Cave Dwellings in Matera
Once upon a time, the Sassi (cave dwellings) that pitted the limestone slopes of Matera in Basilicata were ramshackle peasant dwellings. Not anymore. In recent years, this ochre-stone hill town, located in the instep of the Italian "boot", has had something of a renaissance. The upshot is that plenty of boutique digs are now in this UNESCO World Heritage site.
The first to embrace the trend back in 1996 was Hotel Sassi, full of cozy nooks, stone-vaulted interiors, and windows perfectly framing the cathedral and campanile. The 35 rooms and suites spread across a cluster of Sassi, some of which date to the 1500s. These have been updated with a modern aesthetic and comforts like wifi and air conditioning. Come for the gorgeous old-town views, local produce-driven breakfasts, and a relaxed mood.
If you've come to Italy to tap into your spiritual side, where better to stay than in one of the monasteries or convents with guest quarters? Ranging from spartan digs in the cloisters to comfortable lodgings with heavenly mountain views, you'll find these dotted all over the country.
At the simple end of the spectrum is La Verna, a striking sanctuary in the Tuscan Apennines, perched on cliffs cloaked in forests of fir and beech trees—this is where St. Francis of Assisi is said to have received the stigmata. Speaking of Assisi, in the town of the same name in Umbria, you'll find St Anthony's Guesthouse, a tranquil convent run by kind sisters with countryside views and pretty gardens. An hour north of Rome is Monastero San Vincenzo Martire in Bassano Romano, with space to accommodate 120 guests. Monks tend to the kitchen gardens, and there are pine forests for contemplative strolls.
Floatels in Venice
What better way to see the floating city than on a "floated" or "boatel?" Venice's marble palazzi and domes can be captured from so many different angles, but few are quite as memorable as seeing its skyline from the lagoon. And staying overnight on one of its permanently moored boats or yachts often costs less than a quick spin in a gondola on the canals.
Top billing goes to Yacht Bert, a "boat and breakfast" moored away from the crowds, yet just two vaporetto (water bus) stops from Piazza San Marco. This converted Maltese yacht has panoramic decks and six individually decorated cabins, ranging from slick and simple to superior, with hot tubs, minibars, and ample space. A good alternative is Venezia Boat San Marco, four miles from the center in the Castello district.
Chat with a local specialist who can help organize your trip.
Trulli in Puglia
Seeing whitewashed, beehive-shaped trulli is a sure sign that you've made it to Italy's deep south. In this hot, sun-bleached region, you'll find these loveable Hobbit-like houses tucked between the olive groves and the emerald sea. They are distinctive because of their dry (mortar-less) limestone walls and conical roofs. The oldest trulli date to the 14th century, though many were built in the 19th century as rural shelters and storage rooms.
The cute-as-a-button town of Alberobello is trulli heartland, and many have been given 21st-century makeovers and converted into charming guesthouses. A great starting point is Trully Holiday, with everything from hideaways for two to family-sized suites with private gardens. Or opt for the five-star Le Alcove, with rustic-chic, antique-slung interiors full of romantic nooks.
Igloos in South Tyrol
You don't have to venture to Arctic Scandinavia to get the full-on igloo experience—Italy can do cold, too. In Maso Corto, the highest village in the Val Senales valley in South Tyrol, the views of the Hochjochferner glacier on the border to Austria are nothing short of extraordinary. The backdrop in the Ötztal Alps is a pure winter wonderland, and never more so than at Rifugio Bella Vista, perched at a cool 9,300 feet above sea level.
Book well in advance to snag one of the three igloos built from scratch as soon as the flakes fall in December. What could be more romantic than sipping mulled wine surrounded by the ethereal glow of blue ice, steaming in Europe's highest sauna, and snuggling down in sheepskins for the night? When you wake up in the morning, it will be the first touch of sun on the mountaintops.
Shepherd Huts in Sardinia
The island of Sardinia, off Italy's west coast, preserves its own rich cultural heritage. Despite its sublime coastline, home to some of the country's dreamiest white-sand beaches, this is an island of pastori, non pescatori (shepherds, not anglers), especially in the mountainous interior. An integral part of this heritage is the pinnetta, a round, rudimentary shepherd's shelter built from dry-stone walling and juniper branches.
Sardinna Antiga, just a mile or so from the sea in Santa Lucia di Siniscola in the island's northeast, takes the concept a step further, bringing you back in time in eco-friendly huts that sensitively adhere to the building techniques of Sardinia's Nuragic (Bronze Age) era. Kick back, unplug (no electronic devices are permitted), sip mountain spring water from an earthenware pitcher, and tune into nature.
Wine Barrel Beds in Le Marche
You might enjoy a glass of wine before drifting off to sleep, but have you ever woken up in an oak barrel? No? Well, here's your chance. At Il Rifugio dei Marsi, wine barrels have been converted into super-snug rooms, with lots of loving detail in their timber interiors and embroidered linens. The setting is incredible, too, tucked away in the lushly wooded hills above the Renaissance city of Ascoli Piceno in Italy's unsung Le Marche region. As you might expect, the views up here are magic.
The friendly family who runs the place is full of ideas—from hikes and bike rides in the nearby Parco Nazionale dei Monti Sibillini to truffle hunting (November to March). There's a sauna and hot tub for post-walk chilling, and breakfasts feature organic produce from the family farm.