Southern Italy and Sicily Tour: History & Indulgent Shores

A 11 day trip to Italy 
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All roads lead to Rome, but your unique path begins in the fascinating heart of Sicily. Historic structures shimmer an aged gold. Emerald grapevines carpet the landscape beneath the shadow of Mount Etna’s peak. Ancient Greek temples speckle the landscape, overlooking olive orchards and orange groves. Cave dwellings honeycomb the walls of a ravine, and conical homes create a fairytale ambiance in the rolling hills of the southern Italian scenery. The radiance of Italy’s south bursts with life and culture, history and charm, ensuring your custom tailored Southern Italy and Sicily tour overflows with all the wonders in between.  

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General Information

Detailed Itinerary

Places Visited 

Palermo, Monreale, Agrigento, Giardini Naxos, Taormina, Catania, Mount Etna, Matera, Alberobello, Salerno, Sorrento Peninsula, Amalfi Coast, Minori, Pompeii, Rome 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Start of the Path

Palermo is a city of wonder, containing cultures that have settled on the golden landscape and crossed the cobalt waters of the Tyrrhenian Sea. You arrive at the airport, where your private transfer greets you at baggage claim. The city has a honey hue emanating from the cathedral located in the heart of Palermo. Arab characteristics embellish the Norman architectural design. Rounded arches and curved parapets create a dazzling effect. The structure was erected in the 12th century and maintains a sense of grace fit for kings. Royalty would appear in the west gate after coronations and face the crowd. The wealth of history springs from cobbled streets and rich mosaics displayed in the Archeological museum. A mixture of culture exudes from the Vucceria market, where bright vegetables and fruit shine beneath the tarps shading the length of the bazaar.

What’s Included: dinner, transfer, accommodation

Day 2: Culture Thrives in Palermo

In the morning, the rising sunlight returns to glint on the stonework of the city. The natural light spills through the narrow arched windows along the dome of the Palatine Chapel. Golden mosaics decorate the walls and capture the sunlight, emitting a sensual, ethereal glow. At breakfast, you sip a decadent espresso, accompanied by a freshly baked brioche, stuffed with raisins and topped with sugar. Your guide meets you into the lobby after your meal, ready to take you through the embracing cultural icons and landmarks that make Palermo such a splendid city to explore, blending Norman, Moorish, and Spanish Baroque styles. Consider reading some of our travelers' Sicily tour reviews to gain inspiration to further refine and perfect your personal itinerary. 

In the plaza of Quattro Canti, you find an elegant and marvelous 17th-century creation. Four facades mirror one another in shape, size, and style, each with three stories and niches at the center of each story. A fountain trickles in the heart of the first floor. The second floor contains statues flanked by Greek columns. The top floor contains a graceful female figure, one of four patron saints. The beauty of the square and its homage to classic architecture symbolizes the ancient roots of Palermo, its preserved history, and the forward momentum of the contemporary city.

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

Day 3: Walking with Ancient Steps

In the morning, the marketplace erupts with activity, filled with lush pomegranates and jovial fishmongers calling out to passersby. At breakfast, you indulge in a frothy cappuccino for a taste of what locals enjoy when at a café. After your meal, your private transfer escorts you to the edges of the bustling contemporary city of Agrigento. Outside of the city is the Valley of the Temples, home to an array of preserved ancient Greek structures dotting the hills and valley. A refreshing breeze brings the aroma of citrus, carried from the orange groves along the creek bed.

The incredible Temple of Concordia tops the Acropolis. The Temple of Juno Lacinia stands above the rising stone steps that climb the hill to meet the plateau. There are 25 columns that remain upright, encircling the temple mount. A marble floor was set in the inner area, known as the cella. A large sacrificial altar stands before a ramp leading to the eastern entrance, placed by the Romans during the temple’s restoration. Wandering along the ancient structures provides an ineffable feeling of marvel and inspiration.

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

Day 4: Wandering the Corso

Wake up in your luxurious hotel with a view of the Ionian Sea. At breakfast, you can hear the water brushing against the pebbled shoreline. After breakfast, your guide leads you to the nearby seaside town of Taormina, positioned on a cliff overlooking the Bay of Naxos. You can look down into the layers of crisp blue water and see locals enjoying the sunshine on the white sand beach. The picture-perfect beach touches the edge of Isola Bella, a small nature reserve connected to the mainland by a narrow sandbar.

A stunning Greek theater was built into the hillside and now frames the panorama of the Ionian shore sweeping the landscape. The theater was erected in the 3rd century BC and holds up to 5,400 people inside the dramatic horseshoe architectural design. Palazzo Duca di San Stefano showcases the beauty and drama of Sicilian Gothic Art, blending elements of Arabian and Norman sensibilities.  Follow your guide along Corso Umberto, the main street paved with cobblestones. Designer boutique shops line the pathway, showcasing clothing, ceramics, and decadent handmade pastries.

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

Day 5: Baroque to Volcanic

Today your guide leads you to the active city of Catania, the second largest city in Sicily. In the morning, the famous Pescheria, the fish market, brims with locals in search of the daily catch. Vendors fill the streets from Via Garibaldi to Via Gemelli Zappala. Fishmongers call out to passersby, encouraging a glance at ruby colored prawns and mounds of mussels. You are intrigued and delighted by the atmosphere, finding that the culture of the marketplace alone makes the visit unforgettable.

The wonders of the city continue in the baroque piazzas and black and white layers of the Porta Garibaldi. The 18th-century gate was erected in honor of King Ferdinand IV. Limestone and black lava rocks provide the unique white and black horizontal layers. Glory is symbolized in the two winged figures crowning the gate’s western face. Stunning friezes adorn the pillared frames of Palazzo Biscari, an 18th-century palace known for its ornate windows and lavish doorways. A double staircase leads into the inner courtyard, embodying the former grandeur of the times. Outside of Catania, your guide leads you through the foothills of Mount Etna to showcase the tremendous height and imposing frame of the largest volcano on the European continent.

What’s Included: breakfast, tour, accommodation

Day 6: Passing to the Mainland

At breakfast, you bask in the beauty of the seaside and the luxurious flavor of your freshly brewed cappuccino. The aroma of the coffee beans blends with the soothing scent of the sea. After your meal, you make your way to the harbor of Messina, where you board your ferry to mainland Italy. The Strait of Messina separates Sicily from the mainland, with a width of nearly 200 feet and length of two miles. Your private transfer greets you at the port of Villa San Giovanni, in the region of Calabria.

The water fades behind the golden landscape of rolling hills and tall grass. The hills turn into rugged mountains along the horizon. Your guide leads you to a marvelous local boutique vineyard known for its dedication to agritourismo, agricultural activities that attract visitors. Vines are segmented and comb the hills. The emerald leaves stand out against the russet tones of the hills. The history of viticulture in the region dates back to the Lucans in 1300 BC. The rugged but fertile soil is perfect for producing dry red wines.

The seasoned grass in the distance swirls in the breeze. Your guide takes you inside the cellar to look at the oak barrels in which the fermented wine ages. The oak gives a pleasant aroma to the drafty room. Your guide pours you a sample of the wine produced on the property. An earthy aroma of rosemary and red fruits emanates from the glass. Your sip fills your palate with a complex flavor rich with tannins and a smooth, long finish.

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

Day 7: Bordering Homes

The morning light washes over the town of Matera, a town built on the rugged mountaintop and known for the cave dwellings honeycombing the landscape beneath the medieval façade of town. The San Pietro Caveoso is a church erected on a rocky spur overlooking the ravine, decorated with simple folk-art depicting friendly saints. The cave dwellings burrow into the cliff and were utilized by locals as homes until the 1980s. After breakfast, your guide escorts you to the enchanting town of Alberobello, known for its whitewashed homes with conical roofs that conjure images of fairy-houses, each with a distinct beehive shape.

Locals have used the limestone around town to erect the uniquely styled architecture in the 14th century. The homes are known as Trulli and were once used as domiciles shaded by the olive groves. Stroll along the streets and enjoy the unforgettable view of the connected Trulli rising above the streets like trees, creating a surreal image of the town. It reminds you of a fairy village framed by winding, narrow lands sloping upwards along the hills. Palm trees interrupt the conical roofs at random intervals. In the second Trulli district of Aia Piccola, you find a smaller, and quieter neighborhood to explore.

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

Day 8: On the Road to Stunning Shores

In the morning, you can stand in a particular spot overlooking the honeycomb of caves speckling the cliff underneath Matera, and feel as though you have stumbled upon a different world entirely. After breakfast, your private transfer meets you at the hotel and leads you away from the hillside city and its subterranean remains. You make your way to the gorgeous shores of Sorrento, stopping in Salerno along the way. The city has an undeniable charm emanating from its vibrant historical center. Medieval churches rise over quaint restaurants.

Trees shade the seafront esplanade, providing a view to lavish yachts and colorful fishing boats sharing the marina. Lush mountains slope down to the edges of the city. The cathedral was erected in the 11th century and was remolded in the 17th century with Baroque and Rococo styles. Geometric mosaics frame the pulpit. The exterior bell tower stands nearly 183 feet tall, containing eight large bells. Byzantine-style bronze doors have 56 panels, each depicting a portion of the life of Jesus. The mixture of style and opulent religious depictions show the mixture of generations that have worked to build the church.

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

Day 9: Heartwarming Coastline

The little town of Sorrento has a big, embracing panorama in the morning. The sea from the Bay of Naples laps at the small marina. Craggy cliffs climb to a height of over 180 feet above sea level. Cobblestone streets wind down to the beaches, flanked by noble houses and remnants of Spanish architecture. Brightly painted fishing boats wade in the calm waters of the Marina Piccola. Ferries venture out to take passengers to the shores of the famous island of Capri. After breakfast, your guide meets you at the hotel and leads you along the celebrated narrow winding road, providing an unparalleled view of the Amalfi Coast.

Turquoise water shines against the cliffs of the shoreline, speckled with lush forest and intermittent towns. The coastline stretches for 25 miles, from the town of Vietri sul Mare in the east to Positano in the west. Positano contains the bright citrus aroma of lemons blending into the semi-sweet scent of the Ionian Sea. The photogenic town rests at the top of the cliff with sun-drenched houses shining pink and peach terracotta hues. Wisterias drape over the charming facades. Fashion boutiques display one-of-a-kind outfits in their windows. The town marks the beginning of the dreamlike quality of the Amalfi Coast, a destination where golden aged Hollywood stars would spend the summer, and famous Italian fashion icons would gather inspiration.

What’s Included: breakfast, tour, accommodation

Day 10: Along the Ancient Steps

In the morning, the 15th-century Cathedral chimes the bells in the old bell tower. The Byzantine capitals adorn the columns. The 13th-century Cloister of San Francesco was erected upon even more ancient foundations. Octagonal columns support arches made of tufa stone. The remarkable and historic summit of Mount Vesuvius towers over the horizon on the opposite side of the bay. After breakfast, your guide leads you away from the elegant paths of the coastal city and takes you to the entry portal of the world-famous ancient city of Pompeii. Citrus trees sprout outside of the city walls and grow the largest lemons you have ever seen. The outline of Mount Vesuvius remains in the distance and acts as a constant reminder of the legendary eruption that took place nearly 2,000 years ago in 79 AD.

Your guide leads you into the city, where you arrive at the remnants of the Forum. Large pillars mark the border of the Temple of Jupiter, raised above the square on a platform nearly 10 feet tall. The Stabian Baths are the best-preserved baths in Pompeii, standing beside a colonnaded athletic training ground. Circular cold baths and a changing room, along with hot baths heated by air-ducts in the floor are offered in both the female and male segregated areas. The entire complex was used to train gladiators. The marvels of the ancient world come to light in both daily life and artistic preference cast in the sensational streets and unspoiled mosaics.

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

Day 11: Unforgettable End of the Road

The sunlight washes over the Eternal City, casting a radiant shimmer along the various church domes decorating the historic skyline. The Colosseum towers over the edges of the Roman Forum. The Spanish Steps rise above the Piazza di Spagna with marbled grace. The baroque images of Fontana dei Fiumi in Piazza Navona represent the life-giving rivers of antiquity. At breakfast, you can indulge in a fresh espresso and a sweet brioche baked fresh that morning. The city comes to fulfilling life around you, brimming with the morning market at Campo de Fiori and the flower stalls speckled around town. After breakfast, your private transfer meets you at the hotel, ready to escort you to the airport for your flight home. You could always extend your stay in Italy and take in the wondrous landmarks of Rome, from the Vatican to the Forum of Trajan, before venturing north to Venice.

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.