Highlights
Rome: Discover ancient treasures of Rome. See Circus Maximus and the Ancient Forum, where Ancient Roman political life and law courts mingled with open-air markets and shops.
Pisa: Your Local Expert will show you the baptistery bristling with marble spines, and the colonnaded bell tower lurching behind the 11th-century cathedral - the famous Leaning Tower in the Square of Miracles.
Cinque Terre: Led by your Local Expert, visit the UNESCO World Heritage Site with dedicated time to explore one of the charming fishing villages.
Portofino: Visit this elegant fishing village and admire the coloured houses and yachts moored in the harbour.
Lake Maggiore: Experience the charming traditional social ritual of la passeggiata in the Italian Lake District. All across Italy, in cities, towns and villages people leave their houses to gently walk streets, from babies in strollers to the most senior citizens. Savour a gelato or glass of wine along the way and observe, as new romances, new babies and new shoes are all put on display. Note the ever-stylish Italians love to dress up for the occasion so feel free add a touch of flair to your outfit!
Venice: Join your Travel Director for an introduction to Venice, exploring its canals, lively squares, and historic landmarks. Discover the city’s unique charm as you navigate its maze of streets and take in iconic sights like St Mark’s Square and the Rialto Bridge.
Venice: Glide through Venice’s canals on an iconic gondola ride, passing beneath historic bridges and past elegant palaces. Soak up the city’s romantic atmosphere as your gondolier navigates the tranquil waterways, offering a unique perspective of this timeless floating city.
Florence: Join a Local Expert to view the multi-coloured marble cathedral, bell tower and baptistery, adorned by Ghiberti's Gates of Paradise. Visit the political heart of the city, Signoria Square.
Pompeii: Walk with a Local Expert through the cobbled streets of this ill-fated town, frozen in time since the first century.
Capri: Cruise by jetfoil to this famous isle through beautiful blue Mediterranean waters.
Capri: Explore Capri town with your Local Expert and see the whitewashed houses, winding alleyways, small cafes, fashionable boutiques and artisans studios.
Matera: With your Local Expert explore this town that Mel Gibson chose as the setting for his film 'The Passion of the Christ.'
Alberobello: Led by a Local Expert, explore this UNESCO World Heritage Site showcasing the Trulli of Alberobello. Circular structures with conical roofs that are domed within, built from local limestone and stacked without using mortar.
Messina: Cross the Straights of Messina to Sicily by ferry.
Taormina: Visit the ancient Greek Amphitheatre with your Local Expert. Set on a cliff, open to the sky, take your seats and enjoy the view through the crumbling arches to Mount Etna.
Taormina: Visit Taormina with a Local Expert and enjoy free time to stroll along Corso Umberto to Piazza IX Aprile.
Palermo: Discover the Sicilian capital with your Local Expert. See Pretoria Square and the 16th-century fountain. View the composite architectural styles of the Palermo Cathedral and visit the Palatine Chapel.
Venice: Join your Travel Director for an introduction to Venice, exploring its canals, lively squares, and historic landmarks. Discover the city’s unique charm as you navigate its maze of streets and take in iconic sights like St Mark’s Square and the Rialto Bridge.
Venice: Glide through Venice’s canals on an iconic gondola ride, passing beneath historic bridges and past elegant palaces. Soak up the city’s romantic atmosphere as your gondolier navigates the tranquil waterways, offering a unique perspective of this timeless floating city.
Florence: Join a Local Expert to view the multi-coloured marble cathedral, bell tower and baptistery, adorned by Ghiberti's Gates of Paradise. Visit the political heart of the city, Signoria Square.
Pompeii: Walk with a Local Expert through the cobbled streets of this ill-fated town, frozen in time since the first century.
Capri: Cruise by jetfoil to this famous isle through beautiful blue Mediterranean waters.
Capri: Explore Capri town with your Local Expert and see the whitewashed houses, winding alleyways, small cafes, fashionable boutiques and artisans studios.
Matera: With your Local Expert explore this town that Mel Gibson chose as the setting for his film 'The Passion of the Christ.'
Alberobello: Led by a Local Expert, explore this UNESCO World Heritage Site showcasing the Trulli of Alberobello. Circular structures with conical roofs that are domed within, built from local limestone and stacked without using mortar.
Messina: Cross the Straights of Messina to Sicily by ferry.
Taormina: Visit the ancient Greek Amphitheatre with your Local Expert. Set on a cliff, open to the sky, take your seats and enjoy the view through the crumbling arches to Mount Etna.
Taormina: Visit Taormina with a Local Expert and enjoy free time to stroll along Corso Umberto to Piazza IX Aprile.
Palermo: Discover the Sicilian capital with your Local Expert. See Pretoria Square and the 16th-century fountain. View the composite architectural styles of the Palermo Cathedral and visit the Palatine Chapel.
Itinerary
Let Italy’s artistry and flavors sweep you away on the 'Grand Italy & Sicily' wine tasting tour, stretching 17 days from Rome to Palermo. Marvel at the Vatican Museums and Michelangelo’s Sistine Chapel, explore Rome’s Colosseum, and cruise the colorful villages of Cinque Terre. Savor steak and local wines in Florence, sail from Sorrento to Capri for breathtaking Mediterranean views, and meet a restaurateur in Alberobello for a farm-to-table meal. With experiences led by local experts and a focus on regional cuisine, this tour package offers an unmatched exploration of Italy’s artistic, culinary, and scenic masterpieces.
day 1 - Welcome to the Eternal City of Rome
Welcome to Rome, a glorious city filled with classical antiquities, medieval buildings, Renaissance palaces and Baroque churches. Settle in before joining your Travel Director and get to know your fellow travellers over Roman specialities during dinner at a local restaurant.
day 2 - Vatican City and Rome with a Local
Rome is about art, antiquity, piazzas and palaces. Join a Local Expert for an in-depth experience bringing millennia of history to life. Embark on an enriching journey as you explore the Vatican Museums, home to an extraordinary collection of priceless artworks collected by the Popes over centuries. Marvel at Michelangelo's iconic frescoes in the Sistine Chapel, where the election of new Popes takes place, and admire the dome of St. Peter's Basilica.Journey from the Vatican City across the Tiber river to ancient Rome. See the incredible Circus Maximus and the beautifully preserved Arch of Constantine and discover the history, the construction and the legends of the iconic Colosseum on a guided visit. As you stroll with your Local Expert, imagine the gladiatorial battles and roaring spectators around the arena. Later, perhaps continue your exploration of Rome to see the Pantheon and the stunning piazzas and fountains of Rome.
day 3 - Pisa and Santa Margherita Ligure
Enjoy a delightful drive to Pisa through rolling countryside dotted with cypress trees, passing vineyards and olive groves. With a Local Expert, view the incredible Leaning Tower in the Square of Miracles from which Galileo is said to have conducted experiments on velocity and gravity. See the splendid cathedral and baptistery, decorated with mosaics and designs in solid marble. Your journey continues to the pretty seaside resort of Santa Margherita Ligure.
day 4 - The Charms of the Cinque Terre
Head to the famous Cinque Terre, which translates to Five Lands. This UNESCO World Heritage Site is located on a gorgeously wild yet hospitable part of the coastline. With a Local Expert, approach one of the fishing villages by boat (weather permitting). In Monterosso, spend some time exploring the medieval quarter or the popular sandy beach before continuing to the village of Portofino, famed for its colourful houses. Browse the boutiques and stay a while in the cafe bars on the piazzetta, watching the yachts moored in the harbour. Then cruise along the rugged Ligurian coast to your hotel in the resort of Santa Margherita.
day 5 - Lake Maggiore Relaxed Start
Head north to beautiful Lake Maggiore in the Italian Lakes District and the town of Baveno, noted for its narrow cobbled streets and charming square. On arrival, settle into your hotel and take in the magical scenery. In the afternoon, why not join an Optional Experience cruise to Isola Bella to explore the palace and admire the stunning and immaculate Italian style gardens.
day 6 - On to Venice Relaxed Start
Your Italy and Sicily tour continues past the Soave vineyards, the city of Padua and on to the canals of Venice. In the evening, enjoy dinner with your travelling companions.
day 7 - Venice and the Magic of La Serenissima Relaxed Start
Cruise by private boat on a journey of discovery past churches and palaces reflecting the rich architectural history of Venice from the 13th to the 18th centuries. Marvel at the intricate facades and learn about the stories behind these historical buildings. Arrive close to St Mark's Square and stroll along the waterfront, passing the iconic Bridge of Sighs and the majestic Doge's Palace. It was from here that the infamous Casanova made his daring escape. Turn the corner into St Mark's Square and be captivated by the grandeur of the basilica. Afterwards, board a traditional gondola for a serenade along the romantic canals. Join a MAKE TRAVEL MATTER Experience and witness the artistry of expert glassblowers as they create beautiful, handcrafted glass pieces, preserving centuries-old techniques and traditions.
day 8 - A Scenic Journey to Florence
Bid farewell to Venice and begin your journey to Renaissance Florence. Explore Florence with Insight Choice. Choose to visit the Accademia Museum and see Michelangelos David. After, continue on foot to admire the multicoloured marble cathedral, bell tower and baptistery, where Ghibertis Gates of Paradise have been recreated in all their glory. Continue into the Piazza della Signoria, still the political heart of Florence and an open-air gallery of Renaissance masterpieces. Spend time gazing at statues such as Neptune, Hercules and Cacus along the front of the Palazzo Vecchio. Alternatively, take a stroll with your Travel Director to enjoy a typical Italian treat in a local cafe. End the day with a traditional Bistecca alla Fiorentina steak dinner paired with delicious local wine, a specialty not to be missed.
day 9 - Florence, Birthplace of the Renaissance Relaxed Start
Enjoy a day at leisure to explore Florence. Perhaps join an Optional Experience to explore the hilltop town of San Gimignano?
day 10 - Ill-fated Pompeii and on to Sorrento
Journey south through the volcanic hills of Frascati to Pompeii, which was buried in A.D. 79 by Mount Vesuvius' catastrophic eruption. Walk with a Local Expert through the preserved cobbled streets for a glimpse into the daily life of civilisation during the Roman Empire. Follow the clifftop road to the resort town of Sorrento, overlooking the Bay of Naples.
day 11 - Capri, the Isle of Dreams
Meet your Local Expert and cross the Bay of Naples to reach the beautiful Isle of Capri, a rock rising sheer from the Mediterranean! For 2,000 years, Capri has beckoned visitors from Tiberius Caesar to Gracie Fields. Arriving at the Marina Grande by boat, ascend to Capri town. Explore the narrow alleyways and descend to the port by funicular railway for the return to Sorrento. Later, perhaps explore the Amalfi Coast?
day 12 - Sassi di Matera and Alberobello
After breakfast, discover two UNESCO World Heritage Sites. First, visit Matera for an in-depth guided exploration of the extraordinary Sassi, ancient troglodyte dwellings and churches dug out of the rock. These are the most extensive example of their kind in the Mediterranean and were inhabited by about 20,000 people up until the 1950s. Matera was also used as the setting for the film 'The Passion of the Christ'. Continue to Alberobello, the second UNESCO World Heritage Site, and your home for the next two nights.
day 13 - The Trulli of Alberobello Relaxed Start
Admire another of Italy's record number of UNESCO World Heritage Sites with a Local Expert. The trulli of Alberobello are circular structures with conical roofs that are domed within. They are built from local limestone and stacked without using mortar. In the evening, delight at the freshly prepared Farm-to-Table dinner.Savour a traditional meal and discover regional life through its local cuisine.
day 14 - Alberobello to Sicily
The local roads will take you south, following the shores of the Gulf of Taranto to the mountainous Calabria region. Travel along the Purple Coast to the very 'toe' of Italy and board your ferry bound for Sicily. According to ancient legend, it was here at the Straits of Messina where the twin whirlpools of Scylla and Charybdis carried unwary seafarers away to their doom. After disembarking, continue to Taormina. Join a Local Expert for a visit to the Greek Theatre, graced with the most spectacular of backdrops.
day 15 - The Dawn Coast of Europe to Palermo Relaxed Start
Relax this morning on the stunning Dawn Coast of Europe or choose to join an optional experience to majestic Mt. Etna, Europe's highest active volcano, where youll journey through dramatic volcanic landscapes and enjoy spectacular panoramic views. Later, travel through Sicilys beautiful countryside as you make your way to the vibrant capital city of Palermo, rich in history, culture and architectural splendour.
day 16 - Palermo, Capital of Sicily
Explore with your Local Expert who will show you the highlights of the capital. Venture inside the cathedral of Palermo and appreciate its composite architectural styles. Next, head to the amazing Palatine Chapel in the Palace of the Normans. From the honey-coloured walls glowing in the sun on the outside, enter a world of glittering ancient mosaics on the inside. Enjoy the rest of your day at leisure exploring this fascinating city. This evening, join your travelling companions and Travel Director at a local restaurant for an unforgettable dinner of delicious local cuisine and wine.
day 17 - Depart Palermo
Your grand tour of Italy draws to an end. Departure transfers arrive at Palermo FalconeBorsellino Airport.

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Customer Reviews
Read what other travelers have to say about Grand Italy & Sicily
You get to see so many amazing sights and places. Some i had never heard of!
We saw historical sites most of all the on road team and expects areas were very knowledgeable and explained everything well . Hotels and food was so beautifully prepared and tastey . We were welcomed wherever we visited . I will recommend this strip to anyone who want to tour Italy/Sicily . Insight tours are the best . The couch very comfortable we were always connected on wife . Driver is the expect and we felt so safe
A very extensive itinerary but it needed 2 extra days in Rome and 2 days in Milan considering that we drove past and were literally 50 kilometres away from the city
It was a well organised tour and we saw many wonderful towns and cities. Every thing ran smoothly and we give credit to a wonderful tour director and bus driver.
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