Luxury Tailor-Made Tours in Italy –
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Whether you’re dreaming of Tuscany’s rolling hills, Venice by private boat, or dinner inside a historic palazzo,

we’ll bring your ideal Italy to life—without the crowds, without the stress.

Let’s design your Italy.

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Why Choose
Dragonfly Tours?

At Dragonfly Tours, we don’t just plan trips—we craft unforgettable journeys, designed around your personality, preferences, and passions.

Saving a few Instagram reels or TikTok videos might give you inspiration, but do they truly tell you where to go?

More often than not, those viral spots are where you’ll find 50 people in line for the same photo, missing the essence of what makes Italy special.

Authentic Italy isn’t just about the places—it’s about how you experience them. That’s where we come in.

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We are Italian

We live here. We know the real
Italy—beyond the tourist path

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We handle every detail,
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Private, behind-the-scenes experiences
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Trusted guides, handpicked partners
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Explore Our Exclusive
Italian Destinations

Italy is one country—but feels like twenty different worlds.

Every region has its own personality: landscapes, food, culture, even language. Trying to see it all at once means missing what makes each place special.

That’s why we recommend the right destinations for you—based on your style, your pace, and what you truly want to experience.

Tap on the DragonFly icon to explore the region.

Lombardia Region

Milan & Lakes

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From the pulse of Milan’s fashion and design scene to the peaceful charm of Lake Como, Maggiore and Orta, this region blends cutting-edge creativity with timeless lakeside elegance.

  • Wine: Franciacorta – Italy’s most refined sparkling wine
  • Dishes: Risotto alla Milanese (Order creamy risotto scented with saffron), Cotoletta alla Milanese (Order veal cutlet fried in butter, Milan-style)
  • Essence: Design capital, romantic villas, and art-rich towns along the lakes

Don’t miss: Climbing to the rooftop of the Duomo to see Milan from above, surrounded by marble spires.

Piedmont

Torino, Langhe and Monferrato

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Quietly luxurious and rooted in tradition, Piemonte is a land of noble cities and rolling hills.

From the Baroque charm of Turin to the vineyard-covered Langhe and Monferrato, this is Italy for the discerning traveler.

  • Wine: Barolo & Barbaresco – bold reds from the Langhe
  • Dishes: Tajarin al tartufo bianco (Order a handmade egg pasta with white truffle), Vitello tonnato (Order veal in creamy tuna sauce, a true classic)
  • Essence: Former royal capital, Slow Food cradle, chocolate and vermouth heritage

Don’t miss: A truffle tasting lunch in the Langhe hills during harvest season.

Campania

Napoli, Pompei

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Naples is bold, soulful, and unapologetically alive.

From the buzzing historic center to sweeping views of the Bay of Naples, this city pulses with energy, tradition, and volcanic flavor.

Just a short ride away, the ruins of Pompeii offer one of the world’s most powerful encounters with the past.

  • Wine: Lacryma Christi del Vesuvio – mineral-rich red and white from volcanic soil
  • Dishes: Pizza Margherita (Order the original, with tomato, mozzarella and basil), Sfogliatella (Order this layered pastry with sweet ricotta filling)
  • Essence: Birthplace of pizza, Baroque churches, Vesuvius views, and Pompeii at your doorstep

Don’t miss: Starting your day with an espresso and warm sfogliatella on the waterfront promenade.

Campania

Capri

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Capri is a Mediterranean icon—glamorous, dramatic, and irresistibly romantic.

From the iconic Piazzetta to dramatic cliffs and azure grottos, the island has long enchanted poets, royals, and dreamers.

Anacapri, just up the hill, offers a slower rhythm—hidden gardens, artisan shops, and breathtaking views with none of the buzz.

  • Wine: Falanghina – crisp and floral white from the Campania coast
  • Dishes: Ravioli capresi (Order stuffed pasta with caciotta cheese and marjoram), Torta Caprese (Order a flourless chocolate and almond cake, born on the island)
  • Essence: Jet-set elegance, natural beauty, artisan charm and secret corners above the crowds

Don’t miss: Taking the chairlift to Monte Solaro from Anacapri for a 360° island view.

Campania

Amalfi, Positano, Ravello, Vietri, Cetara, Nerano, Sorrento

positano

The Amalfi Coast is more than a destination—it’s a vertical dream carved into cliffs.

From the pastel beauty of Positano to the serene gardens of Ravello, every village has its own rhythm.

Amalfi bustles with maritime heritage, Vietri sul Mare shines with hand-painted ceramics, Cetara is a haven for anchovy lovers, and Nerano blends gourmet tradition with seaside calm.

On the edge, Sorrento offers a refined gateway with sea views, citrus groves, and easy access to Capri and Pompeii.

  • Wine: Costa d’Amalfi DOC – fresh, mineral whites from cliffside vineyards
  • Dishes: Spaghetti alla Nerano (Order pasta with zucchini and local provolone), Delizia al limone (Order sponge cake with lemon cream, light and fragrant)
  • Essence: Cliffside villages, sea-view terraces, citrus perfume, and timeless Mediterranean charm

Don’t miss: A lazy lunch in Nerano by the sea with spaghetti alla Nerano and wine.

Liguria

Cinque Terre, Portofino

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Between sea and stone, the Cinque Terre villages—Monterosso, Vernazza, Manarola, Corniglia, Riomaggiore—stun with their color and simplicity.

Just beyond, Portofino is a hidden gem for those seeking elegance away from the crowds.

  • Wine: Sciacchetrà – rare sweet wine from steep terraces
  • Dishes: Trofie al pesto (Order twisted pasta with Genovese basil pesto), Acciughe marinate (Order marinated anchovies with lemon and olive oil)
  • Essence: Ligurian lifestyle, seaside trails, exclusive coves and quiet beauty

Don’t miss: Hiking the coastal trail between Vernazza and Corniglia at golden hour.

Lazio

Rome

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Rome isn’t just the Eternal City—it’s a vibrant mix of ruins, rooftops, and rhythms.

Walk from the Imperial Forums to a quiet piazza in Trastevere, and you’ll feel the layers of history come alive. Elegant, chaotic, magnetic—Rome stays with you.

  • Wine: Frascati Superiore – crisp white from the hills south of Rome
  • Dishes: Cacio e pepe (Order pasta with pecorino and black pepper), Carbonara (Order the real Roman version—made with egg yolks, pecorino, and guanciale, not bacon
  • Essence: Ancient monuments, baroque beauty, vibrant neighborhoods and dolce vita flair

Don’t miss: A rooftop aperitivo with panoramic views over domes and ruins at sunset.

Sicily

Palermo, Taormina, Agrigento

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Sicily is a world of its own—sun-drenched, layered with history, and rich in soul.

In Palermo, Arab-Norman architecture meets lively street food culture. In Taormina, dramatic views stretch from Greek theatres to Mount Etna. And in Agrigento, the Valle dei Templi offers one of the most majestic archaeological sites in the Mediterranean. The island’s starring role in The White Lotus only confirmed what travelers have long known—Sicily is magnetic.

  • Wine: Etna Rosso – elegant, mineral red grown on volcanic slopes
  • Dishes: Pasta alla Norma (Order pasta with eggplant, tomato, ricotta salata, and basil), Cannolo Siciliano (Order the iconic ricotta-filled pastry with a crisp shell)
  • Essence: Ancient ruins, volcanic landscapes, baroque cities, and cinematic coastline

Don’t miss: Watching the sunset over the Greek theatre in Taormina with Etna in the background.

Sardinia

Costa Smeralda, Ogliastra, Maddalena Archipelago

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Sardinia is Italy’s wild island—mysterious, ancient, and unexpectedly luxurious.

From the emerald waters of the Costa Smeralda to the pink sand beaches of Spiaggia Rosa, and from hidden coves in Ogliastra to the timeless inland villages, this island is a world apart.

Archaeological sites, intense flavors, and crystal waters make Sardinia one of the Mediterranean’s best-kept secrets.

  • Wine: Vermentino di Gallura – crisp and mineral white from the northern coast
  • Dishes: Culurgiones (Order handmade ravioli stuffed with potato, mint, and pecorino), Porceddu (Order slow-roasted suckling pig, Sardinia’s most iconic dish)
  • Essence: Untamed coastlines, prehistoric ruins, independent soul and turquoise waters

Don’t miss: A boat day along the Maddalena Archipelago, discovering hidden beaches unreachable by land.

Apulia

Lecce, Polignano a Mare, Maldive del Salento

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Puglia stretches along the heel of Italy’s boot, where olive groves, whitewashed villages, and crystal-clear seas define the landscape.

From the baroque splendor of Lecce, to the iconic trulli of Alberobello, to the dramatic cliffs of Polignano a Mare and the peaceful Itria Valley—this region invites you to live deeply and simply.

For beach lovers, the “Maldive del Salento” offer turquoise waters and fine sand that rival the tropics.

  • Wine: Primitivo di Manduria – intense, full-bodied red from Salento
  • Dishes: Orecchiette alle cime di rapa (Order handmade ear-shaped pasta with turnip greens), Fave e cicoria (Order mashed fava beans with wild chicory—Puglia’s humble soul food)
  • Essence: Dry-stone walls, endless coastline, trulli villages and warm southern soul

Don’t miss: Swimming in the turquoise waters of the “Maldive del Salento”.

Dolomites

Alta Badia, Val Gardena, Cortina d’Ampezzo

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The Dolomites are not just mountains—they’re a cinematic alpine experience.

Dramatic peaks, peaceful valleys, and perfectly preserved villages blend nature, design, and tradition.

Whether you’re hiking through wildflower meadows in summer or skiing in style during winter, the region offers beauty with every turn. Areas like Alta Badia, Val Gardena and Cortina d’Ampezzo are perfect for luxury travelers who love the outdoors.

  • Wine: Gewürztraminer – aromatic white from Alto Adige
  • Dishes: Canederli (Order bread dumplings with cheese, herbs or speck), Strudel di mele (Order warm apple strudel with cinnamon and pine nuts)
  • Essence: UNESCO peaks, Tyrolean traditions, alpine elegance and seasonal luxury

Don’t miss: Watching the mountains glow pink at sunset—enrosadira—from a panoramic mountain hut with a glass of local wine.

Tuscany

Firenze, Chianti, Val d'Orcia, Bolgheri

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Tuscany is Italy’s ultimate daydream—golden light, vineyard hills, medieval towns, and Renaissance beauty.

Explore the rolling landscapes of Chianti and Val d’Orcia, the wild elegance of the Maremma, the refined coastal wines of Bolgheri, or the art-filled streets of Florence. Whether you’re sipping wine in a stone farmhouse or strolling seaside in Castiglione della Pescaia, Tuscany speaks to every traveler in a different way.

  • Wine: Brunello di Montalcino – age-worthy red from Val d’Orcia, Bolgheri Superiore – bold coastal blend from the Maremma
  • Dishes: Pici all’aglione (Order hand-rolled pasta with garlicky tomato sauce), Bistecca alla Fiorentina (Order the iconic Tuscan T-bone steak, grilled rare)
  • Essence: Olive groves, stone villages, cypress-lined roads, and timeless elegance

Don’t miss: Driving at dusk through Val d’Orcia’s cypress-lined roads between Pienza and Montalcino.

Emilia-Romagna

Bologna

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This is Italy’s gastronomic heartland, where every town has a dish that made history. From Bologna’s trattorias to Modena’s balsamic vinegar and Parma’s cheese and ham, excellence is the norm.

  • Wine: Lambrusco – dry and sparkling, perfect with cured meats
  • Dishes: Tortellini in brodo (Order tiny filled pasta in capon broth), Tagliatelle al ragù (Order egg pasta with slow-cooked meat sauce – the original “Bolognese”)
  • Essence: Parmigiano Reggiano, Prosciutto di Parma, and the luxury of the Motor Valley

Don’t miss: Lunch at a traditional trattoria in Bologna followed by a visit to a Parmigiano producer.

Umbria

Assisi, Spoleto, Orvieto, Montefalco

umbria_assisi

Known as Italy’s green heart, Umbria is quieter than Tuscany—but just as rich in beauty, food, and spirituality. Rolling hills, medieval hilltowns like Assisi, Spoleto, Orvieto and hidden abbeys await those who travel off the beaten path.

  • Wine: Sagrantino di Montefalco – bold and structured red from the Umbrian hills
  • Dishes: Torta al testo (Order flatbread stuffed with prosciutto or greens), Strangozzi al tartufo nero (Order handmade pasta with Norcia black truffle)
  • Essence: Spiritual roots, olive oil culture, medieval architecture and silence

Don’t miss: A wine tasting at a family-run vineyard near Montefalco followed by a sunset over Assisi.

Basilicata

Matera

basilicata-matera

Matera is like nowhere else in Italy—or the world.

Its ancient cave dwellings, known as Sassi, carved directly into limestone cliffs, create a landscape that feels timeless and cinematic. Once forgotten, today it’s a UNESCO World Heritage site and a symbol of quiet reinvention. Sleep in a cave, dine by candlelight, and walk streets older than Rome.

  • Wine: Aglianico del Vulture – bold, earthy red from nearby volcanic soil
  • Dishes: Pane di Matera (Order the iconic crusty sourdough bread with centuries of tradition), Crapiata (Order this hearty legume soup, born from local peasant culture)
  • Essence: Off the beaten path, ancient stone architecture, soulful silence and cinematic atmosphere

Don’t miss: Spending the night in a restored cave hotel in the Sassi district.

Calabria

Capo Vaticano, Tropea, Aspromonte

calabria

Calabria is Italy’s raw edge—untamed, soulful, and unexplored. It’s not polished for tourism—and that’s exactly its charm.

Washed by two seas and dotted with ancient villages and fishing towns, Calabria feels wild, honest, and full of discovery. From the turquoise waters of Capo Vaticano to the cliffs of Tropea and the silence of Aspromonte, this is Italy for curious travelers.

  • Wine: Cirò Rosso – bold and spicy red made from Gaglioppo grapes
  • Dishes: Fileja ’nduja (Order handmade pasta with spicy Calabrian sausage spread), Tartufo di Pizzo (Order this iconic gelato dessert with a melted chocolate heart)
  • Essence: Wild beaches, hidden hilltowns, fiery flavors and an untouched Mediterranean spirit

Don’t miss: A scenic drive along the Costa Viola, stopping in untouched fishing villages.

Veneto Region

Venezia

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This diverse area includes Venice’s quiet canals, the rich hills of Valpolicella, the UNESCO-protected Dolomites and the Mediterranean charm of Lake Garda. A journey through contrasts—yet harmoniously Italian.

  • Wine: Amarone della Valpolicella – complex, rich and age-worthy
  • Dishes: Sarde in saor (Order sweet-and-sour marinated sardines), Polenta e funghi (Order polenta with sautéed wild mushrooms)
  • Essence: Craftsmanship, faded grandeur, alpine views and lakeside retreats

Don’t miss: Exploring Venice on foot at night, when the crowds disappear and the city returns to silence.

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Milan & Lakes
Piedmont
Naples
Capri
Amalfi Coast
Cinque Terre
Rome
Sicily
Sardinia
Apulia
Dolomiti
Tuscany
Emilia-Romagna
Umbria
Basilicata
Calabria
Venetian
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About Us

Beyond Itineraries. We Curate Emotion. Dragonfly Tours Italy was born over 15 years ago from a shared family vision—to create luxury journeys that go far beyond the ordinary. What began around a kitchen table is now a well-established boutique DMC with offices in Rome and Los Angeles, over 12,000 high-spending American travelers served, and a reputation built entirely on five-star reviews and word-of-mouth referrals.

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