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Country Roads of Southern Italy & Sicily route map

Arrive in Rome and settle in before meeting your Travel Director. Meet your fellow travelers over a dinner of Roman specialties at a local restaurant.

Meals: Dinner

Take a guided passeggiata through Rome’s backstreets with a Local Expert, who explains modern life in the city. Cross the Tiber to explore ancient Rome, enter the Colosseum, and hear stories about how ancient Romans were entertained.

Meals: Breakfast

Travel south to Pompeii Archaeological Park and walk its streets with a Local Expert, learning about the Roman city buried by Mount Vesuvius in A.D. 79. Continue to the Bay of Naples, cross by sea to Capri, then travel to Anacapri for the evening and dinner.

Meals: Breakfast,Dinner

Discover Capri Town with a Local Expert. Choose between visiting the Gardens of Augustus, with views of the Faraglioni and Via Krupp, or a limoncello tasting in the Piazzetta. Later, you may join an optional cruise along the Amalfi Coast and visit Positano.

Meals: Breakfast

Travel from Capri through the landscapes of southern Italy to Puglia, passing olive groves, whitewashed towns and dry-stone walls. In Alberobello, see the traditional limestone trulli houses with conical roofs and explore the town’s narrow streets and UNESCO World Heritage Site.

Meals: Breakfast,Dinner

Explore Alberobello’s UNESCO-listed trulli with a Local Expert, seeing the circular limestone dwellings, domed interiors and conical roofs built without mortar. You may opt to explore Ostuni with a Local Expert, strolling its winding cobbled streets and seeing its whitewashed architecture. Enjoy an evening Farm-to-Table dinner of traditional Apulian dishes made with seasonal produce.

Meals: Breakfast,Dinner

Enjoy a day at leisure or relax at the hotel. Alternatively, join a Local Expert to visit cliffside Polignano a Mare for Adriatic views and a stroll through the historic hometown of singer Domenico Modugno.

Meals: Breakfast

Explore Matera’s UNESCO-listed Sassi with a Local Expert, including its cave dwellings, churches, staircases and arches carved from rock. Continue to Grottole and meet an advocate of a local initiative to revitalize traditional ways of life. On this MAKE TRAVEL MATTER® Experience, explore the historic old town, learn about the village’s history and enjoy an aperitif with local snacks.

Meals: Breakfast,Dinner

Travel to the toe of Italy and board a ferry across the Strait of Messina to Sicily. The strait is associated in Grecian legend with Scylla, a six-headed rock monster, and Charybdis, a whirlpool, which threatened passing seafarers.

Meals: Breakfast,Dinner

Visit Taormina’s Greek Theater with a Local Expert. You may opt to drive through the national park to Mount Etna.

Meals: Breakfast

Early risers may experience the dawn coast of Europe. Spend the day at leisure or join an optional experience to Syracuse.

Meals: Breakfast

Travel to Agrigento and explore the Valley of the Temples with a Local Expert, including the Temple of Concord and the clifftop Temple of Juno overlooking the sea. Continue to Palermo in the afternoon.

Meals: Breakfast

Take a guided walk through Palermo’s old city with a historian. Visit the Palatine Chapel in the Palace of the Normans, with its 12th-century mosaics, and Palermo Cathedral, with its blend of architectural styles. Enjoy free time in the afternoon to explore, shop or continue sightseeing. In the evening, join your fellow guests and Travel Director for dinner of local cuisine and wine at a local restaurant.

Meals: Breakfast,Dinner

The journey ends. Departure transfers arrive at Palermo Falcone–Borsellino Airport.

Meals: Breakfast

What’s included

Scheduled airport transfers on the tour's arrival and departure days, including the departure transfer to Palermo Falcone–Borsellino Airport
An expert Travel Director and professional Driver, with Local Experts for sightseeing and a historian-led walk in Palermo
A Grottole village visit with an aperitif and local snacks, plus a choice on Capri between the Gardens of Augustus and a limoncello tasting
Audio headsets for sightseeing, luggage porterage for one suitcase per person at the hotels, and complimentary coach and hotel Wi-Fi where available
Hotel charges and local taxes
Tips for hotel housekeeping and porters, and restaurant staff for included meals
13 breakfasts and 7 dinners, including a Roman-specialties dinner in Rome, a farm-to-table dinner in Alberobello and a Palermo dinner with Sicilian wine
13 nights in 4- and 5-star hotels: Radisson Blu GHR in Rome, San Michele in Anacapri, Grand Hotel La Chiusa di Chietri in Alberobello, UNAHOTELS MH Matera, Grande Albergo Maugeri in Acireale and NH Palermo
Travel by air-conditioned 40-seat coach with extra legroom and an onboard washroom, plus the jetfoil to Capri and a ferry across the Strait of Messina
Guided sightseeing and visits to Rome's Colosseum, Pompeii Archaeological Park, the trulli of Alberobello, Matera's Sassi, Taormina's Greek Theater, Agrigento's Valley of the Temples, and Palermo's Palatine Chapel and cathedral

What’s not included

International flights to Rome and from Palermo
Visas, where required for your nationality
Travel insurance
All lunches and the 6 dinners not listed in the itinerary; drinks are extra unless specified as part of an included experience or meal
Optional experiences, including an Amalfi Coast cruise and Positano visit, excursions to Ostuni or Polignano a Mare, a Mount Etna drive, a Syracuse excursion and additional Palermo sightseeing
Voluntary tips for the Travel Director, Driver and Local Experts
Personal expenses such as shopping, laundry, phone calls and minibar purchases
Extra hotel nights before or after the tour and any transfers needed outside the scheduled complimentary airport transfer times

Additional information

Travel through Mount Etna’s national park on an optional drive towards Europe’s most active volcano. Observe the changing terrain around the mountain that dominates eastern Sicily’s skyline.

Etna’s volcanic activity has shaped the surrounding landscape over centuries and remains part of life in the region. This scenic excursion offers a closer perspective on the mountain seen from Taormina. It is at additional cost and bookable on tour.

  • 7 Dinner (D)
  • 13 Breakfast (B)
  • Rome: Follow in the footsteps of gladiators for a deeper insight into life in ancient Rome when you enter the Colosseum.
  • Hand sanitizer is freely available on board for you to use throughout the day.

Insight Vacations

  • Business class coach with extended leg room
  • Top-rated dining, from farm-to-table to local restaurants
  • 4 & 5-star stays

Taste Roman specialties at a local restaurant while meeting your Travel Director and fellow travellers. This hosted dinner offers an introduction to the flavours of Lazio in the city where the journey begins.

Roman cooking draws character from straightforward ingredients and well-established traditions, from pasta dishes to seasonal produce. Sharing a meal provides a relaxed setting to hear about the places and food that shape everyday life in the capital.

Walk Rome’s backstreets with a Local Expert on a leisurely passeggiata that explores how contemporary life unfolds among ancient buildings, piazzas and palaces. The Trevi Fountain, Pantheon and Piazza Navona are among the celebrated landmarks associated with this local-style introduction.

Learn to read the city’s layers, from the Pantheon’s Roman origins to the theatrical spaces of baroque Rome. The pace leaves room to notice the smaller streets and daily rituals between its monuments.

Enter the Colosseum and hear stories of the spectacles that entertained ancient Romans. Standing within the amphitheatre, picture the crowds gathering around its arena and the scale of a public building that has endured for nearly two millennia.

Opened in the first century AD, the Colosseum was the setting for gladiatorial contests and other performances. Its surviving tiers and arches offer a tangible insight into Roman engineering, civic life and the place of entertainment in the imperial capital.

Walk Pompeii’s cobbled streets with a Local Expert, passing the remains of homes, shops and public buildings. The unusually intact street plan makes it possible to picture the routines of a Roman town rather than viewing its ruins as isolated monuments.

When Mount Vesuvius erupted in AD 79, ash buried Pompeii and preserved remarkable traces of everyday life. Your expert’s stories give context to the spaces where residents worked, gathered and lived almost 2,000 years ago.

Cross the Bay of Naples by jetfoil to Capri, watching its limestone cliffs rise above the blue Mediterranean water. On the island, reach clifftop Anacapri for views across the bay towards Mount Vesuvius.

Capri’s dramatic coastline has attracted visitors for centuries, while Anacapri offers a higher vantage point and a quieter perspective on the island. The crossing and lookout together reveal the close relationship between Capri’s sea approaches and its rugged terrain.

Discover Capri Town with a Local Expert, getting acquainted with the island’s streets and lively centre. Explore the setting that has made Capri a gathering place for visitors, with compact lanes opening towards the sea and the island’s steep limestone slopes.

The town combines a long-established local community with the cosmopolitan atmosphere for which Capri is known. Expert guidance helps distinguish its everyday character from its reputation as a fashionable Mediterranean retreat.

Visit the Gardens of Augustus as one of two included Capri experiences. From the garden terraces, look towards the Faraglioni sea stacks and see Via Krupp’s tight switchbacks tracing the cliffs below.

The gardens bring Capri’s cultivated spaces and rugged coastline into a single view. Via Krupp, laid out in the early 20th century, adds a striking human-made line to the landscape. Choose this experience for a closer look at the island’s celebrated scenery.

Taste Capri’s limoncello in the Piazzetta as one of two included island experiences. Learn why locally grown, intensely fragrant lemons are prized for the bright citrus liqueur associated with this part of southern Italy.

The tasting offers a flavour-focused alternative to visiting the Gardens of Augustus. In Capri’s central square, discover how a familiar regional drink reflects the island’s produce and the custom of lingering over a small glass in good company.

Explore Alberobello’s trulli with a Local Expert, walking streets lined with whitewashed limestone dwellings topped by conical roofs. See the distinctive forms up close and learn how the stones were stacked without mortar around domed interiors.

These traditional buildings give Alberobello its UNESCO World Heritage status and a townscape unlike anywhere else in Puglia. Expert commentary reveals the construction methods and local heritage behind houses that remain a defining feature of the region.

Enjoy a farm-to-table dinner near Alberobello, featuring traditional Apulian recipes prepared with seasonal produce. The meal places the region’s ingredients at the centre of the experience rather than treating dinner as a routine stop.

Puglia’s food traditions draw on its agricultural landscape of olive groves and small farms. Taste dishes rooted in that setting, with flavours that express the connection between local harvests, home-style cooking and the communities of southern Italy.

Explore Matera’s Sassi with a Local Expert, moving through a maze of rock-hewn dwellings, churches, stairways and arches. The cave districts reveal how generations adapted the steep terrain into a closely connected urban landscape.

Home to thousands of residents into the 20th century, the Sassi are now part of a UNESCO World Heritage Site. Their weathered stone setting has also appeared on screen, including in The Passion of the Christ, but its lived history is the focus of this visit.

Meet an advocate for the Wonder Grottole Project and explore the village’s historic centre. Hear how the initiative works to revive abandoned spaces and sustain traditional ways of life, then enjoy an aperitif with local snacks.

Grottole’s population decline has left parts of its old town quiet. This MAKE TRAVEL MATTER® Experience connects a walk through its streets with the people working to preserve village culture; your visit supports a project aligned with sustainable cities and communities.

Visit Taormina’s ancient theater with a Local Expert and take in its elevated setting above Sicily’s Ionian coast. From the weathered stone seating and arches, look towards the sea and the distant rise of Mount Etna.

Founded in the Greek period and later adapted by the Romans, the theater brings together performance history and an exceptional natural backdrop. Expert insight helps explain how its ancient builders used the hillside and scenery to shape the audience’s experience.

Explore the Valley of the Temples with a Local Expert near Agrigento. See the remarkably preserved Temple of Concordia and the clifftop Temple of Juno, with broad views across the Sicilian landscape.

These monumental ruins recall the wealth and ambition of ancient Akragas, a major Greek city in Sicily. Walking among the columns gives a sense of the scale of its sacred precinct and the lasting influence of Greek culture on the island.

Walk Palermo’s old city with a historian and visit the Palatine Chapel inside the Palace of the Normans. Its glittering 12th-century mosaics cover an interior that gives little hint of its splendour from outside.

Continue to Palermo Cathedral, whose changing architectural styles reflect centuries of adaptation. Together, the sites reveal the city’s layered heritage and the cultural influences that shaped Sicily during and beyond the Norman period.

Share a Sicilian dinner with local wine at a Palermo restaurant, joined by your fellow travellers and Travel Director. Discover rustic dishes and flavours that offer a fitting introduction to the island’s dining customs.

Sicilian cooking reflects the produce of the Mediterranean and a long history of cultural exchange. Around the table, savour the regional character of the meal while enjoying the convivial atmosphere of a shared evening in the island’s capital.

Cruise the Amalfi Coast and visit Positano on an optional outing from Capri. See the coastline from the water, where steep cliffs and settlements meet the Tyrrhenian Sea, and spend time in one of its best-known seaside towns.

Positano’s buildings climb the hillside above the shore, creating a distinctive view from the boat and from within the town. This experience is at additional cost and bookable on tour.

Explore Ostuni with a Local Expert, walking winding cobbled streets among the whitewashed buildings of this hilltop Puglian town. Take time to notice its closely packed architecture and the turns and passages of its historic centre.

Known for its luminous white facades, Ostuni has a street pattern that evokes the atmosphere of a Mediterranean medina. This guided exploration is at additional cost and bookable on tour.

Discover cliffside Polignano a Mare with a Local Expert, strolling through its historic centre and taking in views over the Adriatic. The town’s buildings stand above a coast of limestone cliffs and blue water.

Polignano is also the hometown of singer Domenico Modugno, associated with the song Volare. This outing brings together coastal scenery and a connection to Italian popular culture. It is at additional cost and bookable on tour.

Explore Syracuse on an optional excursion to one of Sicily’s most historically significant cities. Its long Greek, Roman and later history offers a different perspective on the island’s cultural heritage.

Founded as a Greek settlement on Sicily’s southeastern coast, Syracuse became a major city of the ancient Mediterranean. The tour itinerary does not specify which landmarks this outing visits, so the exact programme should be confirmed on tour. It is at additional cost and bookable on tour.

Price & availability

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