SHORTLIST

Country Roads of Southern Italy & Sicily - Classic Group

Indulge in Italy’s finest food and views during this 2-week guided tour. When in Rome, you will toss a coin into the Trevi Fountain during a walking tour with a Local Expert. In Sorrento, settle into a luxurious resort and take in the views of Mount Vesuvius, which buried Pompeii in a pyroclastic cloud of ash and lava stones in 79 A.D. Dine on traditional Apulian cuisine inside a historic trulli house – iconic to the region with their conical stone roofs. Enjoy seasonal dishes such as orecchiette, a traditional pasta of Puglia, honouring age-old recipes, with a deep connection to their land. In Palermo, a historian will take you through the old city, showing you its cathedral and the Palatine Chapel in the Palace of the Normans, where glittering 12th century mosaics will surely take your breath away.
Tour details
Tour Provider Insight Vacations
Price From
$7,260
Number of Days
14
Start Location
Rome, Italy
End Location
Palermo, Italy
Age Range
Avg. 50+
Group Size
30 to 40
Tour Style
Luxury
Tour Themes
Virtuoso
Physical Rating
Easy to Moderate
Itinerary Open all
Welcome to the Eternal City of Rome
2025 marks a Jubilee Year, a momentous Roman Catholic event celebrated every 25 years, turning Rome into a centre of celebration between December 24, 2024, and December 31, 2025. As festivities unfold, itineraries may be adjusted to ensure you make the most of your time as you visit the Eternal City. Welcome to Rome, a glorious city filled with classic antiquities, medieval buildings, Renaissance palaces and baroque churches. Settle in, before meeting your Travel Director and fellow travellers. Tonight, enjoy Roman specialties during dinner at a local restaurant.
Rome with the Locals
Rome is about art, antiquity, piazzas and palaces, and our guided walk with a Local Expert has it in abundance. Sightsee the local way, with a leisurely passeggiata through the backstreets, where a friend in Rome will explain how modern life takes place. Admire the spectacular Trevi Fountain, see the Pantheon, the best-preserved monument from the Roman period. Enjoy a private visit to the Basilica of Saint Praxedes, welcomed by the Rector of the basilica. Enter the Colosseum and imagine the roar of the spectators as you hear stories of how ancient Romans liked to be entertained.
Rome to Sorrento
As you leave the bustling streets of Rome behind, you enter the peaceful charm of the Italian countryside. The roads wind through sun-dappled hills, where fields of golden wheat and rows of olive trees stretch endlessly under a brilliant blue sky. Small villages dot the landscape, their stone houses nestled against rolling hills, offering a glimpse into authentic Italian life and the air carries the scent of wildflowers and citrus groves. The journey southward reveals itself like a beautiful postcard, with views of the sparkling Mediterranean beginning to emerge in the distance. As you approach Sorrento, the dramatic cliffs and coastal views unfold, the town’s pastel-coloured buildings perched above the shimmering sea, welcoming you to this idyllic coastal paradise.
Capri, the Isle of Dreams
The impossibly blue sea welcomes you to the sun-drenched island of Capri as you cruise by jetfoil. On arrival, meet your Local Expert for an orientation walk through the narrow alleyways. Explore Capri with Insight Choice. Choose to visit the immaculate Gardens of Augustus with a Local Expert and admire the views over the Faraglioni Rocks. Alternatively, enjoy a tasting of limoncello, Capri’s famous lemon liqueur.
Pompeii and Alberobello
Start your day in Pompeii, buried in A.D. 79 by the historic eruption of Mount Vesuvius. Walk with your Local Expert through the cobbled streets to see a city frozen in time. Venture on to Alberobello.
The Trulli of Alberobello Relaxed Start
Join a Local Expert to explore one of Italy’s many UNESCO World Heritage Sites — the unique trulli of Alberobello, circular limestone dwellings with domed interiors and distinctive conical roofs, ingeniously built without mortar. You may also wish to join our Local Expert for an exploration of Ostuni, a whitewashed town that echs the charm of a North African Arab Medina. Stroll through its winding cobbled streets and admire its striking architecture. In the evening, enjoy a four-course Farm-to-Table dinner, showcasing traditional Apulian dishes made with seasonal produce.
Alberobello at Leisure Relaxed Start
Today is yours to enjoy at leisure or unwind and make the most of the exceptional amenities at your remarkable hotel. You can also choose to discover cliffside Polignano a Mare with a Local Expert, enjoying Adriatic views and a stroll through the historic hometown of Volare singer Domenico Modugno.
Journey West to Matera
Visit Matera with a Local Expert for an in-depth exploration of the UNESCO World Heritage Site of Sassi - a labyrinth of cave dwellings, churches, staircases and arches, hewn out of the solid rock. You may recognise Matera as the biblical backdrop for the film ‘The Passion of the Christ.’ Continue to the small village of Grottole. Once a thriving community, it has lost most of its activity and population. Meet Andrea, a local striving to bring back the area's traditional way of living. On this MAKE TRAVEL MATTER® Experience explore the historic old town to learn about the fascinating history of the village and enjoy an aperitif with local snacks helping to preserve the culture.
To Sicily and the Taormina Riviera
In the morning, travel along the Violet Coast to the very t of Italy and board your ferry bound for Sicily, across the Strait of Messina. According to Grecian legend, this was home to the mythical sea monsters Scylla, a six-headed rock monster, and Charybdis, a whirlpool, based on either side of the strait. Together, they posed an inescapable threat to passing seafarers as avoiding one meant passing too close to the other. You will soon arrive at your hotel where you will spend three glorious nights on the Taormina Riviera. Join a Local Expert for a visit to the Greek Theater of Taormina, graced with the most spectacular of backdrops. Stroll along the elegant Corso Umberto to the Piazza IX Aprile and admire the panoramic views and hews of blue from the sky to the azure sea. Later, take your pick of specially selected restaurants for your Dine-Around evening.
Free Time on the Taormina Riviera Relaxed Start
The day is at leisure to relax at your resort's private beach, or perhaps explore the medieval quarter? Don't miss the chance of an optional drive through the national park to Mount Etna, Europe's largest volcano.
A New Dawn in Sicily Relaxed Start
Early risers may experience what D.H. Lawrence christened the ‘dawn coast of Europe.' The day is free to explore Taormina at your leisure, or to embark on an Optional Experience to Syracuse.
Agrigento, the Valley of the Temples and on to Palermo
Drive to Agrigento and explore the Valley of the Temples with a Local Expert. See the massive Temple of Concord and clifftop Temple of Juno, overlooking the sea. In the afternoon, continue to the Sicilian capital of Palermo.
Palermo and the Golden Age of the Normans
Join a historian on a guided walk to see the gems of the old city. Visit the amazing Palatine Chapel in the Palace of the Normans. Outside, there are few clues to its astonishing interior, completely covered in glittering 12th century mosaics. Continue to the Palermo Cathedral which has been altered over the years and observe its unique blend of architectural styles. In the afternoon, there is free time to explore or shop in Palermo or continue sightseeing. In the evening, join your fellow guests and Travel Director at a local restaurant for a dinner of delicious local cuisine and wine.
Depart Palermo
Your journey draws to an end. Departure transfers arrive at Palermo Falcone–Borsellino Airport.
Inclusions
  • 7 Dinner (D)
  • 13 Breakfast (B)
Departure dates
All pp pricing is based on twin share occupancy. Single supplements will apply
Start End Availability Price NZD
10 May 2025 23 May 2025 Available $8,325
17 May 2025 30 May 2025 onRequest $8,325
24 May 2025 06 Jun 2025 Available $7,493
12 Jul 2025 25 Jul 2025 Available $7,556
09 Aug 2025 22 Aug 2025 Available $7,425
23 Aug 2025 05 Sep 2025 Available $7,403
30 Aug 2025 12 Sep 2025 Available $7,260
06 Sep 2025 19 Sep 2025 onRequest $8,850
13 Sep 2025 26 Sep 2025 Available $7,788
20 Sep 2025 03 Oct 2025 Available $7,788
27 Sep 2025 10 Oct 2025 Available $9,148
04 Oct 2025 17 Oct 2025 Available $7,853
11 Oct 2025 24 Oct 2025 Available $7,853
11 Apr 2026 24 Apr 2026 Available $8,850
25 Apr 2026 08 May 2026 Available $8,875
02 May 2026 15 May 2026 Available $8,895
09 May 2026 22 May 2026 Available $8,895
16 May 2026 29 May 2026 Available $8,895
23 May 2026 05 Jun 2026 Available $8,895
30 May 2026 12 Jun 2026 Available $8,895
27 Jun 2026 10 Jul 2026 Available $8,975
11 Jul 2026 24 Jul 2026 Available $8,975
08 Aug 2026 21 Aug 2026 Available $8,825
22 Aug 2026 04 Sep 2026 Available $8,795
29 Aug 2026 11 Sep 2026 Available $8,825
05 Sep 2026 18 Sep 2026 Available $9,025
12 Sep 2026 25 Sep 2026 Available $9,025
19 Sep 2026 02 Oct 2026 Available $9,025
03 Oct 2026 16 Oct 2026 Available $8,895
10 Oct 2026 23 Oct 2026 Available $8,895