VIP Tour of Sicily: Beauty, Culinary & Luxury Experience

A 11 day trip to Italy 
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Treat yourself to the luxury and romance of Sicily, from the crystal clear azure sea to the inspiring ancient ruins scattered across the hillside; the splendors of the island await. Baroque palaces decorate historic cities. Private vineyards overtake the hillside of a secluded island getaway. Cobblestone streets lead to remote vistas with immaculate views of the countryside. You can indulge in the pure essences of the cuisine and bask in the alluring flavors of celebrated vineyards on your custom tailored luxury Sicily tour.  

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General Information

Detailed Itinerary

Places Visited 

Catania, Syracuse, Ragusa, Scicli, Modica, Salina Island, Panarea, Lipari, Stromboli, Taormina, Mount Etna, Marzamemi, Noto 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Secluded Corners of Syracuse

The history of Syracuse encapsulates the beauty of Sicily and the timelessness of its culture. Baroque palaces create dazzling spectacles along the streets. Cobblestones pave the medieval streets leading to the shimmering crystal blue sea. Morning markets burst with vivaciousness, each vendor touting the freshest produce and seafood caught that morning. The city once had the largest population in all of antiquity, larger than even that of Athens and Corinth. The historic heritage has influenced the culture of Syracuse and Sicily as a whole. Your private transfer meets you at Catania-Fontanarossa Airport and escorts you to your charming accommodation located in the most historic neighborhood of the city. Consider learning more about your Sicily travel agents who strive to meticulously personalize your itinerary so that it is perfect from the moment you arrive. 

The island of Ortigia has lavish churches and tight-knit lanes overlooking the stunning Mediterranean. The water laps at the ancient walls of the city. Your room provides you a private view of the water, where you and your partner can watch the fishing boats wade in the marina or drift out to sea. Fonte Arethusa is an ancient spring filled with freshwater but sits near the edge of the sea. Wild papyrus has grown in the spring for millennia. Wild ducks roam on the water’s surface and linger in the shade of the papyrus.

What’s Included: dinner, transfer, accommodation

Day 2: Wonders of the Past and Present

In the morning, the sunlight reflects off of the crystal azure Mediterranean Sea. You can hear the calm water lap at the shores of Syracuse. At breakfast, you indulge in the refreshing aroma of espresso and the sweet taste of a traditional treccine, a brioche with a twisted shape and topped with sugar. After your meal, your guide meets you at the hotel, ready to take you on a private tour of Syracuse, introducing you to the past and present splendor of the city. The ancient Greek Theater was carved into the hillside in the 5th century BC and premiered the works of the famous Greek playwright Aischylos, along with housing performances by Sophocles and Euripides.

The crescent shaped architecture has a diameter of 452 feet and could hold an audience of up to 15,000 people. The encompassing greenery offsets the white stone used to construct the theater. The atmosphere is stunning. In the late morning, you continue to charming village of Marzamemi, known for its quiet streets, indigo waters, and fresh seafood. The 10th-century Arab influence remains prominent in the local culture. Your guide leads you to a tranquil restaurant, where you have a view of the sparkling sea. You notice that the painted blue doors adorning each building and the potted geraniums add to the enchanting atmosphere.

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

Day 3: Baroque Villages and Tempting Chocolate

In the morning, the ducks return to the fresh water of Fonte Arethusa. The zesty scent of citrus groves harmonizes with the refreshing aroma of the sea. The historic city of Syracuse glows gold in the early light. After breakfast, your guide escorts you to the exquisite Baroque village of Scicli, which fills you with an unparalleled sense of discovery. The clean stonework of the architecture allows the entire village to camouflage into the surrounding hillside. Churches and monasteries adorn the encircling ridges overlooking the village.

Gargoyles decorate the façade of Palazzo Beneventano. Elegant balconies have iron-wrought gates. The inhabitants of the village once lived in the local network of caves. Remnants of history can be seen across the landscape, still alive with a sense of archaeological prominence. Continue to Modica. The small town feels like a metropolis after your time in Scicli. A fabulous Baroque cathedral adorns the medieval center. The treasures of the town are strewn across the landscape, making every corner captivating and every street enticing.

The locals are friendly, and the steep staircases add an extra layer of uniqueness to the Modica’s design. Your guide leads you to Bonajuto for your chocolate tasting. The Dolceria is considered the chocolate headquarters of the city, boasting flavors such as Arabian orange and special liquors. You learn about the history of chocolate in Sicily and indulge in an exciting tasting that brings sweetness, richness, and sensual texture for you to share with your partner.  

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

Day 4: Sharing the Landscape

In the morning, Syracuse slowly comes to life. The historic beauty of the city continues to shine alongside the captivating colors of the Mediterranean. After breakfast, your guide leads you into the countryside to visit a sensational vineyard to learn about the diversity of soils and the originality of a celebrated winery. The area is known for its red landscape in the sunset and the refreshing winds brushing over the grassland. Vines create verdant rows, decorating the flatlands of the estate. Your guide leads you through the leaves and grapes sprouting in the fields.

The vineyard caretakers explain the unique qualities of the soil. The tannic properties of the land enhance and shape the flavors of the wine. After you explore the fields and learn about the winery’s biodiversity, you find a table set for tasting. The unassuming picnic table provides a private experience overlooking the lush landscape. Cheeses and local charcuterie accompany the wide selection of wines. You take your first sip of a wine made with the famous Nero D’Avola grape. You find an enticing aroma of mocha and dark chocolate, finishing with an herbaceous black licorice.  

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

Day 5: Romantic Island Treasures

The remaining stonework from the 6th-century BC Temple of Apollo glints in the morning light. Partial columns decorate the cityscape standing nearly 26 feet tall. After breakfast, your private transfer meets you at your hotel to begin your journey to the northern Aeolian Island of Salina. The landscape is luxurious, filled with woodlands and blossoming wildflowers. Grapevines lead to yellow gorse bushes and high coastal cliffs. Waves break against the base of the bluffs. The freshwater springs and volcanic soil combine to make the island landscape fertile.

Two extinct volcanoes shape the topography; the taller of the two, Monte Fossa delle Felci, rises 3,156 feet above sea level. Your private transfer escorts you to your fantastic resort-style accommodation located on a vineyard. The island has a remote and romantic ambiance, colored by the natural beauty of the land and sea. In the afternoon, you can bask in the drifting sunlight and enjoy the dreamy view of the vines rushing out to the edges of the sea.

What’s Included: breakfast, transfer, accommodation

Day 6: Amorous Cruise

As you wake up this morning, you can indulge in an unobstructed view of the Mediterranean, looking out to the medley of uninhabited islands and rock formations springing from the water. The sea breaks along the cliffs. At breakfast, you sip a refreshing cappuccino. The earthen aroma of the island blends with the sea breeze. After your meal, your guide meets you at the hotel and escorts you to the marina, where you board a boat eager to set out on your private cruise to the Aeolian Islands. Mist spritzes up from the sea. The breeze is cool and rejuvenating, while the sunlight is warm and embracing. Later in the day, you reach the island of Stromboli.

The landscape emerges from the vast blue sea in a pyramidal shape. A unique cloud forms and dissipates around the island. The conical shape of Stromboli is due to its being the tip of an underwater volcano, with its base being over 4,842 feet below the surface. The rugged beauty of the island is set in the soft black sand of the beaches on the northeastern corner. Once on the island, you can dig your toes into the warm sand and feel the difference between the cool water and the hot earth. The volcano summit rises 1,312 feet above sea level and provides a stunning display of natural light against the evening darkness.     

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

Day 7: Island of 1,000 Colors

In the morning, you find the emerald hue of the vineyard set against the backdrop of the azure sea. The water changes colors with the passing sunlight. You and your partner enjoy the luxury, privacy, and beauty of the island. You take your time in the morning, basing in the warm light passing over the resort. The citrus aroma of freshly made orange juice accompanies breakfast. After your meal, your guide meets you at the hotel and leads you to the vineyard of the estate for an introduction into the complex and passionate flavors of the wine. The vineyard began in the 19th century by Sicilian aristocracy. Today, the wine has a delicate bouquet shaped by its eclectic volcanic soil.

After your tour of the property, you sit down for a tasting with a view of the entire island in front of you. The verdant quality of the landscape enriches the moment and the memories you and your partner are making together. At the end of your tasting, your guide pours the celebrated Capofaro Malvasia de Salina, a dessert wine. The gold color is bright and rich. The aroma of candied raisins and apricots are accentuated by undertones of lilies and mangos. Your guide places macaroons on the table in front of you. The fresh fruit flavor of the wine pairs perfectly with the sweet and light taste of the macaroon. 

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

Day 8: Delightful Treats

The morning on Salina Island is tranquil. You listen to the waves crashing against the cliff below. The breeze blows over the vineyard, rustling the grapes and the leaves. After breakfast, you are escorted to the marina, where you board the ferry back to the large island of Sicily. You and your partner have tasted the finer things in life and will continue to indulge in the luxuriousness of Sicily with lunch at the Michelin-starred restaurant in the seaside city of Taormina.

Your five-star luxury hotel is located in a historic palace, with the vantage point of a cliff overlooking the Bay of Naxos. The elegant dining room leads to a patio with a garden charm and a stunning vista. Your meal is paired with an exquisite wine to provide the perfect combination of flavor and balance. The innovative menu takes you on a tour of traditional Sicilian cuisine with a modern twist. The sweet and sour vegetable ratatouille with smoked beef slices and buffalo mozzarella perfectly balances the bold and the simple, comfort and unconventional in a single dish.

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

Day 9: Distinctly Mount Etna

Traces of historic walls encircle the base of the clock tower and wind along the northern edges of town. The Argonese coat-of-arms is sculpted into the relief over the archway of the gate. Fresh pastries decorate the windows of the bakeries along the main avenue of Corso Umberto. After breakfast, your guide escorts you to the foothills of Mount Etna. Snow blankets the peak throughout the year, as the summit rises to nearly 11,000 feet above sea level. You arrive at a private, family-owned estate encompassing 61 acres. The vines are segmented, overtaking the hillside and looking over the ridges of the valley beyond.

The nutrient rich volcanic soil helps produce quality grapes bursting with unique flavors. Your guide leads you to the grounds, taking in the vast quantity of vines and the cool quality of the climate, due to the varying altitude of the vineyard from 1,263 feet to 1,663 feet above sea level. In the cellars, you find large Slovenian oak barrels, where wine ages for up to 36 months. The cellars are cool in temperature and rustic looking. The tasting room has an open view of the hillside. Your guide pours a sample of the treasured Brunello, which has a subtle orange zest complemented by plum notes with a spiced finish you have never had the pleasure of tasting before.

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

Day 10: Jewels of the City

The morning view from the Public Gardens is unparalleled. The thick vegetation and blossoming flowers frame the brilliant vista overlooking the water. Olive trees line the pathway and arabesque designs decorate the shrine-like towers. Strolling along the shaded paths is a tranquil and romantic experience. After breakfast, your private transfer escorts you to Catania, an 18th-century Baroque city founded in the 8th century BC. The image of Mount Etna looms over the edges of the cityscape, but the streets are filled with vibrant life and welcoming people.

Opulent palaces are colored with unconventional gray hues, which stems from the unique method of using volcanic rock to rebuild the city in the 1700s. Orange and lemon groves flourish in the gardens. Chestnut trees provide a sweet aroma. Discovering the distinctive character of the city with your partner is an enlightening experience that bonds you ever closer together. The seafood market near Piazza Alonso di Benedetto is one of the most celebrated markets in Sicily.

Marvelous displays of freshly caught fish, prawns, and muscles are only the tip of the culinary iceberg displayed by the vendors of the marketplace. Couples stroll along the cobblestone streets in search of a perfect accompaniment to their dinner that evening. The stunning Greco-Roman theater hides in the midst of the cityscape, surrounded by contemporary life. Clothesline dangle outside windows. The bordering 19th-century palace contains artifacts encompassing two millennia. The beauty of the structure is in the remaining architecture and the ability of the local lifestyle to incorporate the ancient structure into an everyday postcard view. 

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

Day 11: Carrying the Passion with You

The morning light washes over the layers of the 18th century monumental gate of Porat Garibaldi. Two angelic figures flank the central clock adorning the structure. The white limestone and black lava material used to erect the monument shimmer in the sunlight. The angels symbolize glory. At breakfast, the aroma of rich cappuccino has become a comforting invitation for the day ahead. The brilliant decorative statues adorning the Neoclassical façade of the Biscari Palace have an opulent white glow. Your private transfer meets you and your partner at the hotel after breakfast. Soon you will make your way to the Catania-Fontanarossa Airport for your flight home, but you can always extend the romance in the passionate city of Venice or the romantic hills of Tuscany.

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.