The 15 Best Chianti & Tuscan Olive Oil Tours

1.Tuscany Bike Tour with Wine, Oil and Food in the Florentine Hills

★★★★★★★★★★5.0 · 209 reviews · 4 hours (approx.) · from $95Our pick

Ride a geared touring bike from Florence’s Oltrarno to Porta Romana, Medici villas, Arcetri, and San Miniato al Monte. Expect four hills, city traffic, country lanes, and a farm stop with Chianti, olive oil, bread, cheese, cold cuts, and honey. E-bikes cost €25 extra when available.

“We had an incredible time! Our guide knew such deep and interesting history of the region, was friendly, funny, caring and looked out for our safety. I can’t say enough good things about our experience only that you should do it - you will not regret it!”

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2.Tuscany Bike Tour with Wine & Olive Oil

★★★★★★★★★★4.9 · 174 reviews · 4 hours · from $100

Leave Florence by bike with an English-speaking local guide such as Giuseppe, Claudio, or Alex, climbing quiet hills toward villas, olive groves, and San Miniato al Monte. The 11-kilometer ride includes four hills, frequent stops, and a generous tasting of Chianti, olive oil, bread, cheeses, and Tuscan cold cuts.

“Our guide Jack was a wonderful guide, full of history and humor! The tour took us on a beautiful path along the Tuscany countryside, with breathtaking views and delicious snacks of fresh olive oil, honey meats and cheeses. The rainy weather didn’t hinder our experience at all! Highly recommend this tour group, We Love Tuscany, to anyone wanting an inspiring experience to make you feel like you are really getting a piece of the beauty of Firenze and Tuscany!”

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3.Great Chianti Wine and Olive Oil Trail with Lunch

★★★★★★★★★★4.8 · 160 reviews · 5 - 7 hours · from $104

Ride from Florence in a Mercedes minivan with an English-speaking guide such as Francesco, Chiara, or Peter. Visit three wineries, an olive oil mill, and Greve in Chianti, then enjoy a three-course lunch with wine pairings. Expect generous tastings, scenic hills, and a full day of food and drink.

“This was a very enjoyable day trip. Our drivers / guides, Tanya and Claudia, were very friendly and knowledgeable. The three boutique wineries that we visited were charming, the countryside was absolutely beautiful and the wines amazing. We were very fortunate to be able to observe the olive pressing process.”

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4.E-Bike Tour with Olive Oil in the Tuscan Hills

★★★★★★★★★★4.8 · 134 reviews · 2.5 hours · from $65

Leave Florence’s Oltrarno by e-bike with a local English or Italian-speaking guide. Ride through Poggio Imperiale and Pian dei Giullari, stop at San Miniato al Monte, then taste fresh bread and house-made olive oil at a countryside restaurant. Small groups are limited to eight.

“Our tour was fantastic. The bikes were comfortable and in excellent condition. Our guide Gabrielle was so knowledgeable about Florence and was able to share so many interesting and fun facts. He took us to some stunning spots with breathtaking views. Such a great way to see Florence. Highly recommend”

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5.Tour through the vineyards and wine and olive oil tasting in Tuscany

★★★★★★★★★★5.0 · 97 reviews · 1 hour 30 minutes (approx.) · from $45

Visit Villa La Ripa near Arezzo for a winery tour, a weather-dependent vineyard walk, four estate wines, and award-winning extra virgin olive oil with Tuscan bread, cheeses, and cured meats. Guides such as Claudia, Marius, Anita, and Virginia explain the family story and winemaking in English.

“We truly enjoyed our day at Villa La Ripa! Claudia was very informative and helpful. Learning about their operation and then getting to try the different wines was so fun. We would absolutely recommend this tour - just know you’ll likely walk out having purchased some wine & olive oil!”

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6.Olive Oil tour with Tuscan dinner

★★★★★★★★★★5.0 · 69 reviews · 3 hours 30 minutes (approx.) · from $78

At Agriturismo Tananei near Montecatini Terme, David Meacci leads a small-group olive oil lesson at an 1800s stone farmhouse. Walk among olive trees, learn professional tasting methods, pair several EVO oils with Tuscan dishes, and finish with a homemade dinner and wine.

“We had a wondeful experience learning about the oil growing process and business, how to identify and properly taste the oils, how to pair them with food etc. David is a charming teacher with a great mix of info and humor. Dinner was stunning and the setting a delight. This is a for sure to do item for anyone with interest in olives, food and clever small entrepreneurs.”

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7.E-bike 2.5 hour Florence & Tuscany With Fresh Olive Oil and Bread

★★★★★★★★★★5.0 · 45 reviews · 2 hours 30 minutes (approx.) · from $66

Leave Florence by e-bike with guides such as Giuseppe, Alexandro, or Luca, then climb into the hills for Medici history, country lanes, San Miniato views, and bread with fresh olive oil. The 2.5-hour ride covers roughly 6 to 7 miles and suits confident cyclists aged 14 and up.

“This was a great tour which led us up and out of the city of Florence into the Tuscan hills. The landscape and scenic overlooks were wonderful (and made for great photo ops). The olive oil was delicious and an enjoyable break. Highlight was bicycling nearly effortlessly up the gorgeous hills. Iocopo, our guide, was friendly & easy going which perfectly matched the rest of the tour.”

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8.Chianti: Wine and Olive Oil Tasting with Cellar Tour

★★★★★★★★★★4.9 · 35 reviews · from $39

Visit Fattoria Santo Stefano near Greve in Chianti for a one-hour private tour of its working cellars. See fermentation tanks, French oak barrels, Vinsanto casks, and the olive oil room, then taste local wines, extra-virgin olive oil, and Tuscan food with an English- or Italian-speaking guide.

“We thoroughly enjoyed this tour. Since no one else showed up we had a private tour. The wine and lovely snacks were fantastic. We strolled around the property afterwards. May even rent a room at this agriturismo (where the winery is) at our next stay in Tuscany. Beautiful property! If you’re thinking about this tour, think no more, just book it. You won’t regret it. 🍷😋❤️”

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9.Frantoio di San Gimignano: tour of the oil mill and tasting

★★★★★★★★★★4.6 · 25 reviews · 1h 30m · from $23

Spend 90 minutes at Frantoio di San Gimignano learning how extra virgin olive oil is made. Walk through the production area, use scent stations and digital quizzes, then taste the mill’s oils with Tuscan bread and regional specialties. English and Italian tours are available.

“The tour was very informative. It would have been nice to see the machinery in action.”

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10.4 Wines & 2 Olive Oils Tasting in Chianti Winery with Tour

★★★★★★★★★★5.0 · 20 reviews · 1 hour 30 minutes (approx.) · from $43

At Terre di Perseto near San Casciano, family members explain wine and olive-oil production, then pour four wines with Tuscan bruschetta dressed in two house-made oils. You may also take a short vineyard walk. Expect a relaxed, small-group visit led by people such as Benedicta, Mattias, Niccolò, or Daniel.

“It was a great experience. I would recommend this to anyone. We came a family where the youngest were 16, so she tasted the oil and just smelled the wine. We all really enjoyed the tastning!”

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11.Olive Oil Mill Tour & EVO Oils Tasting – Sarteano, Tuscany

★★★★★★★★★★4.7 · 19 reviews · 45 min · from $14Best value

At Frantoio Tistarelli in Sarteano, you’ll tour a family olive mill dating to the 1960s, see its traditional machines, and learn how olives become extra virgin oil. A guide in Italian or English leads a three-oil tasting with water and Montepulciano red wine. The visit lasts 45 minutes.

“We very much enjoyed our tour. Our guide was very friendly and knowledgeable. We learned a lot about the history and process that goes into producing oil. We loved the tastings and purchased several items!”

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12.Chianti: Premium Wine, Olive Oil and Vinegar Tasting

★★★★★★★★★★4.8 · 19 reviews · from $36

Your wine expert guides you through six Poggio ai Laghi wines, including Chianti Riserva and Chianti Classico, with Tuscan meats, pecorino, bruschetta, olive oils, and aged vinegars. This 90-minute tasting takes place in a private setting, not on a vineyard or winery tour.

“The guide provided excellent attention and explanations. The facilities are very good.”

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13.Horse ride, Olive Oil and local foods tasting in a Tuscan farm

★★★★★★★★★★5.0 · 19 reviews · 5 hours 30 minutes (approx.) · from $355

Leave Florence with a private driver for Reggello, where an instructor matches you with a suitable horse for a country trail ride. Then visit a historic estate with guide Thomas for olive oil, Chianti, bruschetta, cheeses, and local cold cuts before returning to Florence.

“One of the highlights of our trip. Beautiful scenic and worthwhile trail ride and tjen on to an excellent amd informative tour with thomas at the olive oil estate in the countryside. We bought olive oil after the tasting and also enjoyed a delicious lunch on the porch overlooking the orchard.”

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14.Think of a romantic meal in the Olive Trees shade, accompanied by Tuscan wines!

★★★★★★★★★★4.5 · 15 reviews · 3 hours (approx.) · from $114

Spend about three hours at Agriturismo Sanguineto near Montepulciano, walking among woods and olive trees before a four-course Tuscan meal with matching estate wines. You dine at the meeting point and can add pool access for €10 or a private spa session for €30 per person.

“The people the food the ambiance the length was better than expected and the weather was fantastic price was well worth for the experience”

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15.Winery Visit with Picnic in Olive Grove

★★★★★★★★★★5.0 · 3 reviews · 2 hours · from $59

Spend two hours at a family-run winery near San Gimignano, tour its wine and olive-oil production, then picnic beneath olive trees with wine, cheeses, cold cuts, appetizers, pappa al pomodoro, and water.

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