Olive Oil and Wine Tastings in Florence: Our 10 Favourites

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 through Porta Romana, Medici estates, vineyards, olive groves, and Arcetri. Your guide, perhaps Giuseppe, Eli, Claudio, or Alessandro, leads a small group toward Florence’s finest viewpoints, with Chianti wine, olive oil, bread, cheese, and cold cuts at a countryside farm. Expect four hills and a real workout.

“We had a wonderful ride with Toto as our guide! Seeing Florence from above was thrilling, and all the views were just stunning. I suggest e-bikes, but my husband did okay without one, though it was definitely hilly! Highly recommend!”

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2.Florence: Tuscany Bike Tour with Wine & Olive Oil

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

Ride 11 km through Florence’s southern hills with an English or Italian guide, passing villas, olive groves, and quiet country roads. Guides such as Giuseppe, Claudio, Luca, and Ale add local history along the way. The tour ends with Chianti, olive oil, fresh bread, and Tuscan appetisers. Regular bikes suit active riders; e-bikes cost €20 extra.

“Very good. Nice way to spend a few hours. Definitely pay extra for e-bikes as the hills would be challenging for any athletic person in the heat of Florence. Would recommend!!”

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3.Florence: Great Chianti Wine and Olive Oil Trail with Lunch

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

Spend 5 to 7 hours touring Chianti from Florence with an English-speaking guide, visiting three wineries, an historic olive oil mill, and Greve in Chianti. Expect generous tastings, a three-course lunch, scenic hill roads, and a small-group ride in a Mercedes minivan. Guides such as Francesco, Chiara, and Peter are known for warm, informative hosting.

“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.Florence: Private Vintage FIAT 500 with Wine & Olive Oil

★★★★★★★★★★4.5 · 21 reviews · 2 hours (approx.) · from $204

Set out from Via del Campuccio in a fully equipped vintage FIAT 500, following a private guide through Florence’s hill roads and nearby Tuscan countryside. Stop at San Miniato al Monte for photos, enjoy scenic viewpoints, and pause at a café for rustic bread, extra-virgin olive oil, and a glass of Chianti. The exact driving arrangement should be confirmed before booking.

“Fue descubrir parajes maravillosos, conduciendo como en el pasado un auto clásico. Francesco el guía genial”

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

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

At Terre di Perseto, a family-run winery near San Casciano, you’ll tour the production rooms with guides including Benedicta, Mattias, Niccolò, or Daniel, then taste two IGT wines, Chianti Classico, Riserva, and two EVO oils on six bruschette. A short vineyard walk may be possible.

“A high quality activity. Interesting and clear explanations with a generous tasting in wine as well as olive oil and balsamic vinegars. Warm and friendly experience that we highly recommend!Auto-translated”

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6.Florence: Vintage Fiat 500 Tour with Wine Tasting at Winery

★★★★★★★★★★4.9 · 17 reviews · 2 hours · from $152

Ride with a private driver in a fully equipped 1960s Fiat 500 from Florence to San Miniato al Monte and the Tuscan hills. You’ll stop at a family-run winery for local wine, olive oil, cold cuts, and bread. Guides such as Gabriele, Iacopo, and Nino bring local stories and plenty of personality, but you cannot drive the car yourself.

“A magical afternoon riding through the Tuscan hills with our fantastic guide Iacopo, ending with a delicious aperitivo at golden hour. Great views, great vibes, the perfect way to end the day!”

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7.Florence: Great Chianti Wine and Olive Oil Trail with Lunch

★★★★★★★★★★5.0 · 8 reviews · 7 hours (approx.) · from $162

Spend about seven hours exploring Chianti from Florence with an English-speaking guide and sommelier. Visit an olive oil mill, wineries, and Greve in Chianti, then enjoy a three-course Tuscan lunch with wine pairings. Transport is by Mercedes minibus, with a maximum of 16 people unless you choose the semi-private option for up to 8.

“Wonderful! Tour guide excellent as were the winery families! Don’t miss this trip!! Roads traveled can be a bit bumpy but our driver was excellent”

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8.Florence: The secret of wine, cheese and olive oil at a farm

★★★★★★★★★★5.0 · 3 reviews · 5 hours · from $94

Leave Florence by car for Fattoria Palaia, a farmhouse among Chianti vineyards and olive groves. Taste 10 organic Tuscan wines and 10 Italian cheeses, tour the cellar and cheese room, then sit down to a traditional lunch with pasta, olive oil, balsamic vinegar, and fresh ingredients. An English-speaking sommelier, including guide Leonardo on some departures, leads the tasting.

“Wineing and dining in Tuscan province is always something great but Leonardo - the wine master and the owners of the Factoria Palaia make it exceptional. The setting is picturesque, located at the hill, overlooking vineyards and olive gardens. You can dine outside and experience the sunset over the valley.”

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9.Amazing Lunch in organic Farm with Balsamic Vinegar Olive Oil truffle and Wine tasting Experience in Tuscany

★★★★★★★★★★3.0 · 3 reviews · 2 hours (approx.)

Leave central Florence by private minivan with an English-speaking Tuscan driver and visit Tenuta Casanova. Silvano leads you through the wine cellar and old-vinegar room, followed by optional lunch and tastings of Chianti, olive oil, honey, balsamic vinegar, cheese, pasta, and truffle dishes. Lunch and tastings cost €50 per person.

“Very deceiving, does not include lunch. We paid $414 dollars for transportation (45 min drive) alone for 4 people, you are only paying for the driver to wait 3-4 hours. The vineyard itself was great but it was a completely separate transaction.”

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10.Chianti from Florence:PRIVATE Wine, Olive Oil Tasting in the Tuscan countryside

★★★★★★★★★★5.0 · 2 reviews · from $368

You’ll leave Florence at 9:15 a.m. with an English-speaking driver in a Land Rover or premium van, then visit two family-run Chianti wineries. Expect cellar tours, Chianti Classico, olive oil, Vinsanto, grappa, and a home-cooked lunch with wine. Your driver handles the road, while winery sommeliers lead the tastings.

“Booking this was the best decision we made! It was a great way to see Tuscany and the wineries we visited were incredible! Both were small, family run and made us feel right at home. Our driver made the experience so easy for us and we would highly recommend to anyone visiting the Florence area!”

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