20 nights from $31,826pp
Embark on the ultimate three-week Italian holiday, journeying from Venice to Amalfi and exploring Lake Garda, Milan, Tuscany, and Rome, starting on the Venice Simplon-Orient-Express train. Discover Italy’s unmatched cuisine, rich culture, and world-renowned wine along the way.
Experience luxury rail travel at its very best aboard the Venice Simplon-Orient-Express train and arrive into Venice in style, before taking the water taxi into the heart of Venice’s Santa Lucia.
Relax in your luxury five-star hotel situated right on the Grand Canal before dinner at a local Venetian restaurant.
Free day to enjoy and explore the ambience of Venice, considered one of the most romantic cities in the world.
Visit St Mark’s Basilica, take a guided Venice city tour by gondola, enjoy gourmet tastings of Venetian cicchetti (small plates), or admire the panoramic views from the Campanile di San Marco.
After breakfast in your hotel, embark on a full day’s wine tour of northern Italy’s Prosecco DOCG region – you’ll visit two local wineries, learn the secrets of the production of one of the world’s finest sparkling wines, and, of course, indulge in a number of tastings before a lunch of delicious local specialities.
After a splendid six-course tasting lunch in Sirmione, meet your private driver for transfers to your five-star hotel and spa set amongst the beautiful surroundings of Lake Garda. Take the afternoon to enjoy the hotel’s surroundings, or take advantage of the Mondo Lefay Spa.
Free day to enjoy the picturesque surroundings, take a stroll or relax by the lake in Gargnano. Alternatively, take a dip in a range of swimming pools, saunas, grottos and small lakes.
The resort also benefits of outdoor areas equipped for sporting activities and trails dedicated to wellness and relaxation.
Breakfast in your hotel starts the day, before meeting your driver for private transfers to your outstanding five-star hotel in the very heart of Milan. Take the evening to wine and dine in one of Italy’s greatest cities.
Free day to enjoy and explore the many shops, cafés and restaurants of Milan. Perhaps visit the Santa Maria delle Grazie to see da Vinci’s ‘Last Supper’, climb the famous Duomo or shop and eat at the Galleria Vittorio Emanuele, one of the world’s oldest shopping malls.
Another free day to enjoy and explore the ambiance of Milan. Included in the trip is an evening to enjoy a show at La Scala, one of the very finest of Italy’s legendary opera houses.
Enjoy an exclusive guided visit of Lamborghini’s nearby factory, before relaxing with private transfers to your hotel in Florence via the scenic country roads, passing the towns of Prato and Pistoia. Your accommodation in Tuscany will be an intimate five-star boutique hotel in the centre of the city.
Free day to enjoy and explore Florence, a city of timeless beauty and jewel of the Renaissance. The city is steeped in history, art and architecture, and keeps countless museums, galleries, churches, monuments and other sights within its ancient city walls.
Just a very few of the most impressive include the Gothic medieval Florence Cathedral, the vast Palazzo Vecchio, the shops along the Ponte Vecchio stone bridge and the legendary Uffizi Gallery, which houses works by the world’s most esteemed Renaissance artists. Alternatively, visit some of the many boutique shops that the city boasts.
Relax with a stunning private Tuscan wine tour around Montalcino, visit the Brunello wineries and enjoy lunch in the heart of the vineyards tasting fabulous sangiovese wines.
Drive on to your accommodation in the restored, 10th-century Castello di Velona, and enjoy the luxury spa and pool with magnificent views over the surrounding countryside.
Today continues your tour around Tuscany. You’ll experience visits and tastings at a selection of boutique wineries around the Chianti Classico producing region and a traditional Tuscan lunch with accompanying wine and olive oil tastings.
Drive down to your lunch venue near Rome via Italy’s stunning coastal route, past the towns of Grosseto and Civitavecchia.
After lunch, arrive at your five-star boutique accommodation in Rome, situated by the Tiber and within walking distance of some of Rome’s finest piazzas, restaurants and shops.
Free day to explore one of the world’s foremost global cities. Rome has no shortage of things to see and do. Beyond the most iconic sights – such as the Colosseum, the ruins of the Roman Forum and the Castel Sant’Angelo, the city is also home to countless striking squares, which are themselves populated by a multitude of shops, cafes and restaurants.
Vatican City is also located in the heart of Rome, with St. Peter’s Basilica and the Vatican Museums containing some of the most remarkable artwork and architecture in the Europe’s history.
Take breakfast in your hotel before departing on a private boat from Sorrento Pier to Capri Marina Grande Pier, before meeting your driver for private transfers to your five-star hotel on the island of Capri off the Amalfi Coast, with spectacular views overlooking the town and ocean.
Free day to relax and enjoy the ambience of Capri. Amongst Capri’s most famous sights include the magnificent and world-renowned Blue Grotto on the coast and the nearby Faraglioni Rocks, to which boat excursions are available, as well as the ancient Roman villas, including Villa Jovis and Villa San Michele; once residences of the Emperor Tiberius.
Depart on a private boat from Capri Marina Grande pier to Sorrento pier, before meeting your driver for private transfers to your stunning five-star hotel in Salerno, with views directly onto the sea.
Take the evening to explore Amalfi itself, or relax in the hotel’s spa.
Enjoy a day of wine tasting in the boutique, terraced vineyards of the Amalfi Coast. Take lunch and tastings on the terrace of a winemaker’s home and experience a fascinating and intimate tour around a charming winery in the afternoon.
Free day to relax and enjoy the ambience of Amalfi. We suggest visiting some of the remarkable historical sites along the coast. Amalfi itself is the location of an 11th-century cathedral which uniquely merges Baroque, Romantic, Byzantine and Gothic architectural styles.
The Villa Cimbrone in Ravello, and the views from its Terrace of Infinity, is famed in Italy for its beauty, as is the Emerald Cave in Conca dei Marini and the many churches which stand in further towns, such as Minori and Positano, all over the coast.
Have a day to enjoy the luxury spa and pool with magnificent views over the surrounding Amalfi coast, or explore the town itself.
Meet your local private driver at the hotel’s reception for your private transfer to Naples Capodichino International Airport, before flying home business class to London or Paris (ask for private jet upgrades).
Perched on a hilltop overlooking the UNESCO World Heritage Site of Val d’Orcia, Castello di Velona is a spectacular boutique hotel set in a beautifully renovated 11th century fortress.
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Located in a quiet, residential area of Sorrento and wrapped in fragrant gardens.
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The Grand Hotel Excelsior Vittoria is one of the Leading Hotels of the World and offers an embodiment of Italian grandeur.
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Perched on the cliffs just outside Amalfi, Hotel Santa Caterina is a grand Italian villa with spectacular coastal views.
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Dating back to 1475, The Gritti Palace began as a noble residence.
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A luxury hotel in Florence located in the heart of historic centre, in the magical setting of the stunning Santa maria Novella Square
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Located in the historic heart of Florence on the southern banks of the River Arno, Hotel Lungarno is an exquisite boutique hotel with iconic views over the river and Ponte Vecchio.
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We craft each itinerary just for you. Contact our Travel Designers to plan an unforgettable train journey from Venice to the Amalfi Coast.
Start PlanningOur 21-day Italian itinerary will take you across the north and then onwards down to the south of Italy. Ultimately, the trip is broken down like this:
Whether or not 3 weeks is too long to spend in Italy is entirely subjective! If you’re coming from further away, it can be better value if you have the time to enjoy a longer trip and travelling slowly to savour every moment and maximise your time in the country.
We tend to recommend spending at least two nights in each location on a tour, especially if transfers in between are long, so that you have time to unwind and then feel fresh to continue exploring!
This sample itinerary includes four days of wine tastings and tours, including in the Prosecco region, Tuscany and around the Amalfi Coast.
Of course, because each trip we create is entirely bespoke, we can increase or decrease this to entirely suit your personal preferences!
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An award-winning, owner-managed boutique travel company, we've spent two decades curating bespoke trips across the globe.
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