A view of the orange roofs of Florence, with the stunning Cathedral of Santa Maria del Fiore towering over the rest of the city, on a sunny day in Tuscany, Italy.
A road winding through the stunning, lush fields of the Tuscan countryside, decorated with beautiful, pointy cypress trees, heading into the sunset.
The Picturesque, Medieval arched river bridge crossing the Arno in Florence, during sunset in Tuscany, Italy.
The glorious courtyard space outside the Uffizi Gallery, with the arched entry overlooking two people, in Florence, Tuscany, Italy.
The sun breaking through patches of clouds onto the vibrant vineyards of Radda in Chianti, overlooked by the distant estate in Siena, Tuscany, Italy.

Florence to Chianti Wine Experience

5 nights from $6,434pp

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Get to know everything about Tuscany on this Italy tour, 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, on this luxury Chianti wine experience.

Highlights of our Florence to Chianti Wine Experience

  • Return flights to Pisa or Florence with private airport transfers
  • Relax in a luxury five-star luxury hotel in the heart of historic Florence and explore the city’s countless world-famous churches, galleries, museums and boutique shops.
  • An exclusive wine tour and lunch in Tuscany by helicopter
  • Enjoy a tutored tasting of local wines and canapés at Enoteca wine gallery in the city centre. This is a great way to orient yourself in the wines of the Tuscan region.
  • Visit to one of the famous Antinori vineyards and enjoy a memorable Michelin star five-course tasting menu with accompanying wines with each course
  • 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.
  • Enjoy three nights in five-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.
A view of the orange roofs of Florence, with the stunning Cathedral of Santa Maria del Fiore towering over the rest of the city, on a sunny day in Tuscany, Italy.

Day 1: Arrival in Florence

After arriving by plane into Florence or Pisa International Airports, take a private transfer to your five-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.

The glorious courtyard space outside the Uffizi Gallery, with the arched entry overlooking two people, in Florence, Tuscany, Italy.

Day 2: Explore Florence at Leisure Before your Wine Tasting

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.

The foggy, autumnal landscape surrounding the Abbey of Passignano, in Tavarnelle Val di Pesa, Antinori, Tuscany Italy.

Day 3: From Florence to Chianti

After breakfast, you’ll have the chance to explore some more of Florence’s finest museums, churches and squares before taking a private transfer into the heart of Chianti.

Visit one of the famous Antinori vineyards; from ceiling to vault, the old historical wine cellars of the abbey today host approximately 2000 wooden barrels within which the wine is aged. Following the tour, go deep in the late 19th-century cellars of the Marquises of Antinori to enjoy a memorable Michelin star five-course tasting menu with accompanying wines.

Head to your boutique hotel in Chianti in the afternoon. Spend the afternoon relaxing in your estate in the hills of Chianti with superb panoramic views and then sample the wonderful Tuscan cuisine at the estate’s restaurant.

A warmly lit wine cellar filled with oak barrels stacked throughout the room, in Montalcino, Tuscany, Italy.

Day 4: Exclusive Wine Tour in Tuscany, by Helicopter

Enjoy an exclusive wine tour and lunch in Tuscany, by helicopter in Chianti, Montalcino, Florence and the San Gimignano area.

Discover Tuscany taking off from a prestigious winery near San Gimignano, Fly all over our beautiful and colourful countryside, discover the soaring towers of San Gimignano, the old walls of Certaldo, the famous and renowned city of Monteriggioni and in the end, a low pass over Piazza del Campo in Siena.

Land in a stunning winery where the owner will welcome you with a glass of sparkling wine. They will then take you to have a tour of the cellars and the vineyards, explaining the story of the family that produces wine since 1720. You are going to have a wonderful lunch under the gazebo located in the middle of the spiral vineyard. A truly incredible day!

The Abbey of Sant'Antimo peacefully located amongst the Tuscan countryside, before a hill covered by lush greenery, near Montalcino, Siena, Italy.

Day 5: Wine Tasting in Montalcino

Today, visit Montalcino, a medieval town near Siena and home to the Brunello vineyard, which produces 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 who 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.

The Picturesque, Medieval arched river bridge, bursting with life, crossing the Arno in Florence, Tuscany, Italy.

Day 6: Relax on your Final Day in Tuscany

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.

Why not extend this trip visiting Piedmont in the north with a truffle hunt, or head south to the Amalfi and take a private cruise to Capri?

Where You Could Stay in Tuscany

A foggy road winding through the stunning, lush fields of the Tuscan countryside, decorated with beautiful, pointy cypress trees, heading into the sunset in Italy.
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