Grand Italy & Sicily
Art, food, and scenery combine in this 17-day guided tour through Italy. Revel in Renaissance artwork housed in the Vatican Museums and gaze at Michelangelo’s famous ceiling in the Sistine Chapel. Visit Rome’s iconic Colosseum as a Local Expert shares its history. In coastal Cinque Terre, stop in a fishing village and cruise the rugged Ligurian coast, admiring the colourful homes perched on the cliffs. See statues of Neptune, Hercules and Cacus, and feast on a steak dinner and local wine in Florence. In Sorrento, meet a Local Expert for a cruise to Capri, where you ascend to Capri town for an unapparelled view of the Mediterranean Sea. In the UNESCO World Heritage Site of Alberobello, meet a restaurateur who will share his farm-to-table philosophy and serve you freshly made orecchiette pasta.
- 15 May 2026 – 31 May 2026
from $15,225 pp twin share * - 22 May 2026 – 07 Jun 2026
from $10,755 pp twin share * - 29 May 2026 – 14 Jun 2026
from $10,215 pp twin share * - 12 Jun 2026 – 28 Jun 2026
from $10,650 pp twin share * - 03 Jul 2026 – 19 Jul 2026
from $9,315 pp twin share * - 14 Aug 2026 – 30 Aug 2026
from $9,607.50 pp twin share * - 21 Aug 2026 – 06 Sep 2026
from $10,575 pp twin share * - 28 Aug 2026 – 13 Sep 2026
from $9,985.50 pp twin share * - 04 Sep 2026 – 20 Sep 2026
from $12,750 pp twin share * - 11 Sep 2026 – 27 Sep 2026
from $12,725 pp twin share * - 18 Sep 2026 – 04 Oct 2026
from $12,725 pp twin share * - 25 Sep 2026 – 11 Oct 2026
from $12,395 pp twin share * - 02 Oct 2026 – 18 Oct 2026
from $12,395 pp twin share *
* Prices and category availability are subject to change without notice.
Itinerary
- 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 a city of art, antiquity, piazzas and palaces. Join your Local Expert for an in-depth exploration that brings its layered history to life. Begin at the Vatican Museums, where you’ll see an extraordinary collection of priceless artworks curated by the Popes. Marvel at Michelangelo’s frescoes in the Sistine Chapel and admire the iconic dome of St. Peter’s Basilica. Then cross the Tiber into ancient Rome to visit the Circus Maximus and the Arch of Constantine. Enjoy a guided visit of the Colosseum and uncover the legends, construction and daily life of this monumental arena. Later, you may choose to continue your exploration, from the grandeur of the Pantheon to the fountains and piazzas that define Rome’s vibrant street life. Please note: On some departures, access to St. Peter’s Basilica may be restricted due to the Papal Audience. You’ll still have time to take in the atmosphere of St. Peter’s Square during your visit to Vatican City. - 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:
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:
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:
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 as you travel south to Renaissance Florence. Upon arrival, enjoy an afternoon at leisure to explore the city at your own pace. Later, perhaps join an Optional Experience to the hilltop town of San Gimignano, known for its medieval towers and timeless charm. End the day with a traditional bistecca alla Fiorentina dinner, perfectly paired with local wine—a regional speciality not to be missed. - Day 9 – Florence, Birthplace of the Renaissance:
Today, discover the artisan traditions of Florence with a leatherwork and gold demonstration—crafts deeply rooted in the city’s heritage. Later, you’ll explore the city with Insight Choice. Choose to visit the Accademia Gallery to admire Michelangelo’s David, followed by a guided walk past the city’s marble cathedral, bell tower and baptistery, where Ghiberti’s Gates of Paradise have been recreated in stunning detail. Alternatively, join your Travel Director for a relaxed stroll and enjoy a typical Italian treat in a local cafe. Continue into the Piazza della Signoria, the city’s political heart and open-air gallery of Renaissance sculpture, and pause to view statues of Neptune, Hercules and Cacus standing proudly before the Palazzo Vecchio. This evening, consider an Optional Experience featuring a traditional Tuscan dinner paired with regional wines—including a glass of Chianti from the nearby vineyards. - 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:
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:
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 you’ll journey through dramatic volcanic landscapes and enjoy spectacular panoramic views. Later, travel through Sicily’s 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 Falcone–Borsellino Airport.
Highlights
- Revel in Renaissance artwork at the Vatican Museums and Sistine Chapel.
- Cruise the rugged Ligurian coast and admire the colorful homes of Cinque Terre.
- Savor a steak dinner and local wine in Florence and freshly made pasta in Alberobello.
Art, food, and scenery combine in this 17-day guided tour through Italy. Revel in Renaissance artwork housed in the Vatican Museums and gaze at Michelangelo’s famous ceiling in the Sistine Chapel. Visit Rome’s iconic Colosseum as a Local Expert shares its history. In coastal Cinque Terre, stop in a fishing village and cruise the rugged Ligurian coast, admiring the colourful homes perched on the cliffs. See statues of Neptune, Hercules and Cacus, and feast on a steak dinner and local wine in Florence. In Sorrento, meet a Local Expert for a cruise to Capri, where you ascend to Capri town for an unapparelled view of the Mediterranean Sea. In the UNESCO World Heritage Site of Alberobello, meet a restaurateur who will share his farm-to-table philosophy and serve you freshly made orecchiette pasta.
Inclusions
- Enjoy the comfort of Insight’s luxurious, air-conditioned, 40-seat coach with double the standard legroom and onboard washroom.
- Our customized luxury coaches are sanitized before the start of your tour and are maintained to very high standards.
- Physical distancing measures have been implemented on our customized luxury coaches.
- Hand sanitizer is freely available on board for you to use throughout the day.
- Personal radio headsets give you the freedom to wander during visits to famous highlights, without missing any of your Local Expert’s fascinating commentary.
- Hotel and restaurant tips are included – you’ll never have to worry about how much to give, nor search for foreign currency.
FAQs
- Baia Taormina, Marina di Forza D’Agrò
- Best Western Regina Elena, Santa Margherita Ligure
- Federico II Central Palace, Palermo
- Grand Hotel Dino, Baveno
- Grand Hotel La Chiusa di Chietri, Alberobello
- Hilton Garden Inn Florence Novoli
- Indigo – Sant’Elena, Venice
- Isabella, Sorrento
- St. Martin, Rome
How long is this journey?
This itinerary runs for 17 days and 16 nights.
When can I travel?
Departures are currently scheduled between 15 May 2026 and 18 Oct 2026, subject to live availability.
Are there different departure options?
Yes, multiple departures may be available depending on your preferred travel period.
Are discounts available?
Seasonal or loyalty discounts may be available on selected departures at the time of enquiry.
What is generally included?
Inclusions typically cover guided touring and selected experiences, with exact details listed in the itinerary.
Provided by: Insight VacationsFine Print
Terms and conditions apply. Click here for more details.