Siena · TOUR REVIEWS
170 reviewed
Every tour on the site, one page, the strongest first. These are the 15 bookings that stand out across Siena and the wine towns around it, with what each costs, how long it runs and why it earns a place. The full catalogue sits underneath if none of them fits your dates.
Full-day small-group Florence trip to Siena, Chianti wine tastings with lunch, and San Gimignano towers, with free time to wander.
“Definitely a recommend! Our guide gave useful tips on the way to the destinations and wine tasting was one of the highlight! We liked everything about the day trip!”
Skip-the-line entry to Siena Cathedral and the Piccolomini Library. See Duomo mosaics and Pinturicchio frescoes for $9.
“Amazing place to be !!! Very typical from Italian history !!!”
Small-group Brunello day trip from Siena with 3 wineries, a winemaker lunch, Sant’Antimo abbey, and time in Montalcino.
“We had such a wonderful day! Juliana is a very gifted host with incredible subject matter knowledge. The wine makers we met were personable as well. The lunch we had was amazing! So much more special than we imagined & the food was excellent. Our host there was so fun! The other travelers on the tour were so much fun as well. Altogether an unforgettable experience!”
Skip-the-line Siena walk to San Domenico and Piazza del Campo, then fast entry into the Duomo with a local guide.
“We learned about many of the unique traditions of Sienna and its "animal" neighborhoods, along with wonderful tidbits about the cathedral and the Duomo. 2 hours was a perfect amount of time for us, and gave us a wonderful overview of the beautiful and long history of Siena and its people. Claudia is a learned and upbeat guide and a proud lifelong resident of the city. Go, Unicorns!”
Half-day Chianti castles and wineries from Siena with a small van, hilltop villages, two tastings, and Tuscan bites for $100.
“Absolutely amazing, such a pretty way to experience Chianti. Love the small 8 people group. The first winery ( Poggio ai Laghi) was fabulous, and the second (Lornano) was quaint. We really enjoyed it and would recommend!”
Hands-on Tuscan cooking in San Gimignano: up to six courses with fresh pasta, paired with local wine, optional truffle hunt. Max 8.
“So much fun! Amazing food! Our host was wonderful. Catarina is a great teacher & chef. What a fabulous way to learn Italian cooking. Food was fresh and simple and very tasty!”
One-hour Montepulciano cellar tour with 5 DOC/DOCG Nobile wines, pecorino, bruschetta with olive oil, and barrel-and-tufa history.
“The guide was excellent extremely knowledgeable & entertaining. The location was stunning with the architecture & history. And to finish the wine was excellent. Thank you forcthe experience.”
Small-group Tuscany day trip from Florence to Siena, San Gimignano, and a Chianti winery with lunch, wine tasting, and free time.
“The tour was great! Lorenzo our guide was very knowledgeable & shared interesting information about Siena, San Gimignano & the surrounding areas. With a great sense of humour, he made everyone feel welcomed & well looked after. Props too, to Alex our bus driver, who navigated the tight roads with ease & assisted with taking our photos. The tour was relaxed, it didn’t feel rushed yet we saw & heard about many details. I especially enjoyed the information about the Siena horse race & the rivalry between families. Paying extra for a smaller group is well worth it for a more intimate experience. I would definitely recommend the tour.”
Tour an organic Chianti Classico estate in Radda in Chianti: vineyard, cellar, 5-wine tasting, olive oil snacks and optional grappa.
“Great tour, great guide and most importantly amazing wines 😍”
3-hour private walk in Siena with a guide. Explore Piazza del Campo, palazzi, San Domenico, and optional Duomo visit.
“What a great tour! I learned so much about Siena that I never would’ve known by just walking the city myself. I also loved that it was far more personal given the small size. Seeing the massive tour groups go by made me appreciate this one all that much more.”
Siena by foot with skip-the-line Duomo access. Choose a 2-hour tour or upgrade with OPA SI Pass for Crypt and museum stops.
“Our guide and tour was outstanding. We have taken many walking tours both large and small over the last 15 years and this tours ranks as one of the best. Flo is a great knowledgeable guide.”
A small-group Brunello di Montalcino day from Siena with three winery visits, tastings, a winery lunch, and a stop at Sant’Antimo Abbey.
“Enjoyable day out, and Georgia was a fantastic, knowledgeable guide. The vineyards were all the kind of postcard settings we imagined and the lunch was excellent! The wines - and winemakers - were interesting but not to our taste - which is a very subjective assessment! We would happily have spent a little more at each vineyard instead of the stop in Montalcino. An enjoyable day out and highly recommended”
Small-group Siena vineyard tour with organic wine tasting, cellar education, and a light Tuscan lunch, guided in English for about 3 hours.
“Interesting know how. Excellent tasting . They also have olive oil . Gained some knowledge about the whole process .”
Cook Tuscan classics in Central Siena with Chef Francesco, make fresh pasta, eat your meal with wine, and learn why the recipes matter.
“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.”
A 90-minute Brunello wine tour and lunch in Castello Tricerchi with a sommelier, 3 local wine tastings, and a Tuscan 3-course meal.
“The place, the tour and the lunch were all excellent. However, when we bought a bottle of Montalcino from the estate, it actually costs more than if we were to buy outside, which was disappointing for us.”
