking Class in Chianti Farmhouse
Guest User2024-09-15
We met so many new friends from around the world yesterday at Simone's farmhouse cooking class in Chianti and had SO much fun! It was everything we hoped it would be. 🫶🏼 The event was very well organized, timely, informative, delicious and a super fun experience all around. Chef Simone was great! 😁 We highly recommend it! ♥️🇮🇹🍝
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Reviews: Tuscan Cooking Class in Central Siena
Guest User2025-09-28
We booked this cooking school as it was only a 1 min walk from our accommodation. It was more expensive than other cookimg classes but well worth it. This was the best meal we had on our Itakian vacation and we helped to prepare it but without the hassle of washing up afterwards! It was a 4 course meal with soup, pasta , pork and potatoes and dessert. We were so full! Everything was delicious and we learnt a lot about traditional Tuscan dishes and also some new techniques.
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Reviews: Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
Guest User2024-10-01
Marco was our guide and he was excellent. 5/5 for him. First vineyard explained all the regulations around the brunello di montalcino wines as well as tasting with some bruschetta, in a lovely setting. The second stop was for lunch which was fantastic, cooked by the owners wife. There were further wine tastings with lunch, however there was no look around their winery. There was a very short stop (25 minutes) to briefly look around Montalcino then a stop at the third vineyard. This tour showed the winery then some small tastings. There is sales pitch, understandably, at each location and we did buy 6 bottles overall, ranging from 68 to 120 euros. It was lovely to be on such a small and intimate tour and meet lovely people as part of it. However I would suggest reducing to two vineyards and more time to explore Montalcino.

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