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

10 days from £3,370 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 £1,915 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.

Belmond Cipriani Bar and Pool

Venice by Hotel Cipriani

4 days from £5,375 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 lagoon cruises, food and wine tastings, and private water-taxi transfers throughout.


Florence & the Tuscan countryside in luxury

9 days from £2,625 pp incl. flights

Early booking savings Relais Le Corte de Papi

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

4 days from £4,370 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

5 days from £6,470 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 £6,440 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

7 days from £1,810 pp incl. flights

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

Venice Simplon-Orient-Express: Venice to London

4 days from £3,995 pp incl. flights

March and April 2024 departures savings

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

5 days from £12,280 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.

Castel Monastero, Tuscany

Andrea Bocelli at Teatro del Silenzio & Castel Monastero

4 days from £2,685 pp incl. flights

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 with a traditional pre-concert dinner and a relaxing three-night stay at the stunning Castel Monastero.

Portofino, Italy

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

5 days from £8,960 pp incl. flights

Experience one of the world's most revered trains at its opulent best as you travel aboard the Venice Simplon-Orient-Express to charming Portofino, in the Italian Riviera, including stays in some of Europe's finest hotels.

Roman Forum, Rome

Italy in style: Rome & Florence

7 days from £3,070 pp incl. flights

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.

St Mark's Square, Venice

Venice Simplon-Orient-Express: A taste of luxury

3 days from £4,870 pp incl. flights

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

Grand Canal, Venice

Adriatic in style with SeaDream & the Venice Simplon-Orient-Express

11 days from £11,005 pp incl. flights

A luxury holiday of two halves, this rail and cruise epic pairs a journey aboard the world's most celebrated train with a yacht adventure among the historic delights of the Adriatic Sea.

Venice Simplon-Orient-Express

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

5 days from £4,920 pp incl. flights

Apr 2024 departure savings

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

4 days from £1,445 pp incl. flights

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

5 days from £1,885 pp incl. flights

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

11 days from £7,725 pp incl. flights

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

4 days from £4,895 pp incl. flights

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

4 days from £2,725 pp incl. flights

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.

St Mark's Square, Venice

Northern Italy Cruise & Venice Simplon-Orient-Express

11 days from £6,770 pp incl. flights

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.

Florence, Italy

Venice Simplon-Orient-Express: Florence to London

4 days from £4,540 pp incl. flights

April departures 2024 special savings

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.

Piazza del Nettuno and Piazza Maggiore in Bologna, Italy

Venice Simplon-Orient-Express: Bologna, Food and Ferraris

6 days from £6,150 pp incl. flights

Journey aboard the iconic Venice Simplon-Orient-Express, starting amid the gastronomic centre of Bologna before crossing the Alps in style en route to London.

Brussels, Belgium

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

6 days from £5,440 pp incl. flights

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.

Amsterdam Canal Sunset

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

6 days from £5,505 pp incl. flights

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.

Verona, Italy

Venice Simplon-Orient-Express: Verona to London

4 days from £3,710 pp incl. flights

March and April 2024 departures savings

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.

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