WINE TOURS · SIENA WINE TOURS
The 15 best siena wine tours you can book right now, each with its price, its length and the kind of afternoon it turns into. The first one is first for a reason.
Spend nine hours exploring Siena and San Gimignano, with a guided Chianti estate visit between them. You’ll taste five wines, sample olive oils and balsamic vinegar, and enjoy a Tuscan lunch. Guides such as Marco, Lyla, Marta, and Enrieta are praised for clear storytelling and keeping the day on time.
“We had a great day out. Lots if activity. We were kept very busy.”
Spend nine hours in the Montalcino wine country with a guide such as Mattia, Juliana, or Emanuele. Visit three wineries, taste Rosso and Brunello, share a generous family-style lunch, explore Montalcino, and visit Sant'Antimo Abbey. Your air-conditioned minivan holds no more than eight people.
“Great tour of the area and visits to 3 small family wineries. Each winery has a different character and experience. Lunch at the second winery was in the home of the winemaker and the meal is a delicious, homemade treat. Mattia our guide was fun and very informative”
Travel from Siena in a small van of up to eight people, with an Italian, English, or Spanish-speaking guide. Visit Castellina in Chianti, Monteriggioni, scenic viewpoints, and two wineries. Tastings include Chianti wines, Tuscan snacks, and at some stops, olive oil and balsamic vinegar.
“Our guide was friendly and informative, we had brief stops at two Chianti villages and two wine tasting sessions, the second one was a sit-down with tastings of wines, oils and balsamics…the host was excellent company.”
At Fattoria di Montemaggio, guide Francesco or another English-speaking host leads you from the vineyard roof to the vines, cellar, and tasting room. Learn about organic farming, Chianti Classico’s Black Rooster, fermentation, aging, and proper tasting. Sample five estate products with olive oil, bread, cheese, salami, and possibly grappa.
“The tour was fabulous and the views were spectacular. Most of all,. Francesco was knowledgeable and a storyteller,, and a genuinely kind person. Fluent in English, he went above and beyond to ensure we had an incredible experience. We could not have had a better guide, one who grew up in the region and knew the ins and outs of all elements of wine production. He is a true gem. This is a little winery with a lot of heart. We could tell that much love goes into every part of the winemaking process. I would strongly recommend to have a vehicle to get there because it is in a…”
Travel from Siena in a small group of up to eight, visiting three Brunello wineries, tasting with local producers, and eating lunch at a family-run estate. Your English-speaking guide may be Marco, Georgia, Paolo, or another local host. The day also includes Montalcino and Sant’Antimo Abbey.
“Excellent in every way. Marco had great energy, made us laugh and taught us a lot about Tuscany and Tuscany wines. The three wineries were all a little different and all great.”
Spend about three hours at Azienda Agricola La Lastra outside Siena, learning how organic grapes become wine, tasting four organic wines, and sharing a seasonal light lunch with wine and olive oil. Guides such as Maia make the technical side friendly and easy to follow. Small groups are capped at 12 people.
“Great, host was most informative, friendly and took time to answer questions. Tasted four organic wines and lunch. So much fun, would definitely do it again.”
From Siena, travel by air-conditioned bus or minivan through Chianti and Val d’Orcia. Taste wines with local snacks at two wineries, visit Pienza and Montepulciano, and enjoy free time for lunch, shopping, and views. Guides may speak English, Italian, Spanish, Chinese, or Portuguese.
“Our many thanks to our driver Vincenzo. He was excellent, helpful and with wide knowledge.”
At Trattoria Fonte Giusta in Siena, an English-speaking chef such as Dennis or Natalia guides you through egg pasta, pici, gnocchi, and tiramisu. You begin with Prosecco, cook in an equipped workspace, then sit down with wine to eat the meal you helped make. The three-hour class costs $81 per person.
“We had a wonderful time at the cooking class. The instructor was great and very patient. We learned how to make tagliatelle, ravioli, gnocchi and tiramisu. The restaurant enhanced our homemade pasta with tomato sauce and a meat sauce plus your choice of red or white wine. There was so much food and they offered a doggy bag to take leftovers home. We highly recommend this activity. It’s worth the price and you won’t leave hungry!😋”
Spend four hours at Castello Tricerchi near Montalcino making filled pasta, pici, and a Tuscan dessert with a chef such as Alexandra, Gaia, or Jacomo. Tour the castle and cellar, then eat your meal with Rosso and Brunello on a terrace above the vineyards. Siena and Florence pickup can be arranged for an added fee.
“Our cooking instructor was wonderful, and very patient! The view for cooking and the meal was amazing.”
Spend three hours at Azienda Agricola La Lastra, about 2 kilometers from Siena, learning how organic grapes become wine. Guides such as Maya, Christian, Renato, and Gianluigi explain the vineyards and cellar in plain English or Italian. Taste four local organic wines with seasonal Tuscan food, including homemade pasta.
“This was an amazing tour. Our guide was really great, very informative, friendly and knowledgeable about the vineyard. Walk a little into the olive orchard and the vineyard and did a little tour in the wine cellar. Had a great wine tasting of 4 wines but as people asked questions he gave us tastes of several other wines and the lunch was really good. All made on site with produce grown on site. This was just a great experience”
Spend about 11 hours touring Tuscany from Florence, with free time in San Gimignano, Siena, and Monteriggioni, plus a winery visit, three-course lunch, and three Chianti wines. Guides such as Marta, Sandro, and Riccardo are praised for clear local context. Expect lots of walking and a potentially large group.
“Freddy did a wonderful job guiding 87 people on these tours. He was so kind and patient. San G was as beautiful as I hoped. I wish we had more time there! Siena was also just as beautiful! I would recommend this tour and experience for anyone! Freddy was spot on with his recommendations in each village!!!”
Ride a Vespa convoy through Chianti’s vineyards, olive groves, and hill towns on a 6.5-hour outing from Siena. You can drive your own scooter or ride with an escort, then visit Casale dello Sparviero for wine tasting and a light lunch. An international driving permit and real scooter experience are required.
“We had a very fun and knowledgeable tour guide who made the trip such a great time! It was such a beautiful ride and the wine was amazing! We would definitely do it again!”
Meet your guide at Siena railway station for a gentle countryside walk along the Via Francigena. Guides such as Keko, Giovanni, Francesco, and Alessia explain local history, plants, and winemaking as you walk toward Monteriggioni. Finish with a tutored tasting of local wines, free time in the medieval village, and included transport back to Siena.
“Giovanni our guide for the walk was friendly, helpful and extremely knowledgeable about the flora and fauna as we walked to Monteriggioni. Highly recommended.”
Spend 2.5 hours at Azienda Agricola La Lastra, an organic winery about 2 kilometers from Siena. Guides such as Maia, Mya, and Gianluigi explain vineyard care and winemaking before five wine tastings paired with seasonal Tuscan food. Plan on taking a taxi from central Siena.
“We absolutely loved our experience. Gianluigi was very well informed, explicative and such a pleasant speaker, we could listen to him talking about wine for hours. The winery is beautiful, we tasted several wines together with delicious food. We are very glad we chose this activity during our stay in Siena.”
Travel from Siena in a small group of up to eight, with an English-speaking driver-guide, to two boutique Brunello wineries. Tour historic cellars, taste local wines, pause in Montalcino, and enjoy a three-course wine-pairing lunch. Guides such as Niccolò, Stefano, and Patrizio are praised for their local wine knowledge.
“The only issue was the original description I signed up for makes you think we would go to winery in Montalcino then lunch somwhere with tastings then also to Montepulciano for another tasting. I really wanted to go to BOTH and actually we only went to 2 places (not 3) and never went to Montepulciano so I thought the price I paid $577.92 fo 2 people was way overpriced for this experience.”
A country, a grape or an afternoon with nothing planned.
