100% Tuscany! Chianti, Pinot & Supertuscan Wine Tour

Traveling through Tuscany offers a tapestry of scenic vineyards, charming medieval towns, and world-class wines. This private day tour from Florence promises an immersive experience, combining cultural sights with exquisite tastings, all wrapped up in the region’s unbeatable landscape. While this tour is geared towards wine enthusiasts and culture lovers alike, it’s also a fantastic way for travelers to relax and enjoy Tuscany’s most iconic sights in one day.

What we love about this experience? First, the personalized nature of a private tour means you get a tailored visit, with plenty of opportunities to ask questions and soak in the scenery at your own pace. Second, the combination of scenic stops, wine tastings, and delicious Tuscan lunch makes for a well-rounded, memorable day.

One potential consideration is the long driving stretches—the tour involves some transfers (up to 80 minutes), which might be tiring for those who prefer more walking or less time in transit. Still, for those eager to explore Tuscany’s highlights efficiently, this tour offers excellent value.

This experience suits wine lovers, history buffs, and anyone wanting to see the Tuscan countryside without the hassle of planning multiple visits. It’s ideal for travelers who appreciate comfort, cultural insights, and authentic tastings all in one day.

Contents hide

1 A Detailed Look at the Tour Experience

2 What’s Included and What’s Not

3 Why You Should Consider This Tour

4 The Sum Up

5 FAQ

Key Points

Private group for personalized attention and flexible scheduling
Visit San Gimignano, with time to climb the iconic Great Tower and sample gelato from the world’s champion gelato shop
Two carefully selected wineries offering different styles of wine and comprehensive tastings
Stop in Certaldo, a charming medieval town, with a walk through its historic streets
Includes a full Tuscan lunch with regional specialties and olive oil tasting
Enjoy scenic photo stops along the rolling vineyards and countryside

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A Detailed Look at the Tour Experience

You can also read our reviews of more tours and experiences in Florence.

The Morning: San Gimignano and Its Medieval Charm

The day kicks off with an early pickup from one of several convenient Florence locations. After a roughly 80-minute drive, you’ll arrive at San Gimignano, a town famous for its medieval towers that punctuate the skyline. Here, you’ll have about 90 minutes to explore—plenty of time to wander the narrow streets, marvel at the well-preserved architecture, and climb the Great Tower for panoramic views of the Tuscan hills. Many visitors find this view simply breathtaking, offering perfect photo opportunities.

A highlight at this stop is the chance to taste gelato from the World Champion Gelato shop. We’ve read reviews that emphasize how memorable this treat is, especially after a walk through the ancient town. The atmosphere of San Gimignano, with its blend of history and lively piazzas, makes it a perfect introduction to Tuscany’s charm.

The Winery Visits: From Vineyards to Tasting Tables

Post San Gimignano, the tour continues with a visit to a beautiful winery. Here, you’ll enjoy a full wine tour, gaining insight into winemaking in Tuscany. Expect guided explanations of traditional and modern techniques, and of course, tastings of some of Tuscany’s most renowned wines, including Chianti, Pinot, and Supertuscan varieties.

The inclusion of lunch and olive oil tasting at the winery enhances the experience. The meal typically features regional dishes, allowing you to savor authentic flavors while pairing with local wines. Several reviews highlight that the quality of the food and wine is exceptional, offering excellent value for the price. The atmosphere is often described as warm and welcoming, with knowledgeable staff eager to share their passion.

In the afternoon, you’ll head to a second winery, which provides a different perspective on Tuscan winemaking. This variety helps illustrate the diversity of styles and terroirs, making the tasting experience richer and more educational.

The Afternoon: Certaldo and Additional Sights

After the second winery, the journey takes you to Certaldo, a charming medieval town that many travelers adore. Its winding streets and historical sites make it a pleasant stop for about an hour. You might find the walk through the town’s monotrail a unique way to experience its ambiance.

Some reviews mention that the hike through the monotrail offers lovely views and a chance to stretch your legs after the morning’s vineyards. It’s a brief but worthwhile visit that adds a touch of local flavor to the day.

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Practical Details: Transportation and Group Size

The tour is conducted in a private van, ensuring comfort and flexibility. An English-speaking driver guides you through the day, sharing insights about the region, its history, and its wines. This personal touch is often praised for making the experience more engaging.

With a total duration of 8.5 hours, this tour balances sightseeing and tasting without feeling rushed. The flexible pickup locations in Florence and nearby towns make it easy to join.

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What’s Included and What’s Not

Included are pickup and drop-off at your accommodation, transportation with a driver, visits to San Gimignano and Certaldo, plus the full wine tasting experience with lunch and olive oil tasting. The only notable extra is the ticket to the funicular in Certaldo, which is not included.

The tour offers full flexibility with the option to cancel up to 24 hours in advance, and the ability to reserve now and pay later helps travelers stay adaptable.

Why You Should Consider This Tour

What sets this experience apart is the combination of cultural exploration and wine tasting, all delivered in a private setting that feels personalized. The expert guides and stunning views of the Tuscan countryside make this a well-rounded introduction to Tuscany’s best attributes.

For those who want to see more than just a winery and prefer a day that blends history, food, and wine, this tour hits the mark. The delicious lunch and olive oil tastings, along with the scenic stops, make it a full sensory experience.

While the long drives might not appeal to everyone, most travelers find the comfort of a private vehicle and the variety of stops make the journey worthwhile. If you’re eager for a comprehensive, relaxed, yet enriching day, this tour offers exceptional value.

The Sum Up

For travelers seeking a personalized, immersive experience of Tuscany, this Chianti and wine tour ticks many boxes. It combines historic towns, scenic vistas, and authentic wine and food tastings into a well-paced day. The private group setup ensures personalized attention, while the variety of stops keeps the day interesting and diverse.

If you prefer a balanced mix of culture, nature, and gastronomy, this tour is a great choice. It’s especially suited for those who appreciate guided insights without the rush of large group tours. The inclusion of local wines, regional cuisine, and scenic views makes it a memorable way to savor Tuscany’s essence in just one day.

For travelers who want to learn about Tuscany’s winemaking traditions, enjoy magnificent landscapes, and experience charming towns without worrying about logistics, this tour offers excellent value and a chance to create lasting memories.

FAQ

What is the duration of the tour?
The tour lasts approximately 8.5 hours, including all visits, tastings, and travel time.

Where does the tour pick me up?
Pickup is available at multiple locations, including Florence, San Donato, San Casciano, Prato, Bagno A Ripoli, Tavarnelle Val di Pesa, and Pistoia.

Is this a private tour?
Yes, it’s conducted as a private group, offering a more personalized experience.

Are the tastings included?
Yes, the tour includes wine tastings at two different wineries, plus olive oil tasting, and a full Tuscan lunch.

What can I expect at San Gimignano?
You’ll have about 90 minutes to explore the medieval town, climb the Great Tower, and enjoy a tasting of world-champion gelato.

Is transportation comfortable?
Yes, the tour uses a private van with an English-speaking driver, providing a comfortable ride throughout the day.

Can I cancel if my plans change?
Absolutely, you can cancel up to 24 hours in advance for a full refund.

Are there any additional costs?
Tickets for the funicular in Certaldo are not included, and you might wish to purchase them separately.

This comprehensive, well-structured tour offers a genuine taste of Tuscany, blending scenery, history, and tradition into one memorable day. Whether you’re a wine enthusiast or simply want to soak in the region’s timeless charm, it’s a journey worth considering.