Rail & Sail: Italy with Orient Express

Two icons of luxury travel, one extraordinary Italian odyssey. Journey through the rolling hills of the Italian countryside aboard the magnificent Orient Express La Dolce Vita, before setting sail along the shimmering shores of the Amalfi Coast and Sicily on the world's largest sailing yacht, the Orient Express Corinthian. This is Italy as only a privileged few will ever know it.

Italy, Sicily, Malta
12 nights private tour from SGD $40,900

Journey highlights

  • Two Icons of Luxury Travel, One Seamless Journey. This itinerary uniquely pairs two of the world's most extraordinary and talked-about ways to travel. The legendary La Dolce Vita Orient Express and the world's largest sailing yacht, the Orient Express Corinthian, combine to create a journey that is wholly exclusive and unlike anything else on the market

  • Unrivalled Culinary Excellence. From three-Michelin-starred Chef Heinz Beck's seasonally inspired menus aboard the train, to private villa dinners on Capri and the authentic flavours of Naples, food is woven beautifully and meaningfully throughout every chapter of this journey

  • Be Among the First to Sail on the Orient Express Corinthian. This is a rare and genuinely historic opportunity. As one of the first guests to sail aboard the Orient Express Corinthian during its inaugural season, you will be part of something truly momentous in the world of luxury travel. This is not simply a holiday, it is a place in history, an experience so exclusive and so new that only a privileged handful of travellers in the world will ever be able to say they were among the first to discover her.

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Itinerary

Day 1 - 3
  • Rome

    At a Glance

    Day 1: Aboard La Dolce Vita Orient Express

    Departing July 30th 2026

    Your extraordinary journey begins at Rome Ostiense, where the legendary La Dolce Vita Orient Express awaits. Settle into your beautifully appointed surroundings as Italy begins to unfold beyond your window. Lunch is a celebration in itself, with three-Michelin-starred Chef Heinz Beck crafting a menu of exquisite Italian-inspired dishes, each one a reflection of the season and the landscape you are passing through.

    Arriving into Venice in the late afternoon, the city is yours to discover. We can arrange any number of exclusive experiences to help you uncover the very best of La Serenissima, from private gondola tours to after-hours museum visits. As midnight approaches, the train quietly departs for the picturesque shores of Portofino.

     

    Day 2: Portofino

    Wake gently to the rhythm of the train and begin your morning with an authentic Italian breakfast, unhurried and utterly indulgent. Arriving into Santa Margherita Ligure, a private transfer takes you into Portofino, where the rest of the day is entirely your own. Explore the harbour, wander the pastel-hued lanes, or simply find a terrace and let the beauty of the Ligurian coast wash over you.

    This evening, return to the train for a truly elegant dinner. Exceptional cuisine, live music and a refined atmosphere combine to create something rather special, the perfect way to draw the curtains on a memorable day.

    Where to stay

    La Dolce Vita Orient Express (2 nights)

Day 3 - 5
Day 5 - 13
  • Amalfi Coast & Sicily

    At a Glance

    Day 5: Embarkation Day

    Departing August 3rd 2026

    After checking out of Casa Monti, your private transfer takes you to the cruise port, where the magnificent Orient Express Corinthian awaits. Board in the late afternoon and allow the coastline to slip quietly from view. As dusk settles over the water, a sense of anticipation builds for the journey ahead, one defined by beauty, culture and the most effortless kind of discovery.

     

    Days 6 & 7: Naples

    Naples greets you with all of its wonderful, unfiltered energy. A city that feels entirely and unapologetically alive, it rewards those curious enough to explore beneath the surface. Wander through grand palaces and hidden baroque churches, venture to the haunting ruins of Pompeii where history has been preserved in extraordinary detail, or simply surrender to the pleasure of a perfectly pulled espresso and the rhythms of daily Neapolitan life.

     

    Days 8 & 9: Capri

    Rising dramatically from the glittering sea, Capri has long captivated artists, aristocrats and discerning travellers alike, and it is not difficult to understand why. There is an air of discreet glamour here that feels entirely effortless. Wander through elegant piazzas, marvel at the ethereal beauty of the Blue Grotto, or find a secluded terrace and simply absorb the luminous Mediterranean light. One evening, a private dinner in an exclusive island villa offers a rare and truly memorable glimpse into Capri at its most refined.

     

    Days 10 & 11: The Amalfi Coast

    The Amalfi Coast needs little introduction, yet it has a way of surpassing every expectation. Pastel-coloured villages cling improbably to dramatic cliffsides, lemon groves scent the warm air, and time seems to slow to a pace that feels almost forgotten in the modern world. Explore the magnificent cathedral at the heart of Amalfi town, lose yourself in quiet alleyways, or simply sit and absorb the extraordinary beauty of it all. There is an unspoken understanding here that the finest things in life are best enjoyed without haste.

     

    Day 12: Giardini Naxos & Taormina, Sicily

    Crossing to Sicily, you arrive at Giardini Naxos, where ancient history and laid-back coastal charm exist in perfect harmony. Once a proud Greek colony, this captivating corner of the island invites unhurried exploration, whether through fascinating archaeological sites or along golden stretches of beach. Just above, the hilltop town of Taormina offers sweeping panoramic views and a timeless sense of elegance that has drawn visitors for centuries.

     

    Day 13: Syracuse

    In Syracuse, history does not simply exist, it breathes. Wander through magnificent baroque piazzas and along ancient walls that gaze out over the Ionian Sea, and you begin to understand why this city has inspired writers, philosophers and travellers throughout the ages. From its classical Greek roots to its richly layered more recent past, every corner of Syracuse has a story to tell, and each one feels quietly, profoundly beautiful.

     

    Day 14: Valletta, Malta & Disembarkation

    Your journey draws to a close in Valletta, one of Europe's most captivating and culturally rich capitals. Built from honey-coloured limestone and steeped in centuries of extraordinary history, this compact yet magnificent city rewards gentle exploration. Wander through grand baroque streetscapes and discover hidden courtyards that speak of a fascinating past. It is a fitting finale to an exceptional voyage, leaving you with the feeling that you have travelled not simply across the Mediterranean, but through time itself.

    Where to stay

    Orient Express Corinthian (8 nights)

Why book a Journey by Land & Sea

When to visit

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Best time to visit
Good time to visit
Average time to visit

Southern Italy's climate makes the area a year round destination. It is important to remember that the main tourism season stretches from mid-April to the end of September with July and August being peak months. The best time to visit is in the quieter part of the season, from April to June and from September to October when weather is usually good, prices lower and there are "fewer" tourists. Many have also discovered the advantages of visiting during the "low season" (winter and early spring) as rates are lower and the reduced number of tourists is visible.

Rail & Sail: Italy with Orient Express
Rail & Sail: Italy with Orient Express

We design each itinerary around you, so this suggested itineraryis a starting point that we can tweak or transform into something completely bespoke to you. Call us on +65 6028 0858 to start planning your holiday.

Plan your trip

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