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

If you’re looking to experience Tuscany’s famed wines and olive oils without the hassle of planning, this private tour from Florence is a fantastic choice. For around six to seven hours, you’ll travel through the scenic Chianti countryside in a comfortable, air-conditioned vehicle, visiting two intimate, family-run wineries. Expect guided tastings of Chianti Classico, a delicious Tuscan lunch paired with local wines, and plenty of time to soak in the rolling hills dotted with olive groves and vineyards.

Two things really stand out about this experience: First, the personalized nature of a private tour means you won’t be sharing your experience with strangers — just your group. Second, the quality of the visits, with charming family wineries providing authentic insights and tastings, makes this a memorable way to connect with the region’s culinary roots.

One potential consideration is that, since transportation is provided by a driver who is not a guide, you might want to pay close attention to the guided commentary in the cellars. Also, the tour’s price is higher than some group options; however, the private setting and the quality of visits and meals justify this for many travelers.

This tour suits wine lovers, foodies, and those seeking a relaxed yet immersive day in Tuscany’s countryside. If you value intimate visits, excellent local wines, and authentic Tuscan hospitality, you’ll find this tour a rewarding choice.

Key Points

• Private transportation ensures a relaxed, personalized experience.
• Authentic visits to family-run wineries provide genuine insights.
• All tastings and lunch are included, offering great value.
• Scenic countryside views make for stunning photo opportunities.
• Flexible itinerary with enough time to enjoy each stop.
• Ideal for wine and food lovers wanting an authentic Tuscan experience.

Exploring Tuscany’s Wine and Olive Oil: A Close-Up

When we set out on this Chianti from Florence tour, we knew we were in for a treat. But what we didn’t expect was just how intimate and authentic the experience would feel. For a price of about $368 per person, you get a full day of exploring, tasting, and savoring in the heart of Tuscany — a price that reflects both the quality of what’s offered and the exclusivity of the private setting.

This tour lasts roughly 6 to 7 hours, making it perfect for a day trip. Departing at 9:15 am from Florence, you’re whisked away in a luxury vehicle, which means no worries about navigating or designating a driver. The comfort of your air-conditioned transport is a small detail that makes the entire day more enjoyable, especially as you wind through the rolling hills.

First Stop: Castellina In Chianti

Your adventure begins around 10:30 am with a visit to a small, family-owned winery in the heart of Chianti Classico. This is where the true charm of the region shines through. The family-run operation welcomes you warmly, guiding you through their vineyards, cellars, and olive groves. Here, you’ll sample Chianti Classico vintages, Vinsanto, and Grappa, along with fresh local snacks.

What we loved here was the personal touch — your host family’s pride comes through in their stories and the care they put into their wines and olive oils. The intimate setting makes it easy to ask questions and really understand what makes Tuscan wine so special.

Second Stop: A Family-Owned Winery with a Terraced View

Next, around 12:45 pm, you’ll visit a second winery still in the Chianti region. This family welcomes you onto their terrace, offering sweeping views of the vineyard landscape. Here, your group will enjoy a home-cooked Tuscan lunch, expertly paired with their wines, including a deeper look into food and wine pairing that highlights local flavors.

This meal is more than just a tasting — it’s a true cultural experience, where each dish showcases regional ingredients and traditional recipes. The family’s warmth and hospitality shine through, making the meal feel like a gathering among friends.

Return to Florence

After a leisurely lunch and some free time to enjoy the scenery or shop for local products, you’ll head back to Florence around 3:30 to 4:00 pm. The return journey is relaxed, leaving you full of delicious memories and perhaps a few bottles to bring home.

Deep Dive into the Experience

Transportation & Comfort
The use of a luxury Land Rover or Premium Van ensures a smooth ride through Tuscany’s often winding roads. For travelers wary of large groups, the private nature of this tour means your group gets undivided attention, creating a relaxed atmosphere ideal for conversations and personal questions.

Itinerary and Timing
The tour’s schedule is thoughtfully designed: a morning begins with a visit to a boutique winery, followed by a late-morning stop, and then a hearty Tuscan lunch. Each stop is long enough to explore deeply but not so long that you feel fatigued. The two wine tastings included are ample for tasting the region’s diversity without feeling overwhelmed.

Authentic Wineries
The emphasis on family-run wineries is a major plus — these are places where wine and olive oil production is a labor of love, not just a commercial enterprise. You’ll meet the families and learn about their methods, which adds a layer of authenticity that larger, commercial wineries often lack.

Food and Wine Pairing
The included lunch isn’t just a snack — it’s a full 3-course meal with local ingredients, paired with the winery’s wines. This is a great opportunity to understand how Tuscan wines complement regional dishes, which can be a revelation for those new to food and wine pairings.

Reviews and Feedback
One guest in September 2023 called it “the best decision we made,” highlighting the small, family-run wineries and the feeling of being “right at home.” They also praised the driver’s professionalism and ease, which underscores how stress-free the day is. The fact that all the key items — tastings, lunch, and transportation — are included enhances the value, making it a hassle-free experience.

Practical Tips for Travelers

• Dress comfortably and bring layers — the countryside can be cooler in the morning and warmer in the afternoon.
• Bring a small notebook or camera to capture the stunning vistas and tasting notes.
• Remember that this is a private tour, so it’s ideal for couples, families, or small groups wanting an intimate experience.
• The tour is accessible for most travelers, with no strenuous physical activity required.
• If you’re a wine enthusiast, you’ll appreciate the variety of Chianti vintages and olive oils sampled here.

Who Will Love This Tour?

This experience is perfect for anyone who wants a personalized, in-depth look at Tuscan wine and olive oil production without the crowds. It’s especially suited for food and wine lovers seeking authentic, family-run establishments. If you’re looking to learn how regional wines are made and taste them in a relaxed setting, this tour hits the mark.

It’s also a good fit for travelers who prefer comfort and convenience over DIY planning — the included transportation, tastings, and lunch make it a seamless, enjoyable day.

Frequently Asked Questions

How long does the tour last?
The tour lasts approximately 6 to 7 hours, starting at 9:15 am and returning around 3:30-4:00 pm.

What’s included in the price?
All wine and olive oil tastings, a 3-course lunch, private transportation, and an English-speaking driver are included.

Is the tour suitable for vegetarians or gluten-free guests?
While the description focuses on local Tuscan food, it’s best to contact the tour provider directly regarding special dietary needs, as the main meal is a traditional Tuscan lunch.

Do I need to bring my own drinks?
No, all tastings and beverages are included in the price, so you can relax and enjoy without worry.

What is the meeting point?
The tour starts at Cantinetta Antinori in Florence, at Piazza degli Antinori, 3.

Can children participate?
Most travelers can participate, and service animals are allowed. It’s suitable for those who enjoy wine and scenery.

How many people are in each group?
Since it’s a private tour, only your group will participate — perfect for a personalized experience.

What if I want to cancel?
You can cancel free of charge up to 24 hours before the tour, receiving a full refund.

Final Thoughts

If you’re after an authentic, relaxed, and immersive way to explore Tuscany’s wine and olive oil heritage, this private Chianti tour offers undeniable value. The combination of family-run wineries, delicious regional cuisine, and scenic landscapes creates a memorable experience that you’ll carry with you long after returning home. It’s a wonderful fit for foodies, wine enthusiasts, or anyone wanting a gentle, personal insight into Tuscany’s rural charm.

While the price may seem steep, the intimacy and quality of visits, combined with all-inclusive tastings and meals, make this a worthwhile investment for those who want to truly connect with the region’s culinary soul. If you’re looking for a day that combines comfort, authenticity, and a touch of Tuscan magic, this tour deserves serious consideration.