A Luxury Italian Bucket List Trip

Duration 18 days
Price guide
Travel in style on this exquisitely luxurious 18-day journey across Italy. Taking in Venice, Lake Como, Milan, Florence, the Amalfi Coast and Rome, you'll see Italy’s highlights with exclusive private tours and stays in the finest hotels. Each day brings new marvels, as you explore the birthplace of the Renaissance, admire Italian masterpieces and visit the country's most celebrated vineyards.

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
Sketch of woman in art gallery
  • Days 1–4 Venice
  • Days 4–7 Lake Como
  • Days 7–8 Milan
  • Days 8–11 Florence
  • Days 11–15 The Amalfi Coast
  • Days 15–18 Rome
Luxury Italian Bucket List Trip
Price guide
  • Days 1–4 Venice
  • Days 4–7 Lake Como
  • Days 7–8 Milan
  • Days 8–11 Florence
  • Days 11–15 The Amalfi Coast
  • Days 15–18 Rome

Itinerary in detail

Every Jacada trip is tailored to your personal preferences and interests. Below you’ll find a sample itinerary to inspire your own custom-designed journey.

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.

Canal view in Venice, Italy

Make it mine

On foot

On the water

At the table

Venice Campanile Tower and Doge's Palace

A Venetian walking tour

As you wander Venice’s winding streets and waterways with an expert guide, you’ll learn all about the city’s history. Visit the shimmering, mosaic-filled St. Mark’s Basilica, the mightiest of Venetian monuments, and the lively market on and around the Rialto Bridge.

Gondola in Venice

Private gondola rides and cruises

No visit to Venice would be complete without a gondola ride around sleepy backwaters or a private cruise along the Grand Canal. Getting out on the water gives a new perspective on this remarkable city, spread across some 118 islands between the mouths of Po and Piave rivers, criss-crossed by some 170 canals and 400 bridges.

Vineyard and the old bell tower on the Mazzorbo island

Michelin-starred dining

Sample the finest Venetian produce at Ristorante Venissa on the quiet island of Mazzorbo. The restaurant has been awarded both a Michelin Star and a Michelin Green Star, the atmospheric cellar dining room surrounded by the estate’s vegetable gardens and vines.

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 3–7

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.

Days 7–8

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.

Shopping in Milan

Make it mine

By day

By night

Milan cathedral facada

A privately guided tour of Milan

Explore the highlights of this dynamic city, known the world over for its glamour. The cathedral is the fourth largest in the world and is a spectacular example of Gothic architecture. The Milanese are also known for their style, and you can visit the beautiful Galleria Vittorio Emanuele, one of the world’s oldest shopping malls. The Dominican convent adjoining the church of Santa Maria delle Grazie houses one of the most important masterpieces in the world, Leonardo da Vinci’s Last Supper.

Interior of La Scala opera in Milan

An evening of opera at La Scala

The Teatro alla Scala was founded under the auspices of the Empress Maria Theresa of Austria, to replace the Royal Ducal Theatre which was destroyed by a fire. Designed by the great neoclassical architect Giuseppe Piermarini, La Scala opened in the summer of 1778 and has been hosting world-class opera and ballet ever since.

Days 8–11

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.

The facade of the Duomo in Florence, Italy

Out of the city




Italy's tower of Pisa

Visit Pisa and its famous tower

You’re sure to have seen it in plenty of books, and now you can learn all about the city of Pisa and its leaning tower. The tower itself is the belfry for a magnificent cathedral complex with a baptistry and walled cemetery, and on your tour you’ll hear what inspired the artists and architects of this cathedral square, known as the ‘Field of Miracles’.

Vineyards in the Chianti hills Tuscany

Explore the Chianti region

Discover the beautiful Chianti region with a private driver at your disposal. Learn about – and taste – some of the most excellent Italian wines, or perhaps simply soak up the beauty of Tuscany countryside and its Medieval towns.

Siena skyline in Italy

Spend the day in Siena

Your tour starts at the Piazza del Duomo with the spectacular Romanesque and Gothic cathedral. The square is surrounded by the Santa Maria della Scala Hospital, the Archbishop’s Palace, the unfinished Duomo, Opera del Duomo museum, the crypt and the baptistry. You’ll then reach the Piazza del Campo, a unique shell-shaped area which was paved with bricks in the 14th century. Be sure to look out for the different animals and symbols that represent the city’s 17 contradas.

Days 11–15

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.

The bay of Positano on the Amalfi Coast

Make it mine

Ancient ruins

On the coast

Island life

Ancient ruins of Pompeii

A private tour of Pompeii

To visit Pompeii is as close as you can get to travelling in a time machine. In August of 79 AD, Vesuvius had been rumbling for some days and it is estimated that a large part of the population of 20,000 had been evacuated; those that were left were as if suspended in time, as the plaster casts made of the bodies that were found shows. Today you can walk Roman streets, look into bars and stroll into Patrician villas, complete with frescoes and mosaics.

Amalfi Coast from above in summer

Highlights of the Amalfi Coast

Discover the spectacular Amalfi Coast, situated like an amphitheatre among the mountains and the sea, with a private guide. Visit Ravello and the Villas Rufolo and Cimbrone, two sites not to be missed for their splendour and decorations. Both villas have amazingly beautiful gardens. The wonderful Positano is considered to be one of the most picturesque of all Italy’s coastal resorts.

View of Capri Island from Mount Solaro

Capri by private boat

Head out into the Gulf of Naples across to the beautiful island of Capri, a draw to visitors for thousands of years. The tour will touch Li Galli Islands, the legendary home of the sirens who lured Ulysses to the islands with their enchanted singing. This is also an ideal place for snorkelling with its clear waters and underwater treasures. Tide permitting, you will approach the famous Blue Grotto where it will be possible to get inside using a local small boat.

Days 15–19

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.

Colourful streets in Rome, Italy

Make it mine

Vatican masterpieces

A Papal Audience

Private palaces

The exterior of the Vatican

Early-access Vatican City tour

Arrive early at the Vatican, when the museums are still closed to the public, with your personal guide. You will pass through room after room full of treasures, before the culmination of the visit, Michelangelo’s Sistine Chapel with its ceiling frescoes and Last Judgement on the altar wall. From here, enter St Peter’s Basilica, a testament to Renaissance architecture, showcasing the work of Bramante, Michelangelo, Carlo Maderno and Gian Lorenzo Bernini. One of the first treasures to capture your gaze will be Michelangelo’s Pieta, sculpted by the artist at the age of 23.

The Pope waves at the Papal Audience in Rome

Wednesday's Papal Audience

The Papal Audience is held on Wednesdays if the Pope is in Rome, giving pilgrims and visitors the chance to see the pontiff and receive the Papal Blessing or Apostolic Blessing from the successor of the Apostle Peter during their visit. The Audience with the Pope consists of small teachings and readings mainly in Italian but also in English, French, German, Spanish, Polish, Portuguese. Your guide will help to find the best place for you to enjoy this special moment.

Villa Medici exterior in Rome

Tour Rome's private palaces

Rivalry between noble families has long been a part of Italy’s history, each competing to build the highest tower or the most elaborate palace. Visit some of Rome’s most impressive houses, starting at the Palazzo Colonna, home to the Colonna family for over 1000 years. The visit takes in the private apartments of Princess Isabelle with the famous Grottesche by Pinturicchio, the glorious gallery, the State Apartments and the Throne Room. These contain works by Carraci (the bean eater), Guercino, Poussin, Tintoretto and Ribera, as well as priceless furniture. From here, continue to the Villa Medici with its spectacular 15th-century gardens, once the property of Cardinal de Medici.

Why book with Jacada

Personalised design

We’ll plan your trip around your personal interests, tastes and preferences, providing honest advice based on first-hand knowledge.

Authentic experiences

Our expert guides and brilliant Concierges are hand-picked for their ability to bring your destination to life with care and passion.

Positive impact

We seek out unforgettable experiences that benefit both local communities and the environment.