The rectangular stone tower lies on a spur of rock just at the foot of the Sibylline mountains in Italy’s Le Marche region. Once, it would have been a lookout point for the nearby village of Montefortino, positioned at the bottom of the pass leading to the neighboring Umbria region. Two decades ago, the crumbling structure was one of the few watchtowers still standing in Le Marche. Now, it has been transformed into La Roccaccia, a one-of-a-kind residence thanks to the passion project of Enrico Biondi.

Looking down from the walking path that skirts by the structure and leads up into the mountains, the 11th-century tower protrudes from a sea of dark green woods. Just beyond it, the ground drops down into a deep valley with a burbling stream that can be heard from the tower’s terrace. To one side, the rugged mountains rise up steeply. To the other is a gentler undulating landscape dotted with hilltop towns.

Twenty years ago, the medieval watchtower was a ruin. The land around was wild and unkempt. But Biondi saw the potential for unique guest accommodation in the dilapidated building. He restored the tower and transformed the gardens into a fantastical and eccentric residence named La Roccaccia. He continues to make additions each year, with a current project to restore a nearby structure to house more accommodation and a spa.

Now, the tower has four levels split into two apartments that can house a total of nine guests. The lower single-floor apartment comprises a double bedroom, bathroom, small kitchen, and living area with a sofa bed. The upper apartment has a kitchen, living area, and a large terrace affording breathtaking views. On the two levels above are the bedrooms that can sleep a total of five guests.

The structure is full of delightful quirks. In the master bedroom on the top floor, a remote control lies by the bed that opens an oculus in the roof for nighttime stargazing. The building is crammed with extraordinary antiques, from cannon balls and stone lions to crucifixes and gilded keys. Biondi also retained the original heavy carved wooden doors and cast iron fittings.

The garden is equally as eccentric, a labyrinth of twisting paths, hidden sculptures and shaded seating areas. The latest addition is a stunning outdoor swimming pool with a magnificent view of the Sibylline mountains.

At night, La Roccaccia becomes truly spectacular. Standing on the terrace is like watching a mesmerizing stage set. Below, the lighting illuminates the mini outdoor theatre and the stone patios decorated with antique well heads and stone plinths. Beyond, the mountains loom dark and mysterious while opposite, the valley winks with lights from little hamlets.

For Biondi, the concept of La Roccaccia is an oasis away from crowds. Manager Giacomo Zoppi can arrange a chef to cook evening meals and activities like yoga on the terrace, wine tasting or truffle hunting.

But it is also a base to explore an area of Italy that is off the radar for many tourists. Moreno Moretti, owner of luxury travel site ItalyCharme, hails from the region and is keen to sing its praises.

He can introduce guests to the nearby art cities, natural attractions, artisan workshops and gourmet restaurants. The first stop is Ascoli Piceno, a city of magnificent Baroque buildings and shining white marble pavements. It is also the birthplace of olive ascolane, olives stuffed with minced meat inside a crispy fried coating. At the elegant Art Nouveau bar Anisetta Meletti, customers can order the olives as an accompaniment to the establishment’s renowned liqueur made from aniseed.

In the countryside around, vines line the hills that were home to winemakers even during the ancient Roman Empire, as Pliny the Elder recounts. At Le Senate, Giulio Visi’s organic vineyard overlooks the azure Adriatic sea. With fresh salty breezes from the nearby coast, he produces a crisp white Chardonanny named Scirocco da Mare and a barrique aged Cacinello red made from Cabernet Sauvignon, Petit Verdot and Merlot grapes.

For natural splendor, Moretti recommends hopping over the regional border to Umbria to see the renowned fioritura of Castelluccio di Norcia. Although the hilltop town and several surrounding settlements were devastated by an earthquake in 2016, the valley’s famous lentil flowering continues. In early summer, the lentil fields explode in color, thickly carpeted with bright red, purple and yellow flowers.

For visitors looking to take home a unique souvenir, Moretti suggests Emanuele Bozzi’s pottery workshop in Montottone. Bozzi is a one-man powerhouse, modeling and painting plates, vases and jugs from morning to night. His pieces are sold in a few stores in the US but can be bought for much more reasonable prices in his artistically chaotic studio.

Moretti’s top tip is a tiny gourmet restaurant in Ortezzano that courageously opened last year. At Da Sebastiani, Chef Carlo Sebastiani serves seasonal tasting menus with exquisite dishes like peach cream with raw prawns or pigeon with cherries and beetroot.

Le Marche is often dubbed a cheaper and lesser-known alternative to Tuscany. But in reality, it’s a region with no need for comparisons that often outrivals the holiday favorite.

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