Custom Tailored Sicily Wine Tour

A 8 day trip to Italy 
4.92 out of 5 stars
12 reviews

Your private tailored Sicily wine tour allows you to settle into the captivating life of Sicily, a destination where you can slow down, sample the best varieties of local wine, and explore the depths of ancient cultures that have evolved in the undulating hillsides. Indulge in a sweet confection inside a chocolate shop that has spent centuries perfecting its craft. Grab a handful of the earth that nourishes the lush flavors of the timeless cuisine. Sensational trips to Sicily can be tasted, touched, and experienced; experience it all in this handcrafted tour of a lifetime. 

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Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Mount Etna, Catania, Taormina, Noto, Syracuse, Butera, Modica, Ragusa, Menfi, Agrigento, Marsala, Erice, Palermo, Cefalu

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: A Taste of the Sicilian Coast

The town of Cefalu sits on the shores of Sicily’s north coast, at the base of a looming bluff. The quiet fishing harbor borders the old streets. A Norman cathedral shines the same golden hue as the long stretch of sandy beach. Your private transfer greets you at the Falcone-Borsellino Airport upon your arrival. The short ride to Cefalu provides a panorama of the medieval town’s postcard-like beauty. It was used as the location for the academy award winning foreign film, Cinema Paradiso. The stone buildings have a glow the color of honeydew. The large rock face known as La Rocca rises 885 feet above sea level.

The Cathedral was erected between the 12th and 13th centuries. Various architectural styles, from Arab to Byzantine, along with Latin and Nordic artwork combine to create a harmonious mosaic of the cultures that have settled in Sicily over thousands of years. Two towers frame the entrance, adorned with powerful battlements. One of the two spires symbolizes the royal family’s power. The ambiance is quiet and embracing, personified in the gentle sea breeze sweeping along the streets. The aroma of bright citrus adds to the sound of sizzling seafood emanating from the restaurants along the shoreline. 

What’s Included: dinner, transfer, accommodation

Day 2: Castles and Culture

In the morning, the vibrant Mediterranean sun washes over the shore. Atop the looming summit of La Rocca is the historic Cefalu Castle, which was constructed in the 13th century. The stone frame of the structure remains and showcases the placement of two towers and twelve rooms that once dominated the skyline overlooking the shoreline and the town. After breakfast, your guide escorts you to Palermo, the provincial capital of Sicily. The calm ambiance of the beach shifts into an alluring vivaciousness. The marketplaces buzz with activity during the morning. An impression of North African bazaars radiates from Ballarò Market, winding beneath the tarps decorating the cobbled streets near Piazza Ballarò.

The distinct cultures that once settled and ruled over the island are visible in Palermo’s activity, along with the architectural wonders framing the streets. Within the Norman Palace, you find the Palatine Chapel, a 12th-century construction draped in gold mosaics and marble floors. Ornamented vaulting decorates the ceiling and creates a honeycomb effect. The geometric style was taken from the Arab tradition and highlights the complexity of blending cultures during the Norman’s rule of Sicily. Natural light shines through the windows above the name, causing the golden ceilings to glitter.

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

Day 3: Imbibing the Coast and Flavors

The landscape around Menfi softens from rugged mountains to green hills that fade to tumbling waves on the pristine coast. Rows of vines are neatly combed in the countryside. The 13th-century medieval tower solitarily stands out in the skyline. The quiet streets are refreshing in the morning, as you sip your rich and frothy cappuccino. Your guide meets you in the hotel lobby and escorts you to a prominent vineyard in the region of Marsala, known internationally for its cooking wine but celebrated in Sicily for growing and processing indigenous grapes in the island.

Your guide tours you around a traditional vineyard to explore the vines, touch the soil, and witness the steps of Marsala winemaking. The wine is fortified with brandy. You witness the winery cooking and processing the grapes to create a deep brown color. After your tour, you can sample the variations of the wine, ranging from a sweet but dry flavor that is perfect as a digestif (an alcoholic beverage made to aid digestion), to the memorable taste of a cooking wine used to make zabaglione (an Italian dessert). The day progresses with your visit to Erice, a medieval town located atop a mountain 2,624 feet above sea level.

Cobblestone streets intersect one another along the triangular plateau. A funicular connects the mountain base to the summit. You stroll along the pathways, beginning at Porta Trapani, the town gate, leading to the Castle of Venus. The charming main street of Corso Vittorio Emanuele leads you to the fabulous Real Duomo, a 14th-century cathedral constructed with the building materials that once supported the ancient Temple of Venus, on which the Castle of Venus now stands.

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

Day 4: Memorable Wine and Ancient Connections

Outside of Menfi, the beautiful vineyards of Terre Sikane carpet the undulating landscape. After breakfast, your guide takes you through the sweeping pathways alongside the emerald-colored vines. The soil has a sweet and clay-like aroma. A family established the vineyard outside the town of Butera on 192 acres. The town is located on the hilltop overlooking the valley. Every detail can affect the grapes’ flavor, from the angle of the sunlight to the slope of the landscape. After your tour, you enter into the tasting room to sample wine made from Nero d’Avola, one of the most iconic grapes in Sicily.

The Il Sikano wine has a ruby red hue with traces of violet in the proper light. The nose presents hints of ripe fruits. You enjoy your tasting, finding the full body and harmonious flavors compelling. The day continues with a tour of the ancient grounds of the Valley of the Temples, found outside the city of Agrigento. The temple ruins are superb, offering insight into the Greek settlements and eclectic cultures of Sicily’s past. Wander the footpaths around the archeological site and you can feel how the preservation of the temples practically takes you back in time.

The aroma of oranges emanates from the nearby citrus grove. Sheep graze alongside the creek’s banks. The Temple of Juno was erected from marble in the 5th century. It is more than 125 feet long with columns rising 21 feet high. You can see the remains of the ancient altar through the eastern face. A portion of the original frieze is preserved on the northern colonnade. At dinner, you indulge in a luxurious dinner enhanced by the accompaniment of a sommelier to help pair your wine with an exceptional menu selection focused on the use of local almonds. 

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

Day 5: A Chance to Indulge in Beauty

Today you venture up the hillside of Butera to visit the stunning history and quiet charms of the small town. The city was founded in the 6th century BC and contains a lasting allure with the Butera Castle. The honeyed hue of the exterior connotes the structure’s former power, rising from the midst of trees. The main street leads to the Mother Church of Saint Thomas. The dome frames the vaulted ceilings. A Byzantine cross from the 6th century adorns the wall. You continue to Modica, a Baroque town with a medieval center.

The small town has a big city ambiance; graceful palaces line the main street of Corso Umberto I. Church spires create an immaculate skyline overlooking boutique shops and bohemian cafes. Life-sized statues of the apostles decorate the staircase leading to the Duomo of San Pietro. A 250-step staircase leads to the Chiesa di San Giorgio, a stunning example of Baroque architecture in Sicily. The three-tiered façade towers above the narrow alleyways of the medieval center, adding a layer of glamor to the square. Sunlight pours through the interior to create a kaleidoscope of colors shining across the nave. Your guide tells you to follow the aroma of chocolate. Your curiosity is rewarded with your discovery of Antica Dolceria Bonajuto, a chocolate shop that has been producing variations of global chocolate flavors for centuries. Now it is your turn to try some of their sweet and delectable creations.

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

Day 6: Baroque Morning and Ancient Afternoon   

The city of Ragusa has a noticeable divide between the elevated neighborhood of New Town, and the lower Baroque buildings of Old Town also referred to as Ragusa Ibla. The city was originally constructed by Norman occupiers in the 12th century and rebuilt after a damaging earthquake in the late 17th century, creating the newer neighborhood on the high plateau. Old Town has a series of labyrinthine nooks connected by narrow cobbled alleys. New Town has wide, elegant avenues. The stunning Baroque church of San Giorgio adorns Piazza del Duomo. The church was erected in the 18th century and sits on wide steps.

Three pillars flank the main doorway on each side, connoting an embellished classic architectural view. Palm trees shade the center of the square amidst bustling cafes serving espresso and brioche. In Syracuse, your guide leads you along the fabled lanes of what was once the largest city in all of classical antiquity, greater than that of even contemporary Athens. The city continues to boast the largest Greek Theater in all of Sicily, which was constructed in the 5th century BC. The architects designed the theater to incorporate the natural slope of the hill, carving the stadium seating into the landscape. The stage reaches a diameter of 452 feet long with 61 rows, providing space for over 15,000 spectators. The historical significance of the city radiates from the evolution of its cuisine and wine.

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

Day 7: Beachside Comforts and Mountainous Vineyards

The sunlight washes over the Ionian Sea, filtering into the Bay of Naxos. The seaside city of Taormina provides an exceptional view of the water from atop the cliff at 669 feet above sea level. The soft beach of the sandbar connecting Isola Bella to the Sicilian shore swells with locals and visitors out to enjoy the sunshine. You make your way to the fabulous cobbled streets of Taormina and notice the lanes ascending the hillside reaching the ruins of the castle at Castelmola. A wooden rail lines the walkway up the verdant mountain to the edge of the plateau. The castle was erected in the 15th century to help safeguard the city and the bay.

The small village stands over Taormina, providing a breathtaking view of the bay and Mount Etna in the distance. The castle ruins brush the edge of the cliff. The walkways along the upper reaches of Taormina bypass Byzantine rock-graves. The Public Gardens contain a charming set of gazebos with arabesque designs constructed from lava pumice stone. They rise from the blossoming flowerbeds and tower over the almond and olive trees. After your day exploring the far reaches of Taormina’s stunning pathways, you make your way to a vineyard located on the edges of Mount Etna, the largest active volcano in Europe. The minerals in the volcanic soil enrich the produce grown on the property, making every ounce of wine radiate and every bite of food sing with flavor.

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

Day 8: Ultimate Refreshment 

Catania is the second largest city in Sicily and was founded in the 8th century by Ionian Greeks. The streets bustle with activity, especially at the famous fish market. The vendors present their sensational fresh catches, ranging from crowds of prawns to magnificent swordfish. At breakfast, you enjoy the tranquil morning overlooking the vines reaching the slopes of Mount Etna. The Sicilian culture has been eclectic and captivating, dedicated to tradition but not afraid to evolve from its ancient roots. After your meal, your private transfer escorts you to Catania-Fontanarossa Airport. Soon you will board your flight and take the memories of Sicily’s splendor home with you. Or you could choose to stay in Italy and enjoy another week immersing yourself in the treasures 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.