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Luxury Italian Rail Vacations
Bespoke Luxury Travel designed for you

Discover Luxury Train Tours in Italy

A country of vivid coastlines and stunning cities steeped in history, Italy has long captured the hearts of travelers. At Vacations By Rail, unforgettable explorations against these breathtaking backdrops come standard, and our luxury rail vacations offer a glimpse into the soul of Italy.

Expertly curated details guide each course, taking you to locations where culture, art, cuisine, and tradition create an intoxicating environment for discovery. Enjoy the freedom to soak up Italy's allures with the knowledge that our 20 years of experience backs your adventures.

Utilizing Italy's extensive rail network, our memorable itineraries travel to places like the canals of Venice, the ancient Roman capital, the quaint towns amongst Tuscany's hills, the colorful Cinque Terre, and the breathtaking Amalfi Coast. Open your eyes and heart to Italian splendors with luxury rail tours from Vacations By Rail.

LuxuryLuxury
Ben Nevis
La Dolce Vita, Rome & Montalcino’s Tuscan Vineyards
5 days from $4,825 pp
  • Indulge in a winery experience and tasting of the Brunello variety in Montalcino
  • Stay two nights in Rome, exploring iconic landmarks like the Colosseum
  • Enjoy an overnight round trip on the luxurious La Dolce Vita Orient Express
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LuxuryLuxury
Venice Simplon Orient Express
Venice Simplon-Orient-Express, Rome and Venice
7 days from $6,995 pp
  • Discover historic Rome over three days with a pasta-making class or wine tasting
  • Experience Venice over two days with a guided tour and regional excursions
  • Board the luxurious Venice Simplon Orient Express train in Venice & disembark in Paris
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LuxuryLuxury
Ben Nevis
La Dolce Vita, Rome, Venice & Portofino
7 days from $11,050 pp
  • Discover historic Rome over three days with a pasta-making class or wine tasting
  • Visit a prestigious Venetian Palace before dinner in an ancient Palazzo
  • Stroll around picturesque Portofino and sail along the Mediterranean Sea
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Luxury Train Journeys
Experience opulence, incredible views, and unparalleled hospitality aboard our selection of luxury train journeys.

16 results matching: Luxury Italy Vacations

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Grand Alpine ExplorerGrand Alpine ExplorerGrand Alpine ExplorerGrand Alpine ExplorerGrand Alpine Explorer
4.6 stars(36 reviews)
Escorted
2026MayJunJulAugSep
Escorted

Bask in boundless displays of jaw-dropping views on a spectacular First Class vacation through the Alps. Soak up the atmosphere of historic Munich on a beer tour, marvel at the fairytale Neuschwanstein Castle and indulge in a Mozart concert dinner in Salzburg after a tour. Enjoy a cruise in the Austrian Lake District and explore charming...

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14 days from
$5,695 pp
per person
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Lake ComoLake ComoLake ComoLake ComoLake Como
4.4 stars(15 reviews)
Independent
2026AprMayJunJulAug...
Independent

From Alpine peaks to glacier-fed lakes and beloved cities that exemplify cultural nuances, this journey delves into the wonders of Switzerland and Italy. There is no shortage of beauty to behold as you explore Switzerland from thought-provoking bases in Zürich, Chur, and Lugano and then cross the border into Italy, settling aside beautiful Lake...

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11 days from
$3,995 pp
per person
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InterlakenInterlakenInterlakenInterlakenInterlaken
Independent
2025NovDec
2026AprMayJunJulAug...
Independent

More than two weeks of dramatic alpine scenery, charming destinations and remarkable rail adventures beckon on this independent trip to Switzerland. With an included Swiss Travel Pass providing unlimited travel by train, bus, and boat; complimentary admission to 500-plus museums; select mountain rail excursions; and a 50% discount on many other...

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15 days from
$3,895 pp
per person
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Spanish StepsSpanish StepsSpanish StepsSpanish StepsSpanish Steps
4.6 stars(15 reviews)
Independent
2026AprMayJunJulAug...
Independent

Let ocean views and cities that span the ages capture your heart in beautiful Italy. It is no secret this country is brimming with fantastic offerings, from its gastronomy to its scenery and rich culture, and this independent expedition is your chance to immerse yourself in it all. Throughout the journey, an enticing mixture of private and...

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8 days from
$4,095 pp
per person
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LuxuryLuxury
Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express
Independent
Independent

Experience a truly memorable journey aboard the opulent Venice Simplon Orient Express on this exceptional tour including three iconic trains. Travel on the world-renowned Glacier Express and Bernina Express through the Swiss Alps, passing dramatic jaw-dropping mountains and lakes as you experience this unique journey. After stays in the famed...

9 days from
$9,125 pp
per person
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LuxuryLuxury
Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express
Independent
Independent

Experience the ultimate in luxury trains with a journey on the iconic Venice Simplon Orient Express. On this memorable tour, explore two Italian giants - the 'Eternal City' of Rome and Venice's 'Floating City' - before traveling to Paris on an unforgettable rail route. Start in Rome, where a private tour unveils the city's most notable...

7 days from
$7,445 pp
per person
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LuxuryLuxury
Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express
Independent
Independent

Create unforgettable memories aboard the opulent Venice Simplon Orient Express between the romantic cities of Venice and Paris. Spend time in the 'Floating City' of Venice, wandering its winding streets, grand squares and decorative bridges. Conclude this enchanting experience by boarding the Venice Simplon Orient Express for a world-renowned...

7 days from
$7,865 pp
per person
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LuxuryLuxury
Ben NevisBen NevisBen NevisBen NevisBen Nevis
Independent
Independent

After two wonderful days taking in the sights, sounds and tastes of Rome, your journey on the La Dolce Vita Orient Express begins with a sumptuous dinner by 3-Michelin starred Chef Heinz Beck. As the train travels northwards, an evening of cocktails and live music creates a sophisticated ambience. The next morning, awaken to a luxurious Italian...

7 days from
$10,215 pp
per person
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LuxuryLuxury
Ben NevisBen NevisBen NevisBen NevisBen Nevis
Independent
Independent

Embark on a luxurious journey aboard La Dolce Vita Orient Express, departing from Rome. Indulge in the exceptional culinary creations of 3-Michelin starred chef Heinz Beck, featuring Italian-inspired dishes crafted from seasonal and locally sourced ingredients. Awaken to the allure of an Italian breakfast as you prepare to explore the UNESCO World...

7 days from
$8,660 pp
per person
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LuxuryLuxury
Ben NevisBen NevisBen NevisBen NevisBen Nevis
Independent
Independent

Begin your adventure with three unforgettable nights in the iconic city of Rome, immersing yourself in its rich history and vibrant culture. Then, board the luxurious Orient Express La Dolce Vita Train and travel in opulent style to Venice. Savor a gourmet lunch curated by Michelin 3-star chef Hans Beck as you glide through Tuscany. In Venice,...

7 days from
$11,050 pp
per person
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LuxuryLuxury
Ben NevisBen NevisBen NevisBen NevisBen Nevis
Independent
Independent

Embark on a luxurious journey aboard the Orient Express La Dolce Vita, traveling from Rome into the enchanting heart of Tuscany. In Montalcino, a town that epitomizes Tuscan charm, explore quaint streets and historic landmarks, then delve into a winery experience to taste the acclaimed Brunello wine. As evening falls, the train comes alive with...

5 days from
$4,825 pp
per person
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LuxuryLuxury
Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express Venice Simplon Orient Express
Independent
Independent

Create unforgettable memories on this European vacation featuring a journey on the luxurious Venice Simplon Orient Express and three iconic Italian cities: Rome, Florence and Venice. Stroll through the capital's historic streets, home to timeless landmarks such as the Colosseum and Trevi Fountain, and spend time in the Renaissance gem of Florence.

9 days from
$8,105 pp
per person
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Our customers love our Luxury Italy tours
First Class Grand Alpine Explorer
5/Oct
Debbie Williams
5 stars
“This was our first European trip and it was even better than we could have imagined!
Collected by Trustpilot
Explore Italy: Pompeii, Capri & the Amalfi Coast
21/Oct
JOSEPH EDWARD KOWALSKI
4 stars
“The only thing that I would change about this trip was the location and quality of the hotel in Rome. The hotel in Sorrento was beautiful, clean, amazing breakfast, and great customer service! Vacations by Rail did a great job lining up drivers for us to and from all locations. This...
Collected by Trustpilot
Highlights of Switzerland & Italy by Rail
18/Oct
MARGARET RASMUSSEN SCHOEWE
4 stars
“All train reservations worked. Hotels were good. All hotels but Rome were convenient to the train station. We should have been warned about the down hill from the bus station to the hotel. There is a funicular to the level of the hotel but we didn’t know that. Very steep...
Collected by Trustpilot
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