Discover the true must-sees of Italy, exploring its history, food, natural beauty and architecture

Personalised journeys from start to finish

Every trip helps support Conservation

Every detail taken care of

  • Personalised journeys from start to finish

  • Every trip helps support Conservation

  • Every detail taken care of

Itinerary highlights

  • Explore beautiful countryside and a delicious culinary scene in the pristine Piedmont region
  • Learn about the history, production process and flavours of traditional Italian Gelato
  • Weave around the ancient city of Rome as a passenger on a classic Vespa
  • Head out into the Gulf of Naples on a private speedboat tour of Capri
  • Explore the area around the tallest active volcano in Europe with an off-road tour of Mount Etna

What's included

  • Luxury accommodation throughout
  • Private transfers
  • Private tours and experiences focused around Italy's history, beauty and identity
  • Full support from your travel designer and concierge before, during and after your trip
  • Our help with restaurant recommendations and reservations
  • Expert guides in each destination
Use this itinerary to inspire your bespoke journey

At a glance

A country of incredible diversity, beauty and history, Italy is one of the world’s most fascinating and rewarding holiday destinations. Captivating culture vultures through its ancient cities, satisfying foodies with its sublime cuisine, thrilling nature lovers through blissful natural landscapes and charming romantics with its poetic character, this 21-day adventure is designed to showcase each individual ingredient which contributes to Italy’s undeniable allure.

Your grand tour of Italy will begin in the far north, soaking up the art of Milan and the beautiful foothills of the Piedmont region, before a memorable experience hiking the incredible Cinque Terre, with its famous colourful fishing villages and dramatic coastal vistas. Tuscany is the next port of call, beginning in stunning renaissance Florence where you’ll encounter incredible architecture and delicious gelato, followed by time spent in the Tuscan countryside, discovering the wonderful wine of Chianti.

The awe-inspiring ancient city of Rome awaits, where you will spend three nights encountering its Roman history and grand landmarks, before retreating to the calming and cooling coast for a few days exploring the Gulf of Naples and the Amalfi Coast. You’ll end your tour on the stunning island of Sicily, witnessing baroque architecture, Greek ruins and Europe’s largest active volcano.


Example trip itinerary

Days 1-3


Flights & transfers


Private transfer to your hotel in Milan

Accommodation in Milan

Private guided tour of Milan with The Last Supper Private guided tour of Milan with The Last Supper

This dynamic city is know the world over for its glamour and you'll enjoy a tour which lets you explore its gems. The cathedral is the fourth largest in the world and is a spectacular example of Gothic architecture. The Milanese are known for their style, and you'll visit the beautiful Galleria Vittorio Emanuele, one of the world's oldest shopping malls. Together with Via Montenapoleone and Via della Spiga, it is considered one of the most important areas for shoppers. Continue to the Piazza della Scala, home to La Scala Theatre, and the majestic Castello Sforzesco. 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. Only a small number of people are admitted at a time to help protect the fragile fresco.

Hiking and cycling in the Italian foothills Hiking and cycling in the Italian foothills

In the morning you'll arrive in Buronzo and have a coffee break at Buronzo Castle before choosing to either go mountain biking or hiking in Oasi Zegna Park, along the Mountain Path in the Wild Valsessera Valley. You will stop for lunch at a local mountain refuge. The distance covered with be shorter if you choose to hike rather than mountain bike. On the way to Borgo Ca del Becca you will have the opportunity to visit some local villages on the way, and when you arrive you will take a short walk in the forest and enjoy a "merenda" of local cheese, prosciutto, beers and Bramaterra wine.

Flights & transfers


Private transfer to your hotel in Portofino

Days 3-5


Accommodation in Portofino

Hiking tour of Cinque Terre Hiking tour of Cinque Terre

This walking tour starts in Monterosso with a scenic path up a steep cliffside stairway of 100 steps, the trail then winding up and down through scrubby Mediterranean vegetation bordered by dry-stone walls. Next, from Corniglia, head through vineyards, olive groves and along terraces dotted with scrubby en route to Vernazza, probably the most photogenic of all the Cinque Terre villages.The final trail brings you to the Sanctuary of Montenero.

Private transfer to your hotel in Florence, via Pisa Private transfer to your hotel in Florence, via Pisa

You're sure to have seen it in plenty of books, and now you can learn all about the city of Pisa and its famous leaning tower. The tower itself is the belfry for a magnificent cathedral complex with a baptistry and walled cemetery, and you'll hear what inspired the artists and architects of this cathedral square, known as the 'Field of Miracles'. Inside this square sits the tower, and you'll wind your way to the top, feeling the 'lean' as you ascend.

Days 5-7


Accommodation in Florence

Walking tour of Renaissance Florence Walking tour of Renaissance Florence

Explore Renaissance Florence today, with a tour of the highlights of this exciting period in the history of this fascinating city. Start with the Academia Gallery, home of Michelangelo’s incredible David; you will see copies all over Florence, but this is the real thing! A short walk will bring you to the Duomo, Santa Maria del Fiore with Brunelleschi’s magnificent dome and alongside it, Giotto’s Campanile. With your back to the cathedral, you will be looking straight at Ghiberti’s legendary ‘Gates of Paradise’ bronze doors in the Baptistery. Continue to the Piazza della Signoria, the political heart of the city, and then to Ponte Vecchio, the oldest bridge crossing Arno river.

Gelato tasting Gelato tasting

This tour is all about gelato - Italian ice cream. Learn how gelato was invented, see how it is made on the premises of a gelato parlour, and naturally, lots of flavours will be tasted and compared.

Private transfer to your hotel in Tuscany, via Siena Private transfer to your hotel in Tuscany, via 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 - giraffes, dragons, owl, unicorns and caterpillars all appear on the outside of buildings and competition between them is fierce during the Palio horse race which happens twice a year.

Days 7-9


Accommodation in Tuscany

Cycle through the Chianti countryside Cycle through the Chianti countryside

A bike ride is the perfect way to see the beautiful Chianti countryside. You will be provided with 21-speed mountain bikes, helmets and water bottles and set off on your adventure, riding past rolling green hills along roads lined with cypress trees. You will also have the chance to visit some local churches and small medieval villages and visit a winery for a tasting. The tour ends with a delicious Tuscan meal.

Private transfer to your hotel in Rome, via Orvieto Private transfer to your hotel in Rome, via Orvieto

Located on a hilltop in the beautiful Umbrian countryside, Orvieto is sure to capture your heart with its churches, cobbled lanes, and medieval piazzas; the stunning Gothic cathedral is not to be missed.

Days 9-12


Accommodation in Rome

Early-access and breakfast at the Vatican Museum Early-access and breakfast at the Vatican Museum

Arrive at 7am at the Vatican when the museums are still closed. You'll have the chance to enter with just a few others and enjoy an American breakfast. Then you are ready to start the tour of the museums with your personal guide. You will pass through room after room full of treasures, before the culmination of the visit, Michelangelo's Sistine Chapel, home to the conclave that elects Popes. The ceiling frescoes and Last Judgement on the altar wall are probably the most viewed paintings in the world.

From here, enter St Peter's Basilica, one of the largest churches in the world and a triumph of Renaissance architecture, the work of Bramante, Michelangelo, Carlo Maderno and Gian Lorenzo Bernini. Once inside, having got over the feelings of awe inspired by the sheer size and magnificence of it all, one of the first things you will see is Michelangelo's Pieta. Sculpted at the age of 23, it must be the most moving of all Michelangelo's sculptures; a mother gazing lovingly at her child as if seeing the baby she gave birth to but in fact the body of the 33-year-old Christ. Moving down the church, you will pass the statue of St Peter, whose bronze toes have been completely worn away by the millions of pilgrims who have stroked them and arrive at Bernini's Baldacchino (canopy), under the centre of the dome and behind this, the throne of St Peter.

Tour of Ancient Rome - The Forum, Palatine Hill and the Colosseum Tour of Ancient Rome - The Forum, Palatine Hill and the Colosseum

Discover 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 area 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.

Rome Vespa tour Rome Vespa tour

Astride your own Vespa with a driver upfront, enjoy becoming acquainted with the capital in a totally fun and unique way.

See the sights of Rome from the back of a vintage Vespa, in true ‘Roman Holiday’ style as you weave your way through everything from large avenues to tiny alleyways. The tour will be led by a private bilingual guide and will take in all the most important monuments and neighbourhoods in Rome.

Driven by professional Vespa drivers, passengers are assured complete safety and peace of mind. The tour lasts around four hours with five scheduled stops.

Flights & transfers


Private transfer to Rome’s train station


Train from Rome to Naples

Private transfer to your hotel in the Amalfi Coast, via Pompeii Private transfer to your hotel in the Amalfi Coast, via Pompeii

To visit Pompeii is probably as close as we can get to travelling in a time machine back to ancient Rome. 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. Excavation started in the 18th century and continues to this day.

The first impression, on entering into the Forum, is just how massive Roman structures were; they really dwarf revered Medieval or later sites. You will get to walk Roman streets, look into bars, stroll into Patrician villas, complete with frescoes and mosaics, there is even a mosaic doormat, saying ‘beware of the dog’. Even graffiti (an Italian word) is written on some of the walls, reflecting a forthcoming election. When you see the baths, the central heating systems and the gentle fountains in the courtyards of the villas, you really feel it wouldn’t be too much of a hardship to live there.

Days 12-15

The Amalfi Coast

Accommodation in The Amalfi Coast

Amalfi Coast tour Amalfi Coast tour

Discover the spectacular Amalfi Coast, situated like an amphitheatre among the mountains and the sea. Visit Ravello with its villas, amazingly beautiful gardens and extraordinary views along the coast.
You'll also take in the wonderful Positano, considered to be one of the most picturesque of all Italy's coastal resorts.

Capri day trip by private speedboat Capri day trip by private speedboat

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 the local small boat.

Flights & transfers


Private transfer to Naples airport


Flight to Catania


Private transfer to your hotel in Noto

Days 15-17


Syracuse private city tour including Ortigia Syracuse private city tour including Ortigia

Syracuse was once the most powerful of the Greek cities in Sicily and is now a pretty coastal town boasting an impressive archaeological park with an amphitheatre, temples, catacombs and castles. Ortigia is the ancient city centre and home to the Temple of Apolloneion, Piazza Archimede and cathedral.

Tour of Modica in a Fiat 500 Tour of Modica in a Fiat 500

Modica is a pretty historic town, with tiers of churches and palaces stacked up on the hill. Once you have arrived you will hop into a classic Italian Fiat 500 and spend an hour exploring the city, weaving in and out of the streets discovering its gems.

Chocolate tasting in Modica Chocolate tasting in Modica

Modica is famous for its chocolate, made here in the same way it was made in Mexico by the Aztecs. You'll visit a local historical shop and try some of its delicious creations and receive a chocolate bar to take away.

Private transfer to your hotel in Agrigento, via Ragusa Private transfer to your hotel in Agrigento, via Ragusa

Walk around in Ibla, the old part of Ragusa, built in Baroque style and recreated on a medieval street plan, with its secret shrines, family crests and baroque fountains. Ibla is known for its typical oriel windows, showy staircases, tawny-coloured mansions and filigree balconies, secret arches and yellowing palm trees.

Days 17-18


Accommodation in Agrigento

Tour of Agrigento and the Valley of the Temples Tour of Agrigento and the Valley of the Temples

Founded as a Greek colony in the 6th century BC, Agrigento became one of the leading cities in the Mediterranean. The area is home to the Valley of the Temples, one of the world’s most impressive and important archaeological sites. The temples are spread over 1,300 hectares of land and most are situated on rocky crests south of modern day Agrigento. The best preserved is the Concordia temple, one of the most impressive examples of a Greek Doric temple.

Private transfer to your hotel in Taormina, via Villa Romana del Casale tour Private transfer to your hotel in Taormina, via Villa Romana del Casale tour

Visit the incredible remains of the Villa Romana del Casale, a 4th century Roman villa and UNESCO World Heritage Site. One of the most opulent residences in the Empire, it contains the richest, largest and most complex collection of Roman mosaics in the world.

Days 18-21


Accommodation in Taormina

Off-road tour of Mount Etna and winery visit Off-road tour of Mount Etna and winery visit

Enjoy an off-road excursion on a comfortable 4WD, and explore the area around the tallest active volcano in Europe with a vulcanologist as your guide. As you ascend to the summit at 2,000m, you'll pass through enchanting forests and experience a walk through tubular lava caves. Once you're at the top, you'll enjoy breathtaking views over the Ionian Sea and the vineyards and orchards that sprawl across the lower slopes. After soaking up the incredible and striking landscapes of Mount Etna, you'll enjoy lunch at a local winery. While here, you can sample the delicious wines that are produced on the fertile slopes of Etna.

Taormina walking tour Taormina walking tour

Taormina sits on the east coast of the island and has long been home to artists and intellectuals. It is also favoured by Hollywood stars who are charmed by its beauty and on this walking tour, you'll see why. The town is filled with pretty churches, a Norman cathedral, impressive clock tower and a main square which overlooks the Gulf of Messina. It is also home to the Palazzo Corvaja palace, which housed the first Sicilian parliament in the 15th century. A real highlight is the Greek theatre from where you will get stunning views of Taormina’s two bays and across to Calabria, with Mount Etna as a backdrop in the other direction. You'll also enjoy some time to go shopping and explore the streets at your leisure.

Flights & transfers


Private transfer to Catania Airport

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Grand Tour of Italy

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We create fully personalised trips from start to finish, working with you to pick locations, accommodation and guides that suit you.

Every trip helps support Conservation.

From in-depth private tours to restaurant reservations, we take care of every detail so you can make the most of your journey.

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