Discover Sicily Tour: A Feast for the Senses

A 14 day trip to Italy 
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The discoveries of Sicily are endless on an island bursting with ancient wonders and vivacious culture, stunning landscape and iridescent beaches. Medieval towns crown towering mountains offering unparalleled views. Breathtaking Doric temples rise from valleys overlooking wild olive groves. Celebrated chocolate shops share with you their recipes passed down for hundreds of years. Cobblestone paths wind through antique buildings and into open elegant piazzas adorned with graceful churches. Your custom-tailored discover Sicily tour lets you explore Sicily like a local, relishing the thrill of adventure, the excitement of discovery, and the soothing calm of daily life. 

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Most tours are customized for private travel.

General Information

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Detailed Itinerary

Places Visited 

Palermo, Taormina, Erice, Syracuse, Ragusa, Agrigento

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: A King’s Capital

Palermo is a city of kings from around the world, having been ruled by Phoenicians and Carthaginians, Arab caliphates and Spanish empires. The streets brim with excitement teeming along the golden hued buildings. The old city bursts with architecture filled with details showcasing the preferred styles of invaders who once claimed the city as their own. The vibrant markets burst with jovial calls from vendors trying to grab the attention of passersby. Bright produce highlights the Mediterranean topography and climate. Stalls fill with pomegranates and oranges, figs and apricots. Your private transfer meets you at Falcone-Borsellino Airport.

Once in the city, the Norman Palace adorns the historic center. The structure was rebuilt in the Norman style in the 11th century after the Normans overtook the Arabs. Elements of the original structure are visible in the foundation. The Astronomical Observatory is a Pisan tower that houses 19th-century telescopes and astronomical instruments. In the 1800s, observers in the tower discovered the first dwarf planet of Ceres. The unique history of Palermo is captivating, and the culture of the city is illuminating. Consider reading some of our travelers' Sicily vacation reviews to gain additional ideas to further complement and perfect your own itinerary. 

What’s Included: transfer, accommodation

Day 2: Proper View of Palermo

The city of Palermo is over 2,700 years old and sits at the edge of the Tyrrhenian Sea, which is a region of the Mediterranean. The aroma of rich espresso drifts along the streets. The bustling marketplaces resume their active selling, now including the traditional breakfast pastries baked fresh that morning, such as ciambelle, a large donut dusted with sugar. Your guide meets you at the hotel and leads you on a spectacular tour of the city. The Teatro Massimo has a grand neoclassical design and houses the famous Palermo opera.

The structure was erected in the late 19th century and remains the third largest opera house in Europe, holding up to 1,350 people. The design symbolizes the eclectic history of Sicily, incorporating elements of Greek and Arab styles that have influenced the culture of the city. The 17th-century chapel of Oratorio de Santa Cita showcases brilliant stuccowork emblematic of the Rococo style. On the entrance wall, you notice hundreds of cherubs holding the stucco drapes that frame a fresco, depicting the Battle of Lepanto when a Christian army defeated the Turks.

What’s Included: breakfast, tour, accommodation

Day 3: The Tranquil Seaside at Taormina

In the morning, you find the delightful citrus aroma of freshly squeezed orange juice. Wild orchards speckle the island near olive groves and almond trees. After breakfast, your private transfer leads you away from the historic capital city and to the town of Taormina, located on a cliff overlooking the Bay of Naxos and the Ionian Sea. Cobblestone streets wind along the hillside bordered by colorful Baroque and medieval architecture. The clock tower stands at the center of town. The tower was erected in the 17th century but the foundation dates back to the 4th century BC, to when the town was first founded.

Your guide leads you along the walkways until you come to the edge of the Greek Theater. The ancient site was carved into the hillside in the 3rd century BC, using the natural incline of the topography to support the structure. The semicircular construction gives the theater a diameter of 357 feet. From the top level, you can see the azure waters of the Bay of Naxos and a panorama that includes the looming image of Mount Vesuvius and its powerful peak. 

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

Day 4: The Beauty of Choice

In the morning, you can look out over the Bay of Naxos and find the calm waters brushing against the shore of Isola Bella. A narrow sandbar connects the small island to the mainland. The Ionian Sea has a crystal clear azure color that allows you to see all the way to the seafloor. The breeze rustles citrus trees and carries the slightly salty aroma of the ocean. The day is yours to delight in the charms of Taormina as you prefer. Venture to Mount Etna on an adventurous trek to visit the mountains’ many craters or stroll along the streets of the city to indulge in the various pastry shops specializing in Sicilian specialties.

The beach of Lido Mazzarò is a mixture of soft sand and gravel, once frequented by the Hollywood stars of the “Golden Age” of film. You venture down the cliff in a gondola, taking in the remarkable view along the way. The boardwalk has a lively atmosphere of bustling restaurants and charming cafes offering views of the water. The sea laps at the beach. You can dig your toes into the sand and feel the warmth of the earth contrasting the refreshing temperature of the water.

What’s Included: breakfast, tour, accommodation

Day 5: Sensational Syracuse

At breakfast, you sip on a remarkable cappuccino, a favorite of Sicilians indulging in a complete meal before beginning their day. The frothy and rich flavor elevates the morning, promising an enriching experience to come. Your guide meets you at the hotel and escorts you to the remarkable city of Syracuse, which overtook its contemporaries of Athens and Corinth as the largest city of Antiquity. Syracuse retains one of the largest theaters from ancient Greece and possesses meandering catacombs that surpass the greatness of those found in Rome. The vivid splendor of the city rises along the small island of Ortigia, where an ancient spring continues to provide freshwater to the historic neighborhood. Papyrus trees grow out of the spring.

Syracuse is one of three locations in Europe where papyrus grows naturally. Your guide leads you along the cobbled streets of the historical neighborhoods of the city, allowing you to take in the magnificent antiquity surrounding you. The church of San Giovanni was erected in the 6th century and rebuilt in the 12th century by the Normans. However, the façade now stands in ruins after numerous earthquakes, leaving a scene from a romantic painting, filled with blossoming flowers overtaking the exterior. The catacombs underneath the church date back to the 6th century and contain a Greek-style crypt with frescoes decorating the walls and inhabitants ranging from Byzantine to Norman eras. Niches honeycomb the catacombs that connect ancient Greek cisterns to former Christian chapels.

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

Day 6: Basking in Noto

The citadel of Castello Maniace stands at the far edge of Ortigia. In the morning light, the 13th-century edifice has a soft glow against the shimmering azure water of Syracuse Bay. At breakfast, you can relax with a refreshing espresso and enjoy the aroma of fresh citrus carried by the sea breeze. Your guide meets you at the hotel and escorts you to the enchanting city of Noto, known for its Baroque architecture and unique town design. Palaces and churches line the cobbled streets and create a gorgeous skyline.

Bright limestone used to construct the buildings adds to Noto’s lively and radiant image. The Cathedral of San Nicolò borders the Piazza del Municipio. The church’s opulent form overtakes the square from atop a flight of steps. An elegant palace, the Palazzo Ducezzio, faces the church and helps frame the square with historic grace. Outside of the city, the calm crystal waters of Lake Avola are located in Cavagrande del Cassibile Nature Reserve and opens up to panoramic views of the Syracuse province.

Visit the area and explore the natural beauty of the province like a local. The path to the water is a little over a mile winding along the gorge. When you reach the lake, you find crystal clear indigo freshwater. The Cassibile River feeds the lake by trickling down the smooth stone banks that hold the water. On your way back to Syracuse, you can see the Baroque city of Noto. At sunset, the shifting layers of light bounce off of the buildings, draping the city in a golden-red glow. 

What’s Included: breakfast, tour, accommodation

Day 7: Province from Up High

In the morning, the markets of Syracuse bustle with locals in search of the perfect ingredients for the remainder of the day. Old women dressed in shiny black coats squeeze oranges. Elderly men sit at the cafe tables lining the cobblestone paths and sip their espresso, read newspapers, and play dominoes. After breakfast, you explore the expansive streets of the neighboring city of Catania, known for its radiant fish market, before continuing to the hilltop town of Enna. The provincial capital offers stunning views of the undulating hills and valleys beneath the 3,054-foot summit.

The town looks impregnable atop the mountain. The air is crisp and clean when you arrive in the city center. The medieval lanes wind through historic buildings and provide unforgettable views. The Duomo was erected in the 15th century with a stunning Baroque façade crafted from yellow tufa stone. Corinthian columns inside the cathedral separate the aisles. The polygonal apses remain from the original church. Bright frescoes decorate the concentric layers of the dome, lit by the natural light pouring through the top.   

What’s Included: breakfast, tour, accommodation

Day 8: Old and New Side-by-Side

In the morning, the Market in Ortigia is in full swing. The sea is close and lends its aroma to the marketplace. Seafood vendors showcase their magnificent fish, vibrant prawns, and large amounts of shellfish pulled fresh from the water that morning. Wild asparagus and bright tomatoes are displayed beside blood oranges and grapefruits. Beneath the shady awnings, the aroma of basil and olive oil is mouthwatering. Your guide meets you after breakfast, and leads you away from the Syracuse Bay. You travel along the undulating landscape to the interior of Sicily to arrive at the hilltop city of Ragusa. A noticeable division separates the upper and lower halves of the city, creating the new neighborhood of New Town and Old Town.

Your guide leads you along the meandering narrow streets of Ragusa Ibla, or Old Town. Much of the city was rebuilt after a 17th-century earthquake, scattering stunning 18th-century architecture along the streets amongst the remaining ancient structures. The surrounding landscape rises and falls with remarkable cliffs, rushing rivers, and marvelous canyons. The Church of San Giuseppe was erected in the 17th century in the Baroque style. Four saintly statues adorn the semicircular portal along the façade. The interior has an elliptical shape topped with a cupola decorated with a lavish fresco.

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

Day 9: The Richness of Modica

The morning light gently illuminates the Palazzo Mediterraneo, a museum with exhibits on prehistoric Greek and Roman artifacts discovered in the countryside around Ragusa. Ceramics from the 6th-century BC city of Attica show mythological figures and heroes. After breakfast, your guide leads you to the enchanting city of Modica, which was restructured in the 18th century to emanate Baroque beauty. The beauty of the city is spread along the hillside, ascending and descending with the landscape.

Staircases connect the upper and lower reaches of the city, none more celebrated than the 250 steps that make up the grand staircase leading to the Church of San Giovanni. Colorful tiles decorate the edges of the stairs to create a unique mosaic decorating the cityscape. The extravagant Baroque façade of the church has a curved central bell tower. The garden erupts with blossoming roses and wisteria. Palm trees shade the footpaths. The aroma of chocolate is compelling.

The city is known as the home of the best chocolate in Sicily, with the most famous dolceria being Bonajuto. Elaborate displays line the shelves in the window. When you enter the shop, the rich, slightly bitter, and indulgently sweet aroma fills the comfortable space. The shop has created Arabian and Spanish cakes for a plethora of customers, the recipe having been passed down for centuries. The pastry chef introduces you to the history of chocolate in Sicily and the variety of the treats produced in the store, from nutty to fruity, and all the pleasurable combinations in between.

What’s Included: breakfast, tour, accommodation

Day 10: Finding Wonder in Ancient Remains

The morning blankets the old and new neighborhoods of Ragusa in a pristine light. The large palm trees in Piazza del Duomo provide luxurious shade in front of the raised base of the Church of San Giorgio. After breakfast, your private transfer escorts you to the edges of Agrigento, where you find the stunning Valley of the Temples. The beauty of the archeological site is in the number of ancient Greek ruins, along with their exceptional preservation. The sounds of the bustling streets of the city of Agrigento fade away. The brilliance of the undulating landscape peppered with Greek temples comes into focus.

Olive groves and almond trees rise above the silver bush shrubs. Your guide leads you along the pathways connecting the remaining pillars that mark the elaborate temple complex that once stood there. The area was settled between the 6th and 4th centuries BC. The best-preserved temple stands atop the hill and is known as the Temple of Concordia. The structure has a six-column façade and 13-column flanks. The semicircular decorative wall surfaces known as tympani have been perfectly preserved. Standing in front of such a magnificent ancient structure is breathtaking. The roof was once covered in marble tiles that reflected the sunlight, making the temple glint. 

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

Day 11: Returning to the Sea

The morning light washes over the white rock cliff known as Stairs of the Turks, which overlooks the clear water of the Ionian Sea. The eroded limestone left layers that resemble steps, wrapping around the edges of the coast. The drifting sunlight changes the colors along the landscape from white to gold. After breakfast, you make your way to the sensational seaside town of Cefalu, located across Sicily on the Tyrrhenian Sea. The stone buildings have a radiant honey hue. Mosaics adorn cathedrals. The relaxed pace and picture-perfect scenery allow you to settle in the city and relish the beauty at your leisure.

La Rocca is an imposing cliff nudged against the town, rising 882 feet above sea level. On clear days, you can see the Aeolian Islands in the distance, including the conical peak of the Stromboli volcanic island. The Norman castle battlements provide a perfect viewpoint for an unparalleled panorama of the coastline. Stroll along the medieval laundry center in the heart of the old city. Women once gathered to wash and rinse clothing on the distinct elevated area made of lava stones. Water springs from 22 spigots into the basins and overflow would rush into the sea. Cefalu is a mixture of historical intrigue and natural charm.

What’s Included: breakfast, tour, accommodation

Day 12: In the View of the Hilltop 

The sunlight washes over the Valley of the Temples and brings the ancient structures back to life. The markets of Agrigento open, and locals fill the cafes in search of a quick espresso and sweet brioche. After breakfast, your private transfer leads you to the seaside city of Trapani, which hugs the famous harbor where Peter of Aragon docked his ships in the 13th century to begin the Spanish occupation of Sicily.

You can see the towering summit of Mount Eryx standing 2,460 feet above sea level. The Medieval town of Erica adorns the plateau. The neighborhood of Old Town Trapani was once the heart of trade with the surrounding Mediterranean Sea, connecting Carthage in North Africa and Venice in northern Italy. A gondola connects the base of the nearby mountain to the top. After exploring Trapani, you venture up the hillside to find the cobblestone streets bisecting the triangular plateau.

Historic walls continue to wind around the outer layers of the cityscape, connecting to old castles that once protected the citizens. Venus Castle was named due to its placement over the temple once dedicated to the goddess of love. Artifacts of the Elymians and Phoenicians have also been found on the mountaintop. You can see the northern edge of Sicily. Stroll along the luxurious green park to the medieval Pepoli Castle to find the ancient acropolis. Capo San Vito, a protruding rock, magnificently edges the Tyrrhenian Sea. 

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

Day 13: Relishing the Coastline

The sun rises over the water and casts a shimmering light across the Mediterranean Sea. The clear water is stunning in its opulence. After breakfast, you venture to the enchanting seaside town of San Vito lo Capo, located at the northern edge of Sicily or set sail on a Catamaran excursion of a lifetime exploring the Egadi islands.

San Vito lo Capo is nestled between the mountains, sandy beach, and the local olive groves. Caverns honeycomb the mountainside and provide ample discoveries to rock climbers and spelunkers. Locals and visitors from mainland Italy come to enjoy the refreshing water, soft sand, and bright sunlight. The mountain towers 1,745 feet above the sea, providing unparalleled views of the water. In the afternoon, you visit the ancient ruins of Segesta on your way back to Erice.

The ruins occupy a tranquil area in the hills. A temple crowns the hilltop encircled by a remarkable gorge on three sides. The temple was erected in the 5th century BC and has 14 columns running along the flanks. Along the nearby hillside of Monte Barbaro is the semicircular theater erected around the same time as the temple. The marble seating looks out to the encircling countryside, creating an exceptional natural backdrop for the plays that were once performed there. During the summer, the region continues to use the venue for plays, concerts, and festivals, offering people a deeper connection to the history encompassing Sicily.

For your second option, you will be escorted to the port of Trapani where you will meet your local guides at Alien Cat Tours. You’ll embark on an adventure of a lifetime, sailing a catamaran along the Mediterranean Sea discovering the marvelous Egadi islands. Your sailing catamaran captain will drop anchor in stunningly beautiful “secret” destinations, giving you the luxury to peacefully relax in the warm Mediterranean sun, go for a swim, and taste delicious homemade Sicilian food. Take a few moments to deeply observe the surrounding scenery and enlighten yourself with the bright baby blue water as it hugs the ancient island shores. Your guides at Alien Cat Tours will truly give you an experience you will never for forget.

What’s Included: breakfast, tour, accommodation

Day 14: Final Days of Sicily

In the clear morning sky, you have a perfect view of Sicily, reaching from the port of Trapani to the rolling hills across the central landscape. The crisp air perfectly complements the glistening aroma of the sea below. Your private transfer meets you at the hotel and escorts you back to Palermo. The antique stalls in Piazza Peranni provide insight into the history of Palermo and the splendor of Sicily. Stunning chairs padded with hand-sewn tapestry decorate the market. Strong brass candelabras stand atop desks made of rich dark wood. History in Sicily is a part of everyday life. You continue to Falcone-Borsellino Airport to board your flight home. Your exploration doesn’t have to end. You can continue discovering the beauty of Italy and the history of Europe by extending your vacation to visit Rome or the unique southern region of Apulia.

What’s Included: breakfast, transfer 

Price

Starting Price 

$3,845
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.