Why should you travel to Italy with us?

Italy fires your imagination; with the slick purr of an Alfa Romeo, and the staggered terraces of the Amalfi Coast. It’s a country that sells itself. So why go with us?

Details, details, details – that’s why. A sommelier-guided tour of Rome’s best enoteche (wine bars). A private table at Sarah Cicolini’s Appio-Latino restaurant. In Sicily, a private picnic amongst the 2,000-year-old ruins of the Valley of Temples, and in the wild North: a trek into the dramatic ‘pale hills’ of the Dolomites, searching for mountain air, natural wine, and a canopy of stars. This is ideal stuff for families, friends, lovers, and solo travellers. But wherever you decide to go, it’s our job to create a perfectly bespoke travel itinerary, and not simply to sell you what’s gone before. That would be far too easy. And very un-Italian.

Key facts

  • Population Population 61,000,000
  • Capital Capital Rome
  • Language Language Italian
  • Currency Currency Euro
  • Time Difference Time Difference GMT+1| ET+6
  • Best Time Best Time Apr - Oct

Example Itineraries

These are simply suggestions for the kind of holiday you might have. Yours will be tailored, altered, and refined until it matches you completely.

A luxury Tuscany and Amalfi Coast holiday: La Dolce Vita

Rolling hills, crystal waters and food fit for the gods; Tuscany, Sorrento and Amalfi are a breathtaking trio. You’ll begin in the north of Italy, sampling the sun-fuelled foods and wines of Tuscany before heading sout...

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Rome, Florence & Puglia: Gladiators & Gelato with the Family

Roman gladiators, handmade gelato and vintage Vespas, this ten-night adventure through Italy has everything and more to keep the whole family entertained. Perfectly balancing culture with cuisine, history with hijinks, o...

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Como, Tuscany & Amalfi: The Ultimate Italian Honeymoon

Italy, synonymous with romance, has always made for an irresistible honeymoon The soft pearlescent glow of Lake Como at sunrise; the Tuscan air heavy with the scent of cypress; the sweltering haze of a summer's evening ...

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Emilia Romagna & The Langhe: A Luxury Hiking Adventure from the Best Restaurant in Italy

Hike between Barolo wineries and white truffle hunts to discover a new culinary destination in Italy Italy is famous for many things: its centuries-old culture, its renaissance masterpieces, its charming towns in a perf...

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Lake Garda, The Dolomites & The Prosecco Hills: A Luxury Summer Holiday in Northern Italy

Shake off thoughts of the Mediterranean - for Northern Italy is having its time in the sun. It's long held a reputation as home to Italy's most inimitably stylish cities, however, it's keen to show off it's got the lands...

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Switzerland & Italy: A Luxury Holiday in the Alps, Lakes and Coast

Starting way back in the Golden Age of Travel, a luxury holiday in Europe has, over the years, become synonymous with luxury. Whilst everywhere has it's own take on that trademark timeless elegance, for us, few do it as ...

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Puglia: The Perfect Italian Getaway

Fancy being the envy of colleagues around the coffee machine? Puglia should do the trick. Our favourite Italian getaway, we've been retreating down to the heel of Italy's boot for several years now, but no matter how man...

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Highlights of Italy: A luxury holiday in Rome, Florence & Venice

This nine-night holiday to Rome, Florence and Venice will see you sample the delights of this culturally rich and passionate country in true Black Tomato style. Rest your head in some of Italy’s most romantic urban hid...

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Palermo, Agrigento & Taormina: A Luxury Holiday in Sicily

Stumbled upon by mythical Odysseus but hastily left due to the native Cyclops, we found Sicily to be a paradise of sun, sea, sand and olive groves. One that no Cyclops could chase us from. Flee to the countryside, slumbe...

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Milan, Como & Bologna: A Gourmet Escape to Northern Italy

Let us introduce the Italian region of Emilia Romagna. Not only does it produce some of our favourite culinary delights (balsamic vinegar, Parma ham and Parmigiano, to name a few) but it’s also the birthplace of Ferrar...

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Siena: Experience Il Palio in Style

The summer sun beats down on the tiles of Tuscany. Flags and banners sway in the breeze. Men and women garbed in the colours of their ward pageant around a city that looks a lot like a theatrical backdrop. Troupes and fa...

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Piedmont: Discover Truffles on a Luxury Holiday in the Italian Countryside

We have created an exclusive experience tempting you with the best of north Italian cuisine in the heart of truffle country, Piedmont. Take a break in the tranquil countryside and get a unique insight into how the white ...

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The Aeolians: Island Hop in Style in Italy

White-washed villages, honeysuckle-swathed paths and a phenomenal natural fireworks display: Sicily is our sizzling-hot secret. For a dose of barefoot island glamour, these stylish, rustic Aeolian Islands have an innocen...

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Portofino: A Luxury Holiday to the Italian Riviera

Shopping vs beach: the eternal quandary. Or is it? We've tailored the perfect 'Capital to Coast' Italy experience for you to spend a few days sharpening your warrior-like shopping skills in Milan, before escaping to the ...

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EATER Journeys: Rome & Florence

As luxury travel experts, we know a thing or two about getting around the world in style. That's why we've combined our round-the-world travel expertise with the culinary insight of Eater. This slice-by-slice tour of It...

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The Young Pope: Italy

Forget ‘La Dolce Vita’, here at Black Tomato we’re all about La Vita Alta - the Italian high life where you'll tour the country by private jet. In celebration of 2016's smash-hit series ‘The Young Pope’, our tr...

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What to see & do in Italy

If you can’t see it here we’ll still plan it for you.

Rome's rooftops

MORE ABOUT LUXURY HOLIDAYS IN ITALY

Italy – the land of renowned renaissance masterpieces, rich gelato, rolling vineyards, and azure waters. Arguably the ...

Italy – the land of renowned renaissance masterpieces, rich gelato, rolling vineyards, and azure waters. Arguably the most infatuating country in Europe, there is something for everyone, from the gastronomic delights in Modena to the dazzling labyrinths of Venice, the striking ruins of Pompeii to the designer storefronts in Milan. Both romantic and family focused, your luxury Italian holiday awaits.

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Trevi Fountain, Rome

UNCOVER THE ANCIENT STORIES OF ROME

Thanks to the dazzling ceiling frescos at the Vatican and the gaping hole in the Pantheon, Rome doesn’t limit its wond...

Thanks to the dazzling ceiling frescos at the Vatican and the gaping hole in the Pantheon, Rome doesn’t limit its wonders to eye-level. Be it tossing a coin into the Trevi Fountain or standing small underneath the impressive Colosseum, Rome is a fascinating place that has you peering upwards in wonder. Here you’ll explore tales of emperors, gladiators, wealth, and war with our family-friendly adventure.

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Capri at sunset

GRAPES AND GROTTOS ON HIDDEN PEAKS

Italy is diverse – from the snow-capped peaks of the Alps to the urban metropolis of Milan – there’s no shortage o...

Italy is diverse – from the snow-capped peaks of the Alps to the urban metropolis of Milan – there’s no shortage of landscapes to get lost in luxury. Experience some of the best wine in the world with our private Tuscany tours, or set up shop on the island of Capri, where turquoise waters lap onto sun-soaked beaches. The choice is yours.

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The Italian Dolomites

A WINTER ESCAPE INTO THE MESMERISING DOLOMITES

While Italy doesn’t scream Winter Wonderland, we think it should. Cosy and homey, it’s not just for the skiers – t...

While Italy doesn’t scream Winter Wonderland, we think it should. Cosy and homey, it’s not just for the skiers – think wellness spas, hot tubs with unbeatable vistas, sauna sessions and Turkish baths for your luxury holiday this time. Nights can be filled with horse-drawn carriage rides to charming villages, cluttered with Christmas markets and illuminated castles. It may not be your average Italian holiday, but it will be one that delivers everlasting memories.

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Tuscany in Italy

Rolling hills of Tuscany

If Italy was an art gallery then Tuscany, both rural and urban, would be its masterpiece. Learn the little-known stories...

If Italy was an art gallery then Tuscany, both rural and urban, would be its masterpiece. Learn the little-known stories hidden in the Renaissance architecture of Florence on a private guided tour. Take an exclusive hot air balloon ride over Val d’Orcia’s calm and colorful hills en route to wine tasting at the region’s best-in-class vineyards before joining a truffle hunt with some locals.

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Verona, Italy

Romantic Verona

Romance runs through the city that provided the setting for Shakespeare’s Romeo and Juliet. Around the corner from eve...

Romance runs through the city that provided the setting for Shakespeare’s Romeo and Juliet. Around the corner from every busy photo op are quaint streets and piazzas peppered with alluring architecture and fine dining. Private table at the much-loved Bottega del Vino? Space is limited and we make no guarantees about how much room you’ll have for dessert after you’ve mopped up the exquisite Baccalà con Polenta and Risotto con Vino Amarone.

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Milan duomo cathedral, Italy

Fashionable Milan

The home of Italian futurism and the motor car, Milan is an evolving city steeped in history. Why not experience its bes...

The home of Italian futurism and the motor car, Milan is an evolving city steeped in history. Why not experience its best contradictions? Indoors, you can get lost in an endless supply of 20th-century art, treat your taste buds with the aroma and soft taste of infused risotto alla Milanese, or stroll the Quadrilatero d’Oro for retail therapy via the world’s most exclusive brands, such as Salvatore Ferragamo and Bottega Veneta.

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Magna Pars Suites, Milan

Magna Pars Suites, Milan

This former perfume factory turned hotel is designed to awaken your senses with its secret garden and perfumed suites. L...

This former perfume factory turned hotel is designed to awaken your senses with its secret garden and perfumed suites. Located in the heart of Milan’s design district, Magna Pars’ state-of-the-art contemporary interiors echo the stitch-perfect style of the surrounding locale

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Sumptuous Italian living at COMO Castello del Nero

Como Castello Del Nero, Tuscany

Recharge your batteries in the ultra-modern spa, dine on Michelin-starred cuisine or venture out for a cooking class to ...

Recharge your batteries in the ultra-modern spa, dine on Michelin-starred cuisine or venture out for a cooking class to learn a nonna’s secret recipes in her authentic farmhouse. The calming retreat that is Castello Del Nero will leave you as relaxed as the rolling landscape you’re surrounded by.

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Luxury camping with Black Tomato

Blink luxury camping

We don’t limit you to bricks and mortar hotels. Luxury Blink camping lets you spend a night anywhere. Explore breathta...

We don’t limit you to bricks and mortar hotels. Luxury Blink camping lets you spend a night anywhere. Explore breathtaking Tuscan hilltops, escape to alpine serenity at Lake Lugano, or head into the untouched wilderness along the Amalfi Coast. Whether you’re planning a remote retreat or simply getting away from city life for a night of bliss, Blink allows you to experience a different side to Italy and feel true tranquility.

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Vatican museum tour in Rome

Enjoy exclusive access to the Vatican

Soak up the history of the Sistine Chapel and stroll around the Raphael Rooms at your leisure, enjoying the papal city i...

Soak up the history of the Sistine Chapel and stroll around the Raphael Rooms at your leisure, enjoying the papal city in complete privacy. The iconic St. Peter’s Basilica presents the finest hour of Renaissance architecture and is also the ideal spot to appreciate panoramic views of the Vatican gardens.

Visit as part of ‘The Young Pope’ tour (inspired by the landmark 2016 series) and spend eight nights in the lap of luxury, with your very own private jet, prestige hotels, unique dining experiences, and more.

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Lake Como in Italy

Explore Lake Como from a private helicopter

Take to the air with a unique helicopter tour over Lake Como and enjoy the neoclassical architecture set against the hyp...

Take to the air with a unique helicopter tour over Lake Como and enjoy the neoclassical architecture set against the hypnotic waters from above. Survey the striking green hills and take in the dramatic scenery with the wind running through your hair. When you’re ready to take a break, stop off for a bite to eat at the breathtaking Isola Bella island, privately catered for with fresh-caught pesce persico ready to satisfy your taste buds.

This is just one of our many exciting experiences on Lake Como.

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Climb Mount Etna in Sicily

Get close and personal with Europe’s highest volcano

With a private Jeep tour taking you through the winding slopes, explore the ever-changing lunar-esque environment of the...

With a private Jeep tour taking you through the winding slopes, explore the ever-changing lunar-esque environment of the explosive Mount Etna. From bubbling lava to the smoking cap, feel the heat of the active volcano like nothing else, with exclusive views of the wondrous Sicilian landscape, this is like nowhere else in Italy and our all-inclusive trip is one to remember.

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“Our clients have a thirst for feeling like a local; for shrugging off the crowds and going beneath the surface. It’s why we arrange for them to learn the art of cucina contadina. To get their hands dirty with a truffle hunter – or to experience the Sistine Chapel in absolute privacy.”

Sunil Metcalfe, Italy Travel Expert

Top Locations in Italy

If we were asked to choose our top three places in Italy, we’d go for these.
Rome in Italy

Rome

Welcome to the ‘eternal city’ – sacked, burnt to the ground, and rising resplendent.

The Vatican City, the Spanish Steps, the Colosseum and the modernist abandon of the EUR district. Our trips to Rome do justice to its curious and ancient history; with cucina povera and enotecas (rustic cooking and on-trend wine bars, in effect).

Rifugio in the Dolomites

The Dolomites

The so-called pale mountains are the home of thrilling climbs and slow food.

Steep, rugged, beautiful, otherworldly. This is a very different Italy to Sicily and the Amalfi coast. Some come for its slow food, others for its ski resorts and local obsession with via ferrata (pre-roped, semi-climbing routes). For hikers, the remote villages and stunningly clear air are reason enough. 

Puglia in Italy

Puglia

This is where the Italians go to relax.

Limestone clifftop towns and patient Adriatic waters. Puglia is the calm ‘breadbasket’ of Italy – providing much of the country’s olive oil and wheat. The food is roughly beautiful and amazingly fresh. Towns like Ostuni and Matera are a honeycomb of labyrinths and mazes. At Borgo Egnazia, you’ll encounter one of the world’s most immersive hotels.

Best Hotels in Italy

Nothing but the best. Browse our handpicked, tried-and-tested Italy hotels.

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