Day 1 (Saturday) Airport pickup, introduction to the Conventino and Anghiari and the truffle festival at Citta di Castello

The good times start as soon as your bags are delivered to your room, as it will be off to  taste truffle crostini and sampling the new wine at the truffle festival in nearby Citta di Castello. After a siesta at Conventino, we will tour the ancient walls and subterranean springs of Anghiari as well as the Marzocco museum displaying the sketches of the Battle of Anghiari (1440) by Leonardo da Vinci, and then enjoy a light-crust pizza with porcini mushrooms at a famous local haunt.

Day 2 (Sunday): The haunts of hermits, monks and birthplace of Michelangelo: Caprese Michelangelo and La Verna

After an early breakfast, we will set out on a two-hour walk from the Conventino up through the surrounding hills of Monti Rognosi (an ancient range of mountains where gold and native copper was mined by the Etruscans) and then along the escarpment towards Sasseto and the mediaeval castle of Montauto, with wonderful vistas down towards the Montedoglio Lake and Sovara valley beyond.

After a quick coffee, we will then drive up to the prominent rock fortress of La Verna, sanctuary of St. Francis of Assisi, to visit his secluded bed of iron and spiritual retreat under a cleft of rock, as well as spectacular ceramics from the della Robbia school. We will return via the eyrie of Caprese Michelangelo where we will enjoy a spectacular thirteen course Sunday lunch at a restaurant overlooking the valley, being treated to local specialities of porcini mushrooms and truffles amidst the hubbub of local crowds, or depending on the season, drive across to the Alpe della Luna along the ancient route of the transhumance, the Via Marecchia, to savour the 18 course truffle menu at a famed restaurant in the mountains.

Following a well-deserved siesta, we will attend the chestnut festival up at Caprese, browsing the booths and sampling roast chestnuts, chestnut pancakes with nuts, flambéed chestnuts and local cheeses, washed down with the new caniola wine for supper and then wine by the fire at Conventino.

Day 3 (Monday) Arezzo, Sansepolcro and Monterchi: the paintings of Piero della Francesca

First, we will drive early in the morning to Arezzo to see the frescoes entitled “The Legend of the True Cross” and the haunting XIIIth c. Cimabue cross at the Church of San Francesco, proceeding on to the portrait of St. Mary Magdalene in the Arezzo Cathedral, both compelling works by the celebrated Piero della Francesca. After cappuccino in an elegant café in Arezzo, we will then drive on to Sansepolcro to see the famous Xth c. sculpture entitled the Volto Santo in the XIIth c. Duomo or Cathedral (according to legend, brought back from Palestine where it was seized during the Crusades) and the haunting fresco of St. Thomas a Becket who allegedly took refuge in Anghiari.

We will then enter the Civic Museum where some of the best frescoes by Piero including the stunning “Resurrection” are displayed. We will conclude with a selection of dishes at lunch in an atmospheric enoteca or wine cellar specialising in carpaccio (finely sliced meat or fish marinated in extra virgin olive oil), daubed with either truffles or porcini.

After a short siesta, we will be treated to a cooking lesson with truffles conducted by Mariella and Santina in Italian (with running translation), watching the preparation of crostini with porcini mushrooms and truffles, tagliatelle with truffles, roast duck stuffed with fennel cooked in the wood oven and Torta della Nonna. We will then indulge in this feast at a banquet in the XIth c. chapel of the Conventino where the food will be accompanied by organic wine selected from the “Il Conventino” winery from the Vino Nobile di Montepulciano region.

Day 4 (Tuesday) Trip to the Etruscan town of Chiusi and Montalcino, home of the famous Brunello wine

We depart early for Chiusi and on arrival, descend into the subterranean labyrinth believed to be the tomb of King Porcenna from the VIIIth c. BC, visit the VIth c. Cathedral of “San Secundiano and Santa Mustiola”, one of the earliest Christian churches in Italy and then pop across to the fascinating Etruscan museum, grabbing a quick cappuccino en route.

We will then descend into a couple of painted tombs outside Chiusi (the only Etruscan tombs in Tuscany still visible in their original context) and proceed to Montalcino for a gourmet lunch -- the menu de degustazione washed down with “Brunello di Montalcino” wine-- in a small osteria featured in Gourmet magazine that enjoys a panoramic view over the valley. We will walk off the lunch by strolling through the lanes of Montalcino and drop down to the XIIth c. Abbey of S. Antimo, a monastery originally built in the VIIIth century by Charlemagne (or so the legend goes) a pristine construction of alabaster and white stone where monks even now sing Gregorian chants.

We will head home via Montepulciano, arriving at the Il Conventino winery for a tour of the estate and tasting of their organic olive oil and reserve wines from the “Vino Nobile di Montepulciano” DOC region, accompanied by with bruschetta and cheese. On arrival home, those who wish will enjoy a light supper at the Conventino.

Day 5 (Wednesday) Anghiari

After breakfast, we will depart for Anghiari and the weekly market, drink cappuccino in the heart of the main square and tour the ancient walls, nipping into the XIIth c. monastery (the Badia) and the Palazzo Pretorio, now site of the Commune or Town Hall, to catch the superb vista of the Tiber valley below. We will then tour the original textile mills at Busatti which still produce gorgeous Italian damask, followed by truffle oil tasting at the traditional XIVth c. Ravagni oil press near the ancient church of Micciano. We will then adjourn for a truffle-laden pasta lunch at an exceptional restaurant inside the walls of Anghiari.

After a short siesta, we will head off to the hilltown of Monterchi to see the Madonna dell Parto, a famous painting by Piero della Francesca and then to an enoteca encased within the ancient walls of Anghiari. There we will be invited to taste different wines from the Val di Chiana region, accompanied by a selection of cheeses and condiments. After this teaser, we will then return for a light supper of salamis and salads around the log fire at the Conventino.

Day 6 (Thursday) Mushroom and truffle hunting near Anghiari

After breakfast, armed with boots and sticks, we will follow an experienced mushroomer and guide into the forests beyond Anghiari to discover the often secret locations of these fabled ‘fruits of the forest’. This will be followed by a light lunch at the Conventino, the usual siesta and then shopping along the elegant passageways of Sansepolcro prior to a dinner at an ancient Osteria, specialising in mushrooms, wild boar and game specialities, once a hostel on the two thousand year old route of the transhumance.

Day 7 Siena

After an early breakfast, we will depart for Siena, passing by ancient olive groves and vineyards into the undulating, lunar landscape of the crete. On arrival ( about 2 hours later), we will walk from the spectacular Porta Camollina, dropping into the stark XIIth c. Templar church of Magiona, and stroll through the “Contrada of the Istrice” or “porcupine”, the street of one of the brotherhoods who compete in Siena’s famous palio or horse race, named after both real and fabulous animals,. After cappuccino at the elegant Nannini café, we will then walk on to the shell-shaped Piazza Grande where the palio takes place, visiting the spectacular Duomo and the Palazzo Pretorio to see the ironic XVth c. frescoes of Good and Bad Governance as well as stunning examples of religious art.

After a short shopping break, we will all meet up for a truffle or porcini lunch with home-made pasta and salad, accompanied by local wine, in an intimate trattoria overlooking the Mangia and the Piazza Grande. Afterwards we will stroll through the lanes ogling antiques and textiles, as well as the superb pan forte and other sweets famous from the area. This afternoon will be free for everyone to amble around, sit in the piazza café’s or take in other superb monuments of the city. Back at the Conventino, we will enjoy a relaxing supper at the Conventino, tasting several wines from the Siennese Chianti region, hopefully with a few porcini cooked by ourselves!

Alternative Day 7 (Friday) Florence (if preferred by a majority of guests)

After breakfast, we will set off for Florence by train and on arrival, will walk via the extraordinary Profumo-Farmeceutica of S. Maria Novella with its ancient herbal potions, to the Duomo and under-church dedicated to Diva Severina, crossing over finally to see the stunning “Baptistery”, erected originally as a Roman temple.

1:00 pm: Walking via the Piazza della Signoria, we will then stop to have a typical Tuscan lunch of the season with antipasto and pasta with salad, embellished with porcini and truffles, at a jewel of a restaurant just beside the Duomo. After this feast, we will then make our way to the Uffizi gallery for a selective viewing of masterpieces of Giotto, Botticelli, Titian, Leonardo and Piero della Francesca where we have reservations and then to the Ponte Vecchio for a stroll and coffee. Afterwards, as preferred we will either stroll through the lanes seeking out little leather boutiques, relax in the piazza café’s, or head for the Accademia to see Michelangelo’s original “David”.

When back home, we will enjoy a farewell dinner at the Conventino with tasting of wines from San Gemignano and the Florentine Chianti region and hopefully, a few porcini cooked by ourselves!

Day 8 (Saturday)

Breakfast and drop off from starting point.

When is truffle season?

Tour 1: Oct. 15th - Sat. Oct. 22rd (to coincide with the Caprese Michelangelo chestnut festival and the Citta di Castello truffle fair)

Tour 2: Oct. 22nd - Oct. 29th (to coincide with the Caprese Michelangelo chestnut festival and the Citta di Castello truffle fair)

Tour 3: Oct. 29th- Nov. 5th (to coincide with the truffle festival on the Via Marecchia, dates to be confirmed)

Call for pricing, based on numbers travelling. Ideal numbers 5-6...