Luxury Italy holidays

From <i>trattoria</i> kitchen to lakeside palace, from Tuscan countryside to Sicily’s seaside idyll and from Roman ruin to Renaissance cathedral, Italy has allure in abundance. With 51 UNESCO-listed treasures to its name, no country features more World Heritage Sites.

Indeed, when confronted with Italy’s sheer abundance of 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 contours 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 religion 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 dot a rolling countryside broken only by wineries.

That’s they joy of Italy. One moment you could be relaxing in a Belle Époque palace on the Italian Lakes, and the next looking out over Amalfi's bright patchwork. Here, centuries-old houses spill down 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

Countryside views in Tuscany, Italy

Discover the unmatched beauty of Tuscany

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

Florence, Italy

The Tuscan Coast & Florence

8 days from £1,595 pp incl. flights

Tuscany is famous for Renaissance art and architecture, with the city of Florence at its forefront. Less well known perhaps are the region’s beaches, each as lovely as the Botticelli Venus. This trip combines the beauty of both.

Capri, Italy

Capri and the Amalfi Coast

8 days from £2,125 pp incl. flights

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

8 days from £1,440 pp incl. flights

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.

Venice Simplon-Orient-Express

Venice Simplon-Orient-Express: London to Venice

4 days from £3,505 pp incl. flights

Between indulgent fine dining, champagne receptions and private city tours, this elegant journey pairs the ultimate in luxury rail travel with a palace stay in the heart of ancient Venice.

Belmond Hotel Cipriani

Venice Simplon-Orient-Express: Venice & London in Luxury

4 days from £3,515 pp incl. flights

This version of the classic the Venice Simplon-Orient-Express's northbound route pairs the world's most iconic rail experience with luxury stays in both Venice and London.

Belmond Hotel Cipriani

Venice by Belmond Hotel Cipriani

4 days from £2,345 pp incl. flights

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

Tuscan countryside

Florence & the Tuscan countryside in luxury

7 days from £2,360 pp incl. flights

With ultra-luxury stays in a millennium-old castle and a monastery designed by Michelangelo himself, this curated itinerary showcases Florence and Tuscany at their very best.


Venice Simplon-Orient-Express & Venice’s Islands

4 days from £3,260 pp incl. flights

Save up to £115 pp – ends 31 January

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

Verona Opera & the Venice Simplon-Orient-Express

4 days from £3,975 pp incl. flights

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.

Lake Como, Milan, Italy

The Venice Simplon-Orient-Express & Lake Como

6 days from £4,155 pp incl. flights

Save up to £330 pp – ends 31 January

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

6 days from £950 pp incl. flights

The coast of Italy has long been known as the epitome of romance and charm, but this is perhaps nowhere more apparent than among the pastel-hued villages, rugged cliffs and charming yacht-lined harbours of world-famous Cinque Terre. Explore it all on this tailor-made, luxury trip.

Kefalonia island, Greece

Venice Simplon-Orient-Express & Seabourn: London to Athens

14 days from £7,855 pp incl. flights

Combine one of the world's greatest rail journeys with an equally spectacular cruise to some of Europe's most iconic cities.

Pont Alexandre III , Paris, France

Venice Simplon-Orient-Express: Venice, Paris & Berlin

7 days from £6,335 pp incl. flights

Save up to £735 pp – ends 31 January

Experience the elegance and glamour of the Venice Simplon-Orient-Express on this three-centre itinerary, travelling on board the world's most luxurious train between Venice, Paris and Berlin.

Grand Canal, Venice

Venice Simplon-Orient-Express: Venice to London

4 days from £2,545 pp incl. flights

Save up to £470 pp – ends 31 October

A counterpoint to the classic London-Venice route, this journey aboard the Venice Simplon-Orient-Express starts among the exquisite architecture of Italy's floating city before the traversing the high passes of the Austrian Alps.

Venice Simplon-Orient-Express

Venice Simplon-Orient-Express: Return to Venice

5 days from £4,825 pp

Travel from London to Venice, and back again, aboard the Venice Simplon-Orient-Express, enjoying all the luxury and elegance of the world’s most famous train.

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

Venice Simplon-Orient-Express Grand Suite Experience

4 days from £7,985 pp incl. flights

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.

Bar Car, Venice Simplon-Orient-Express

Venice Simplon-Orient-Express with Belmond Hotel Cipriani "The Party"

3 days from £3,975 pp incl. flights

Combine a golden era of travel with a night of revelry; "The Party" will take you back to the magic of the 1920s to celebrate a new decade.

Verona, Italy

Venice Simplon-Orient-Express: Verona to London

4 days from £3,080 pp incl. flights

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.