Luxury Classic Italy by Train vacations

Classic Italy by Train

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At a glance

? Don't forget that all of our itineraries are totally customized and so this is just an idea of what we can build for you.

Discover the highlights of Italy over two unforgettable weeks on this customizable grand train tour. Travel in comfort aboard Italy’s excellent high-speed rail network as you explore world-famous cities, admire iconic art and architecture, and soak up “la dolce vita” along sunny coastlines.

Begin your Italian adventure in romantic Venice, the Floating City of canals and gondolas. Wander narrow alleys crossed by graceful bridges, admire Byzantine mosaics and Renaissance frescoes, and indulge in delicious seafood. Don’t miss St Mark’s Square and Basilica, the Doge’s Palace, and the vibrant energy of Carnevale if you visit in February.

Next head to magnificent Florence, the birthplace of the Renaissance. Marvel at Brunelleschi’s dome crowning the Florence Cathedral, Michelangelo’s stunning David sculpture, and masterpieces in the Uffizi Gallery. Stroll across the Ponte Vecchio and indulge in Florence’s famed gelato. Consider a day trip to Pisa to see the iconic Leaning Tower.

Continue south to the Eternal City of Rome. Explore ancient Roman ruins like the Colosseum, Roman Forum, and Pantheon. Throw a coin in the Trevi Fountain, climb the Spanish Steps, and soak up the atmosphere in bustling piazzas. Discover Vatican City’s Sistine Chapel and St. Peter’s Basilica. Rome has a small but lively gay scene in areas like Testaccio.

End your Italian sojourn along the spectacular Amalfi Coast, the perfect place to enjoy “la dolce vita”. Enjoy cliffside villages like Positano and pastel-hued Ravello. Go hiking in the Lattari Mountains, sample limoncello liqueur, and feast on fresh seafood by the shimmering blue Mediterranean. The Amalfi Coast epitomizes the beauty of Italy.

Discover the best of Italy in 2024 with this meticulously planned and inclusive itinerary. Whether you’re interested in gay Italy travel, luxury tours, or personalized vacations, Out Of Office provides exceptional service for an unforgettable journey.

In detail

? Don't forget that most of our itineraries can be totally customized. Our expert team will be able to talk you through all the options.

Days 1-3: Venice

Embark on a romantic three-day stay in Venice, renowned as ‘the floating city’ with its enchanting waterways. When you arrive, you’ll board a private water taxi to your accommodation. Absorb the beauty of Venice’s unique architecture, winding canals, and historic landmarks during the journey.

In Venice, you can immerse yourself in the city’s charm with a private walking or gondola tour led by a knowledgeable and friendly local. You can also take a trip to the nearby island of Murano, known for its beautiful glass blowing. We’ll also recommend you take a private nighttime tour of the famous Basilica – this exclusive experience offers a unique way of seeing this iconic building.

You’ll stay at the opulent Cipriani, A Belmond Hotel on Giudecca island. This stunning five-star property boasts unparalleled views of St Mark’s Square, ensuring a luxurious start to your European vacation.

Days 1-3: Venice

Days 3-7: Florence

As your adventure continues, board a first-class, high-speed train to Florence, the epicenter of the Italian Renaissance. This train takes just two hours and 15 minutes, and you can upgrade your journey to travel in an executive train cabin, giving you a private room from which to watch the Italian countryside speed by.

Check into The Grand Hotel Minerva, a beautiful hotel based right in the heart of Florence city center, boasting a refreshing rooftop pool. It sits beside the captivating façade of Santa Maria Novella, Florence’s exquisite cathedral. Suites here blend classical art and modern Italian craftsmanship.

Florence is famed as the home of so much of Italy’s greatest Renaissance art. If you’re an art-lover, the galleries here are a must-do – we recommend you visit the The Uffizi, where you’ll find the famous painting, The Birth of Venus – and also the Accademia Gallery, where you’ll find Michelangelo’s David.

A local guide will take you on a private day trip to Siena and San Gimignano, the nearby Tuscan wine regions of Italy. In both of these beautiful regions, you can sample wine from local vineyards, as well as delicious Tuscan cheeses.

Days 3-7: Florence

Days 7-10: Rome

Hop on your first-class, 90-minute train to Rome, the Eternal City, for an exquisite three-night stay. You’ll check in to one of our favorite luxury hotels in Rome, Leon’s Place. This boutique hotel boasts design-focused rooms, with second-to-none service that’ll make you feel special.

Most cities are packed with history, but Rome is on another level. You’ll want to take a trip to the Roman Colosseum, the largest ancient amphitheater ever built – as well as the iconic Roman Forum. You can take private tours of both of these historic gems. If you’d like to take a deeper dive into Rome’s history, take a trip to Palatine Hill, the former stomping ground of the Roman elite.

If you’d like a more unique way of seeing the city, consider a golf-cart or side-car private tour. These fun-filled tours are a great way to see the best sights of Rome in a speedy timeframe, without compromising on comfort. You can also take a day trip to Vatican City from Rome, where you can get a private tour of the famous Vatican.

Days 7-10: Rome

Days 10-14: Amalfi Coast

Take a first-class train to Naples to begin your Amalfi Coast adventure. You’ll be met in Naples by an Out Of Office representative who will privately transport you to Sorrento, a quaint coastal town on Italy’s gorgeous Amalfi Coast. Here, you can enjoy views of the beautifully blue sea while you sip on an Aperol Spritz, and witness unbeatable sunsets in the evenings. You’ll stay at the Bellevue Syrene, a luxe 5-star hotel that’s well-located, with panoramic views across the Gulf of Naples.

Sorrento can be called the ‘gateway to the Amalfi Coast’ as it’s so easy to access other parts of the area from here. It’s easy to take a day trip to neighbouring Positano, a colorful cliffside village with cobblestone streets lined with classy cafes and cute boutiques. You can also visit the wonderful island of Capri via a short ferry ride – we think it’s one of Italy’s crown jewels.

History lovers can also enjoy an excursion to Pompeii – it’s conveniently located on the journey between Naples and Sorrento, so can easily be fit into your itinerary. We’d recommend a private tour with an expert guide, which will mean you can make the most of your visit.

You can also enjoy a private sunset yacht cruise around the Amalfi Coast, which we’d highly recommend. Sail to the best parts of this stunning coastline, and sip on a glass of champagne as the sun sets behind you.

Days 10-14: Amalfi Coast
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