Italy · SIENA TOURS
The 15 best siena tours you can book today, with what each costs, how long it runs and who it suits. Number one is top for a reason; start there.
Explore Siena, Chianti, and San Gimignano from Florence with wine, Tuscan lunch, free time, and an air-conditioned ride.
“12 hours very well splited which led to beautiful memories. We were lucky to have Marta as a guide. She shared with us the history of the region and some old legends. Sienna, Colle di Val d’Elsa and San Gimignano worth for sure spending more than one day to feel them.”
Enter Siena Cathedral and the Piccolomini Library with fast-track access, Renaissance art, Michelangelo sculptures, mosaics, and a digital audio guide.
“Amazing interior. Overwhelming pieces of religious artwork. Missed explanations.”
Explore Siena’s Duomo, crypt, library, museum, baptistery, and Facciatone with a three-day pass and smartphone audio guide.
“The cathedral was stunning! We never received an audio guide but felt we did not need it. The beauty spoke for itself!”
Walk medieval Siena with a local English-speaking guide, learn the Palio story, and enter the spectacular Duomo without the ticket-line wait.
“Elio is fantastic! V informative. Next time I’d choose a longer tour as 2 hours is not enough. Nothing to do with the guide, but we paid almost $100 for the two of us and I thought that was a bit steep for only 2 hours (granted, it included entrance to the duomo). Highly recommended!”
Taste Brunello at three Montalcino wineries, enjoy a homemade Tuscan lunch, visit Sant’Antimo Abbey, and return to Siena by minivan.
“This tour was a wonderful experience! We visited three distinct wineries and tasted a variety of Rosso and Brunellos. We had a great lunch that was homemade in the family kitchen. The drive was beautiful and Emanuel, our “professional drive” (as he calls himself), is fantastic! He made our day showing us the sights and offering lots of history about the area. Don’t miss this tour!”
Explore Siena’s contrade, Piazza del Campo, and the Duomo with a local guide, skip-the-line entry, and two hours of focused walking.
“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!”
Tour Chianti from Siena in a small van, visit Castellina and Monteriggioni, and taste regional wines at two Tuscan wineries.
“Daniel was a fun informative guide . We visited beautiful little villages and 2 wonderful wineries with amazing views of the Chianti wine region .The wine we tasted was lovely and each winery gave us a different experience. Highly recommended.”
Spend a day in Tuscany visiting Siena, a family winery, and San Gimignano, with lunch, wine tasting, guided walks, and free time.
“Lorenzo was a fantastic tour guide and Alessio made the ride very comfortable. Such a great day well spent at a comfortable pace with a good amount of historical information and lots of free time to shop around and take photos.”
Tour an organic Chianti winery, taste five estate wines, learn wine skills, and enjoy Tuscan views with cheese, salami, bread, and olive oil.
“the guide was very freindly and he really created an experience we will not forget.”
Explore Siena with a private guide, from Piazza del Campo and Saint Catherine’s shrine to the optional marble-filled Duomo.
“My guide Mare was wonderful! I prefer to be guided as a traveler and want to learn the inside story of a few key places in a city. Mare taught me about Saint Catherine of Siena, the Paleo and all of its details and the Duomo of Siena. I told her I knew how to be guided and she smiled and became good friends which is essential for this type of experience. I highly recommend this tour!”
Explore Siena’s medieval streets, Palio districts, and Duomo on a guided walk with skip-the-line tickets and an optional OPA SI Pass.
“pur guide Elio was absolutely charming and tailored the tour with great consideration to all members of our small group. We learned about the history, culture and customs of Siena in a very engaging way - the right balance of info and fun! it was a great tour!”
Spend nine hours in Montalcino with three Brunello wineries, a family-run Tuscan lunch, Montalcino town, and Sant’Antimo Abbey.
“What a great tour! We visited 3 fantastic wineries and had the pleasure of trying several selections of their wines. And Georgia was a wonderful tour guide; very insightful, knowledgeable, and accommodating. We couldn't have asked for a better day.”
Tour Siena’s organic vineyards, learn winemaking from grape to bottle, taste four wines, and enjoy a seasonal Tuscan lunch at La Lastra.
“Wonderful! A small group, the sommelier was informative and kind. The winery is beautiful and the meal was fantastic. 10/10 would go back!”
Learn to make fresh pici, Tuscan soup, meat, and dessert with Chef Francesco in central Siena, then enjoy your meal with Tuscan wine.
“Excellent chef and helper. Our experience was helpful. All was delicious and easy to understand. Highly professional and talented. Made us feel comfortable.”
Spend a full day from Siena tasting Chianti and Nobile di Montepulciano wines while exploring Pienza, Montepulciano, and Tuscany’s hill roads.
“I had great time on this tour, met some amazing people and get to see Montelcino, Pienza and Montepulciano which are all amazing little villages. both of the wineries we visited were amazing in their own way, great wine to taste/purchase. the tour guide was amazing, so overall I received more than I paid for, amazing day out.”
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