Day 1 – Saturday

Private gourmet wine paired dinner at your villa

In the morning rendezvous with your diVino sommelier and chauffeur and transfer to your luxury villa nestled in the quiet Tuscan countryside. Free time to relax and settle in before moving on to a ‘Welcome to Tuscany’ intro to winemaking in Tuscany and aperitivo followed by a private gourmet dinner catered at the villa and paired to an array of DOCG wines from Tuscany.

Day 2 – Sunday

Monte Oliveto Maggiore & Siena by Night

In the morning travel by private chauffeur to the Benedictine abbey of Monte Oliveto Maggiore to see the world famous frescos by Sodoma and listen to the Sunday morning Gregorian chants.

After the mass, return to your villa for a light buffet lunch and free time to rest and relax. In the afternoon we’ll travel to the beautiful gothic masterpiece of Siena for a 2 hour private guided tour with our partnering local art historian guide, who will tell you about the history and unique traditions of Siena including the world famous Palio horse race.

Enjoy free time in the early evening to shop, explore and soak in Siena’s magical atmosphere before we move on to a gourmet dinner at one of the city’s finest restaurants, where we’ll enjoy a tasting menu paired to top class wines.

Day 3 – Monday

Brunello di Montalcino wine tour

In the morning we’ll head to the medieval hill-top city of Montalcino, home to Italy’s most famous wine, Brunello di Montalcino.

We’ll meet the owners of one of Montalcino’s leading estates and tour the vineyards and cellars before enjoying a fabulous private lunch prepared especially for us and accompanied by estate wines. 

After lunch we’ll visit the 9th century Benedictine Abbey of Sant’Antimo followed by a walk through the cobblestone streets of Montalcino and a visit to its 14th century fortress castle.

Return home to your villa with a free evening to relax at the villa with optional transfer to a local restaurant for dinner.

Day 4 – Tuesday

Montepulciano & Pienza

In the morning we’ll depart for the beautiful hill-top town of Montepulciano, enjoying free time to explore and shop.

Then we’ll travel to the quiet village of Montefollonico where we’ll enjoy a light lunch at one of our favorite enotecas where you will sample locally produced pecorino cheeses and other Tuscan delicacies along with a tasting of Vino Nobile wines.

After lunch visit the Renaissance village of Pienza and meet Linda, a local terracotta painter, for a demonstration of hand-painted ceramics in her historic grotto.

Enjoy free time to explore Pienza on your own before returning to the villa.

That evening we’ll travel to the southern border of the Chianti Classico region for a special dinner at enoteca La Vinsantaia, where Andrea will prepare an olive oil tasting followed by a tasting menu paired to olive oils from various areas of Tuscany. We’ll wrap up our meal with a tasting of wonderful artisan chocolates paired to one of the world’s finest (and too often underappreciated) pleasures – grappa.

Day 5 – Wednesday

Free day to explore with your chauffeur

Enjoy a free day to relax at the villa or explore the area with your chauffeur. You might head to Cortona or Arezzo or to the nearby region of Umbria to explore Assisi or Perugia.  In any case your driver will accompany you to the destinations of your choice and wait for you while you explore on your own.

Day 6 - Thursday

Rare farms tour & fresh seafood dinner at the villa

In the morning we’ll travel to the beautiful hills above Siena to visit two of Tuscany’s most unique farms Santa Margherita – a goat cheese farm specializing in wonderful organic cheeses and a Cinta Senese farm producing delicious cured meats from this rare native Tuscan breed of pig.

After touring the farms with the owners we’ll enjoy  a private lunch of farm products paired to locally produced organic wine.

After lunch enjoy an optional stop at one of Tuscany’s most beautiful hill-top villages: San Gimignano. Once home to over 70 stone towers, today its 17 remaining giants mark the horizon with a spectacular medieval skyline. Enjoy free time to shop and explore on your own.

Return home to the villa to rest and relax before enjoying a very special seafood dinner prepared at your villa with the freshest ingredients brought that morning from the seaside to your villa and paired to an array of fantastic Italian white wines.

Day 7 – Friday

Florence

After enjoying a relaxing morning at the villa, we’ll travel to Florence city center  to meet our partnering art historian for a very special private guided walking tour of some of Florence's greatest Renaissance treasures.

After our art and history tour we’ll move on to a local Florentine enoteca for a delicious dinner paired to more of our favorite Italian wines.

Day 8 – Saturday

Departure

AM farewell to your Villa transfer to Florence airport for departure.

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This itinerary can be completely customized to fit the individualized needs of your private group.  Prices for all our luxury private tours vary according to the number of people in your group and final custom itinerary.