Tuscany is the heart of Italian wine tourism. It’s a great idea to start by discovering some of the region’s finest wineries. In Tuscany, the Mediterranean diet comes alive, celebrating fresh, local ingredients in every bite. In this tradition, extra virgin olive oil isn’t a garnish—it’s the foundation. It carries flavor, softens acidity, and deepens every note on the plate.
Freshly pressed, it’s peppery, clings to the tongue, and hums with life. Tuscany knows this best—where olive oil and wine share the spotlight as equals. The groves often stand beside the vines, and the presses hum just meters from the fermenters. For travelers, a single day can take you from barrel to bottle, from branch to bread. If you know where to go, you can taste both worlds in one smooth itinerary.
Enjoy a day in Tuscany where olive oil tours and wine tastings come together in perfect harmony. These premier wineries and carefully selected experiences offer the balance of rich history, authentic flavors, and stunning landscapes—all conveniently bookable through Winera.com. Discover the essence of Tuscany with an itinerary crafted to captivate your senses and deepen your connection to its finest delights.
Here’s how to plan it — with stops you can book directly on Winera.com
Fattoria Casa Sola – Vineyard & Cellar Tour with Olive Oil Tasting
Chianti’s hills are all curves and light, and Casa Sola sits right in their flow. The 90-minute guided walk begins in the vineyards, where the soil is stony underfoot. You step into the olive groves, silver leaves flickering in the breeze. Inside the cellar, barrels line up in perfect symmetry. The guide speaks in simple terms — no lecture, just stories about how wine and oil live side by side.
The tasting is clean and precise: three wines, each with its moment, followed by their extra virgin olive oil. It’s not rushed. You get time to swirl, sniff, and dip bread still warm from the oven. Easy to book online, easier still to enjoy in person.
Castello La Leccia – Chianti Classico Riserva Vertical Tasting & Olive Oil Tour
Castello La Leccia has the quiet authority of a place that’s been doing this for centuries. The tour moves from stone cellars to panoramic gardens. You hear the corks pop as the Chianti Classico Riserva is poured in three different vintages. Each glass is a different snapshot in time. You notice how the tannins soften, how the fruit changes shape, how the structure holds.
Then the shift — a table set for olive oil. Small cups of gold, each one catching the light in a swirl. Sip it straight, and the spice kicks in at the back of your throat. Pair it with cheese, and the creaminess rounds off the bite. It’s all in small groups, which keeps the pace personal.
Podere La Quercia – Wine & Olive Oil Tasting with Light Lunch
Near San Gimignano, the road turns narrow and the air smells of herbs. Podere La Quercia is small, warm, and welcoming. The family walks you through their Vernaccia, Chianti, and a Super Tuscan — each poured with a short explanation, no fluff. The olive oil arrives with slices of country bread, still rough around the edges. Fresh, green, with that grassy lift that tells you it hasn’t sat in a bottle long.
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The light lunch is exactly right: cured meats, pecorino, seasonal vegetables. That is enough to satisfy without slowing you down for the afternoon. Organic methods aren’t advertised here as a trend. They’re just how things have always been done. Book it on Winera, turn up, and let them handle the rest.
Villa Il Pozzo – Boutique Wine & Olive Oil Tasting in the Chianti Hills
Nestled between San Gimignano and Certaldo, Villa Il Pozzo is as much an open-air painting as it is an agriturismo. Vineyards and olive trees roll into the horizon, and the villa itself, a restored 15th-century residence, overlooks landscapes that inspired Renaissance masterpieces. Here, wine and olive oil are treated as two expressions of the same terroir. Your guided visit begins in the olive groves, where centuries-old trees still yield a luminous, peppery extra virgin olive oil with vivid green aromas of artichoke and wild herbs. In the cellar, small-batch wines—crafted with minimal intervention—mirror the elegance of the land.
Tastings are slow and deliberate: Sangiovese with bite, Vernaccia with freshness, and the estate’s silky olive oil drizzled over fettunta. It’s an experience wrapped in quiet luxury, where every pairing feels like a conversation between land, history, and flavor.
Le Vigne di Silvia – Bolgheri Wine & Olive Oil Tour
Bolgheri has a different rhythm. Closer to the coast, the air tastes faintly of salt. Le Vigne di Silvia leans into that freshness. The 90-minute walking tour takes you through both vines and olive groves, pointing out how they work in harmony under the same sun. Sustainability isn’t a brochure word here — they show you how it works, from soil management to harvest timing.
Tastings are focused: three premium wines and the estate’s olive oil. You learn to smell the oil first, noting the green almond, the artichoke, the fresh-cut grass. Book it online, walk into the landscape, and leave knowing more than you expected.
Fattoria Svetoni – Montepulciano in a Glass and on a Plate
In Montepulciano, Svetoni keeps things intimate. The tour winds through the winery, pauses in the cellar, then moves straight to the tasting. Three wines, poured with precision. The Sangiovese here is deep and steady.
Then comes their olive oil — bright, with a snap of pepper on the finish. The contrast with the wine is part of the point; each one makes the other taste sharper, cleaner. The estate’s history runs through the experience without weighing it down. You leave feeling like you’ve been let in on a local secret.
Castello di Meleto – History, Architecture, Taste
Some wineries keep their focus strictly on the glass. Castello di Meleto adds the stones, the rooms, the weight of centuries. The tour starts in the castle itself — high ceilings, faded frescoes, the kind of silence that makes you lower your voice. From there, it’s down to the wine shop.
Three estate wines are poured; each matched with its olive oil. It’s a simple close to a rich visit, and the setting alone would be reason enough to come. Booking through Winera keeps it straightforward.
Tenuta Valdipiatta - Guided Wine Tasting 5 Wines
At Tenuta Valdipiatta, enjoy a guided tasting of five organic wines, each paired with the estate’s rich, organic extra virgin olive oil. Served with slices of traditional Tuscan bread, this 30-minute experience highlights the seamless connection between the region’s wines and its prized olive oil. Perfect for those wanting an authentic, concise taste of Tuscany, all shared with warm hospitality in English or Italian.
Conte Guicciardini Castello Di Poppiano - Tower Tour Poppiano Castle
Start your visit in the Aging & Maturation Cellar to explore the wine aging process, then head to the Olive Oil Mill to learn how the prized Laudemio extra virgin olive oil is crafted. Next, ascend to the Vinsantaia in the Grand Tower, where traditional “caratelli” barrels line the room and panoramic views of the Florentine hills await.
Enjoy a tasting of four carefully selected premium wines paired with Laudemio olive oil, traditional Fettunta bread, local cold cuts, cheeses, Vin Santo, and Cantuccini. Finish your experience with a stop at the wine shop, where you can take home the authentic flavors of Tuscany. The tour lasts about two hours, is available in English and Italian.
Icario - Platinum Tour & Tasting Experience
Experience an elegant winery tour with a guided visit to the modern cellar, followed by a tasting of seven exceptional Tuscan wines, accompanied by premium olive oil, grappa, and local delicacies. From crisp whites and refreshing rosés to rich reds and aged vintages, each sip reveals the depth and character of the region’s finest offerings. Traditional cheeses, olive oil-drizzled bruschetta, and savory cold cuts perfectly complement the tasting, bringing Tuscany’s flavors to life.
Set against breathtaking landscapes, this experience is a celebration of wine and food, inviting you to savor the authentic tastes and heritage of the region. Lasting just under two hours, the tour is available in English and Italian, offering private and public options for groups of 2 to 20 visitors, guided by experts who bring each wine’s story to life.
Why Combine Wine and Olive Oil in Tuscany?
It’s not just about efficiency. Olive oil here is treated with the same reverence as wine—each has its harvest, its press, and a unique flavor profile that shifts with the weather and the seasons. Tasting them side by side reveals the full story. You begin to see how the land shapes both, and how the same soil and climate leave their signature on every drop.
For travelers, this pairing offers a way to get under Tuscany’s skin in a single day. The wines speak of patience and time spent in barrels, while the oils capture the essence of freshness and immediacy. Together, they create a rich, sensory narrative that tells the complete tale of this remarkable region.
How to Plan Your Day
Choose two or three experiences. Begin with a morning tour and tasting, enjoy a light lunch, then try a different style or region in the afternoon. Winera keeps it simple — every experience above has direct booking, and you can lock in times without back-and-forth messages.
And remember: tasting olive oil is an active process. Sip it straight before you dip bread. Let it roll over your tongue. Wait for the pepper to hit the back of your throat. That’s quality talking.
A Sensory Journey Through Vineyards and Olive Groves
Tuscany rewards the curious—those willing to follow winding roads through sun-kissed hills where olive groves meet sprawling vineyards. Take your time to savor what grows here, in every form it takes. Each taste connects you deeper to the land, revealing stories written in soil and sun, captured in every bottle and drop of golden oil.
Don’t just collect bottles—gain the skill to savor them like a true connoisseur. Join this journey and unlock Tuscany’s secrets with every sip and drizzle. Ready to taste the soul of Tuscany? Start planning your perfect day with Winera and let your senses lead the way.
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