The villages and art cities of Chianti

6 days

from 3.300 euro


An exclusive itinerary in the heart of Tuscany to discover Chianti through art, nature, and traditions. The 6-day stay at the prestigious Como Castello del Nero combines the charm of a historic residence with the wellness of an excellent spa.

The journey begins in Siena, a city of medieval art, with its Gothic cathedral and Piazza del Campo, followed by a stop in the fortified village of Monteriggioni. It continues through the iconic villages of Chianti—Greve, Radda, Gaiole, and Castellina—surrounded by vineyards and olive groves, with a stop at a winery to taste the region's renowned wines.

The fourth day is dedicated to relaxation: rejuvenating treatments at the Como Shambhala Retreat or a visit to San Gimignano, a UNESCO World Heritage Site, with its medieval towers and 14th-century frescoes.

The experience culminates with a day on a farm: truffle hunting guided by expert truffle hunters, a cooking class on fresh pasta, and a typical lunch overlooking the olive groves, to experience the most authentic Tuscany through its flavours.

A tour that combines luxury and tradition, perfect for those who want to experience the soul of Chianti with exclusive comfort and unforgettable moments.

Tour itinerary

Day 1, arrival in Tuscany

Travel to Como Castello del Nero during the day.

Arrival at the hotel and free time to enjoy the facilities.

Overnight stay.

Day 2, the art cities of Chianti

After breakfast, head to Siena, where time seems to have stood still in the heart of the Middle Ages. Strolling through charming alleys and red brick buildings, you will find yourself in front of the magnificent Duomo, one of the finest examples of Gothic architecture in Italy, enriched with works by Michelangelo, Donatello, and Pinturicchio and featuring an incredible marble mosaic floor (uncovered according to the calendar).

The tour continues to the unmistakable Piazza del Campo, dominated by the Torre del Mangia, with its shell shape and unique atmosphere, the setting for the famous Palio.

Here you will discover the fascinating history of the seventeen districts of Siena. On the way back, we suggest a stop in the village of Monteriggioni, which welcomes you with its imposing, perfectly preserved medieval walls.

Walking along the walls, you can admire panoramic views of the Sienese hills. In the village, among cobbled alleys and atmospheres of times gone by, you can visit the main square and the armor museum, breathing in the history of an authentic Tuscan fortress.

Return to the hotel for overnight stay.

Day 3, the villages of Chianti

Starting from Castello del Nero, today we suggest a tour in the heart of Chianti, along scenic roads that wind through neat vineyards, centuries-old olive groves, and villages rich in history.

The first stop is Greve in Chianti, with its characteristic porticoed square and artisan shops where you can discover typical products and quality wines. Continuing towards Radda in Chianti, an ancient, fortified town, you will immerse yourself in an authentic atmosphere, strolling among medieval walls and picturesque views of the Tuscan countryside.

The journey continues to Gaiole in Chianti, renowned for its historic wineries, perfect for learning more about the local winemaking tradition.

The last stop is Castellina in Chianti, dominated by an imposing fortress and crossed by the picturesque Via delle Volte, a covered walkway carved out of the ancient walls.

As we are in the heart of the Chianti Classico area, a stop at a winery is a must: here you can taste some of the region's excellent wines. The return to Castello del Nero offers a final view of the rolling hills of Chianti.

Overnight stay.

Day 4, relaxation at the castle

Today, you will have free time to rejuvenate your body and spirit in the hotel's spacious spa or participate in a yoga class.

The COMO Shambhala Retreat is an elegant wellness sanctuary in the heart of Tuscany that pampers its guests with personalized massages, revitalizing wellness experiences, and a 25-meter heated outdoor pool (open only during the summer season), surrounded by the enchanting landscape of the Tuscan hills.

If you wish to continue exploring the region, we recommend visiting nearby San Gimignano, a UNESCO site located a short distance from Siena and a well-preserved example of a fortified medieval town. An independent visit allows you to explore the historic center, characterized by 13th- and 14th-century towers that define the urban skyline. Of particular note are the Collegiate Church of Santa Maria Assunta, with cycles of frescoes from the Sienese school, and the Palazzo Comunale, home to the Pinacoteca and access to the 54-meter-high Torre Grossa.

Overnight stay at the hotel.

Day 5, Tuscan cuisine

Enjoy an authentic Tuscan experience on a characteristic organic farm in close contact with nature, actively participating for about an hour and a half in the search for the prized “black gold,” the truffle, accompanied by expert truffle hunters and their trusty four-legged friends who will reveal the secrets of this ancient tradition rooted for centuries in the Tuscan territory.

Mid-morning, you will return to the farm, where you will prepare fresh pasta on a beautiful panoramic terrace. The experience ends with a typical lunch served on the terrace, overlooking a picturesque olive grove, where you can savor the fruits of your morning's labor in a relaxing and authentic atmosphere.

The afternoon is free for you to relax at your hotel or continue exploring the villages of Tuscany.

Day 6, return

After breakfast, we will begin our journey back to our places of origin.


Travel info

The price includes:

- 5 nights' accommodation with breakfast at Como Castello del Nero

- Private guided tour (approx. 2 hours) of Siena's historic center, including admission to the Duomo on day 2

- Visit to a Chianti winery with wine tasting on day 3

- Truffle hunting followed by a cooking class on a Tuscan farm on day 5ù

The price does not include:

- Transportation to and from your place of origin

- Medical/luggage insurance

- Tourist tax

- Lunches and dinners, unless otherwise indicated under “the price includes”

- Beverages with meals

- Anything not expressly mentioned under “the price includes”


Retreats combined with the tour
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