Catania, Taormina, Noto, Syracuse, Butera, Modica, Ragusa, Menfi, Agrigento, Marsala, Erice, Palermo, Cefalu
Dates are flexible and customizable for private departures.
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...
Sicily – 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.
Palermo – 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.
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.
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. At dinner, you can 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.
Modica – 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.
Ragusa Ibla – 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.
Taormina – Beachside Comforts and 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.
Catania – 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.
- Revel in an unforgettable traditional Sicilian dinner with dishes paired with select wines chosen by a renowned sommelier
- Enjoy a fabulous wine tasting at a celebrated local vineyard in Marsala to sample a variety of wines, providing a full spectrum of flavors in the region
- Indulge in an elaborate chocolate tasting at a historic chocolaterie located in the baroque town of Modica
- Witness the beautiful Greek ruins at the Valley of the Temples on a unique night tour, accompanied by an exceptional performance at the Teatro della Posta Vecchia
- Discover the lavish and rich history of Syracuse on a private guided tour of the distinctive city
- View the elegant glistening golden mosaics of the Palatine Chapel found inside the Norman Palace of Palermo
- Relax on the tranquil and picturesque shores of the seaside town of Cefalu
- Stroll along the historical and elegant cobbled streets of Taormina
Sample the fragrant grapes and witness the lush produce on display in the active morning markets. Stroll alongside an ancient Greek theater and dip your toes into the hot sand of a gorgeous Mediterranean beach. Your 8-day Sicily wine tour lets you experience the flavors of the island that have inspired the world, from its traditional cuisine to its unique culture, the distinctive details that shape the daily life of a Sicilian begin to inspire you. Your tour starts with your arrival at the Palermo airport. Your private transfer escorts you to the nearby seaside town of Cefalu. The remainder of the day is yours to relax on the shoreline and enjoy the picturesque atmosphere.
Relish your first meal paired with a sampling of wines from around the region. The following day, your guide leads you on a fabulous historical tour of Palermo. Visit the stunning churches and view the Baroque facades of the city before exploring the impressive Duomo del Chiostro in the nearby village of Monreale. In the evening, you settle into the quiet streets of Menfi for another fabulous meal and wine accompaniment. You venture to the nearby region of Marsala for a guided tour of a traditional vineyard that produces Marsala wine. Continue to the exceptional medieval hilltop town of Erice, where you can sample from a collection of the local pastry shops serving typical regional delights.
The next day, you discover the wonderful grounds of the Terre Sikane vineyard on a guided tour and wine tasting before continuing to the Valley of the Temples, located outside the contemporary city of Agrigento. Enjoy a fine dinner with a focus on the differences an almond can make in the cuisine, with wines paired by a local sommelier. Return to the Valley of the Temples for an evening tour, along with a performance at the Teatro della Posta Vecchia. Then, you traverse the charming streets of Butera. Continue to the Baroque town of Modica to sample the stunning confections of a historic chocolaterie. Travel along the rambling cobblestone streets of Ragusa to see a city shaped by both time and the elements. At dinner, you enjoy the traditional regional dishes of Ragusa. Consider reading some of our travelers' Sicily vacation reviews to acquire additional inspirations to perfect your own trip.
Your guide escorts you to Noto, the Baroque capital of Sicily. You continue to discover the ancient foundations of Syracuse before arriving at your hotel on the foothills of Mount Etna. Enjoy another fabulous meal paired with a delicious local wine. You visit the exquisite seaside town of Taormina to explore the winding streets at your leisure. Return to Etna for dinner, where you sample the splendid wines of Tenuta San Michele with your meal. On your final day, your private transfer meets you at your hotel near Etna and escorts you to the airport in Catania for your flight home.
$2,195 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Reviews of Zicasso's Referral Service
4.88 stars based on 4533 reviews
"Laura was crucial in making the agenda and listening to...
Reviewed By Tim L.
"Every detail of the trip was meticulously planned and executed."
Reviewed By kimberly e.
"Our travel planner was on top of every little detail, which...
Reviewed By Gabriel G.
"[Our travel planner was] always accessible during our trip...
Reviewed By Elliot A.
"It was truly the trip of a lifetime. Thank you, Devaki,...
Reviewed By Michael B.
"ETAV was very responsive and helpful in the planning process."
Reviewed By Nicolle G.
Get Weekly Inspiration and Expert Advice on Travel
during the COVID and post-COVID era