Wine Lovers Sicily Tour: History, Tasting & More

A 8 day trip to Italy 
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Uncover the secrets to a perfect bottle of wine in the unparalleled landscape of Sicily. Follow the trail of an open-air museum dedicated to the different grapes of the island. Sip a sensual red or robust white in an antique farmhouse. Discover the ancient civilizations that settled the hillsides and shores. The subtle flavors of wine are influenced by the soil and elements, nurtured to absorb the qualities of its surroundings. Embark on a luxurious Sicily wine tasting experience that will introduce you to the Planeta estates and has you fall in love with the distinctive characteristic of each property’s wine and production. 

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General Information

Detailed Itinerary

Places Visited 

Catania, Palermo, Etna, Taormina, Syracuse, Noto, Vittoria, Ragusa, Agrigento, Menfi 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Surrounded by Vines

The history of the vineyards in Sicily spans thousands of years. In Palermo, remnants of an ancient lifestyle have combined with millennia of settlements from cultures around the world. The honey hue of the city glistens in the sunlight. The shimmering blue Tyrrhenian Sea brushes against the boats in the harbor. Women stroll along the paths of the marketplaces, listening to the shouts of the vendors vying for their patronage. The Cathedral has a 15th-century Gothic-Catalan portico. A single column contains an Arabic inscription connecting the structure to its former role as a mosque during the city’s Arab rule.

The bell tower was erected in the 12th century. The Baroque beauty of the city emanates from the Quattro Canti. The 17th-century plaza was erected with four mirroring corners rising three stories tall. A fountain decorates the lower floor, with sculpted figures adorning the upper floors, each flanked by elegant Greek columns. Your private transfer escorts you through the vibrant city and leads you to the town of Menfi. You settle into the comforts of your lavish resort, encircled by lush vines combing the hillside. The aroma of recently fried arancini, Sicilian stuffed rice balls, drifts from the kitchen. The elegance of the landscape and private accommodation is soothing. Consider reading some of our travelers' Sicily vacation reviews to further inspire and refine your perfect Sicily trip.

What’s Included: transfer, accommodation

Day 2: In the Lap of Luxury

In the morning, you wake up to the sun-drenched vines carpeting the hillside. The emerald leaves glint in the light. The breeze carries the aroma of the sea, which is noticeable in the distance. From your patio, you notice the azure water lining the horizon. At breakfast, you sip on a delightful frothy cappuccino and enjoy the aromas wafting from your cup. Your guide leads you to the edges of Sambuca di Sicilia, a town founded in the 9th century by Arab settlers and rising nearly 1,150 feet above sea level.

Palm trees stand as tall as church facades. The light captures the golden colors of the buildings bordering the piazzas. You reach the Ulmo Estate. The winery was inaugurated in 1995 as Planeta’s first, covering nearly 230 acres, incorporating approximately 24 different types of grapes. Your guide leads you through the rows of grapes, showing you the differences in color and size from the varietals found on the property. The 16th-century farmhouse was recently remodeled to incorporate a wine cellar.

In the tasting room, your guide pours a sample of the Chardonnay. Ulmo Estate is known for its premium wines, often aged in Bordeaux barrels for the wine to absorb extra flavor. After your tasting, you venture along the Grapevine Route known as the Vitis Museum. An antique stone building envelops the open-air exhibit dedicated to the rich history of Sicilian viticulture, along with celebrating the indigenous grape varieties found around the island. Vines surround the museum, illustrating the ease at which the grapes can grow in the Sicilian climate.  

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

Day 3: Following in the Footsteps of the Ancients

Elements of the past are all around Sicily, from traditional recipes that have evolved with time to the seamless blending of wine’s significance to the culture of the island. At breakfast, you find variations of brioches decorating the table. The sweet and flaky textures of the baked pastry complement your rich espresso. Your guide meets you in the hotel lobby and leads you away from your wine resort near Menfi to the ancient grounds of the Valley of the Temples, located outside of the contemporary city of Agrigento. Olive trees grow along the creek bed. The lingering citrus scent stems from the orange groves lingering near the olive orchards.

The Temple of Concordia crowns the hilltop. A pathway winds along the Doric ruins speckling the landscape. The old city of Akragas was founded around the 6th century BC. The Temple of Hercules was the second largest temple in the area, measuring 220 feet long by 83 feet wide. 15 columns line the length of the temple. A stone staircase flanks the interior shrine. Legend states that the temple once held a coveted painting of an infant Hercules strangling a serpent. The Romans erected three small cult rooms near the back of the shrine, embracing the temple as their own. The splendor of antiquity captivates you in the image of marble statues and graceful pillars that have withstood the test of time.

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

Day 4: The Journey Continues

The town of Ragusa is divided between the old and new districts set along the hillside. In the morning, the aroma of freshly baked pastries drifts along the cobblestone streets. In the distance, remnants of the ancient city of Kamarina look out to the sea. Your guide leads you to the Dorilli Estate, to sample the unique flavors of the celebrated wine. The vineyard encompasses 84 acres, including a rose-colored farmhouse erected in the early 1900s. The varietals of grapes are simply Nero d’Avola and Frappato, distinct to Sicily and known for their aromatic profiles. Inside the wine cellar, you notice both aged steel-coated cement vats and modern stainless steel tanks.

You enter the tasting room, where your guide pours a sample of the Cerasuolo di Vittoria Classico. The vineyard was the first wine in Sicily to receive the “controlled designation of origin guaranteed” mark. You taste bright acidity with hints of light fruit and lingonberry. The medium body is refreshing. Once in Ragusa, you notice the distinct differences in the two faces of the town. The neighborhood of Ragusa Superiore is laid out on a grid pattern. The streets in the older district of Ragusa Ibla wind along the sloping hill, intermixed with gray stone houses and Baroque palaces. Sunlight washes over Piazza Duomo, where the local cafés sell a celebrated wine-flavored gelato. 

What’s Included: breakfast, tour, accommodation

Day 5: Keeping the Flavors in the Family

The Baroque cathedral in the heart of Ragusa Ibla was erected in the 18th century. The lavish tiered stairway rises to meet the pillars flanking the central portal. At breakfast, you enjoy the familiar indulgent flavors of a freshly brewed cappuccino before venturing out to Buonivini Estates. You can see the Baroque charms of the towns of Noto and Modica en route to the vineyard, which spans 126 acres. Your guide takes you to a door deep inside the hillside, escorting you to the Invisible Wine Cellar.

Stainless steel tanks line the modern, sleek cellar. The aroma of grapes emanates from the vats. You continue deeper underground to find the barrel room. Several rows of oak barrels surround you. It feels as though you have seen into the future of wine and it all starts here. The contrast between the chic and modern elements of the winemaking process from the parched hills and ruined houses along the landscape outside the vineyard are striking. You can’t help but find the juxtaposition alluring.

The winery produces a dessert wine known as passito di noto. It has a golden color with notes of dried apricots and pistachio, along with a creamy, full-bodied texture and a predominate sweetness. After your subterranean tour of the vineyard, you make your way to Noto, the Baroque capital of Sicily. In the late afternoon, the sunlight casts a red and gold hue across the palaces and churches lining the main street of Corso Vittorio Emanuele. The dome of Cattedrale di San Nicolo has a peach color and remains the central focus of the city’s spire-based skyline. 

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

Day 6: Clear Remnants of the Past

The sunlight washes over the ancient buildings of Syracuse located on the small islet of Ortygia. The ancient fountain trickles with fresh water bubbling from a spring used for thousands of years. Papyrus grows wild around the water, and ducks glide across the surface, finding shade in foliage. Your guide leads you on a remarkable tour of the contemporary life surrounding the remaining architectural wonders of the city. Orange and olive trees grow in the magnificent hallows of the Latomia del Paradiso, a limestone quarry with an opening to let the sun shine through. 

The Greek theater was built into the hillside. Ancient engineers used the natural slope of the landscape to carve the stone seats, allowing for seating of up to 15,000 spectators and is subsequently the largest theater in Sicily. The diameter of the theater reaches a width of nearly 453 feet at its widest point. You can imagine the plays of Sophocles and Euripides being performed in their heyday, as the auditorium remains mostly intact. Elements of the 6th-century Temple of Apollo remain in the heat of the city. Pillar bases stand atop a staircase, hinting at the grandeur of the former house of worship and persisting in front of a small surviving portion of the wall.  

What’s Included: breakfast, tour, accommodation

Day 7: Succulent Lava Soil

The powerful summit of Mount Etna looms over the region, reaching a height of 10,911 feet above sea level. The volcanic soil is rich with nutrients affecting the flowers, produce, and vines that grow along the landscape. In the winter, snow turns the rugged summit into an opulent white. In the summer, you can see smoke rising from the numerous craters peppering the mountain’s peak. Today your guide leads you along Feudo di Mezzo Estate, where you can taste the difference the rich soil makes in enriching the crops.

The winery has designated particular zones of the foothills to yield the best flavors, beginning at Sciara Nuova, located at an altitude of 2,854 feet. The uniqueness of the vineyard goes beyond the sensational tastes of the wine and into the ambitious architectural design of the winery. The building was constructed in the path of an antique lava flow, blending modern design with traditional rustic elements of the region. The soil helps produce a distinct, spiced aroma. Your guide pours a sample of Eruzione 1614, a Chardonnay emanating a nose of honeysuckle and ginger.

You find a hint of lemon zest and green apple on your palate that pleasantly lingers. You continue to the seaside city of Taormina, a beautiful town situated on a cliff overlooking the Bay of Naxos. The water shimmers like a gem and the cobblestone streets winding along the mountainside are enchanting. You can sit in the public garden and enjoy the panoramic view encompassing the calm waters of the bay and the inspiring peak of Mount Etna.

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

Day 8: After the Feast

The tranquil water of the Ionian Sea brushes against the soft-sand beaches below. Blossoming flowers adorn the second-story balconies lining the streets of the city. The scent of coffee drifts from the Bar Mocambo, a café where Truman Capote and Tennessee Williams would enjoy a fresh espresso to start their days when visiting. Your guide meets you at the hotel after breakfast and escorts you to Catania. The monumental gate crowns the city center with an 18th-century Baroque style, crowned with winged figures. The fish market brims with activity, showcasing the fresh catches of the morning and the abundance of quality seafood brought by local fishers. You reach Catania-Fontanarossa Airport where you board your flight home, taking the memories of the wines and wonderful ancient ruins with you.   

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.