Wine country · WINE TOURS IN SIENA
This is the shortlist you would send a friend: 15 wine tours in Siena worth the money, each with its price, its traveller verdict and the one thing to know before you commit.
Leave Florence for Siena, a Chianti estate, and San Gimignano in nine hours. You’ll taste five wines, sample olive oils, eat Tuscan specialties, and explore each town with guidance plus free time. Guides may include Marco, Lyla, Marta, or Emma.
“The guide was very informative and engaging. We had a fantastic day and got what we wanted, history, fantastic surroundings and wine yard.”
Travel from Siena in a small minivan to three Montalcino wineries, with tastings, cellar visits, a family-made Tuscan lunch, free time in Montalcino, and Sant’Antimo Abbey. Guides such as Mattia, Giorgia, Juliana, and Emanuele bring wine, history, and humor to the day.
“The entire day exceeded expectations! Guillermo was amazing and I am still in awe of his knowledge from history to wine. He was so generous with his information - I was blown away.. The wineries we visited were all special with genuine hospitality. Having lunch at the home of a winemaker was an unforgettable experience and not one you would have in the States! And Brunello.. wow! Highly recommend!”
Ride from Siena in a climate-controlled minivan with up to eight people, stopping at Castellina in Chianti, Monteriggioni, scenic viewpoints, and two wineries. Guides such as Fabio, Daniel, and Tsvetelin lead the route in English, Italian, or Spanish, with tastings paired with Tuscan snacks.
“The tour was great. The ease of booking, drivers and tour guides at both wineries were excellent. Five hours was the perfect amount of time to see the Siena countryside and learn about the Italian wine making process.”
At Fattoria di Montemaggio, Francesco, Ilaria, or Stefano leads you through the vineyard and cellar, explaining organic farming, Chianti Classico, fermentation, and aging. You taste five estate products, often including red, white, rosé, sparkling wine, and grappa, with local snacks and olive oil.
“Amazing, Francesco is definitely an expert on wine making and story telling. 100% recommended”
Travel from Siena in a small minivan to three Brunello wineries, meet winemakers, taste local wines, and enjoy lunch at a family-run estate. Guides such as Marco, Georgia, Paolo, and Daniele add local history and wine know-how. The day also includes Montalcino and Sant’Antimo Abbey.
“All around a terrific day. Thought the tour might be too long, but time flew, wine was amazing, lunch delicious and Mattieo, a former vintner, was extremely knowledgeable and passionate about Tuscany and the wine and olive oil that it produces. Highly recommend!”
Join a multilingual guide for a roughly 10-hour trip from Siena through Chianti and Val d’Orcia. Taste wines with local snacks at two wineries, then enjoy free time in Pienza and Montepulciano. Guides may include Marta, Vincenzo, Alberto, or Lizzia, depending on the departure.
“Great way to experience the wine and beauty of the countryside!!”
At Trattoria Fonte Giusta in Siena, an English-speaking chef such as Dennis or Natalia guides you through egg pasta, pici, gnocchi, and tiramisu. Start with Prosecco, cook in a small group, then sit down to eat your pasta and dessert with a glass of wine.
“This class was amazing. The teacher was so good at institutions. And we had a fun group to spend time with. Definitely worth the money. I’ll be able to cook these foods when I return home. Best part was eating with we prepared.”
At Azienda Agricola La Lastra, 2 kilometers from Siena, you’ll walk through organic vineyards, visit the cellar, taste four local wines, and share a seasonal Tuscan lunch. Guides such as Christian, Renato, Maya, and Maia explain the work in plain English or Italian.
“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 2.5 hours at Azienda Agricola La Lastra, about 2 kilometers from Siena, with guides such as Maia or Gianluigi. Walk through organic vineyards, learn cellar methods, taste five wines, and share seasonal Tuscan food, including fresh vegetables from the farm garden.
“It was a wonderful experience which I can highly recommend. From the picturesque location to the wonderful guide, Maya, to the exquisite wine and food - a true Tuscany treat. Grazie mille!”
Meet at Siena railway station at 6 PM and ride into Chianti for a sunset aperitivo, winery visit, chapel stop, and candle-lit four-course dinner. Guides such as Valeska, Marco, or John may lead the evening, with wine, roast meats, grilled vegetables, dessert, and return transport included.
“amazing, would really recommend this if you want good food, amazing wine and excellent staff who will teach you alot about the wine and how to taste it. thank you so much for the wonderful evening”
Spend 2.5 hours at family-run Winery San Giorgio a Lapi with guides such as Jesse, Gabriele, or Giuseppe. Walk through Chianti vineyards to an 1100s church, visit the cellars, then enjoy wine pairings and a substantial Tuscan lunch on a panoramic terrace.
“Seeing more than just the process of wine , we were showed about olive and fig trees. Of course the wine tastings and pairings of food.”
Join Balloon Team Italia for a roughly one-hour flight above Siena or the Chianti countryside, guided by an English or Italian-speaking pilot such as Guido, Ollie, Gigi, or Federico. Help prepare the balloon, admire vineyards and hill towns from 500 to 3,000 feet, then return to the field for prosecco.
“The balloon ride was everything we could have hoped for. The pilot and his crew were amazing. The scenery was beautiful, the landing so smooth, and the Prosecco afterwards was a perfect ending. And we truly appreciated the pickup”
Join Elena or another member of the Poggiarello family for a two-hour visit through castle gardens, a 16th-century chapel, and an organic cellar. Finish with four or five wines, water, and snacks in a relaxed setting. English, Italian, and French tours are available.
“The tour was impressive. The guide was very informative and interactive. The story of the castle is very interesting. We had fun exploring the property”
Join an English-speaking guide such as Domenico or Kekko for a six-hour, small-group e-bike ride from Siena through Chianti. Expect 20 kilometers of quiet roads, vineyards, forests, Monteriggioni fortress, and a farm lunch with wine and olive oil.
“Dom was a brilliant guide. Safe, knowledgeable, funny and friendly. Great day!!”
Spend four hours driving a manual vintage Fiat 500 through the Chianti Hills with an English or Italian guide. Stop in Castellina in Chianti, visit a private winery, taste regional wines, and enjoy countryside views. Drivers need a license, credit card, and confidence with a classic car.
“Fantastic is an understatement. Gabriele was a great guide. Very knowledgeable and passionate about Tuscany and the region. Highly recommend.”
Cellar doors, tasting rooms and the long lunches in between.
