Luxury Italy Vacations & Tailor-Made Trips
Why choose Black Tomato for your luxury Italy holiday
Our luxury Italy holidays are designed around the details that fire 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.
Details, details, details – that’s why. A sommelier-guided tour of Rome’s best enoteche (wine bars). Exclusive access to the Vatican. In Sicily, a luxury 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 world-class wines, and a canopy of stars. This is ideal stuff for families, friends, and lovers. But wherever you decide to go, it’s our job to create a perfectly bespoke travel itinerary for your Italy holiday, and not simply to sell you what’s gone before. That would be far too easy. And very un-Italian.
Example Italy trips
These are simply suggestions for the kind of luxury holidays you might have. Your itinerary will be tailor-made for you, altered, and refined until it matches you completely.
Speak to an expert
Meet our Italy Team
Call our experts or schedule a video consultation for inspiration and expert guidance.
Experiences our clients love
Call us to add any of these activities to your trip or for a consultation on our exclusive experiences
What to see and do in Italy
If these luxury Italy holidays aren't quite what you're looking for, our Italy destination experts will plan you a personalised trip. Just for you.
More about luxury Italy holidays
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.
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 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, and wealth with our Italy family holidays.
The best of 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 city breaks and 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). Most Italian itineraries include a stop in Rome and, once you’ve been, you’ll understand why.
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 north for its good life and 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
This is where the Italians go to relax on their own Italy holiday.
Limestone clifftop towns and patient Adriatic waters. Puglia is the calm ‘breadbasket’ of southern 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.
FAQs
Everything you need to know about visiting Italy with Black Tomato
Independent travel has its appeal, but Italy’s logistics — historic city driving restrictions, top restaurant reservations, experiences well beyond the tourist trail — can quietly consume your trip. A private holiday handles all of that while preserving the freedom that matters: a tailor-made itinerary designed around you, with local expertise opening doors you didn’t know existed.
The Langhe wine region delivers Barolo without the Tuscan crowds. Matera’s ancient cave dwellings are unlike anything else in the country. Puglia’s whitewashed towns feel genuinely undiscovered. The Dolomites rival the Alps with a fraction of the visitors. The best itineraries weave these lesser-known moments alongside the icons rather than choosing between them.
April to June offers mild weather, landscapes in bloom, and manageable crowds — ideal for Rome, Florence, and the Amalfi Coast. September and October bring harvest season and a more relaxed pace. December to March suits Alpine skiing. August is worth avoiding in the cities, when many Italians head out of town and the heat can be punishing.
Italy is one of the most welcoming destinations in the world for families. Children are genuinely embraced here, and the experiences tend to captivate all ages — pizza-making in Naples, gladiator school in Rome, gondola rides in Venice. Private villas with pools give families the space to decompress, and the best hotels here go well beyond tolerating children to actively catering to them.
Start with how you want to feel, not just where you want to go. Italy offers coastal relaxation, cultural immersion, and culinary adventure — often within a single region. A specialist who knows the country well can design around your interests and unlock experiences that simply aren’t available to independent travellers.
Luxury Italy holidays with Black Tomato start at £7,000 per person per week, with final costs based on your travel preferences since all trips are customised. Pricing varies based on location(s), time of year, hotels, transfers, experiences and more. For an accurate quote built around your specific travel dates and preferences, submit an enquiry and we’ll connect you with one of our Italy travel experts.
Looking for inspiration?
“Everything was seamless and easy. We had a great experience in Italy and had several adventures that I'm not sure we could have figured out…”
“Our first time using Black Tomato (BT). Celebrating a 40th wedding anniversary in a luxury manner was on the agenda. With the excellent support of…”
“Another wonderful BT trip - their 'boots on the ground' folks, in each city, were outstanding. The itinerary was carefully curated with all our hopes…”
“My husband and I just got back from a trip Alys planned for us to Italy. It was easily the most wonderful, stress free and…”
