Unchartered Territory: Italy’s New Frontier

Written By Kayla Douglas

Few destinations elicit a ubiquitous, knowing smile amongst friends quite like the top places to go in Italy; whether it’s family ties, an appreciation for Italian wine and cuisine, or simply an infatuation with la dolce vita, there’s little need for debate about the merits of a return to “Bel Paese.”

But after the requisite trips to Rome, Florence, Venice, Milan, Tuscany, the Amalfi Coast, and Lake Como, what’s left undiscovered? It turns out, plenty. Or, perhaps you’re closely following the possibility of a digital nomad visa in Italy in the near future and already angling where you’ll base yourself. Either way, with demand for Italy outpacing inventory across the country’s most sought-after regions, savvy travelers are seeking lesser-known destinations across the country they’ve long loved. Our on-the-ground Italian partners paired with first-hand perpetual research (did someone say work trip to Italy?) empowers SmartFlyer to remain at the pulse of the trending destinations you won’t want to miss.

Come along for a #smartflyertakemeto dive into six spots beyond the top places to go in Italy that you’ll be eagerly adding to your trip queue in no time.

  1. Dolomites
  2. Pantelleria
  3. Piedmont
  4. Puglia
  5. Sardinia
  6. Umbria


Oftentimes, a trip to Italy conjures images of the summer months. We envision warm Mediterranean waters, fragrant lemon trees, and your gelato melting faster than you can possibly finish it. But Italy should be thought of as a year-round destination, particularly for those who relish nature and winter sports. If you’re the type of skier who is looking for new mountains to maximize your runs on multiple slopes per day, we’ve got just the ticket: a Ski Safari with Dolomite Mountains.

Our partners local to the Dolomites have crafted an impressionable five-day itinerary moving from resort to resort where you’ll ski from rifugio to rifugio and stay at a different cozy mountain inn nestled into the slopes each night. Spend your days passing through the wide variety of pistes in the Dolomites Superski. Pass your evenings savoring the alpine inns that represent this region’s mix of Italian, Austrian, and Ladin cultures. Of course, your Ski Safari will be led by a professional mountain guide who ensures you hit the best runs. Oh, and will advise on what wine to order along the way!

…design blends four key elements: pure spring water, fresh mountain air, exposure to sunshine, and a mild climate.

Envisioning more of a laid-back immersion into the nature of the Dolomites? Our friends at the family-owned property, FORESTIS, have taken their vision of serenity to new heights in Italy’s South Tyrol, Dolomites. The architecture of this stunning new build lets nature do the work. The design blends four key elements: pure spring water, fresh mountain air, exposure to sunshine, and a mild climate. Guests are invited to reconnect with their body and soul within nature, sure to be aided by their cutting-edge spa and cuisine philosophy following the principles of variety, naturalness, and authenticity. Another family-owned property within the Dolomites to consider is Rosa Alpina, an Aman Partner Hotel. It is the ideal base for exploring the region’s natural beauty and outdoor pursuits in the warmer months. The 3-Michelin-starred restaurant and expansive spa make for the ultimate Alpine stay.

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The ideal destination for the traveler who wants to be the first of their friend group to touch down in a place that “no one has heard of,” (yet) Pantelleria delivers. This tiny, oval-shaped island off the coast of Sicily is actually closer to Tunisia than Italy. Its location only further fuels intrigue for the discerning jetsetter seeking a secret hideaway. Of course, getting there is half the fun! Fom mainland, there are direct flights from Milan, Bergamo, Rome, Venice, Verona, Turin, and Bologna during the high season. Or, if you’re combining with Sicily, there are direct flights from both the western and eastern parts of the island departing from Palermo, Catania, and Trapani.

It wouldn’t be worth the trip without a stunning property to call home, which is where our partners at Sikelia come in. This boutique, 20-room retreat is housed in a porcelain-white dammusi – an ancient stone building typical of this part of Italy – with monastic architecture and striking, modern interiors. Spend your day enjoying the gorgeous palm-lined pool or take out the Esperanza Boat. But being back on the property for sunset is the ultimate treat as you soak up a rooftop sunset. Take in the evocative island under the burnt orange sun before the sky turns illuminated with bright stars.

…phone signal is scarce which lends itself nicely to the entire point of Pantelleria: to do nothing.

Here, phone signal is scarce which lends itself nicely to the entire point of Pantelleria: to do nothing. The main road of the island will lead you to rocky coves and secluded beaches with thermal springs. It’s not hard to see why Homer once called Pantelleria “the navel of the Mediterranean” for this island is rich in contrasts – a place that melds Arabic influences with Southern Italian hospitality.


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After exploring nearby Lake Como, Milan, or the Cinque Terre, the northwest corner of Italy calls. Bordering Switzerland and France, Piedmont literally translates to “foot of the mountain.” The region remains predominantly untouched by the American market despite offering some of the finest white truffles in the world. Those in the know draw parallels between what Tuscany offered before its rise in popularity; here, travelers can indulge in the region’s wine, truffle hunting, culinary offerings, and stunning scenery.

When it comes to a SmartFlyer selected property, the newly opened Casa di Langa is more than a hotel – it is a sustainable stay where you can spend your time wandering 42 hectares of working vineyards or venture out to explore the neighboring UNESCO World Heritage Site. Foodies and budding chefs alike will relish the chance to learn new skills at their wine academy and cooking school. But the true treat is a meal at the on-property restaurant, Fàula where each dish is crafted with local ingredients with special attention to sustainable agriculture and conservation practices.

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No matter how much time you have in the heel of Italy’s boot, we’ll wager you’ll be left wanting more…

As you venture south, Puglia’s sun-drenched peninsula straddles the Adriatic and the Ionian Sea. While we’d be hard-pressed to say Puglia is still up and coming, there’s a lot to unpack. No matter how much time you have in the heel of Italy’s boot, we’ll wager you’ll be left wanting more. This is a region in which many of our clients opt for long-term villa rentals to really settle in. Through our network of vetted partners, we offer a wide variety of serviced, amenity-rich homes to suit groups of any size. But if it’s a Puglia road trip and some hotel hopping you’re after, of course, that’s in our wheelhouse, too.


Unlike in many other regions of the country, large-scale hotels aren’t prevalent in Puglia. The masseria – a fortified farmhouse typically dating back anywhere from the 15th to 18th century – concept helps to make the region still feel authentic and untouched in many ways. Such is the case with Rocco Forte’s gem, Masseria Torre Maizza, a 16th-century farmhouse transformed into a heavenly retreat in the picturesque area of Savelletri di Fasano. Alternatively, there’s Masseria San Domenico which balances its storied history in the 15th-century farmhouse with updated amenities including an outdoor swimming pool, state-of-the-art Thalassotherapy Spa, tennis courts, and a challenging 18 hole golf course. Another family-owned option nearby is Borgo Egnazia, designed to replicate a traditional Apulian village – or borgo – this hotel offers an authentic experience that’s replete with unexpected design, contemporary touches, and luxurious features.

otrano + ostuni

If your Puglia journey takes you beyond Fasano even further south, there are some exciting openings on the horizon. The Baglioni family is set to unveil their latest project, Masseria Muzza just a few minutes from Otranto, deep in the Salento countryside in late May 2022. Make this your homebase to explore the stunning scenery in Lecce. Here, Baglioni blends the simplicity of Salento traditions with the excellence that the luxury Italian hotel group is known for; the venue is prime for destination weddings or celebratory events. And with an even firmer look to the future, Four Seasons is developing property just a short drive from Ostuni. The Four Seasons in Puglia will be one of the very few hotels in the region with direct beach access. The property plans to house accommodation in villa-style units all facing the sea.

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Despite being the second largest in the Mediterranean, Sardinia’s white-sand beaches met by turquoise water remained lesser known until the 1950s when Costa Smerelda began to be developed as an eco-paradise worthy of royalty. Those familiar with the vast coastline are first to divulge that chartering a yacht is ideal to discover hidden gems. In that case, SmartFlyer works with a handful of trusted partners to arrange your time at sea. But if you prefer to keep your feet on shore, rest assured, there’s a slice of Italy for every speed.

…home to some of the most stunning beaches, villas, and hotels which cater to billionaire jetsetters and casual vacationers alike.

The northeastern Sardinian coast is home to stunning beaches, villas, and hotels catering to billionaire jetsetters and casual vacationers alike. The newly opened Baglioni Resort Sardinia has quickly become a SmartFlyer favorite with easy access to one of the island’s most breathtaking beaches, Lu Impostu. The property has just 78 rooms in addition to a private villa rental option. For fine dining, look no further than the 1 Michelin Star restaurant, Gusto by Sadler, right on the property.

As far as activities, adventure seekers will gravitate towards windsurfing, exploring marine caves or hiking the rugged coastline. If history is more your thing, don’t miss the cylindrical towers marking relics of the Nuragic civilization south of Olbia. There are also the fortified villages that stand as a testament to Sardina’s storied history. Another new property on our radar is the soon-to-open 7Pines Resort Sardinia, part of Destination by Hyatt. It is located in a tranquil cove in Baja Sardinia ensuring some of the best sunset views across the Mediterranean. Even further afield, Rosewood Porto Cervo will make its debut in 2023.

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We round out our recap with Umbria. You’re likely to associate it with nearby Tuscany thanks to their shared knack for rolling hills, olive groves, medieval towns, and sparkling lakes. But let us assure you that landlocked Umbria benefits from its underground reputation. Whereas Tuscany’s most beautiful rural areas have become famous, Umbria’s best offerings still remain little known or traversed. These tiny towns like Montefalco, Amelia, and Perugia are all yours to discover. As an added benefit, Umbria is equally easy to access from Rome and Florence on your next Italian road trip.

As far as a place to call home on your countryside adventure, Reschio Estate is a destination in and of itself in this unspoiled corner of Umbria. A forward-thinking family recently renovated the ancient, Millennium-old castle as a passion project. Their energetic drive has ensured that Reschio continues to be a haven of wilderness. The transformed castle has developed into 36 accommodations complete with fine dining, outdoor swimming pool, library, Bathhouse, and Palm Court. And in terms of activities, guests will have no shortage of things to do. Horseback riding, cooking lessons, tennis, biking, a lake day, fishing, truffle hunting, and wildlife watching all available during your stay. Of course, with the help of your SmartFlyer travel advisor, you’ll never be alone in planning your tailored Umbria getaway.

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Ready to begin planning your off-the-beaten-path Italy trip? Contact a SmartFlyer travel advisor to begin the booking process.

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