Pontassieve is a charming town in Tuscany that offers more than just stunning views and a peaceful vibe. It’s a prime base for exploring some of the region’s best wine and olive oil tours. What makes Pontassieve stand out is its proximity to authentic producers and family-run estates, giving visitors a chance to taste local products straight from the source. One tour we especially like is the Chianti Rufina: Discover the tradition of extra virgin olive oil and organic wines, which combines scenic vineyard visits with the chance to learn about biodynamic winemaking and traditional olive oil production. It’s a hands-on experience that appeals to anyone curious about Tuscany’s culinary staples.
In this guide, we’ve picked two standout tours: one focusing on organic wines and olive oils with a touch of history, and another offering a more casual tasting session with food. Both provide unique insights into Tuscany’s rich agricultural traditions, helping you decide which fits your style and schedule better. Here’s what you need to know.
1. Chianti Rufina: Discover the tradition of extra virgin olive oil and organic wines

At number 1 on our list, this tour offers a guided visit of vineyards and olive groves, with professional tastings of biodynamic wines and extra virgin olive oils. Over three hours, you’ll tour the estate’s historic windmill and hear about the noble Strozzi family’s role in shaping this land’s agricultural heritage. What makes this experience truly stand out is the combination of educational tastings with breathtaking views of the Florentine hills.
You’ll learn how biodynamic farming influences wine quality and how traditional olive oil production methods have been preserved. The guide’s storytelling makes complex topics accessible, and the tasting sessions are led by experts eager to share their passion. This tour is perfect for foodies and anyone interested in sustainable agriculture, offering great value at $51 per person.
Bottom line: This tour blends history, taste, and scenery into an enriching experience that’s ideal for curious travelers wanting a deeper connection with Tuscany’s culinary roots.
2. WINERY AND VINSANTAIA TOUR + TASTING + PLATTER

Next up is the WINERY AND VINSANTAIA TOUR + TASTING + PLATTER, which takes you about 12 km from Florence into a working winery. This shorter, one-hour tour strikes a different chord—more casual but still packed with interesting sights.
It begins with a visit to the winery’s production and aging rooms, where you can see how Veroni wines are made from grape to bottle. The highlight is the guided tasting of Veroni wines and olive oil, paired with a cold cuts and cheese platter. The guide is praised for being well-informed and energetic, making the visit lively and engaging.
While reviews note the tour is a bit brief, the quality of the wine and the food pairing makes it a good choice for those wanting a quick, authentic experience without a hefty time commitment. It’s a great option if you’re looking for local flavors in a friendly setting.
Bottom line: A solid choice for lovers of wine and food who want a relaxed, informative tasting with a personal touch.
How to Choose Between These Tours
When deciding between these options, consider your priorities. If you’re eager to learn about biodynamic wines and traditional olive oil production in a scenic, historical setting, the Chianti Rufina tour offers a comprehensive experience. It’s ideal for travelers who want to deepen their appreciation of Tuscany’s food heritage and enjoy a more immersive outing.
On the other hand, if you prefer a shorter, more relaxed visit with an emphasis on tasting and pairing local wines and cheeses, then the Winery and Vinsantaia Tour may be better suited. It’s perfect for those on a tight schedule or looking for a fun, informal experience.
Both tours are accessible and full of genuine Tuscan flavor. Remember to check availability ahead of time, especially for the shorter tasting options, and consider booking early during peak seasons.
Final Thoughts
Pontassieve offers a delightful mix of wine, olive oil, and scenic beauty, making it an excellent hub for these engaging tours. For travelers interested in deepening their understanding of Tuscany’s culinary traditions, the Chianti Rufina tour stands out with its comprehensive approach and historical insights. If you’re after a quicker, fun tasting experience with food, the Winery and Vinsantaia tour delivers that in a lively, approachable package.
Both options suit different travel styles—whether you want a detailed, educational adventure or a casual, flavorful tasting. Early booking is recommended, especially during the busy season, so you can secure your spot and enjoy a truly authentic taste of Tuscany. No matter which you choose, these tours promise a memorable journey into the heart of Tuscany’s food and wine culture.



