Siena · TOURS
86 reviewed
Good tours fill up fast in high season around Siena. Here are the 15 best, with current prices and what makes each one different, so you can lock yours in before the calendar closes.
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 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!”
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 .”
From Siena, tour Pienza and Montepulciano in Val d’Orcia with two winery tastings, Chianti and Nobile di Montepulciano, plus snack pairings.
“I love Montepulciano! It was my favorite. I was blown away out when they give only crackers in the wine tasting. Then biscotti with Monsanto. The driver was rough and the bus did not have any oxygen because AC was not working properly. I was dizzy and nauseous most of the time. I told one of the guides but nothing changed. That old bus is not good for tours.”
Siena on foot with a local guide: Piazza del Campo, palio stories, and Siena Cathedral entry included for $34.
“Coming to Siena just for a day, this 2-hour tour was perfect: it gave us enough important information in the very beginning of the day, after which we could explore the city and its treasures on our own. Highly recommend for first-time one-day travelers.”
Tour Montepulciano’s underground tufa cellar, learn local wine traditions, then taste 3–6 wines with bruschetta in a small group.
“This was a fantastic tour! We throughly enjoyed it. We liked hearing about the history of the business.”
A guided wine and olive oil tasting at Tenuta Torciano in San Gimignano with Chianti, Vernaccia, small bites, and optional meal upgrade.
“We were late for our booked schedule but they accommodate us with good food and wine. The property and the people are nice”
Private 2–3 hour walk in Siena with a licensed guide: San Domenico, Piazza del Campo, Palio contrade, and the Duomo plan.
“Personal, insightful & helpful. Pit guide was knowledgeable & relatable. We enjoyed our time with Julia.”
