Luxury Italy holidays

From trattoria 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 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

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 £2,540 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 £2,115 pp incl. flights

Save up to £130 pp – ends 31 October

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 £3,405 pp incl. flights

Save up to £210 pp – ends 31 October

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 £3,560 pp incl. flights

Save up to £145 pp – ends 31 October

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

5 days from £3,030 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

9 days from £3,310 pp incl. flights

Save up to £205 pp – ends 31 October

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 £3,195 pp incl. flights

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

4 days from £3,815 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.

Varenna, Lake Como

Venice Simplon-Orient-Express & Lake Como

6 days from £4,065 pp incl. flights

Save up to £495 pp – ends 30 November

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 £1,330 pp incl. flights

The coast of Italy has long been the epitome of romance and charm, and this is perhaps nowhere more apparent than among the pastel-hued villages and yacht-lined harbours of Cinque Terre.

Zykanthos, 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.

Grand Canal, Venice

Venice Simplon-Orient-Express: Venice to London

4 days from £3,135 pp incl. flights

Save up to £200 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 crossing the Alps in style en route to London.

Venice Simplon-Orient-Express

Venice Simplon-Orient-Express: Return to Venice

5 days from £4,965 pp

Save up to £1,000 pp – ends 31 October

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.

Casa Angelina, Amalfi Coast

Amalfi Coast with private chef experience

4 days from £2,330 pp incl. flights

Save up to £315 pp – ends 31 January

A short break for foodies. Spend three nights at an adults-only retreat, coupled with an exclusive sunset dinner experience in the company of a private-chef.

Fiat 124 Spider, Amalfi Coast

Amalfi Coast with sports car experience

4 days from £1,525 pp incl. flights

Save up to £285 pp – ends 31 January

Explore Italy's Amalfi Coast in style, with a stay at an adults-only hotel and a day's use of a Fiat 124 Spider.

Burano at sunset, Italy

Venice Simplon-Orient-Express & Northern Italy River Cruise

11 days from £5,325 pp incl. flights

Save up to £1,225 pp – ends 16 November

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

Vltava River, Prague

Venice Simplon-Orient-Express: Venice-Prague-London

7 days from £5,725 pp incl. flights

A journey on the legendary Venice Simplon-Orient-Express, from the historic waterways of Venice to medieval Prague and onwards to London. Enjoy city nights in luxurious hotel accommodation between stays onboard the train itself.

Venice, Italy

Venice Simplon-Orient-Express: Venice to London via Vienna

7 days from £5,360 pp incl. flights

Save up to £320 pp – ends 31 October

Extend your time aboard this iconic train to showcase two of Europe’s greatest cities between afternoon teas and bar-car drinks.

Verona, Italy

Venice Simplon-Orient-Express: Verona to London

4 days from £2,995 pp incl. flights

Save up to £155 pp – ends 31 October

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