Florence to Chianti Wine Experience

6 days

Get to know everything about Tuscany, from the timeless beauty of Florence to the rolling hillsides to the town of Montalcino, and all of the wineries, restaurants and cultural wonders in between with two full days of wine tours into the Chianti vineyards.

Trip Highlights

  • Return flights to Pisa or Florence (hold luggage not included) and private transfers to Florence

  • Relax in a luxury 5 star luxury hotel in the heart of historic Florence and explore the city’s countless world-famous churches, galleries, museums and boutique shops

  • Enjoy a tutored tasting of local wines and canapés at a Enoteca wine gallery in the city centre. This is a great way to orient yourself in the wines of the Tuscan region

  • Embark on two full day’s wine tasting in the vineyards with an expert wine guide visiting four prestigious wine estates and one olive oil producers over the two days. Enjoy traditional Tuscan lunches with perfectly paired wines

  • Enjoys 3 nights in 5 star luxury with panoramic views in the Chianti Hills

  • Meet the makers and learn about the production process and taste their produce; both chianti and brunello wines

  • Visit the medieval town of Montalcino, and the 12th century Romanesque Abbey di Sant’Antimo

from $3,760 per person

This is a guide price based on 2 people travelling together and sharing a room. Flights are included with this package.


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Trip details

Day 1

After arriving by plane into Florence or Pisa International Airports, take a private transfer to your 5 star hotel in the very heart of Florence.  Spend the afternoon unwinding or exploring your surroundings. For the evening, we provide a list of recommended restaurants and would be happy to make a reservation for you.

Day 2

Take the day to explore Florence, a city of timeless beauty and jewel of the Renaissance. Florence is steeped in history, art and architecture – perhaps visit the cathedral or the legendary Uffizi Gallery, or some of the many boutique shops that the city keeps within its walls.  In the evening, enjoy a wine tasting in a typical Enoteca in central Florence, where you will taste a selection of local wines and canapés – the perfect way to orient yourself with the wines of the region and the tastes and terroirs to come.

Day 3

After breakfast, you’ll have the chance to explore some more of Florence’s finest museums, churches and squares before taking a private transfer to your hotel in Chianti in the afternoon. Spend the afternoon relaxing in your 5 star estate in the hills of Chianti with superb panoramic views and then sample the wonderful Tuscan cuisine at the estate’s restaurant.

Day 4

Your local English-speaking wine guide will meet you at the estate after breakfast for a full day wine tasting experience to some of the most prominent wine producers in the region. Sample the best local Chianti wines (amongst other Super Tuscan wines), and, after a tasting lunch, visit the charming village of Castenuovo Beradenga, a local olive oil producer and one more superb wine producer on the southern border of Chianti Classico.

Day 5

Today, visit Montalcino, a medieval town near Siena and home to the Brunello vineyard, which produce the Sangiovese wine of the same name, before enjoying a relaxing wine tasting at a local family estate. After lunch, take a tour around another local winery, meet the family which owns it, and hear about the secrets of Brunello wines. At the end of the day, visit the beautiful Abbey di Sant’Antimo, a Romanesque building constructed in the 12th century.

Day 6

Take the chance to relax in your accommodation – enjoy the pool and the local scenery – before leaving in the late morning for your transfer back to Pisa or Florence airport.

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Recent Google Reviews

SmoothRed planned a truly fabulous trip from Paris through Brittany to Normandy and back to Paris. Every part of the trip was wonderful and seamlessly executed. It was a trip of a lifetime! Without any hesitation or qualifications, we heartily recommend SmoothRed. They customized an extraordinary family trip.

Dorothy Weinstein

Very well organised trip to Tuscany, getting in 2 wine regions. Lovely hotel with amazing view. The best part was our guide Paula who ensured our wine tasting tours were with smaller wineries which have authenticity and care for the environment. Highly recommend SmoothRed!

Warren De Villiers

To Adam & the SmoothRed Team. Our recent trip to Bordeaux and the Medoc/St Emillion has been a wonderful trip & experience. One I would have no hesitation in saying is top class. I would certainly use SmoothRed & their travel associates in future wine tasting trips. The entire group…

Paul Green

SmoothRed did an outstanding job providing chauffeured driven wine tour through Bourgogne and the Rhone valley (France). The multiple vendors they used were all Courteous, Prompt, and very fluent in English. This 7 day trip went without problems. I would highly recommend SmoothRed.

Dan Lepley

We came to Bordeaux for part of our honeymoon and took the First Growth Bordeaux tour. SmoothRed worked with us to curate a trip based on our desires. The 8 Chateaux we visited, the 3 delicious lunches, and the hotel were wonderful, but what set the trip apart was our…

Tibita Kaneene

“Thanks for taking the time and trouble to call. You really have set the standard by which we compare all other companies!! Thank you so much for organising a fantastic itinerary with such an interesting and varied range of stop-overs. We are already starting to think about next year’s trip to France so would welcome any suggestions.”

Hilary Alder

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