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-day tailor-made holiday from £3,445 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-day tailor-made holiday from £1,870 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.

Tuscany

Florence & the Tuscan countryside in luxury

9-day tailor-made self-drive holiday from £2,700 pp incl. flights

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

Assisi, Umbria

Tastes of Umbria

5-day tailor-made holiday from £1,705 pp incl. flights

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.

contemporary building among green vineyards with gated entrance

Sicily: Vineyards and Volcanoes

5-day tailor-made city break from £2,020 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.

Alberobello

Puglia & Matera: Urban charms & rural delights

11-day tailor-made self-drive from £2,595 pp incl. flights

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.

Cinque Terre

Cinque Terre in Style

7-day tailor-made break from £1,770 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.

Forio, Ischia island, Italy

Neapolitan treasures: Ischia & the Bay of Naples

8-day tailor-made break from £2,665 pp incl. flights

This seven-day itinerary takes you on a luxurious journey through the vibrant streets of Naples and the serene landscapes of Ischia. Experience the best of both worlds as you explore ancient ruins, sample authentic Italian cuisine, and unwind in idyllic island surroundings.

Roman Forum, Rome

Italy in style: Rome & Florence

7-day tailor-made holiday from £2,735 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.

Sardinia coast

Best of Sardinia

11-day tailor-made self-drive from £3,145 pp incl. flights

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.

S.S. La Venezia
Special offer

Verona & Northern Italy Cruise

10-day tailor-made cruise holiday from £3,750 pp incl. flights

Save up to £285 pp – ends 31 Oct

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.

Villa Cordevigo, Verona

Lake Garda: From Grape to Glass

4-day tailor-made holiday from £1,440 pp incl. flights

Indulge in 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.

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

Amalfi Coast with private chef experience

4-day tailor-made break from £5,640 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-day tailor-made break from £2,135 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.

Belmond Cipriani Bar and Pool

Venice by Hotel Cipriani

4-day tailor-made city break from £5,370 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.

Murano, Venice Islands
Special offer

Venice Simplon-Orient-Express & Venice’s Islands

4-day luxury rail journey from £5,220 pp incl. flights

Save up to £370 pp – ends 31 Oct

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

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

7-day luxury rail journey from £6,820 pp incl. flights

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.

Grand Canal, Venice
Special offer

Venice Simplon-Orient-Express: Venice to London

4-day tailor-made holiday from £4,635 pp incl. flights

Save up to £1,275 pp – ends 31 Oct

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-day luxury rail journey from £12,250 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.

Cefalu

Western Sicily & the Aegadian Islands

14-day tailor-made holiday from £3,865 pp incl. flights

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.

Castel Monastero, Tuscany

Andrea Bocelli at Teatro del Silenzio

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.

Vineyards near Montalcino, Italy

La Dolce Vita Orient Express: Rome & Tuscany

4-day luxury rail journey from £3,915 pp incl. flights

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

5-day luxury rail journey from £7,010 pp incl. flights

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.

Matera

La Dolce Vita Orient Express: Rome, Matera & Palena

5-day luxury rail journey from £5,940 pp incl. flights

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

5-day luxury rail journey from £7,400 pp incl. flights

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.

Venice Simplon-Orient-Express
Special offer

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

5-day luxury rail holiday from £4,825 pp incl. flights

Save up to £1,240 pp – ends 31 Oct

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.

Burano at sunset, Italy
Special offer

Venice Simplon-Orient-Express & Northern Italy River Cruise

12-day tailor-made holiday from £8,650 pp incl. flights

Save up to £925 pp – ends 31 Oct

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

St Mark's Square, Venice
Special offer

Northern Italy Cruise & Venice Simplon-Orient-Express

11-day tailor-made holiday from £7,500 pp incl. flights

Save up to £1,225 pp – ends 31 Oct

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.

Roman Forum, Rome
Special offer

Venice Simplon-Orient-Express: Rome to London

4-day tailor-made holiday from £4,695 pp incl. flights

Save up to £390 pp – ends 31 Oct

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.

Amsterdam Canal Sunset

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

6-day tailor-made holiday from £5,945 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.

Florence, Italy
Special offer

Venice Simplon-Orient-Express: Florence to London

4-day tailor-made holiday from £4,955 pp incl. flights

Save up to £470 pp – ends 31 Oct

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.

Brussels, Belgium

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

6-day tailor-made holiday from £6,450 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.

Verona, Italy
Special offer

Venice Simplon-Orient-Express: Verona to London

4-day luxury rail journey from £4,470 pp incl. flights

Save up to £1,240 pp – ends 31 Oct

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.

Sant'Angelo, Ischia island, Italy

Ischia and the Amalfi Coast

Pair a luxury seafront stay on the Amalfi Coast with an idyllic island escape in Ischia on this delightful twin-centre Italian getaway.

Vulcano

Volcanic wonders of Vulcano & Sicily

8-day tailor-made holiday from £2,035 pp incl. flights

Discover the wild and rugged volcanic landscapes of Vulcano in the Aeolian Islands before spending a couple of nights in the verdant foothills of Mount Etna on this delightful, off-beat Italian escape.

Arena di Verona

Italian opera experience at Arena di Verona

4-day tailor-made holiday from £1,785 pp incl. flights

Experience the pinnacle of Italian culture with a night of Opera at the iconic Arena di Verona on this luxury getaway, alongside a stay in a historic 14th-century palace, time to explore a city steeped in history and romance, and a visit to the Soave wine region, renowned for it's white wines.

Turquoise stone beach in Rovinj, Croatia
Special offer

Adriatic Odyssey with Ponant & the Venice Simplon-Orient-Express

14-day luxury rail and cruise holiday from £9,065 pp incl. flights

Save up to £540 pp – ends 31 Oct

From the medieval walls of Dubrovnik to the romantic waterways of Venice, experience the best of the Adriatic aboard Ponant's L'Austral. Following a stay in the city of canals, conclude your epic journey with a truly unforgettable experience on the world-renowned Venice Simplon-Orient-Express.

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