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Country Roads of Southern Italy and Sicily

Two Week Tour to Rome, Alberobello & Sicily | Operated by InsightVacations

  • 15 Days

  • 1 Country

    Italy
  • 15 Cities

    Rome, Alberobello, Matera, Pompeii, Sorrento, Capri, Villa San Giovanni, Giardini Naxos, Taormina, Cefalu, Palermo, Agrigento, Ragusa, Syracuse, Catania
  • 22 Meals

    6 Dinner with Wines, 14 Breakfasts, 1 Lunch with Wine, 1 Dinner
  • Pace: Comfortable

    Mainly 2–3-night stays in each location. Comfortable travel days with numerous stops. Requires 1-3 miles of walking per day that might involve some uneven surfaces, such as cobblestones and stairs.

Trip Itinerary

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. Transfers depart from Rome's Fiumicino Leonardo da Vinci Airport for your hotel. Relax and settle in before joining your Travel Director and getting to know your fellow travelers over a delicious Welcome Dinner with wine at a local restaurant.

Hotel: Kolbe Hotel Rome
Included Meals: Dinner with Wine
Authentic Dining: Rome Welcome Dinner Enjoy a Welcome Dinner with your fellow travelers at a uniquely Roman local restaurant.
Notes
Day 2: Rome with the Locals

Rome is about art, antiquity, piazzas and pizza, 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. Toss a coin into the spectacular Trevi Fountain, see the Pantheon, the best-preserved monument from the Roman period, and enjoy free time to do as the Romans do. Perhaps join a tour to discover the incredibly characteristic Roman quarter of Trastevere. Get off the beaten track and explore Rome’s most untouched and unique districts and most consistently unchanged medieval neighborhoods, Trastevere is dotted with ancient and dimly lit churches, crumbling buildings and streets barely wide enough for a Fiat. With your Local Expert, explore the medieval labyrinth of alleyways and pause from time to time to take in this very atmospheric area. A maze of food shops, art galleries, cafes, apartment buildings and pretty squares, this district was once rather run-down and working-class, but has now become one of the city's liveliest and most popular neighborhoods.

Hotel: Kolbe Hotel Rome
Included Meals: Breakfast
Top Rated Highlights: Rome City Tour Sightsee the local way, with a leisurely passeggiata through the backstreets, where a friend in Rome will explain how modern life takes place, around ancient treasures like the Trevi Fountain, the Pantheon and Piazza Navona. 
Notes
Day 3: Vatican and Alberobello

With your Local Expert, visit the Vatican Museums. Inside the Sistine Chapel, admire Michelangelo’s famous ceiling before visiting St. Peter’s Basilica. Next, journey to Alberobello.

Hotel: Grand Hotel La Chiusa di Chietri
Included Meals: Breakfast, Dinner with Wine
Insight Experiences: Vatican Visit with Fast-Tracked Entry Gain Fast Track access into the Vatican Museums and admire the famous Bramante Staircase. Witness the genius of Michelangelo in the Sistine Chapel and view the splendid dome of St. Peter's Basilica.
Notes
Day 4: 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, join a MAKE TRAVEL MATTER® Experience using home-grown organic and locally sourced, seasonal produce, you sit down to a delicious four-course, Farm-to-Table Highlight Dinner.

Hotel: Grand Hotel La Chiusa di Chietri
Included Meals: Breakfast, Dinner with Wine
Top Rated Highlights: Trulli of Alberobello Visit 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.
Make Travel Matter: Organic Farm-to-Table Meal at Terre Madre Alberobello Dine at Trattoria Terra Madre, where owner Alessandro and his nonna have built a restaurant that focuses on sustainability and creating jobs for locals. Everything is grown organically and harvested on site, and excess produce is donated to their community. The restaurant sources their produce locally, implements a strategy to reduce their food waste and promotes sustainable agricultural practices. Trattoria Terra Madre, advances UN Sustainable Development Goal 12: Responsible Consumption & Production.
Notes
Day 5: Free Time in Alberobello

The day is free for you to enjoy this extraordinary town as you wish. Why not join an Optional Experience to the stunning city of Ostuni? With its dazzling white houses and fascinating history, it is a true delight. Your Local Expert experience reveals this town reminiscent of a North African Arab Medina. Admire the stark white-washed buildings, narrow cobbled streets and arched stairways. Set against three hills and perched high above the beautiful sea; 'The White Town' is a photographer's delight. Afterwards, visit a Mill to taste the renowned olive oil produced in this area that incorporates olives from the ancient groves of Puglia. Or, join an optional Masseria Dinner in Puglia, a food lovers' paradise. You’re off to the countryside to a local 'Masseria', a typical ancient fortified 'Farmhouse'. Enjoy an authentic dinner in a 'country roads' experience all served up with great wines form the region.

Hotel: Grand Hotel La Chiusa di Chietri
Included Meals: Breakfast
Notes
Day 6: Journey South 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 traditional way of living of the area. On this MAKE TRAVEL MATTER® Experience explore the historic old town to learn about the fascinating history of the village. Later, enjoy a light lunch with wine, helping to preserve the local culture.

Hotel: MH Matera Hotel
Included Meals: Breakfast, Lunch with Wine, Dinner
Make Travel Matter: Participate in the Wonder Grottole Project Participate in the fascinating Wonder Grottole project. This regeneration initiative works to rehabilitate the abandoned historic center and preserves traditional village life.
Top Rated Highlights: Visit Sassi di Matera With your Local Expert, visit the famous Sassi or cave dwellings, which were home to approximately 20,000 people until 1950 and are now a UNESCO World Heritage Site.
Notes
Day 7: Pompeii and Sorrento

Journey to the region of Campania to visit 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 the picturesque resort of Sorrento, perched upon the southern cliffs of the Bay of Naples and looking over to Mount Vesuvius.

Hotel: Hotel Isabella
Included Meals: Breakfast
Top Rated Highlights: Pompeii City Tour Walk with a Local Expert through the cobbled streets of this ill-fated town, frozen in time since the 1st century.
Notes
Day 8: Capri, the Isle of Dreams

Cruise by jetfoil across the impossibly blue sea to the sun-drenched island of Capri. On arrival, enjoy an escorted ride in an iconic, open-top taxi to Capri Town and meet your Local Expert for an orientation walk through 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. Descend to the port by funicular before returning to Sorrento.

Hotel: Hotel Isabella
Included Meals: Breakfast
Top Rated Highlights: Visit the Gardens of Augustus in Capri Discover the luxuriant Gardens of Augustus with a Local Expert and admire views of the Faraglioni rocks.
Authentic Dining: Limoncello Tasting in Capri Enjoy a tasting of limoncello, Capri's traditional lemon liqueur.
Top Rated Highlights: Cruise by Jetfoil to the Isle of Capri Cruise by jetfoil to this famous isle through beautiful blue Mediterranean waters to meet your Local Expert.
Top Rated Highlights: Isle of Capri Open-top Taxi Ride Relax and enjoy the views as you are driven in an iconic open-top taxi.
Notes
Day 9: To Sicily and the Taormina Riviera

In the morning, travel along the Purple Coast 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. You will soon arrive at your hotel where you will spend three glorious nights on the Taormina Riviera.

Hotel: RG Naxos Hotel
Included Meals: Breakfast, Dinner with Wine
Top Rated Highlights: Ferry to Sicily Cross the Straights of Messina to Sicily by ferry.
Notes
Day 10: Taormina and the Dawn Coast of Europe

Your hotel faces east, so early risers may learn why D.H. Lawrence christened this 'The Dawn Coast of Europe.' After breakfast, perhaps take an Optional Experience through the vineyards to Mount Etna, Europe's largest active volcano. Travel to the old town of Taormina, which clings to the side of Mount Tauro, overlooking the Ionian Sea and Mount Etna. With your Local Expert, visit the Greek theater set on a cliff and open to the sky. Take a moment to sit in this ancient theater and admire the view through the crumbling arches to Mount Etna. Stroll through the old town and admire Taormina's grandest building and along the elegant Corso Umberto.

Hotel: RG Naxos Hotel
Included Meals: Breakfast
Top Rated Highlights: Admire the Taormina Sunrise Should you awake early, you may see why this is known as 'The Dawn Coast of Europe.'
Top Rated Highlights: Taormina Greek Ampitheatre Visit Visit the ancient Greek Ampitheatre 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.
Top Rated Highlights: Taormina Riviera Orientation During your orientation with your Travel Director, visit the courtyard of Palazzo Corvaja, seat of the first Sicilian parliament, and stroll along Corso Umberto to Piazza IX Aprile.
Notes
Day 11: Cefalu and Palermo

Travel to the quaint fishing town of Cefalu. The town's imposing cathedral was erected to fulfill a vow made by the Norman King Roger II. Stroll down to the medieval stone fountain and seek out the Gothic arch of the Porta Marina for a picture-perfect view of the little harbor. Later, travel onwards to Palermo.

Hotel: NH Palermo
Included Meals: Breakfast
Top Rated Highlights: Cefalu Orientation Your Travel Director will show you the cathedral, built to fulfil a vow. Walk to the medieval stone fountain in the old fishermen's quarter, find the Gothic arch of the Porta Marina and see the harbor.
Notes
Day 12: Palermo & the Golden Age of the Normans

Explore Palermo with Insight Choice. Choose to visit the spectacular 12th-century Palatine Chapel with a Local Expert. Alternatively, join the Anti-Mafia tour of Palermo, part of a MAKE TRAVEL MATTER® Experience, and find out how locals are working together in modern day Palermo. In your free time this afternoon, you could visit Palermo Cathedral which has been altered many times over the years and observe its unique blend of architectural styles. For your dining pleasure, you are offered a selection of local restaurants on your Dine-Around Evening.

Hotel: NH Palermo
Included Meals: Breakfast, Dinner with Wine
Make Travel Matter: Uncover Palermo's Rich History Learn about the civil anti-mafia movement and discover the lesser known history of Palermo. 
Authentic Dining: Palermo Dine-Around Evening Sample a variety of cuisine on your Dine-Around evening.
Top Rated Highlights: Palermo Local Market Visit Join your Local Expert for a walk through the lively Vucciria market. 
Top Rated Highlights: Palatine Chapel Visit Visit the spectacular 12th Century Palatine Chapel. Its sombre exterior gives away few clues to the riches inside. Step into a world where the walls glitter with 12th century mosaics, the best of their kind in the world.
Notes
Day 13: Explore the Valley of the Temples and on to Ragusa

Journey to Agrigento. Explore the Valley of the Temples with a Local Expert and see the massive Temple of Concordia and the clifftop Temple of Juno overlooking the sea. Your travels continue to the hilltop town of Ragusa.

Hotel: Mediterraneo Palace
Included Meals: Breakfast
Top Rated Highlights: Agrigento City Tour A Local Expert will lead you through the magnificent remains of the Greek colony in the Valley in the Temples. See the massive Temple of Concord and clifftop Temple of Juno.
Notes
Day 14: Ancient Syracuse and Catania

Sightseeing with your Local Expert takes you to Syracuse’s Paradise Quarry with its unusual Ear of Dionysius, an ear-shaped grotto with an unusual echo. See the superb Greek theater, carved out of solid rock, one of the largest of the ancient world. There is time to explore the atmospheric Old City, a maze of narrow streets lined with palaces, sprawling over the island of Ortygia. It was here that the famous geometrician Archimedes ran naked through the streets, crying ‘Eureka!' Continue to Catania to celebrate your time in Sicily over Dinner with your fellow travelers.

Hotel: NH Catania Centro
Included Meals: Breakfast, Dinner with Wine
Top Rated Highlights: Syracuse City Tour Walk through the gardens of Paradise Quarry, listen to the acoustics in the mysterious Ear of Dionysius and visit the Greek theater.
Top Rated Highlights: Catania Orientation During an exploration with your Travel Director see the Duomo, Piazza and the noble buildings of Palazzo Senatorio.
Notes
Day 15: Depart Catania

Appreciate views of Mount Etna on your way. Departure transfers arrive at Catania Airport at 06:30 and 08:30.

Included Meals: Breakfast
Notes
This itinerary is for reference only. Upon booking with GET, guests will receive tour documents which will list all confirmed hotels and itineraries based upon the guest's departure date.

Price Includes

Dining Summary
  • - 6 Dinner with Wines (DW)
  • - 14 Breakfasts (B)
  • - 1 Lunch with Wine (LW)
  • - 1 Dinner (D)
Authentic Dining
  • Enjoy a Welcome Dinner with your fellow travelers at a uniquely Roman local restaurant.
  • Enjoy a tasting of limoncello, Capri's traditional lemon liqueur.
  • Sample a variety of cuisine on your Dine-Around evening.
Top Rated Highlights
  • Sightsee the local way, with a leisurely passeggiata through the backstreets, where a friend in Rome will explain how modern life takes place, around ancient treasures like the Trevi Fountain, the Pantheon and Piazza Navona. 
  • 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.
  • With your Local Expert, visit the famous Sassi or cave dwellings, which were home to approximately 20,000 people until 1950 and are now a UNESCO World Heritage Site.
  • Walk with a Local Expert through the cobbled streets of this ill-fated town, frozen in time since the 1st century.
  • Discover the luxuriant Gardens of Augustus with a Local Expert and admire views of the Faraglioni rocks.
  • Cruise by jetfoil to this famous isle through beautiful blue Mediterranean waters to meet your Local Expert.
  • Relax and enjoy the views as you are driven in an iconic open-top taxi.
  • Cross the Straights of Messina to Sicily by ferry.
  • Should you awake early, you may see why this is known as 'The Dawn Coast of Europe.'
  • Visit the ancient Greek Ampitheatre 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.
  • During your orientation with your Travel Director, visit the courtyard of Palazzo Corvaja, seat of the first Sicilian parliament, and stroll along Corso Umberto to Piazza IX Aprile.
  • Your Travel Director will show you the cathedral, built to fulfil a vow. Walk to the medieval stone fountain in the old fishermen's quarter, find the Gothic arch of the Porta Marina and see the harbor.
  • Join your Local Expert for a walk through the lively Vucciria market. 
  • Visit the spectacular 12th Century Palatine Chapel. Its sombre exterior gives away few clues to the riches inside. Step into a world where the walls glitter with 12th century mosaics, the best of their kind in the world.
  • A Local Expert will lead you through the magnificent remains of the Greek colony in the Valley in the Temples. See the massive Temple of Concord and clifftop Temple of Juno.
  • Walk through the gardens of Paradise Quarry, listen to the acoustics in the mysterious Ear of Dionysius and visit the Greek theater.
  • During an exploration with your Travel Director see the Duomo, Piazza and the noble buildings of Palazzo Senatorio.
Insight Experiences
  • Gain Fast Track access into the Vatican Museums and admire the famous Bramante Staircase. Witness the genius of Michelangelo in the Sistine Chapel and view the splendid dome of St. Peter's Basilica.
Make Travel Matter
  • Dine at Trattoria Terra Madre, where owner Alessandro and his nonna have built a restaurant that focuses on sustainability and creating jobs for locals. Everything is grown organically and harvested on site, and excess produce is donated to their community. The restaurant sources their produce locally, implements a strategy to reduce their food waste and promotes sustainable agricultural practices. Trattoria Terra Madre, advances UN Sustainable Development Goal 12: Responsible Consumption & Production.
  • Participate in the fascinating Wonder Grottole project. This regeneration initiative works to rehabilitate the abandoned historic center and preserves traditional village life.
  • Learn about the civil anti-mafia movement and discover the lesser known history of Palermo. 

Optional Experiences

Optional Experiences are subject to change. Your Travel Director will supply you with a final list of Optional Experiences available on your trip. Optional Experiences cannot be booked online; they can be purchased during your trip through your Travel Director.

Discovering Trastevere (Available on Day 2)

Get off the beaten track and explore Rome’s most untouched and unique districts, Trastevere. One of Rome's most consistently unchanged medieval neighborhoods, Trastevere is dotted with ancient and dimly lit churches, crumbling buildings and streets barely wide enough for a Fiat. With our local expert, we’ll explore the medieval labyrinth of alleyways and pause from time to time to take in this very atmospheric area. A maze of food shops, art galleries, cafes, apartment buildings and pretty squares, this district was once rather run-down and working-class, but has now become one of the city's liveliest and most popular neighborhoods!

Adult Price: €34 Roman Dinner Party (Available on Day 2)

Enjoy an evening of delicious Roman cuisine with drinks and a great Italian ambiance.

Adult Price: €71 Visit Polignano a Mare (Available on Day 4)

This afternoon we'll visit the picture-perfect 'Pearl of the Adriatic' Polignano a Mare with our Local Expert. A quaint and delightful town built upon cliffs with breath-taking views of the turquoise Adriatic Sea below, it's also the hometown of Domenico Modugno, who sang and co-wrote Volare. We'll take a stroll in the historical center, where traces of the town’s Arab, Byzantine, Spanish, and Norman past still coexist.

Adult Price: €38 The White Town of Ostuni and Olive Mill (Available on Day 5)

In the company of our Local Expert experience the town of Ostuni which is reminiscent of a North African Arab Medina. Admire the stark white-washed buildings, narrow cobbled streets and arched stairways. Set against three hills and perched high above the beautiful sea; 'The White Town' is a photographer's delight. Afterwards, we'll visit a Mill to taste the renowned olive oil produced in this area that incorporates olives from the ancient groves of Puglia!

Adult Price: €38 Masseria Dinner (Available on Day 5)

Puglia is a food lovers paradise, famous for its local dishes using the freshest of ingredients! Tonight it's off to the countryside to a local 'Masseria', a typical ancient fortified 'Farmhouse' of Puglia. We enjoy an incredible, authentic Puglian style dinner in a beautiful setting! A wonderful 'country roads' experience all served up with great wines form this region!

Adult Price: €70 Island Tour of Capri (Available on Day 8)

Experience the spectacular cliffs and famous turquoise waters of Capri during a relaxing cruise to the most beautiful part of the island, the southern side. View the beautiful grottoes and unique coastline before ascending to Capri town. This optional experience is weather dependent and may be replaced by a minibus tour of the Island with a visit to Anacapri and the Villa San Michele.

Adult Price: €52 Amalfi Coast Drive & Positano Visit (Available on Day 8)

Drive along the clear blue waters and picturesque resorts of the Amalfi Coast, arguably the most glamorous and scenic stretch of coast in Europe. Minibuses wind their way down serpentine roads to the exclusive artists' paradise, Positano. Explore elegant shops, watch artists at work, or enjoy an aperitivo in a beachside cafe.

Adult Price: €66 Mt Etna (Available on Day 10)

Where myth and legend merge to reality! With a Local Expert we'll drive up Mt. Etna, Europe's largest active volcano. Ascend through the fertile foothills, bypassing small villages, lush forests, ancient craters and lava flows to see amazing lunar landscapes and houses surrounded by lava. Admire astonishing panoramic views over the eastern Sicilian coast and Ionian Sea whilst discovering the history of Sicily’s most popular attraction and its eruptions. (Footwear such as trainers or boots advised)

Adult Price: €61 Dinner in the Clouds (Available on Day 10)

With one of the most incredible rides of your lives, you will arrive high above the sea, a world apart from the areas that tourists tread. You'll arrive in your terraced authentic local restaurant for a truly educational meal of delicious regional specialties, with accompanying local wines.

Adult Price: €83 Dinner in Palermo (Available on Day 11)

Sicilian dining is one of life's true pleasures! We'll indulge in great food made from the freshest ingredients, accompanied by the island's delicious wines.

Adult Price: €70 Dinner In Ragusa (Available on Day 13)

Indulge in the varied and complex flavors of Sicily, at this evening's dinner. Sicillian shores are washed by three different seas, so fish is a must (meat alternative available). The large greenhouses around Ragusa also produce a wide range of fruit and vegetables to enjoy. Arabian settlers brought sugar with them and now the island's dolci are considered among the best in Italy. Of course any Italian meal wouldn't be complete without the wonderful local wine. Buon Appetito!

Adult Price: €63 Guided Tour Of Ragusa Ibla (Available on Day 14)

Join a Local Expert to explore the jumble of churches, houses, old squares and civic palazzi that make up Ragusa Ibla. Devastated by the earthquake of 1693, this part of town was rebuilt along the lines of the old medieval layout. With most of the nobility and wealthier citizens choosing to live in the new upper town, the fortunes of Ibla waned. Now you can step back more than three hundred years into the past, where every turn of the winding streets and stairways comes with the promise of another fantastic discovery.

Adult Price: €28