Siena · TUSCAN WINE TASTINGS & WINERY TOURS
74 reviewed
The heart of a Siena trip is a day among the vines, and the right winery tour makes or breaks it. Here are the 15 best across Chianti, Montalcino and the Orcia valley, with the grapes each estate pours, how many tastings you get, whether lunch is included and what a seat costs.
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!”
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!”
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.”
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 😍”
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 .”
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.”
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.”
5 pm Siena wine class for Tuscan classics: taste 6 wines with bites and learn to read Chianti and Brunello on menus in 2 hours.
“Terrific class. Had a ton of fun. So convenient being in the city walls. Drank, laughed and learned a great deal. Manuel was a terrific teacher and good natured person. No pressure sale. If you don’t know much about wine from Tuscany, want to learn and drink with a friendly group, this tour is for you.”
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”
Three-hour organic vineyard and cellar lesson near Siena, tasting four wines and a light Tuscan lunch for $100.
“Amazing experience. You learn a lot while drinking and eating delicious wines/meals. Highly recommend !!!”
Taste four Montepulciano DOCG wines in a 16th-century cellar with a sommelier and Tuscan appetizers in 1.5 hours for $41.
“We enjoyed the wine tasting and touring the cellar very much. Fantastic guide. My wife had walking difficulties and the descent down the cellar steps was challenging. At the end of the tour he opened the door to the street, which would have been a good option for her at the beginning (to avoid difficult brick stairway) as well.”
A 1.5-hour Montepulciano wine tasting with lunch in a 14th-century cellar, featuring 4 local DOCG wines and Tuscan specialties.
“Very nice small group gathering in a beautiful setting. Host was knowledgeable and friendly. Food was excellent”
Enjoy a Chianti winery lunch or dinner near San Gimignano with guided wine and olive oil tasting in a beautiful setting.
“Amazing! Wine, scenery and food all top quality n. Highly recommend!”
Ride Montepulciano’s hills by e-bike, stop at San Biagio, then taste eight Montepulciano wines at two cellars, guided by your phone.
“This is not for anyone who hasn’t been on an e-bike and it’s not off road as the photos would represent. We traveled main roads between wineries. That said, Italians are kind to bikers/cyclists and I never felt unsafe. Both wineries we visited were lovely. We had one of our best meals in Italy during this excursion! Urban Bikery was an upscale store with great staff. A unique experience for sure and be sure to leave yourself extra time to explore the town!”
