Culture, Tradition & Beauty of Southern Italy Tour

A 9 day trip to Italy 
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This is the Italy of ruin and prestige, artistry and strongholds, an Italy steeped in culture deriving from ancient life. Your custom tailored tour immerses you in the majesty of Southern Italy, from Naples to Palermo, connecting the heritage of the past with the traditions of the present. Greek temples tower over rocky promontories. Roman villas provide insight into the wealth and opulence of emperors. Lush citrus groves grow on terraces stretching beneath limestone cliffs, and the Mediterranean Sea shines with turquoise water against gold-sand beaches. Follow the trails of history to discover the welcoming traditions of Southern Italy. 

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General Information

Detailed Itinerary

Places Visited 

Sorrento, Pompeii, Positano, Ravello, Amalfi, Conca dei Marini, Vietri sul Mare, Capri, Anacapri, Palermo, Agrigento, Erice, Noto, Syracuse, Taormina, Forza d’Agro, Catania 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Positano – Reaching Southern Italy

Naples is a city rich in history both inside the city center and bordering the harbor. Lavish churches overlook cobblestone streets, and the Castel dell’Ovo stands proudly at the edge of a rocky promontory with roots dating back to the 6th century BC. Your flight lands and Naples International Airport where you meet your private transfer. On the outskirts of the bustling city, you find the aroma of citrus emanating from lemon groves thriving in the Mediterranean climate. The turquoise sea laps at the coastline of the Bay of Naples.

The scent of rich espresso drifts out of small corner cafes. You stop at the entrance to Pompeii Archeological Park as your introduction to the marvelous history of Southern Italy. Your guide meets you at the entrance eager to show you the highlights of the Roman port city once covered in ash and pumice from the volcanic eruption of Mount Vesuvius in 79 AD. Excavations have revealed that the layers of ash have kept the city intact, complete with sailor hotels, bars, public baths, and taverns. The fragrance of rich soil rises from the Roman Forum.

Portions of pillars frame the piazza leading to the Basilica, which once housed the city’s courts. As you stroll along the cobbled streets, your guide points out homes in which frescoes continue to decorate the walls. Pillars crowned with Corinthian capitals flank the House of Meander. The interior contains frescoes depicting scenes from Homer’s Iliad. A wooden roof hovers over the small temple in the corner of the atrium. You are not only seeing ancient history but walking in the footsteps of a citizen of Pompeii, with the image of Mount Vesuvius’s conical peak ornamenting the sky on the horizon.

What’s Included: tour, transfer, accommodation

Day 2: Positano – Traversing the Gulf of Salerno

The town of Positano climbs along the steep hillside, beautifying the rugged promontory with pastel-painted homes and narrow winding lanes twisting beside terraced gardens. The scent of fresh lemons and oranges garnishes the air, blending seamlessly with the aroma of the Tyrrhenian Sea. The water shimmers turquoise in the spreading morning light, embellished with brightly decorated fishing boats wading in the marina. After breakfast, you meet a private guide at the hotel for a day traversing the celebrated Amalfi Coast, strung with small villages and charming towns edging Italy’s southern shores.

The gold-pebbled coast of Praiano fills with locals basking in the shade of their beach umbrellas beneath the pastel-colored cottages. A steep stairway traverses the vertical town leading from Vettica beach to the town center at Piazza San Gennaro. Cafes set out tables and chairs along the cobblestone square, providing stunning views of the radiant water leading outwards to the shores of Capri. In the town of Conca dei Marini, you discover the serene charm of the cream-colored houses tucked into the base of the cliff.

A 16th-century watchtower continues to keep an eye out for pirates. Venture down the steps to the marina to board a small boat. The water is crisp and refreshing against your skin when you dip your fingers into the gentle wake. The boat takes you into the Grotto dello Smeraldo, the Emerald Cave. The sunlight refracts off the water to fill the 100-foot tall cave with enchanting hues glowing like precious stones. The walls flicker with colors that remind you of a kaleidoscope.

What’s Included: breakfast, tour, accommodation

Day 3: Positano – Island in the Sun

In the morning, you find the delightful aromas of refreshing espresso and freshly baked brioche, offering a mixture of sweet, buttery, and earthy notes to bring in the new day. After breakfast, you make your way to the Positano marina to board the ferry to Capri. The swift ride brings into view the stunning cliffs of the island, which reach upwards of 200 feet above sea level. The rugged, limestone glints in the sunlight, embellished with intermittent greenery growing around natural terraces and over the top cliff tops. The ferry docks at Marina Grande.

Pastel-hued homes frame the waterway. A funicular leads visitors and locals atop the steep mountain framing the marina to Piazza Umberto I, which contains a series of café tables offering espresso, morning cappuccino, and captivating aromas. The aroma of lemon gelato emanates from out of a local gelataria. Boutique shops lining the meandering cobblestone streets provide elaborate window displays. Travel the recently reopened trail known as the Hunter’s Path, offering a route to the caves once utilized by locals to store hay.

The path takes you between the natural rocky archway and the cliffs of Mount Tiberius offering a view of the Stack of Matermania from a height of nearly 820 feet above sea level. The coastline of the island shines with verdant grass, a thriving canopy, and sporadic outcroppings of limestone boulders set against the cobalt Mediterranean. For a more cultural view of the island, you can visit Villa Jovis, an estate once belonging to Roman Emperor Tiberius.

What’s Included: breakfast, lunch, tour, accommodation

Day 4: Palermo – Beyond the Toe of Italy’s Boot

The shops of Positano open their doors to the morning light. A traditional sandal maker continues his craft with his door open to a small cobblestone lane off the central piazza. His workshop fills with shoes, slippers, and sandals he both makes by hand and fixes for customers. The scent of leather and polish emanates from the doorway. After breakfast, your private transfer meets you at the hotel and escorts you around the Bay of Naples, passing beside the looming figure of Mount Vesuvius before arriving at Naples International Airport for your brief flight to Palermo, Sicily.

Once at Falcone Borsellino Palermo Airport, you meet your private transfer at baggage claim. Sicily feels like an entirely different country from the Italy you have visited along the Bay of Naples and the Amalfi Coast. Palm trees grow alongside Arab architecture. The aroma of pomegranates and oranges swirl through the air. The Cathedral in the heart of the historic city center contains a 15th-century gothic Catalan portico erected over the foundations laid by the Norman-Hohenstaufen dynasty. The stone glints with gold hues beneath the Mediterranean sun.

Your guide points out an early Arabic inscription on a column supporting the doorway. In the treasury, you discover the priceless artifact of the Crown of Constance of Aragon, a headpiece decorated with strings of pearls and precious stones, connoting prestige and power on the historically preserved grounds of the cathedral. The city maintains a history spanning more than 3,000 years, from the medieval port expanded by Arab settlers to the impressive ogival arches and blind arcades of the Norman Palace. 

What’s Included: breakfast, transfer, tour, accommodation

Day 5: Agrigento – A Rich History of Tradition

In the morning, the Ballaro Market fills with both vendors and patrons eager for a sale. Stalls overtake the mixture of narrow and wide cobblestone lanes extending between Piazza Ballaro and the Church of San Nicolo. Ruby tomatoes fill crates. Seafood, from freshly caught mollusks to impressive marlins, sit in ice baths. The aroma of arancini, fried, stuffed rice balls, emanates from street vendors who call out to passersby. The outdoor market is a tradition influenced by the souk of the former Arab settlers. After breakfast, your private transfer escorts you from the hotel to the mountaintop town of Erice, located at more than 2,600 feet above sea level.

A cable car ferries you to the top of the mountain, framed by the medieval gate of Porta Trapani. The settlement was erected in a triangular formation, with the main street leading uphill to Piazza Umberto I, the historic principal square. The cool breeze blows against the polished stone of the centuries-old structures, including the walls leading to the 12th-century Castle of Venus at the furthest end of the triangle. A café terrace offers a pristine panorama of the valley below and the coastline. The castle was erected over a foundation of a former Roman temple dedicated to the goddess Venus, of which provides the structure with its name. Descend the medieval town and continue to the Valley of the Temples, beside the city of Agrigento, which contains the three perfectly preserved Greek temples.  

What’s Included: breakfast, tour, transfer, accommodation

Day 6: Taormina – The Baroque in Sicily

The grandeur of Sicilian culture spans thousands of years and countless architectural aesthetics. In the morning, you can look out on the Valley of the Temples for an instant reminder of the stunning preservation of one of Italy’s oldest settlements. The image of the columns, along with a restructured statue of Zeus, brings to mind the elaborate and intricate details of the former religious grounds. Your view of Sicilian culture jumps nearly two millennia with your arrival in Noto, the baroque capital of Sicily.

The luster of the architecture makes the street resemble a film set. The main boulevard of Corso Vittorio Emanuele contains an elegant walkway adorned with shimmering palaces and marvelous churches. Much of the city was rebuilt in the 17th century after a wave of earthquakes. Balconies with wrought iron rails frame colorful window shutters. The stairway leading to the cathedral has three tiers before reaching the columned portico. The pillars remind you of the gorgeous classical architecture at the Valley of the Temples.

The Cathedral of San Nicolo has a dome shimmering with a peach hue, making it the focus of the city’s skyline above the surrounding church spires. You continue to the city of Syracuse, one of the oldest, largest, and best-preserved ancient of the ancient Greek cities in Sicily. The city also houses a remarkable Greek theater carved into the hillside. The architects utilized the natural grade of the landscape to erect a complex able to seat nearly 15,000 spectators in the 5th century BC. 

What’s Included: breakfast, tour, transfer, accommodation

Day 7: Taormina – A Day on the Cliff

In the morning, locals and visitors alike venture to the beaches at Spisone. The quiet turquoise water in the bay laps at the smooth sand. The crystal clear surface allows swimmers to look down to the seafloor without constraint. Striped umbrellas shade the lounge chairs and segments of the beach from the Mediterranean sun. The day is yours to enjoy the splendors around Taormina at your leisure. Take a trip to Mount Etna to trek around the craters and fumaroles or venture to the Alcantara Gorge to witness the unique rock shapes and rushing river.

Spend a relaxing day wandering the cobblestone streets of Taormina to view the historic architecture and splendid views looking out to the bay. The aroma of olive groves, palm trees, and azaleas fills Piazza IX Aprile. A terrace opens to a stunning view of Mount Etna in the distance, framed on one side by the pink baroque façade of San Giuseppe church. The interior contains an ornate décor of white stucco waving across the walls resembling cake frosting.

Open-air cafes offer views to the rugged slopes and glowing waters in the refreshing breeze. The scent of espresso and freshly baked cakes drifts out of the café doors. For the best view of Mount Etna, you make your way to the Greek Theater, which was erected in the 3rd century BC under the rule of Hiero II of Syracuse. The semicircular structure has an upper diameter of more than 355 feet, with an impressive view of the surrounding countryside, sweeping from the bay to the volcanic peak. 

What’s Included: breakfast, tour, accommodation

Day 8: Catania – Holding to Tradition

In the morning, you leave behind the stunning views and historic streets of Taormina for the traditional lanes of Forza d’Agro, where Francis Ford Coppola filmed scenes for The Godfather. The traditions and history of Sicily’s past remain strong, taking you to a different time than when you were in Taormina. Bar Vitelli, a filming location of the famous movie, has beaded curtains dangling in front of the doorway. The typical, unspoiled culture sweeps through the streets. The aroma of lemon Granita emanates from the bar. The tart, sweet, and refreshing treat helps soothe the rugged heat washing over the golden landscape. The 12th-century castle stands atop the hillside overlooking the town frozen in time. The structure was erected over the foundations of a Roman fortification with the walls and interior used as a quarry for local materials in the early 20th century. 

A lookout tower provides a view of Sant’Alessio Castle. You continue to Catania, a contemporary city with a majestic edge. Youthful restaurants surround the white and black tiled palaces and magnificent baroque squares. Marvelous domes overtake the skyline and ancient ruins more than 2,500 years old lay beneath the foundations of the historic center. The Benedictine monastery was erected in the 16th century and incorporates an array of architectural styles, most notably late-baroque features on the façade. Pilasters and sculptures windows stand beside details sculptures of angels. The historic monastery now houses the Department of Humanities for the University of Catania, an educational system first established in the 15th century.

What’s Included: breakfast, tour, transfer, accommodation

Day 9: Catania – Out of Time In Antiquity

Mornings in Catania brim with activity at La Pescheria, the city’s famous fish market. Vendors call to one another and to passersby with their voices echoing through the streets behind Piazza del Duomo. Tables look as though they will buckle under the weight of gigantic swordfish, ruby prawns, and trays almost overflowing with shellfish. Locals search for the perfect fish for dinner and vendors offer extra mussels after weighing the bag. Catania is a contemporary city rooted in its traditions, whether in the architectural majesty or the vibrant life of the fish market. Your private transfer meets you at the hotel when you are ready and escorts you to Catania-Fontanarossa Airport for your flight home.

What’s Included: breakfast, transfer 


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.