ITALY · CITY
The most popular, first.
The 15 most popular siena tours, with what each one includes, who runs it, and what you can expect on the day.
Florence to Tuscany in a small group: Siena sights, a Chianti estate with five wine tastings and lunch, then San Gimignano’s towers.
“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.”
Skip the line in Siena Cathedral and visit the Piccolomini Library with Pinturicchio frescoes, plus an official QR-code audio guide.
“Building to the Lord, in great magnificence and splendour can never be out of the question. I pray that that Romanesque structure and the libraries inspire the faithful until the end of time”
OPA SI PASS lets you explore Siena’s Duomo complex with a self-guided digital audio guide and access to crypt, libraries, museum and viewpoint.
“Very good experience - line to get tickets printed can be a bit busy in peek period.”
2-hour Siena walking tour with skip-the-line Duomo tickets, English guide stories on the Contrade and Palio, plus major art inside.
“Very good. However if I knew better I would have brought my headphones because earpieces were very difficult to hear everything”
Small-group Brunello di Montalcino day trip from Siena with 3 winery visits, winemaker lunch, town time, and Abbazia di Sant’Antimo.
“This was an AMAZING experience!! We spent all day tasting high quality wine at very small family vineyards and enjoying authentic Italian food made in their kitchens. Our guide, Mattia, was so great! He was knowledgeable (a wine-maker himself) and SO funny! Our group was small (8) and we became fast friends. We cannot recommend…”
Skip the line to Siena’s Duomo and walk car-free through contrade, Piazza del Campo, and red-brick churches with a local guide.
“So glad we did this tour. We were very fortunate that it was only myself and a friend so we had Georgia to ourselves! She was a fantastic guide and so knowledgeable about the history of Siena. Georgia made the tour very specilaised and answered lots of our questions. It was wonderful learning about this…”
A 5-hour small-group van tour from Siena through Chianti towns and vineyards, with 2 winery tastings and classic Tuscan stops.
“A wonderful small group tour visiting the beautiful Chianti region & several wineries snd hill top Tuscan villages. Momo our tour guide was an excellent host- very informative, friendly and helpful. Enjoyed some beautiful Chianti wines. It was a most enjoyable and relaxing five hours! Excellent value.”
Small-group Florence day trip to Siena, San Gimignano and Chianti with guided walks, winery lunch and tastings, plus time to explore.
“Beautiful day in Tuscany! Our guide and driver were both wonderful. The winery staff were great too; the food and wine at lunch were delicious. We had such a great day.”
A 2-hour Chianti organic winery tour in Tuscany with vineyard and cellar visits, 5 wine tastings, olive oil snacks, and optional grappa.
“Our guide Francesco was awesome. He was knowledgeable, passionate and entertaining.”
3-hour private Siena walk with a local guide and optional Duomo visit. UNESCO stops, Palio stories, and photo-worthy sights.
“Our guide was knowledgeable and interesting throughout the tour. She was able to bring important events like the Palio to life for us and helped us understand the culture of the Contradas. It was just long enough and ended in front of the beautiful cathedral where we could then enter on our own if we…”
Walk Siena with skip-the-line Duomo tickets, then choose OPA SI Pass for crypt, Opera Museum, Baptistery, and Facciatone views.
“Very knowledgeable guide. Lots to see. Definitely include the Duoma and Cryptic. Was worth the additional cost!”
Small-group Brunello tour from Siena with vineyard walks, 3 estate tastings, a real Tuscan lunch, plus Montalcino and Sant’Antimo.
“Mattia was incredible. He was knowledgeable not just regarding wine but also history and geography of the area. I had the most enjoyable and informative wine tour. I would definitely bring my family and friends back.”
Small-group organic wine tour outside Siena: vineyard walk, cellar science, tasting 4 wines, and a light Tuscan lunch with olive oil.
“Great value - generous pours and lovely large lunch! We enjoyed being in the vineyards as well as the fermentation room”
Hands-on Tuscan cooking in central Siena with chef Francesco, a full 4-course menu, and wine at the end in a small group.
“Such a fun experience! My wife and I really enjoyed ourselves. The group of people we were with were very friendly and we all were the best of friends at the end of the evening.”
Full-day wine tour from Siena with two winery tastings, plus Pienza and Montepulciano in Val d’Orcia. Great views, long day.
“The mixture of two winery visits and tastings, along with two beautiful towns and the scenery.”
