Wine country · WINE TOURS IN SIENA
This is the shortlist you would send a friend: 5 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”
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.
