Grand Tour of Italy

Duration 21 days
Price guide
Scroll to video
A country of incredible diversity, beauty and history, Italy is one of the world’s most fascinating and rewarding holiday destinations. This 21-day adventure is designed to showcase each individual ingredient which contributes to Italy’s undeniable allure.

Trip 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
  • Go mountain biking or hiking in Oasi Zegna Park, along the Mountain Path in the Wild Valsessera Valley

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
  • Days 1–3 Milan
  • Days 3–5 Portofino
  • Days 5–7 Florence
  • Days 7–9 Tuscany
  • Days 9–12 Rome
  • Days 12–15 The Amalfi Coast
  • Days 15–17 Noto
  • Days 17–18 Agrigento
  • Days 18–21 Taormina
Grand Tour of Italy
Price guide
  • Days 1–3 Milan
  • Days 3–5 Portofino
  • Days 5–7 Florence
  • Days 7–9 Tuscany
  • Days 9–12 Rome
  • Days 12–15 The Amalfi Coast
  • Days 15–17 Noto
  • Days 17–18 Agrigento
  • Days 18–21 Taormina

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

Welcome to 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 under the surface. This long and rich history is encapsulated in the Duomo, Milan’s grand gothic cathedral that is the city’s centre. Built on the site of the Roman basilica, it was extended and refaced numerous times throughout the middle ages, with final flourishes and iconic pinnacles added under Napoleon’s orders that were finally completed in the 20th century.

Make it mine

Art and shopping

Fresh air

Private guided tour of Milan with The Last Supper

Milan’s cathedral is the fourth largest in the world and is a spectacular example of Gothic architecture. You’ll also visit the beautiful Galleria Vittorio Emanuele, one of the world’s oldest shopping malls. Together with Via Montenapoleone and Via della Spiga. 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. 

Hiking and cycling in the Italian foothills

Begin with 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. Stop for lunch at a local mountain refuge. On the way to Borgo Ca del Becca you will have the opportunity to visit some local villages, 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.

Days 3–5

Riviera living

The magnificent Italian Riviera has been attracting rich and beautiful since the days of Byron, Shelley and Keats who spent time here swimming, finding inspiration and drinking around what became known as the Golfo dei Poeti. Portofino, perched on its own peninsular, is Liguria’s glamorous heart and one of the most perfect fishing ports in the Mediterranean. Attracting small fleets of glittering yachts, the pretty Piazzetta by the harbour is lined with cafe and restaurant tables.

Make it mine

Explore on foot

Lean in

Hiking tour of Cinque Terre

Five perfectly preserved fishing villages, laced together with hiking paths that meander between vineyards and the deep blue sea; this is the UNESCO World Heritage Site of Cinque Terre (Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore). Over the centuries, people have carefully built terraces on the steep landscape, right up to the cliffs that overlook the sea.

Visit Pisa

On the way to Florence, you’ll stop in the city of Pisa to see its famous leaning tower. It 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

Enchanting 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.

Make it mine

Renaissance ramble

Sweet treats

Siena sights

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.

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.

Siena tour

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.

Days 7–9

Tuscan countryside

Few scenes are more evocative of Italy than that of rural Tuscany, undulating hills, dotted with stoic stone farm houses, dark green cypress trees and ranked vines, all under a shawl of a dawn’s mist.

Make it mine

Pedal power

Into the hills

Cycle through Chianti

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 local churches and small medieval villages and visit a winery. The tour ends with a delicious Tuscan meal.

Visit Orvieto

On the way to Rome, make a stop in Orvieto. Located on a hilltop in the beautiful Umbrian countryside, this town 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

When in Rome

Rome, Italy’s capital and largest city, needs little introduction. One of the most historied locations in the world, we can help you discover its incredible past with a luxury trip focused around expert guided tours and local insight.

Make it mine

Avoid the crowd

Back in time

On two wheels

Early-access and breakfast at the Vatican Museum

Arrive at the Vatican early when the museums are still closed. You’ll have the chance to enter with just a few others and enjoy an American breakfast before your tour with your personal guide. The culmination of the visit is 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 where one of the first things you will see is Michelangelo’s Pieta.

Tour of Ancient Rome

Discover the great Roman Forum, for centuries the centre of civic life. Then, along the Via Sacra (Sacred Way), head to the Palatine Hill, one of the most ancient areas of the city, where you’ll enjoy a breathtaking view of the Circus Maximus. Finally, 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

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.

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. Excavation started in the 18th century and continues to this day.

Days 12–15

Head to the coast

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

Head out into the Gulf of Naples across to the beautiful island of Capri. The tour will take you to Li Galli Islands, the legendary home of the sirens who lured Ulysses to the islands with their enchanted singing. With its clear waters and underwater treasures, this is an ideal place for snorkelling. Tide permitting, you will approach the famous Blue Grotto where it will be possible to venture inside on a small boat.

Days 15–17

Sicilian baroque

The beautiful town of Noto is a UNESCO World Heritage site, considered the capital of Sicilian baroque style. It is filled with pretty honey-coloured buildings and a main corso where you’ll find spectacular baroque palazzi and churches. You’ll also spend time in nearby Syracuse, once the most powerful of the Greek cities in Sicily which 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.

Make it mine

Fiat adventure

Sweet tooth

Secret shrines

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

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.

Ragusa tour

On the way to Agrigento, you’ll stop in 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

Temples and more

This hilltop city is best known for the nearby the Valley of the Temples, one of the world’s most impressive archaeological sites. The temples are located along a ridge between the higher modern hilltop town of Agrigento and the sea. Between the town centre and the temples is a peaceful green vale where agriculture is interspersed with ruins and excavations.

Make it mine

Into the past

Roman mosaics

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. The temples are spread over 1,300 hectares 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.

Villa Romana del Casale tour

On the way to Taormina, 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

Coastal Taormina

Settled on a hill of the Monte Tauro, this pretty coastal town enjoys a prestigious position on the east of the island. As well as streets and squares lined with churches and beautiful old buildings, it is home to an impressive Greek amphitheatre that looks out over Taormina’s two bays and out towards Calabria.

Make it mine

Volcano adventure

Explore on foot

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. Enjoy breathtaking views over the Ionian Sea and the vineyards and orchards that sprawl across the lower slopes. You’ll enjoy lunch at a local winery and  sample delicious wines.

Taormina walking tour

Taormina sits on the east coast of the island and has long been home to artists and intellectuals. 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.

“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…

Published 25th October 2022 on Trustpilot
Bob W.

Start planning
your adventure

How it works

  1. Simply click ‘Start Planning’ or give us a call.
  2. We’ll get in touch within 24 hours and work with you to perfect the details of your trip.
  3. Sit back and relax while we plan a bespoke itinerary for you.

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.