A Cultural Journey to Sicily Tour: Past & Present

A 11 day trip to Italy 
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Sicily is a very distinctive region of Italy, filled with unique personality stemming from architecture that spans thousands of years. The coastline undulates between pristine beaches to remarkable cliffs. Mount Etna looms over wineries and cities, puffing smoke and spouting lava. Baroque palaces line charming piazzas. Marvelous frescoes decorate historic churches. Greek temples continue to stand tall along the edges of a modern city. Cobblestone streets twist and turn alongside medieval homes. Your custom tailored Sicily culture tour brings you to the unforgettable wonders of Sicily, embodied in the buildings, cuisine, and scenery scattered across the island.

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General Information

Rooftop Terrace at El Mosaico del Sol. Photo Credit: El Mosaico del Sol
Diving Lampedusa Reefs. Photo Credit: Marina Diving Center
Suit at El Mosaico del Sol. Photo Credit: El Mosaico del Sol
Diving with Marina Diving Center. Photo Credit: Marina Diving Center
Pool at El Mosaico del Sol. Photo Credit: El Mosaico del Sol
Diving Underwater Statues. Photo Credit: Marina Diving Center
Detailed Itinerary

Places Visited 

Palermo, Agrigento, Syracuse, Taormina, Catania, Monreale  

Departure Dates 

Dates are flexible and customizable for private departures. 

Detailed Itinerary 

Day 1: Introducing Palermo

Palermo’s uniqueness stems from its vibrant architecture, stunning setting, and radiant culture. The jovial calls of vendors at La Vucciria market echo off of the historical walls encompassing the stalls. “Vucciria” means voices in Sicilian dialect, and rings true in the boisterous and jubilant atmosphere of the marketplace. Produce native to the Mediterranean and North African climate thrives in both color and size. Herbs bring a sensual aroma to the pathways. Fresh seafood caught earlier that morning showcases the variety and abundance of what the oceans has offered residents of Sicily for millennia. Your private transfer greets you at the airport and escorts you to a luxurious hotel situated near the heart of the city. You quickly notice that the markets of Palermo offer more than just insight into the local shopping habits and vendor practices of the Italian province. They also embody the eclecticism of the cultures that have traversed and shaped the island.  

What’s Included: dinner, transfer, accommodation

Day 2: The Apparent Wonders of Palermo

In the morning, the calls of Vucciria market return to the streets. The palm trees rustle in the sea breeze sweeping in from the port. The city has a golden hue glinting off the cobblestone streets and bright historic buildings. In the heart of the city stands the vibrant Norman Palace embellished with an Arab design and erected on a Phoenician base. Palermo Cathedral embodies original Norman architectural elements showcasing three apses, crossover rounded arches, and curved parapets along the eastern façade. The splendor of the city’s Arab-Norman past brims in the marble interior, which houses impressive royal Norman tombs.

You find hints of myrrh filling the nave. Gothic décor accentuates the 13th and 14th-century southwestern façade. In the treasury, you find the glistening jewels of the gem-encrusted crown of Constance of Aragon. Outside Quattro Canti, the circular space open to the city was erected in the 17th century at the junction of two of the Palermo’s major streets. A nook at each of the four corners of the façade holds a fountain, and sculpted figures adorn the upper floors. The neo-Classical allure offers passersby an elegant look into the glamorousness of Palermo’s past.

What’s Included: breakfast, tour, accommodation

Day 3: Delighting in the Days of Palermo or Lampedusa

The morning light washes over the verdant trees and manicured hedges of the Botanic Garden. The broad boulevard of Foro Umberto I opens to a sensational view of the Bay of Palermo. The sweet aromas of coconut palms and banana trees drift from the gardens blending with the sea breeze. After breakfast, the day is yours to indulge in a free day exploring the city. Consider reading some of our travelers' Sicily tour reviews to gain some insight into the possibilities available to you. Venture to the Archeological Museum to visit some Egyptian and Phoenician artifacts, along with stunning Roman mosaics and Greek friezes.

Stroll along the vibrant Ballarò market, filled with the aroma of freshly cooked food and colorful clothing. Walking around Palermo is a fantastic way to enjoy the architecture and embrace the culture. Teatro Massimo was erected in the 19th century with an auditorium that can hold up to 3,200 people. The first performance in the opera house was Verdi’s “Falstaff,” which solidified the performance hall as one of the major opera houses in Sicily. The upper tiers envelop the main gallery in a horseshoe arrangement that helps the music of the orchestra and singers resonate harmoniously.

You also have the option to discover the amazing depths of the Mediterranean Sea on an epic SCUBA diving adventure. Your guide meets you at your hotel lobby and escorts you to the airport for a short flight to the gorgeous island of Lampedusa. Local dive-masters from Marina Diving Center guide you around the beautiful island, taking you to some of the best dive spots in the Mediterranean Sea. Swim along spectacular underwater rock formations, caves, and drop-offs that are home to magnificent fish like brown groupers, moray eels and brown meagres. After your amazing day of diving through the grand limestone structures of the Mediterranean Sea, your guide will accompany to El Mosaico del Sol for a wonderful nights stay.

What’s Included: breakfast, accommodation at El Mosaico Del Sol

Day 4: Fascinating Greek Ruins in Italy

In the morning, the aroma of arancini, deep-fried rice balls, filters through the streets of the Palermo. Locals enjoy the popular street food throughout the day, especially when shopping in one of the vivacious marketplaces filling the cobblestone streets and public piazzas. After breakfast, your guide meets you at the hotel. You say goodbye to Palermo and venture away from the golden hues of the Norman palace and the lavish neo-Classical architecture of the cityscape. You reach the edges of the contemporary town of Agrigento to find the Valley of the Temples. Ancient Greek ruins speckle the dell surrounded by rolling rugged hills.

Each ruin stands in contrast to the modern buildings of the city of Agrigento. The Temple of Castor and Pollux was erected between the 6th and 5th centuries BC. Four columns and a fragmented pediment remain today. The original edifice had a large colonnade adding grandeur to the historic edifice. The Temple of Herakles was once revered as one of the most beautiful temples of antiquity. Today, the building maintains a modicum of its former glory due to its visibility from a distance, adding an extra layer of mystique to its current form. The wide rectangular platform measures 242 feet long and is mounted atop four steps. The original temple stood more than 53 feet tall.

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

Day 5: Preserved Piazza

In the morning, the sunlight sweeps over the valley and once again highlights the former glories of the Greek ruins. After breakfast, your private transfer leads you away from the Valley of the Temples and into the City of Piazza Armerina. The city was developed during the 11th century but maintains a proud history of flourishing during Roman times. Norman and Gothic architecture decorate the city streets, along with a Baroque Cathedral erected between the 17th and 18th centuries.

You make your way to Villa Romana del Casale, a Roman villa located two miles outside of town. The mansion was constructed in the 4th century AD. A landslide covered part of the villa in the 12th century. More than 37,673 square feet of mosaics depicting 40 separate scenes decorate the grounds. North African motifs influenced the artistry. “The Great Hunt,” is a single mosaic stretching 200 feet long, depicting the hunt, capture, and also the gladiatorial games in which the animals fought inside the Colosseum. Each artistic interpretation provides another unique perception of the times.

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

Day 6: Taking in Syracuse

The city of Syracuse has a timeless beauty, encapsulating the wonders of Ancient Greece and Baroque piazzas. Medieval lanes weave through the city and open to stunning blue waters of the Ionian Sea. Life in Syracuse has continued for nearly 3,000 years. The city once boasted the largest population of any city in Classical antiquity, greater than that of even Athens. The marketplaces brim with excitement in the morning. The sea crashes against the rugged shores beneath the fortified walls of the city. Your guide meets you at your hotel after breakfast. Exploring the main street takes you in front of the cathedral where you find the ancient spring of Fontana Aretusa.

Charming buildings encircle the pool where fresh water continues to bubble up as it has since ancient times. Papyrus grows in the heart of the fountain and lingers in the quiet grotto. Ducks glide across the fountain’s surface. It is a quiet moment in the bustling streets of an ancient city. The Greek Theater was erected in 470 BC. The ancient construction uses the natural slope of the landscape to frame the sensational theater, which has 61 rows, carved from the rock, with capacity for 15,000 people. A colonnade once stood on the terrace protecting visitors from the elements.

What’s Included: breakfast, tour, accommodation

Day 7: Deeper into the Splendor of Syracuse

In the morning, the Piazza del Duomo fills with locals. The cathedral was erected on the former site of the Temple of Athena. The edifice absorbed the Doric columns into the main structure, connecting the past and present grandeur of the city. After breakfast, the day is yours to discover the continuing beauty of Syracuse at your preferred pace. Visit the Baroque Palazzo Beneventano in the Piazza del Duomo or visit the stunning I Sapori Gusti Smarriti, which means the “Flavors of Lost Tastes,” a delicatessen specializing in Sicilian cheeses and cured meats.

The Crypts and Catacombs of San Giovanni continue to captivate visitors from around the world. The church was originally erected in the 6th century and has been rebuilt numerous times over the centuries. The 14th-century portal wall is one of the oldest elements of the church. The crypt is cool and hidden from the natural warmth of the sunlight. Remnants of Ionic column bases remain in the vault. The underground necropolis dates back to the 4th century and connects to a network of roads and piazzas around the city. The honeycombed tunnels and empty niches leave traces of the church’s Norman history and lavish riches that were once accompanied the burial ceremonies.

What’s Included: breakfast, accommodation

Day 8: The Draw of Taormina

Taormina has a romantic ambiance rising from its incredible panorama and historic ruins. After breakfast, your private guide whisks you away from the embrace of Syracuse. The beauty of Taormina comes into view quickly. The city sits atop towering cliffs overlooking the Bay of Naxos. In the distance, you can see the snowcapped peak of Mount Etna climbing into the sky. Walls of ancient stone hide secluded gardens. Terraces overlook the pristine Ionian Sea. In the old neighborhood of the city, Palazzo Santo Stefano glows with archeological monuments and medieval homes, including a view of the 12th-century Norman-Arab castle. Your guide leads you on a fabulous tour of the city, strolling along the circuit of walls looking out towards Messina. The clock tower was erected in the 15th century. Ruins around the base of the tower show a defensive wall dating back to the 4th century BC.

What’s Included: breakfast, transfer, accommodation

Day 9: Independent Taormina

In the morning, the water in the Bay of Naxos changes from azure to turquoise as it reaches the coastline. You can see the small rock-bound island of Isola Bella. The nature preserve has a small and narrow sandy beach that connects the islet to the mainland. The day is yours to enjoy Taormina and its surroundings at your leisure. Locals sit in the open-air cafes and sip espresso. The aroma of fresh brioche blends into the sea breeze. You can make your way down to the Isola Bell and dig your toes into the hot sand.

The water is calm and still against the shoreline. The sun is warm on your skin. When you dip your feet into the water, the refreshing temperature cools you down. A walkway surrounds the perimeter of the island overlooking the coves and beaches of Taormina. You can see the cable car connecting the cliff top to the resort of Mazzaro. The zesty scent of lemon mixes with the sweet aroma of coconut. The sporadic trees provide lovely shade in the heart of the afternoon.

What’s Included: breakfast, accommodation

Day 10: Luxuries of Taormina

When you wake up in the morning, the summit of Mount Etna is too alluring to pass up. You choose to venture up the mountainside on an exhilarating excursion to a number of craters to see the active volcano up close. The summit rises to an elevation of 10,958 feet. A cable car ferries people as far as 9,842 feet above sea level. The lush and fertile soil of the foothills changes to a rugged lunar landscape. The rocks turn black, showcasing the intensity of cooled magma. White puffs of smoke rise from the active craters around the craggy peak.

The higher you climb, the more the atmosphere thins, bringing a colder afternoon. It is hard to differentiate the puffs of volcanic smoke and the clouds drifting past the mountain. Your guide leads you to the Valle del Bove, which provides an impressive view of the summit craters. When the volcano last erupted, lava flowed from the basin. At the edge of Valle del Bove, you can look down into the lava desert and feel the lava ash slipping down the slopes.

What’s Included: breakfast, accommodation

Day 11: Taking the Culture with You

Via Roman connects to the municipal gardens of Villa Comunale, where rare species of plants grow over Victorian stone architecture. Flower petals blossom in the vast greenery. The trees open to expansive views of the water. The quiet ambiance makes it a preferred escape for locals who wish to stroll along tranquil walkways away from the bustling piazzas and absorb the beatitude of nature. Soon you will soar over the Tyrrhenian Sea, but for now, you relax with the indulgent aroma of fresh espresso and the wondrous images of Taormina. After breakfast, your private transfer meets you at the hotel, ready to escort 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.