Luxury Italy holidays

From trattoria kitchen to lakeside palace, from Tuscan countryside to Sicily’s seaside idyll, Italy is one of the world's great masterpieces. And, with a history steeped in the Romans and the Renaissance, along with more than 50 UNESCO-listed treasures to its name, it has a history to match its abundant natural allure.

Indeed, when confronted with Italy’s myriad cultural delights, it’s often easiest to think of the country as a collection of 20 regions, each with its own distinct identity. Sicily is a case in point; Greek temples crouch in valleys, vineyards terrace green hills and playful Mediterranean cuisine is served up in seaside villages. It’s a world away from Rome’s architectural exuberance – where you can trace the source of whole empires and religions between the crumbling colonnades of the Roman Forum and the Michelangelos of the Vatican’s Sistine Chapel. Then there’s the rural charm of Tuscany where medieval towns and wineries are dotted across rolling countryside.

That’s the joy of Italy. One moment you could be relaxing in a Belle Époque palace on the Italian Lakes, and the next looking out over the Amalfi coast. Here, centuries-old houses overlook dramatic cliffs to the beach-fringed waters below. And our multi-stop itineraries will bring you between the country’s richly varied highlights in style, enjoying stays in luxury accommodation and the services of private drivers and guides throughout. But, there’s one thing that’s found throughout the country – an appreciation of la dolce vita, the good life. You’ll be well looked after whether you’re feasting on a Fiorentina steak, sipping prosecco in Venice or waking up to an espresso in a piazza-side café.


Special experiences in Italy

Enjoy a private gozzo tour of the Amalfi Coast to a secluded restaurant or explore the region’s bohemian towns – whether you cruise around in a classic sports car or on a Vespa is up to you. Alternatively, take a hot air balloon and float over the ancient village towns and vineyards of the rolling Chianti hills. Let your charismatic guide bring alive the days of the Roman Empire while you investigate the eerie remains of Pompeii and Herculaneum or ask about how to visit after the crowds have departed. Explore the striking coastlines of the Aeolian Islands on a gullet-style tall ship or discover Sardinia’s pristine beaches and glamorous nightlife aboard a super yacht. Wander between the villas and gardens on the shores of Lake Como or explore the Italian Lakes aboard a timelessly elegant Riva yacht. Take to the roads of northern Italy and drive the route of the Mille Miglia in a classic Gran Turismo sports car. Lose yourself in the mystique of the masked carnival in Venice, we can even help you to arrange your own private masked ball in a palazzo, and experience a behind-closed-doors visit to St Marks or the Sistine Chapel. Enjoy a private visit to the most prestigious Murano glass factories or see behind the scenes of a fashion superbrand. Join a local and his dog to look for truffles in the Abruzzo or learn how to make the most amazing pasta in a cookery lesson with either a local family or an Italian Mamma. Imagine the stories you’ll tell.

Italian food

Discover the delights of Italian food on a cookery course

The canals of Venice

Take a gondola through the canals of Venice

Lake Como, Italy

Discover grand villas and scenic beauty on the shores of Lake Como

Where to stay in Italy

Spoil yourself with a stay in an opulent Venetian palazzo such as Baglioni Hotel Luna or base yourself in a private Roman residence. Take time out in a traditional Tuscan farmhouse or restored fort, experience life in a converted Franciscan monastery or traditional Puglian masserie and immerse yourself in a restored alberghi diffusi in the Abruzzo. Indulge yourself with vintages available at your hilltop winery retreat or bask in the luxury and privacy on offer at your private lakefront Como villa or stunning coastal escape. Ask us too about travelling on the Venice Simplon-Orient-Express to experience old world glamour and serious style on a great rail journey across Europe. 

When to go to Italy

Because Italy can be exceptionally busy, ask us about how to explore the country in the shoulder seasons, travelling to the cities and countryside in spring or autumn instead of high summer. Alternatively, grab a towel to travel to the beach in June or September. Otherwise, look out for annual events such as the Venice Carnival in February or the Palio in Sienna in July and August and plan ahead to secure the best bases from which to experience these exceptional events.

Suggested itineraries

Capri, Italy

Capri and the Amalfi Coast

Guide price from £3,530 pp

Capri and the Amalfi coast are characterised by vertiginous cliffs and grand, salt-encrusted villas. Crescent beaches in secluded coves line an aquamarine sea, and there’s history at every turn.

Taormina, Sicily

Best of Sicily

Guide price from £1,915 pp

From glorious swathes of golden sand to millennia-old ruins framed by scented lemon groves and sun-soaked vineyards, Sicily’s highlights are as enchanting as they are varied. Take it all in with stays in iconic hotels and scenic country drives.

Belmond Cipriani Bar and Pool

Venice by Hotel Cipriani

Guide price from £5,505 pp

Not only will this city break see you stay in one of Italy’s most iconic hotels, but you’ll indulge with lagoon cruises, food and wine tastings, and private water-taxi transfers throughout.


Florence & the Tuscan countryside in luxury

Guide price from £2,765 pp

With luxury stays in a historic country houses, this curated itinerary showcases Florence and Tuscany at their very best.

Murano, Venice Islands

Venice Simplon-Orient-Express & Venice’s Islands

Guide price from £4,370 pp

Before travelling on the world’s exclusive train, hop between Venice’s archipelago, centring on a luxury stay on your very own private island.

Arena di Verona

Venice Simplon-Orient-Express & Verona Opera

Guide price from £6,470 pp

This spectacular short break combines a journey on the world’s most elegant train with a stay in a converted palace and of opera at the iconic Arena di Verona.

Varenna, Lake Como

Venice Simplon-Orient-Express & Lake Como

Guide price from £6,890 pp

Travel from London to Verona onboard the world’s most famous train, finishing off with a truly opulent stay on the shores of Italian lake country.

Cinque Terre

Cinque Terre in Style

Guide price from £1,810 pp

Explore the myriad coastal delights of Cinque Terre on this luxury tour, enjoying everything from wine tasting in world-class vineyards to sampling local bruschetta in cosy trattorias.

Grand Canal, Venice
Special offer

Venice Simplon-Orient-Express: Venice to London

Guide price from £4,845 pp

Save up to £1,245 pp – ends 31 Jul

A counterpoint to the classic London to Venice route, this journey aboard the Venice Simplon-Orient-Express starts in Italy's floating city before crossing the Alps in style en route to Paris, then via Eurostar to London.

Grand Suite (Artist's Impression), Venice Simplon-Orient-Express

Venice Simplon-Orient-Express Grand Suite Experience

Guide price from £12,280 pp

From free-flowing champagne to complimentary caviar, experience the ultimate in luxury rail travel with the butler-served indulgences of the new Venice Simplon-Orient-Express Grand Suites.


Puglia & Matera: Urban charms & rural delights

Guide price from £2,160 pp

Combine the historic treasures of Matera with an in-depth exploration of Puglia’s urban and rural delights, including visits to the trulli houses of Alberobello, a cheese tasting experience and a peaceful stay on the Adriatic Coast.


Western Sicily & the Aegadian Islands

Guide price from £3,960 pp

Visit ancient temples, medieval hilltop villages and gorgeous beaches on this in-depth adventure around Western Sicily and the Aegadian Islands, along with stays in stylish, boutique accommodation throughout.

Sardinia coast

Best of Sardinia

Guide price from £3,225 pp

Discover Sardinia’s historic cities, rural villages, ancient archaeological sites and idyllic beaches on this self-drive adventure, starting on the south coast and ending up in the far north.

Assisi, Umbria

Tastes of Umbria

Guide price from £1,735 pp

Delve into the rich culinary heritage of Umbria and discover its medieval hilltop towns on this food-themed journey into the green heart of Italy.

Castel Monastero, Tuscany

Andrea Bocelli at Teatro del Silenzio

Guide price from £3,435 pp

Enjoy VIP tickets to Italy's greatest musical showpiece as you travel to Tuscany to experience Andrea Bocelli performing at the picturesque Teatro del Silenzio in the hills of Tuscany. Pair it all with a three-night stay at the stunning Castel Monastero.

Roman Forum, Rome

Italy in style: Rome & Florence

Guide price from £2,795 pp

Discover two of Italy's most beautiful and historic cities. Start by discovering the likes of the Pantheon and Trevi Fountain in the iconic city of Rome, before exploring the gothic piazzas of romantic Florence.

Vineyards near Montalcino, Italy

La Dolce Vita Orient Express: Rome & Tuscany

Guide price from £4,015 pp

Enjoy a unique journey aboard Europe's latest ultra-luxury train – La Dolce Vita Orient Express – pairing the famous hills and vineyards of Tuscany with the Eternal City of Rome.

Venice, Italy

La Dolce Vita Orient Express: Rome, Venice & Siena

Guide price from £7,195 pp

Enjoy an epic journey through Venice, the Tuscan city of Siena and the Eternal City of Rome on board Europe's latest ultra-luxury train – La Dolce Vita Orient Express – taking in the myriad wonders of some of Italy's most admired regions.


La Dolce Vita Orient Express: Rome, Matera & Palena

Guide price from £6,095 pp

Discover little-known Palena, the ancient city of Matera and the Eternal City of Rome on board Europe's latest ultra-luxury train – La Dolce Vita Orient Express – taking in the myriad wonders of some of Italy's most admired regions.

Orient Express La Dolce Vita

La Dolce Vita Orient Express: Rome, Venice & Portofino

Guide price from £7,590 pp

Experience the wonders and secrets of Rome, Venice and Portofino on this epic journey on board the brand new one-of-a-kind train – La Dolce Vita Orient Express.

St Mark's Square, Venice

Venice Simplon-Orient-Express: A taste of luxury

Guide price from £4,870 pp

Enjoyed across three unforgettable days, this itinerary is perfect for those looking to experience the Venice Simplon-Orient-Express but are short on time

Venice Simplon-Orient-Express

Venice Simplon-Orient-Express: London to Paris & Venice

Guide price from £4,860 pp

With Eurostar included, this is the iconic southbound journey from Paris to Venice aboard the Venice Simplon-Orient-Express, paired with stays in two luxury hotels.

Villa Cordevigo, Verona

Lake Garda: From Grape to Glass

Guide price from £1,470 pp

Indulge on fine wines, dine on Michelin-starred Italian cuisine and explore Lake Garda's stunning scenery from the 18th-century charm of Villa Cordevigo – a truly luxurious gourmet getaway.

contemporary building among green vineyards with gated entrance

Sicily: Vineyards and Volcanoes

Guide price from £2,065 pp

Escape to Sicily for four nights of relaxation at a romantic boutique resort. Experience the island like a local, tasting authentic foods and wines throughout.

Zadar, Croatia

Treasures of the Adriatic with Regent Seven Seas Cruises

Guide price from £7,850 pp

Discover the ancient treasures and natural wonders of Croatia, Greece and Turkey on this luxurious Mediterranean cruise, sailing in all-inclusive style with Regent Seven Seas Cruises.

Restaurant at Grand Hotel Convento Di Amalfi at sunset overlooking Amalfi coast.

Amalfi Coast with private chef experience

Guide price from £5,865 pp

A short break for foodies. Spend three nights at a luxurious coastal hotel, coupled with an exclusive culinary experience in the company of a private-chef.

Fiat 124 Spider, Amalfi Coast

Amalfi Coast with sports car experience

Guide price from £2,185 pp

Explore Italy's Amalfi Coast in style, with a stay at a luxury clifftop hotel and a day's use of a Vintage Alfa Romeo Spider.

S.S. La Venezia
Special offer

Verona & Northern Italy Cruise

Guide price from £3,615 pp

Save up to £1,075 pp – ends 31 Jul

This spectacular itinerary combines a luxurious all-inclusive Uniworld cruise among the waterways of Venice with a stay in the heart of Shakespeare's city – Verona.

St Mark's Square, Venice
Special offer

Northern Italy Cruise & Venice Simplon-Orient-Express

Guide price from £8,400 pp

Save up to £730 pp – ends 31 Jul

Experience one of travel's great pairings as you combine a cruise among the treasures of Northern Italy with the luxurious delights of the Venice Simplon-Orient-Express.

Burano at sunset, Italy
Special offer

Venice Simplon-Orient-Express & Northern Italy River Cruise

Guide price from £9,025 pp

Save up to £485 pp – ends 31 Jul

Discover Venice and its surrounds in unmatched style as you pair the Venice Simplon-Orient-Express with a five-star cruise.

Florence, Italy

Venice Simplon-Orient-Express: Florence to London

Guide price from £5,235 pp

Journey aboard the iconic Venice Simplon-Orient-Express, starting amid the exquisite architecture of Florence before crossing the Alps in style en route to London.

Amsterdam Canal Sunset

Venice Simplon-Orient-Express: Venice & Amsterdam to London

Guide price from £6,395 pp

This journey aboard the Venice Simplon-Orient-Express starts among the exquisite architecture of Italy's floating city before crossing the Alps in style en route to the canals and museums of Amsterdam.

Brussels, Belgium
Special offer

Venice Simplon-Orient-Express: Venice & Brussels to London

Guide price from £5,845 pp

Save up to £465 pp – ends 31 Jul

This journey aboard the Venice Simplon-Orient-Express starts among the exquisite architecture of Italy's floating city before crossing the Alps in style en route to the gastronomy, architecture and cafe culture of Brussels.

Roman Forum, Rome

Venice Simplon-Orient-Express: Rome to London

Guide price from £5,100 pp

A counterpoint to the classic London-Venice route, this luxury journey aboard the Venice Simplon-Orient-Express takes you in unmatched style between Rome and London.

Verona, Italy
Special offer

Venice Simplon-Orient-Express: Verona to London

Guide price from £4,485 pp

Save up to £1,240 pp – ends 31 Jul

Beginning with a luxury city stay and included walking tour in Verona, you'll board the Venice Simplon-Orient-Express for an unforgettable journey across Europe, steeped in the elegant traditions of 1920s rail travel.

Get in touch and let a personal travel consultant help book your bespoke holiday