Private Wine Day in the Chianti Hills from Florence

Enjoy an intimate day trip tasting wine and organic food from local farms and vineyards in Tuscany

4.99 (122) Travel Flexibly 7h Max 8 guests Max 8 Florence, Italy

What You Get With This Tour

  • Unwind with slow-food dining
  • Expert English-speaking driver
  • Private climate-controlled luxury transportation
  • Hotel pickup and drop-off in Florence
  • Guided winery tour and wine tastings
  • Organic farmhouse visit
  • Traditional organic Tuscan lunch with wine
  • Visits to historic Tuscan villages & Castellina in Chianti
  • Free time to explore local villages
  • Private group experience
  • Guide tips

Tour Itinerary

  • 1

    Your tour begins at your Florence accommodation

    Your tour begins with direct pickup at your Florence accommodation, where your private driver welcomes you aboard a climate-controlled vehicle. As you leave the urban streets behind, roll past silver olive groves and gentle vineyard slopes into the heart of rural Tuscany.
  • 2

    Explore historic Castellina in Chianti

    Next, stop in Castellina in Chianti, a fortified village with origins stretching back to Etruscan and Bronze Age settlements. Walk the ancient cobblestone streets, admire medieval architecture, and soak in sweeping vistas over the surrounding valleys where winemaking traditions have thrived for centuries.
  • 3

    Taste oil and wine at an organic farmhouse

    Then, arrive at an operating Chianti farmhouse to meet local producers and tour the property. Taste cold-pressed extra-virgin olive oil alongside small-batch wines, gaining insight into biodynamic agriculture and the family passion behind every bottle produced on the estate.
  • 4

    Indulge in an organic Tuscan lunch

    Afterward, sit down for an authentic multi-course lunch adhering to Italian slow-food traditions. Savor dishes prepared from fresh, farm-grown ingredients, perfectly paired with regional vintages. Take your time enjoying every bite while surrounded by iconic Tuscan countryside views.
  • 5

    Discover a tranquil medieval village

    Next, visit a quiet village in the Chianti hills where time seems to have stood still for centuries. Enjoy free time to wander narrow stone alleyways, discover artisan shops, and capture photographs of romantic arches and stone towers untouched by modern development.
  • 6

    Compare vintages at a second vineyard

    Then, head to a second estate to experience a contrasting approach to winemaking. Guided by a wine expert, you will tour the production facilities, learn how terroir shapes Sangiovese grapes, and sample a distinct selection of estate vintages to compare flavors with your earlier tasting.
  • 7

    Your tour ends with a return journey to Florence

    Your tour finishes with smooth, door-to-door transportation back to your Florence accommodation. Sit back and unwind after a full day of countryside exploration, taking home fond memories and an enhanced appreciation for authentic Tuscan food and wine culture.

Additional Information

Discover what to expect, what’s included, and everything you need to know before booking.

Good to know:

  • Accessibility: As this is a private tour, the itinerary can be accommodated to be wheelchair or mobility accessible. Please contact us to make the proper arrangements.

  • Please note: The itinerary of a private tour can be adjusted to your needs. Please reach out if you do not see a start time that fits for your party. We would be happy to check with our ticketing team to see if we can accommodate you.

  • Dietary Restrictions: Please contact us with any special dietary restrictions or allergies, so we can do our best to accommodate you.

  • Alcohol Consumption: This tour includes local wine; participants consuming alcohol should be of legal drinking age in Italy (18). Please bring a government-issued ID if you plan to partake.

  • Check-in: Arrive 15 minutes early for check-in at the meeting point so the group can enter sites on time.

Your tour includes:

  • Expert English-speaking driver

  • Private climate-controlled luxury transportation

  • Door-to-door hotel pickup and drop-off in Florence

  • Guided winery tour and wine tastings

  • Organic farmhouse visit

  • Traditional organic Tuscan lunch with wine

  • Visits to historic Tuscan villages and Castellina in Chianti

  • Free time to explore local villages

  • Private group experience

What to bring:

  • Government-issued ID

  • Comfortable walking shoes

  • Camera

  • Water bottle

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Customer Reviews

4.99 (122)
Leave a review
Outstanding!
Aaron M., 09 May 2026

Booked this for my wife who loves the wine, we both thoroughly enjoyed the experience. Mike, our driver, was amazing. Our first stop seemed very special in today’s world. Loved our tour.

Clifford M., 22 April 2026

Great drive into Tuscany and fantastic lunch at the Casanova winery. Marlon our driver was top notch and very accommodating. The first stop for lunch was at the Casanova family farm and winery. Interesting to learn the process to make Balsamic vinegar. The winery also has great wine, truffles, honey, lavender all from the farm. Hospitality at the farm is more than you can wish for. Highly recommend this tour.

So Many Tastes
Samantha N., 04 November 2025

Tried more wines than I expected! From red to white, each one had its own story. Left with a new favorite variety.​

Calm
Erik J., 01 November 2025

This tour had no rush at all. Just easy travel, beautiful scenery, and great company. Felt like a full day of peace.

Advait P., 01 November 2025

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Frequently Asked Questions

What if I want to see Tuscany, but I don't like wine?

If you're not interested in a wine-focused day trip from Florence, feel free to contact us so we can make alternate plans for your travel to the countryside.

I'd love to go on this tour, but it's kind of last minute. What should I do?

If you would like to do this tour, but it is less than two weeks away, please contact us and we will do our best to accommodate you. You can either drop us an email or call us at +1 888 290 5595.

Is a guide included on this day trip?

No, but a personal, private driver is included for the entire day. You will also meet locals and wine producers at the winery stops.

Is lunch and wine included in the price of this day trip?

Yes, absolutely. It's all included in the total price.

What if I have dietary restrictions or allergies?

Please contact us in advance with any dietary restrictions or allergies and we will do our best to accommodate you.

Is this tour family friendly?

As this is a private tour, we can adjust it to your specifications. Younger crowd? Contact us and we can work out an itinerary that best suits your party.

Start From: $1,359.60

Available days Discounted days

Free cancellation up to 7 days in advance!