Grand Tour of Italy
- Duration
- 21 days
- Price guide
- From $35,418 per person
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

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
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.

Days 4-5
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.

Where you could stay

Traditional agriculture at La Portofinese
Embark on a full-circle journey through traditional Mediterranean agriculture in Portofino, witnessing how sustainable farming methods can sustain local communities in the process. You’ll start at Eco-Farm, set within the National Park, where you can explore the carefully restored olive groves and vineyards, coaxed back to life after being abandoned for decades. Learn about the organic farming methods and advanced renewable energy systems that allow the estate to operate with minimal carbon footprint. Finish your experience by completing the agriculture circle at Osteria dei Coppelli, where you’ll sample the best of locally grown produce during a picnic lunch or early dinner.
Days 6-7
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.

Where you could stay
Days 8-9
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.

Where you could stay
Days 10-12
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.

Where you could stay
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 13-15
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.

Where you could stay
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 16-17
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.

Day 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.

Where you could stay
Days 19-21
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.

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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