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Country Roads of Southern Italy & Sicily - Insight Tour
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Insight Guided Tour

Country Roads of Southern Italy & Sicily

14 Days 37 Departures
From $4,905 per person

Departure Dates & Pricing

37 departures available

Departure DateEnd DateStatusInsight Price Per PersonPavlus Discounted Price
Apr 10, 2027 Apr 23, 2027 Available $6,150per person Get Our Discounted Price
Apr 24, 2027 May 7, 2027 Available $5,535per person Get Our Discounted Price
May 8, 2027 May 21, 2027 Available $6,050per person Get Our Discounted Price
May 15, 2027 May 28, 2027 Available $5,445per person Get Our Discounted Price
May 29, 2027 Jun 11, 2027 Available $6,050per person Get Our Discounted Price
Jun 26, 2027 Jul 9, 2027 Available $5,378per person Get Our Discounted Price
Jul 10, 2027 Jul 23, 2027 Available $5,333per person Get Our Discounted Price
Aug 7, 2027 Aug 20, 2027 Available $4,905per person Get Our Discounted Price
Aug 21, 2027 Sep 3, 2027 Available $5,450per person Get Our Discounted Price
Aug 28, 2027 Sep 10, 2027 Available $4,946per person Get Our Discounted Price
Sep 4, 2027 Sep 17, 2027 Available $6,450per person Get Our Discounted Price
Sep 11, 2027 Sep 24, 2027 Available $6,450per person Get Our Discounted Price
Sep 18, 2027 Oct 1, 2027 Available $6,450per person Get Our Discounted Price
Sep 25, 2027 Oct 8, 2027 Available $6,450per person Get Our Discounted Price
Oct 2, 2027 Oct 15, 2027 Available $6,450per person Get Our Discounted Price
Oct 9, 2027 Oct 22, 2027 Available $6,325per person Get Our Discounted Price
Apr 8, 2028 Apr 21, 2028 Available $6,450per person Get Our Discounted Price
Apr 15, 2028 Apr 28, 2028 Available $6,450per person Get Our Discounted Price
Apr 22, 2028 May 5, 2028 Available $6,450per person Get Our Discounted Price
Apr 29, 2028 May 12, 2028 Available $6,450per person Get Our Discounted Price
May 6, 2028 May 19, 2028 Available $6,350per person Get Our Discounted Price
May 13, 2028 May 26, 2028 Available $6,350per person Get Our Discounted Price
May 20, 2028 Jun 2, 2028 Available $6,350per person Get Our Discounted Price
May 27, 2028 Jun 9, 2028 Available $6,350per person Get Our Discounted Price
Jun 10, 2028 Jun 23, 2028 Available $6,275per person Get Our Discounted Price
Jun 24, 2028 Jul 7, 2028 Available $6,275per person Get Our Discounted Price
Jul 8, 2028 Jul 21, 2028 Available $6,225per person Get Our Discounted Price
Jul 22, 2028 Aug 4, 2028 Available $6,225per person Get Our Discounted Price
Aug 5, 2028 Aug 18, 2028 Available $5,725per person Get Our Discounted Price
Aug 19, 2028 Sep 1, 2028 Available $5,725per person Get Our Discounted Price
Aug 26, 2028 Sep 8, 2028 Available $5,775per person Get Our Discounted Price
Sep 2, 2028 Sep 15, 2028 Available $6,775per person Get Our Discounted Price
Sep 9, 2028 Sep 22, 2028 Available $6,775per person Get Our Discounted Price
Sep 16, 2028 Sep 29, 2028 Available $6,775per person Get Our Discounted Price
Sep 23, 2028 Oct 6, 2028 Available $6,775per person Get Our Discounted Price
Sep 30, 2028 Oct 13, 2028 Available $6,775per person Get Our Discounted Price
Oct 7, 2028 Oct 20, 2028 Available $6,650per person Get Our Discounted Price

Tour Overview

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, honoring 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 Summary

Duration14 Days / 13 Nights
OperatorInsight
Departures37 in 2027–2028
Starting From$4,905 pp
View All Departure Dates

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Tour Route

Map of your 14-day journey

Country Roads of Southern Italy & Sicily route map

Day-by-Day Itinerary

14 days through your journey

Day 1

Welcome to the Eternal City of 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 travelers over Roman-specialties dinner at a local restaurant.
Day 2

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. 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.
Day 3

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 the bay of Naples, the dramatic cliffs and coastal views unfold, the pastel-colored buildings perched above the shimmering sea, welcome you to the sun-drenched island of Capri as you cruise by jetfoil.
Day 4

Capri, the Isle of Dreams

This morning, 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.
Day 5

Pompeii and Alberobello

Start your day in Pompeii, buried in AD 79 by the historic eruption of Mount Vesuvius. Walk with your Local Expert through the cobbled streets to see a city frozen in time. Then venture on to Alberobello.
Day 6

The Trulli of Alberobello

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 opt to join our Local Expert 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.
Day 7

Alberobello at Leisure

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.
Day 8

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 recognize 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.
Day 9

To Sicily: 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.
Day 10

Taormina

Join a Local Expert for a visit to the Greek Theater 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.
Day 11

A New Dawn in Sicily

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.
Day 12

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.
Day 13

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.
Day 14

Depart Palermo

Your journey draws to an end. Departure transfers arrive at Palermo Falcone–Borsellino Airport.

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