A Luxury Italian Bucket List Trip
- Duration
- 18 days
- Price guide
- From $59,518 per person
Trip highlights
- See Venice from the water on a romantic gondola ride
- Cruise sparkling Lake Como on a private tour
- Drink in the rolling hills and fine Chiantis of Tuscany
- Lunch at a Michelin-star restaurant surrounded by vineyards
- Enjoy a night of opera at the world-famous La Scala in Milan
- Relax in style on the glittering Amalfi Coast
- Explore the ruins of Pompeii with a personal guide
- Get early access to the treasures of Vatican City
Bespoke trips with Jacada
We design one-of-a-kind journeys incorporating luxury in all its forms. Our bespoke trips include:
- Luxury accommodation throughout
- Privately guided tours
- Private transfers
- Meticulously selected experiences
- Expertise and support from your Jacada Concierge

Itinerary in detail
Every trip is shaped around you. Below is a sample route to start from; we change any part of it to suit you.
Days 1-3
Soak up the romance in Venice
Enjoy three nights in Venice, one of the world’s most romantic cities, exploring its maze of canals and seeing St. Mark’s Square, the Doge’s Palace and Rialto Bridge. Romantic gondola rides beckon, but you could also see inside a private palace on the Grand Canal, discover tucked-away galleries, or visit quieter islands such as Burano and Torcello out in the lagoon, where traditional Venetian culture still runs deep. The entire city is considered a World Heritage Site, an extraordinary architectural masterpiece in which even the smallest building may contain works by some of Europe’s greatest artists.

Where you could stay
A pause in Valpolicella

On your private transfer onwards towards Lake Como, stop in this hilly, agricultural and marble-quarrying region famous for its wine production. A variety of wines are produced here, including a Recioto dessert wine and Amarone, both made from dried grapes. Several light and fragrant styles are also typical of the region. You’ll visit a local winery to learn all about the processes and techniques used in the production – and enjoy a tasting.
Days 4-7
Three nights by Lake Como
Lake Como has been a popular retreat since the time of the Roman Empire, and its popularity shows no signs of waning. Shaped like an inverted ‘Y’, the lake is long and slender and one of Europe’s deepest. Surrounded by the Rhaetian Alps and close to the border with Switzerland, its enviable position means few fail to be charmed by its beauty. This is one of Italy’s prettiest destinations, with picturesque towns, grand villas and beautiful gardens dotted around the lake.
Take to the water on a boat tour to truly appreciate Como’s beauty from the best angle. You’ll see the small wooden island of Comacina as well as the characteristic bell tower of Santa Maria Maddalena, before proceeding to Bellagio, known as the pearl of the lake, where you can walk along the narrow streets.

Where you could stay
Day 8
One night in Milan
An arbiter of international style, Milan is Italy’s financial and industrial heart, a thoroughly modern European city with a great history not far beneath the surface. Whether shopping, seeing Leonardo da Vinci’s Last Supper, dining out or discovering hip canal-side bars, Milan is a city with an overlooked charm hiding just beneath the chic surface.

Days 9-11
Three nights in Florence
Surrounded by rolling Tuscan hills, the beautiful city of Florence is one of Europe’s most enchanting and historically influential cities. If anywhere in the world can claim to have shaped modern Western consciousness, it is Florence’s grand piazzas and palazzos. The world’s greatest Renaissance artworks and sculpture can be found at every turn in the historical centre.
Start by exploring on a private guided walking tour. Begin with the church of Santa Maria del Fiore – the famous Duomo – to view Brunelleschi’s magnificent dome. Nearby you’ll see the Campanile of Giotto (bell tower) and Ghiberti’s enchanting ‘Gates of Paradise’, the door to the Baptistry. A short walk next takes you to the Medici Palace, from where the powerful dynasty ruled over the Golden Age of Florence. You’ll can also visit the Academia Gallery, home to Michelangelo’s ‘David’, one of the finest sculptures ever created.
Florence is also a great jumping-off-point for exploring the nearby cities of Pisa and Siena – and the vineyards of Chianti.

Days 12-15
Four nights on the Amalfi Coast
Draped along the cliffs on the southern side of the Sorrento Peninsula, between Salerno and the city of Sorrento, the Amalfi Coast is one of the most dramatic and glamorous spots in Italy. Between the two, Positano, Amalfi and Ravello’s candy-coloured buildings spill their way down into blue bays.
The peninsular combines affluent sophistication with an honest simplicity, where super yachts and gurgling Italian sports cars next sit amidst an unchanging rural way of life. The food gloriously reflects this and some of Europe’s finest restaurants can be found here, thriving on fresh local produce, whilst the Neapolitan food found everywhere here to many epitomises Italian cuisine. The views and food are perhaps the main draw here, but there is a rich history to explore too, hidden beaches to discover and pristine trails in the Lattari Mountains to climb.

Where you could stay
Days 16-18
Three days in Rome
Rome, Italy’s capital and largest city, needs little introduction. In one of the most storied locations in the world, glorious reminders of Rome’s illustrious past, from ancient Roman wonders to Renaissance masterpieces, are all on show. That’s not to say that its cosmopolitan streets do not embrace the now; Rome is as exhilarating and forward-thinking as ever.
No trip is complete without a guided tour of Ancient Rome, taking in the Forum, Palatine Hill and the Colosseum. Start at the great Roman Forum, for centuries the centre of civic life as the site of triumphal processions, elections, public speeches and criminal trials. Then, along the Via Sacra (Sacred Way), head to the Palatine Hill, one of the most ancient parts of the city, where you’ll enjoy a breathtaking view of the Circus Maximus, an ancient Roman chariot racing stadium Last but not least, enter the magnificent Colosseum, considered one of the greatest works of Roman architecture and Roman engineering, and capable of seating up to 50,000 spectators.

Where you could stay
★★★★★
“Fantastic trip to Italy”
We researched several travel sites and decided to go with Jacada based on the reviews. This review is adding to the outstanding service and amazing trip they arranged for us. This was our first time ever using a service like theirs and we were nervous about it but they did not disappoint! It was our 25th wedding anniversary and our…
Bob W. · Trustpilot
Why book with Jacada
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Personalised design
We’ll plan your trip around your personal interests, tastes and preferences, providing honest advice based on first-hand knowledge.
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Authentic experiences
Our expert guides and brilliant Concierges are hand-picked for their ability to bring your destination to life with care and passion.
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Positive impact
We seek out unforgettable experiences that benefit both local communities and the environment.
Start planning your trip
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