TUSCANY · DESTINATION
Tuscany's standouts.
The 10 siena tours travellers book most often across Tuscany. Each one with the price you pay, the operator behind it and the day you actually get when you turn up.
Tuscany day trip from Florence with Siena, Chianti wine tastings and lunch, plus San Gimignano towers. Small-group transport and 5 wines.
“We traveled to multiple beautiful towns. The views were breathtaking and our guides were very fun and communicated well. The wine was incredible as was the host. I highly recommend the tour.”
Half-day Chianti castles and wine tastings from Siena with a small-group minivan, two winery stops, and scenic hilltop towns.
“Fabio was an excellent tour guide with great insight into the region and a good sense of humour. Fabio took us around the Chianti area countryside safely and expertly and made our visit to the region an enjoyable one. Thank you Fabio, you were excellent !!”
Small-group Tuscany day trip: Siena’s cathedral and Palio square, a Chianti winery lunch with wine tasting, then San Gimignano towers.
“Beautiful day wonderful guides and lunch highly recommend”
2-hour organic Chianti Classico tour at Fattoria di Montemaggio: vineyard and cellar walks, five wines, snack pairings, optional grappa.
“The tour was great! We have not only received a detailed information about the winery but also tried a lot of different (including aged) wines with a tasty plate of cheese/cold cuts. Big thanks to our guide Francesco for making this tour fun!”
Full-day Siena wine tour to Monteriggioni, Pienza, and Montepulciano with two tastings of Chianti and Nobile, plus free time in town.
“Our many thanks to our driver Vincenzo. He was excellent, helpful and with wide knowledge.”
Taste 4–5 iconic Tuscan wines in a small Siena class, learn how to read wine lists, and pair pours with local cheese and bread.
“Although avid wine lovers, we still learned a lot in the class. The food pairing was delicious and the instructor was fun and knowledgeable.”
Small-group food and wine walk in Siena with Tuscan charcuterie, pici cacio e pepe, pappa senese, and sweet ricciarelli.
“We loved it.! Our guide Alexandra was so knowledgeable, kind and gracious. She made it a wonderful experience! A must do in Siena. Thank you Alexandra!”
Small-group Tuscany day trip from Siena to San Gimignano towers, Chianti tastings, UNESCO Val d’Orcia, and Brunello in Montalcino.
“Beautiful tour and wine tastings. Luca our guide was great. Small group of 8 was perfect. about 9 hrs with lunch. Great value.”
A small-group Siena horseback ride through vineyards, rivers, olive groves, and cypress roads, with guide-led nature stories and optional picnic or wine.
“We had a lovely time on this tour. The horses were sweet and very well behaved, the guide was excellent, and the views were stunning. It was very easy to find using google maps to the designated start point. Highly recommend this tour.”
A 5-hour small-group Chianti day from Siena with two winery tastings, olive oil, and free time in hilltop villages.
“We had such a wonderful time on this tour! Valesca and Luigi were the best! Valesca speaks fluent Italian, English and Spanish and was extremely pleasant and kept the group running on time. The wineries were excellent. The two towns were amazing. Luigi was a fantastic driver who kept us all safe. I recommend this…”
