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Country Roads of Southern Italy & Sicily

14 Days

  • Tour Description
  • Itinerary
  • Dates & prices
  • Enquire Now
  • Travel Insurance by Allianz

Tour Description

Indulge in Italy’s finest food and views during this 2-week guided tour. In Rome, explore the city on foot with a Local Specialist, uncovering its layers of history and architecture. On Capri, settle into Anacapri and enjoy views across the Bay of Naples towards Mount Vesuvius. In Puglia, explore Alberobello, a UNESCO World Heritage Site known for its whitewashed trulli houses and distinctive conical stone roofs. Savour traditional Apulian cuisine, including seasonal dishes such as orecchiette, a pasta closely associated with the region’s culinary heritage. In Palermo, a historian will guide you through the old city, including its cathedral and the Palatine Chapel in the Palace of the Normans, where 12th-century mosaics reveal the city’s rich cultural legacy.

Priced From:

$ 8820pp *

From: 2027-04-10

To: 2027-10-09

Start Location: Rome, Italy

End Location: Palermo, Italy

Trip Type: Country Roads

Tour Advisors

Beccy Hayes

Travel Specialist

Tiffany McCrea-Lennon

Managing Director

Russell Mein

Travel Specialist

Caitlin Lennon

Travel Coordinator

Gaylyn Murdoch

Administration Manager

Holly Skene

Travel Co-ordinator

Kim Thomas

Broker

Itinerary

Welcome to the Eternal City of Rome
Day 1
Duration: 1
Accommodation: Radisson Blu GHR, Rome
Welcome to Rome, a glorious city filled with classic antiquities, medieval buildings, Renaissance palaces and baroque churches. Settle in, before meeting your Travel Director. Later today, get to know your fellow travellers over Roman-specialities dinner at a local restaurant.
Rome with the Locals
Day 2
Duration: 1
Accommodation: Radisson Blu GHR, Rome
Rome is about art, antiquity, piazzas and palaces, and our guided walk with a Local Specialist 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. Cross the Tiber river to enjoy ancient Rome. Enter the Colosseum and imagine the roar of the spectators as you hear stories of how ancient Romans liked to be entertained.
Rome to Capri
Day 3
Duration: 1
Accommodation: San Michele, Anacapri
The journey south brings you to Pompeii Archaeological Park, where your Local Specialist reveals a Roman city preserved beneath the ash of Mount Vesuvius since A.D. 79. Walk streets once lined with homes, shops and public buildings, gaining a vivid picture of everyday life almost 2,000 years ago. Continue to the Bay of Naples and cross to Capri, approaching the island by sea as its limestone cliffs rise from the water. From here, make your way to Anacapri, set high above the coastline, where you’ll settle in for the evening and enjoy dinner.
Capri, the Isle of Dreams
Day 4
Duration: 1
Accommodation: San Michele, Anacapri
Begin the day discovering Capri Town with your Local Specialist before exploring further with your choice experience. Visit the Gardens of Augustus, where terraces overlook the Faraglioni, Capri’s three limestone sea stacks, and see Via Krupp, the remarkable switchback path carved into the cliffs in the early 20th century. Alternatively, enjoy a limoncello tasting in the Piazzetta and learn why the island’s intensely fragrant lemons are so prized. Later, you may choose to join an Optional Experience cruising the Amalfi Coast and visiting Positano.
Pompeii and Alberobello
Day 5
Duration: 1
Accommodation: Grand Hotel La Chiusa di Chietri, Alberobello
Capri gives way to the landscapes of southern Italy as you travel towards Puglia, where olive groves, whitewashed towns and dry-stone walls define the countryside. Your destination is Alberobello, known for its extraordinary trulli: traditional limestone houses with conical roofs unique to this part of the region. Wander through the town’s narrow streets to see these distinctive homes up close and learn why Alberobello has been recognised as a UNESCO World Heritage Site.
The Trulli of Alberobello
Day 6
Duration: 1
Accommodation: Grand Hotel La Chiusa di Chietri, Alberobello
Join a Local Specialist 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 opt to join our Local Specialist for an exploration of Ostuni, a whitewashed town that echoes the charm of a North African Arab Medina. Stroll through its winding cobbled streets and admire its striking architecture. In the evening, enjoy a Farm-to-Table dinner, showcasing traditional Apulian dishes made with seasonal produce.
Alberobello at Leisure
Day 7
Duration: 1
Accommodation: Grand Hotel La Chiusa di Chietri, Alberobello
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 Specialist, enjoying Adriatic views and a stroll through the historic hometown of Volare singer Domenico Modugno.
Journey West to Matera
Day 8
Duration: 1
Accommodation: UNAHOTELS MH Matera
Visit Matera with a Local Specialist 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 the advocate behind a local initiative dedicated to revitalising the traditional ways of living in the area. 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: Acireale
Day 9
Duration: 1
Accommodation: Grande Albergo Maugeri, Acireale
In the morning, travel to the very toe 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.
Taormina
Day 10
Duration: 1
Accommodation: Grande Albergo Maugeri, Acireale
Join a Local Specialist for a visit to the Greek Theatre of Taormina, graced with the most spectacular of backdrops. Don't miss the chance of an optional drive through the national park to Mount Etna.
A New Dawn in Sicily
Day 11
Duration: 1
Accommodation: Grande Albergo Maugeri, Acireale
Early risers may experience what D.H. Lawrence christened the ‘dawn coast of Europe'. The day is free to explore at your leisure, or to embark on an Optional Experience to Syracuse.
Agrigento, the Valley of the Temples and on to Palermo
Day 12
Duration: 1
Accommodation: NH Palermo
Drive to Agrigento and explore the Valley of the Temples with a Local Specialist. 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
Day 13
Duration: 1
Accommodation: NH Palermo
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
Day 14
Duration: 1
Your journey draws to an end. Departure transfers arrive at Palermo Falcone–Borsellino Airport.

Dates & prices

Start Date: 2027-04-10
End Date: 2027-04-23
twin
Child Price: 9835
Adult Price: 10895
twinShare
Child Price:
Adult Price: 10895
triple
Child Price: 9605
Adult Price: 10665
single
Child Price:
Adult Price: 12515
Start Date: 2027-04-24
End Date: 2027-05-07
twin
Child Price: 9835
Adult Price: 10895
twinShare
Child Price:
Adult Price: 10895
triple
Child Price: 9605
Adult Price: 10665
single
Child Price:
Adult Price: 12605
Start Date: 2027-05-01
End Date: 2027-05-14
twin
Child Price: 9835
Adult Price: 10895
twinShare
Child Price:
Adult Price: 10895
triple
Child Price: 9605
Adult Price: 10665
single
Child Price:
Adult Price: 12605
Start Date: 2027-05-08
End Date: 2027-05-21
twin
Child Price: 9635
Adult Price: 10695
twinShare
Child Price:
Adult Price: 10695
triple
Child Price: 9405
Adult Price: 10465
single
Child Price:
Adult Price: 12405
Start Date: 2027-05-15
End Date: 2027-05-28
twin
Child Price: 9635
Adult Price: 10695
twinShare
Child Price:
Adult Price: 10695
triple
Child Price: 9405
Adult Price: 10465
single
Child Price:
Adult Price: 12315
Start Date: 2027-05-29
End Date: 2027-06-11
twin
Child Price: 9635
Adult Price: 10695
twinShare
Child Price:
Adult Price: 10695
triple
Child Price: 9405
Adult Price: 10465
single
Child Price:
Adult Price: 12315
Start Date: 2027-06-26
End Date: 2027-07-09
twin
Child Price: 9515
Adult Price: 10575
twinShare
Child Price:
Adult Price: 10575
triple
Child Price: 9285
Adult Price: 10345
single
Child Price:
Adult Price: 12095
Start Date: 2027-07-10
End Date: 2027-07-23
twin
Child Price: 9435
Adult Price: 10495
twinShare
Child Price:
Adult Price: 10495
triple
Child Price: 9205
Adult Price: 10265
single
Child Price:
Adult Price: 12015
Start Date: 2027-08-07
End Date: 2027-08-20
twin
Child Price: 8590
Adult Price: 9650
twinShare
Child Price:
Adult Price: 9650
triple
Child Price: 8360
Adult Price: 9420
single
Child Price:
Adult Price: 10980
Start Date: 2027-08-21
End Date: 2027-09-03
twin
Child Price: 8590
Adult Price: 9650
twinShare
Child Price:
Adult Price: 9650
triple
Child Price: 8360
Adult Price: 9420
single
Child Price:
Adult Price: 11080
Start Date: 2027-08-28
End Date: 2027-09-10
twin
Child Price: 8665
Adult Price: 9725
twinShare
Child Price:
Adult Price: 9725
triple
Child Price: 8435
Adult Price: 9495
single
Child Price:
Adult Price: 11055
Start Date: 2027-09-04
End Date: 2027-09-17
twin
Child Price: 10365
Adult Price: 11425
twinShare
Child Price:
Adult Price: 11425
triple
Child Price: 10135
Adult Price: 11195
single
Child Price:
Adult Price: 13045
Start Date: 2027-09-11
End Date: 2027-09-24
twin
Child Price: 10365
Adult Price: 11425
twinShare
Child Price:
Adult Price: 11425
triple
Child Price: 10135
Adult Price: 11195
single
Child Price:
Adult Price: 13045
Start Date: 2027-09-18
End Date: 2027-10-01
twin
Child Price: 10365
Adult Price: 11425
twinShare
Child Price:
Adult Price: 11425
triple
Child Price: 10135
Adult Price: 11195
single
Child Price:
Adult Price: 13045
Start Date: 2027-09-25
End Date: 2027-10-08
twin
Child Price: 10365
Adult Price: 11425
twinShare
Child Price:
Adult Price: 11425
triple
Child Price: 10135
Adult Price: 11195
single
Child Price:
Adult Price: 13045
Start Date: 2027-10-02
End Date: 2027-10-15
twin
Child Price: 10365
Adult Price: 11425
twinShare
Child Price:
Adult Price: 11425
triple
Child Price: 10135
Adult Price: 11195
single
Child Price:
Adult Price: 13045
Start Date: 2027-10-09
End Date: 2027-10-22
twin
Child Price: 7990
Adult Price: 9050
twinShare
Child Price:
Adult Price: 9050
triple
Child Price: 7760
Adult Price: 8820
single
Child Price:
Adult Price: 10670
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