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Tuscany & Umbria for the Connoisseurs

Verdant vineyards, rolling hills, olive groves and medieval hill towns provide the setting for "La Bella Vita". Explore Tuscany & Umbria with us on a true connoisseur's journey to experience authentic wine pursuits, enjoy some of the finest cuisines and visit astonishing UNESCO sites. 


Stay in charming boutique hotels surrounded by vines and olive groves

Visits to some of the best wineries in Tuscany & Umbria

Insiders experiences with a local angle

Savour Michelin-dining experiences



We leave Rome today for a scenic drive to the colorful and seaport town of Porto Santo Stefano for your first glimpse of "Tuscany by the Sea". From a local's perspective, we talk a walk through the town famous for fine fish restaurants, wonderful olive oil, luxury yachts and a very laid-back atmosphere. Witness the unloading of fresh fish at the busy port area where we will also notice the Mediterranean Aquarium of Argentario where it begins the path of the promenade designed by Giorgetto Giugiuaro. Consider a walk up the picturesque alleys and stairways of the historic center to reach the old 17th Century Spanish Fortress, in a commanding position overlooking the town and offering panoramic views. 

We then continue on the coastal road witnessing the shimmering Tuscan coast seeing remnants of several medieval towers built during the Spanish domination. Eventually, we make a stop in the fishing village of Talamone where enjoy the company of local fisherman, Paolo Fanciulli on his fishing boat to gain insights into the traditions of fishing on a "Pescatourism" mission, advocating sustainable fishing and an inviting seafood lunch onboard his boat. Thereafter, a short drive arrives us at the stunning setting of L'Andana where we spend 2 beautiful nights. 

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Overnight: L'Andana, Castiglione della Pescaia

Meals: Seafood Lunch


A magnificent day starts with an introduction of the seaside town of Castiglione della Pescaia, overlooking the Tyrrhenian Sea, features some of the most beautiful sand beaches of Tuscany. On a walk, discover the ancient medieval fortress that originally belonged to Pisa, then to Aragon, and to Siena. Thereafter, a scenic coastal drive leads us inland before arriving at the stunning architectural beauty of the 300 hectares Petra Winery, founded in 1997 by Vittorio Moretti and his daughter Francesca. The winery, which sits 150m deep in the ground with a tunnel-like wine cellar, as well as the vineyard, were designed by the famous Swiss architect Mario Botta, who built the San Francisco Museum of Modern Art. Enjoy a interactive tour of the facilities and a tasting flight of its signature super Tuscan wines. 

Next, head on to the city of Vetulonia, once an important Etruscan city that was rediscovered in the 1800s in an archaeological research. Enjoy an immersive visit of the ancient necropolis, one of the largest and most well-known burial grounds dating back to the 7th Century BC. Our day then ends with a visit to the incredible Le Mortelle winery, belonging to the Antinori family. Be impressed by its striking design that blends perfectly into the surroundings underground, in efforts to reduce the impact on the environment to a bare minimum, built using natural materials, harnessing the heat regulation of the rock deep down in the ground. The underground cylindrical-shaped building is on three levels: inside, all the various winemaking stages take place, from the arrival of the grapes to winemaking, storage and ageing in barriques in the cellar. 

We then return back to L'Andana where this evening, enjoy a degustation dinner in the Michelin starred La Trattoria Enrico Bartolini, a stylish gourmet restaurant dedicated to the most authentic local Maremma cuisine, interpreted creatively and delicately for an impression of Tuscany by the sea. 

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Overnight: L'Andana, Castiglione della Pescaia

Meals: Breakfast & Michelin Dinner


We leave L'Andana today for a scenic drive inland to the fairytale hill-perched town of Pitigliano, one of the most beautiful villages in Italy sitting atop high walls of volcanic tuff. Known as "Little Jerusalem" for its quaint narrow streets, the Jewish Ghetto and Synagogue. There has been a “Hebrew quarter” for more than half a millennia, and there is still a synagogue, kosher shops and traditions intact. Thereafter, continue to the impressionable town of Sorano, adorned with lovely cobbled streets, winding alleys and steep staircases leading from the hilltop. The Medieval old town of Sorano was first established as an Etruscan centre in the middle of the “Tuff land” spreading at the foot of the 14th century Orsini Castle, one of the largest military constructions built in that period. 

From here, our drive takes us temporarily out of Tuscany and into the domains of Umbria where we arrive at the impeccable Borgo dei Conti Resort, in the green and rolling countryside of Perugia where you will spend the next 2 nights in this refurbished ancient medieval fortress and retreat. 

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Overnight: Borgo dei Conti Resort, Montepetriolo

Meals: Breakfast 


Start the day with a visit to the picturesque Umbrian town of Todi, which is exemplified by its encircling three concentric rings of walls, which provide evidence of the town's size in the Umbrian-Roman, Roman and medieval periods respectively. Todi's lofty position and solid defense system saved it from destruction during the barbarian invasions, and it was able to live in relative peace during the turbulent early Middle Ages. Our day then continues nearby to the ancient fortified art town of Spoleto, originally a Roman colony before it was taken over by Theodoric, king of the Visigoths, and then by the Byzantine Belisarius. Marvel at its medieval atmosphere which has remained largely unchanged and inspiring the annual celebration of art, music and theater. 

We continue next into the domains of Montefalco, long renowned for its astonishing and signature Sagrantino wines, a strong contender rivaling Tuscany's Chianti and Brunello wines for its bold and dry flavors. We visit the Cantina Le Cimate, born in 2011 and situated on a splendid hill top with a 360 degree panorama view of on one side the Monti Martani mountains and on the other side the city of Montefalco. Enjoy a authentic insight into the Sagrantino wine production and the story behind the Bartoloni family that has specialized in agriculture since the 1800 before culminating in an exceptional tasting flight of its wines. 

Our final visit of the day is the hilltop town of Assisi, designated a UNESCO World Heritage site. Famed as the birthplace of Italy's catholic patron saint, St Francis of Assisi, the sleepy town documents the highs and lows of his life. Embark on a walking tour to uncover the life of St Francis as well as his follower, St Clare. Visit the Convent of Santa Chiara, the Basilica di San Francesco as well as the Piazza del Commune with its turreted palace - Palazzo del Capitano del Popolo and the Roman Temple of Minerva.

Overnight: Borgo dei Conti Resort, Montepetriolo

Meals: Breakfast 

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We leave the Borgo dei Conti with a drive back into Tuscan territory to the hilltop village of Montepulciano, probably the most beautiful medieval town in Tuscany with elegant Renaissance palaces, ancient churches, charming squares, hidden alleys and exceptional panoramas of the Val d'Orcia. Thereafter, we visit the Salcheto Estate, a modern contrast to the rustic Tuscan estates. Visit the vines and cellar and sample the exquisite Vino Nobile Riserva. Thereafter, a short distance away is the UNESCO World Heritage-listed town of Pienza, in the heart of the prized Val d'Orcia of Tuscany. Pienza is an architectural jewel as well as a formidable resource for local gastronomic products, particularly sold both fresh and seasoned. In the fifteenth century Pienza was a small fortified town on top of a hill, without distinction and with certain economic problems, until Pope Pius II (Enea Silvio Piccolomini - 1458) decided to turn Pienza into an ideal Renaissance city. 

We then enter into the domains of Montalcino in the rustic heart of the Val d'Orcia, completely encircled by fortified walls and its dominating fortress, providing the allure of probably the most beautiful hilltop Tuscan town surrounded by rolling vineyards, olive groves and cypress trees. Make a visit to the 12th Century Abbey of Sant'Antimo, a beautiful and evocative abbey where legend has it that the abbey was founded by Charlemagne a/k/a Charles the Great in 781. The king and his army stopped here on the way back from Rome as the soldiers were afflicted by an unknown pestilence. An angel appeared to Charlemagne, telling him to make his men drink an infusion with a local herb. The cure worked and the army was saved so the king decided to build the church in gratitude. Finally, a short drive away arrives us in the legendary Castello Banfi with its revered winery and an impeccable Tuscan style accommodation where we spend the next 2 nights. 

Overnight: Castello Banfi II Borgo, Montalcino

Meals: Breakfast 

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Enjoy a mid-journey break with a well-deserved enjoyment at Castello Banfi. No experience of Tuscany is complete without a dedicated tour of the Castello Banfi estate where you will be accompanied on a path that will start with a walk through the vineyards to continue in the cellar and end by visiting the Balsameria, where you get to witness the balsamic vinegar ageing cellar, and continue with a walk through the vineyards and a visit to the winery. After the tour, you will enjoy a tasting of four special vintages of Castello Banfi's most representative wines followed by a 5-course wine pairing lunch at its Tuscan restaurant “La Taverna”.

Overnight: Castello Banfi II Borgo, Montalcino

Meals: Breakfast & Lunch



Leave Castello Banfi today as we journey on to Siena with its UNESCO-listed old town. Join a walking tour beginning with the Piazza del Campo, regarded as the most beautiful square in Europe. Explore the historic areas as you see the Palazzo Tolomei, Basilica of San Domenico and the spectacular Siena Duomo - an opportunity to admire the works of Donatello, Bernini and Michaelangelo. 

Thereafter, we continue to the UNESCO World Heritage-listed San Gimignano. Join a walking tour beginning with a walk down the "Via Francigena" strip to learn about the ancient pilgrimage route of the Christians travelling from Italy to England. Admire the medieval architecture  and charming monuments in Piazza del Duomo and as you walk, learn about San Gimignano's fascination for saffron!

Finally, we retreat to the stunning COMO Castello del Nero in Tavarnelle Val di Pesa, a stunning 12th Century restored castle in the heart of the Chianti wine region sitting over 300 hectares of rolling vineyards and lush olive groves where we spend the next 2 nights. This evening, tuck into a sumptuous degustation dinner at the Michelin-starred La Torre Restaurant overseen by Executive Chef, Giovanni Luca Di Pirro. Dishes are made with the finest Tuscan ingredients, sourced from local farmers, or directly from the estate’s organic garden. 

Overnight: COMO Castello del Nero

Meals: Breakfast & Michelin Dinner

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Two agendas for the day. First, we visit the impeccable Antinori nel Chianti Classico, a winery that reveals the past, present and future of the Antinori family; designed to welcome wine enthusiasts into its wine-making legacy that began in 1385. Overlooking the countryside from a terrace surrounded by vineyards planted with Chianti Classico’s most typical grape, Sangiovese, together with other varieties that were historically planted nearby, the winery not only impress with its innovative architecture designed to have a low environmental impact and maximum energy savings blending into the harmonious Chianti landscape but also a sacred place of wine pilgrimage dedicated to the ancient rituals of wine-making while using cutting edge technology and innovations to produce some of the finest and most revered wines on the planet. 

The second agenda will be the visit to the Badia di Passignano Monastery, a historic abbey dating back to the 11th Century embarking on a historical wine cellar tour of the estate followed by a sumptuous Michelin-dining lunch experience at the revered Osteria di Passignano accompanied by classic Antinori signature wines, preceded by extra-virgin olive oil tasting. 

Overnight: COMO Castello del Nero

Meals: Breakfast & Michelin Lunch

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We say goodbye to a week of spectacular wines, epicurean pursuits and inspiring landscapes of Tuscany and Umbria with a pleasant transfer into the Renaissance city of Florence where you may continue your journey. 

Meals: Breakfast


The former hunting lodge of Leopold II, Duke of Tuscany, L’Andana is located in Italy`s stunning Maremma region, celebrated for its lush countryside that stretches to the Tyrrhenian Sea. Not surprisingly, food and wine are the focal points of a stay: Trattoria Enrico Bartolini and its wine cellar makes the most of the property`s desirable location. A laid-back ambience and impeccable service are the trademarks of L’Andana. 

L'Andana, Castiglione della Pescaia


Borgo dei Conti is a charming resort that has combined its centuries of aristocratic history to modern concepts of hospitality and elegance. A real village in the vastness of its 20 hectare park, made up of the villa and Colonica structures that host 55 rooms in 4 different typologies. 

Borgo dei Conti, Montepetriolo


A hamlet perched on a hill south of Siena, Castello Banfi Il Borgo proudly reigns over its prestigious vineyards. Along the rolling landscape of the estate, discover a classic and romantic Tuscan kaleidoscope of grapevines, plum orchards and woodlands. The decor of the former farm buildings was designed by Federico Forquet showcasing suites and spaces in warm tones and elegant decor, bringing to life for tasting of the exquisite wines by the Mariani family. 

Castello Banfi II Borgo, Montalcino


COMO Castello del Nero, The Chianti


Hidden among the rolling hills of Tuscany lies COMO Castello Del Nero, Tuscany — in easy driving distance of the Renaissance cities of Florence and Siena. At the heart of this historic 740-acre estate is a twelfth-century castle layered with Renaissance frescoes and contemporary design, with interiors by Paola Navone. The resort offers Michelin-starred dining experiences with estate-to-table Tuscan produce, as well as meaningful wellness therapies at COMO Shambhala Retreat.


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