A Luxury Wine Tour of Sicily

A 9 day trip to Italy 
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The luxuries of Sicily emanate from every sip of wine, each bite of food, and the unforgettable panoramas of the landscape. Your Sicily wine tour is custom tailored to ensure comfort and elegance, flavor and culture. The sea shines a deep sapphire blue. The hills transition between golden grasses and verdant vineyards. The exquisite snowcapped peak of Mount Etna rises over the sandy beaches, and immense columns of ancient Greek temples continue to stand stoically against rolling hills surrounding the valley. From the moment you arrive, you will relish the splendor of Sicily.

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General Information

Detailed Itinerary

Places Visited 

Palermo, Marsala, Erice, Monreale, Sambuca di Sicilia, Valle del Belice, Agrigento, Ragusa, Modica, Taormina

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Cultural Sample of Sicily

The city of Palermo has a wondrous allure set against the pristine lulling waters of the Tyrrhenian Sea. You arrive at the airport, where you find your private transfer waiting to escort you to the lavish resort-style hotel outside of Marsala. The city is famous for its wine but has a long and illustrious history of which its citizens are proud. The marble streets gleam in the bright sunlight. Baroque buildings encircle elegant piazzas. Locals enjoy the cool breeze of the evening and stroll along the charming streets or sit in small cafes watching passersby while sipping an aperitif. The Complesso Monumentale San Pietro is a remarkable art center housed in a refurbished 15th-century convent.

The complex of museums contains weapons and documents used in the reunification of the two kingdoms of Sicily, along uniting the island with mainland Italy. Numerous cafes stand opposite the stunning Marsala Cathedral known as the Duomo. The cathedral was reconstructed in the 1950s but maintains strong Norman foundations. You settle into your hotel on the outskirts of town to find a comforting spa and wellness center on property. The pool sets a tranquil ambiance with its constant trickling of water. The sea brushes against the shores golden sands of the beach for an undeniably luxurious stay.

What’s Included: dinner, transfer, accommodation

Day 2: Becoming Acquainted with the Unfamiliar

The sunlight sweeps across the lush vineyards stretching across the landscape outside your resort. The relaxed pace of Marsala resounds across the shoreline and low-lying hills near the city. After breakfast, your guide greets you the lobby, eager to introduce you to the culture and history surrounding Marsala. Your day begins with an introduction to the flavors of Marsala, where you can enjoy the simple pleasures of a wine tasting at a celebrated local winery. The family who owns the vineyard has been in the wine industry for more than 160 years.

The cellars in Marsala provide a spacious courtyard filled with citrus and olive trees, bringing a delightful zest to the day. The particular cellar which houses the barrels was carved out of the natural tuff rock, providing a temperature controlled area maintained by the earth’s climate. Exploring the historical grounds and processes involved with creating the wine pairs perfectly with the floral profile and perfumed style of the white wine. In the afternoon, you ascend the mountainous terrain to the town of Erice, at 2,463 feet above sea level. Medieval buildings line the streets.

Verdant trees encircle the rugged granite cliffs. Pepoli Castle and Venus Castle offer breathtaking panoramas of the rolling hills and expansive sea. The Norman edifice of Venus Castle has impressive towers climbing over the already powerful mountaintop. On a clear day, you can look out over the shoreline and see Africa’s coast in the distance. The 15th-century Gothic church of Chiesa Madre was erected in the shape of a Latin cross. Baroque altars and lavish paintings add to the enriching ambiance. The Duomo was built in the 14th century. The view from the mullioned windows makes the entire moment feel taken out of a storybook.

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

Day 3: Heart of the Market

In the morning, Palermo bustles with open-air markets overtaking the historic cobblestone streets and piazzas. The monuments of the city predate the Roman Empire. The lavish Norman Palace has Phoenician foundations. The Arab influence on the Cathedral’s design is prominent in the form of geometric embellishments. You arrive in the city and meet your guide. You are eager to explore the depths of the culture that has amalgamated various values and traditions from traveling societies from around the globe. One of the best places to experience the vibrant lifestyle of Palermo is at Cap market, the oldest market in the city.

Stalls edge the old city wall and the backside of Teatro Massimo. Vendors call out to passersby and one another, filling the streets with a boisterous and jubilant atmosphere. Packaged spices provide a savory aroma and refreshing brightness. The marketplace maintains a connection to the Arab traditions of past inhabitants. Vendors hold out large lemons to you, urging you try the alluring scent. Mountains of olives rise over stalls. The colors of the produce are vibrant and fresh. Your guide points to the freshly made arancini, deep-fried rice balls that offer a savory crunch throughout the day. After your exploration of the market, you continue to the restored 18th-century palace overlooking the sea.

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

Day 4: Visiting the Valleys

You wake up to the rejuvenating sounds of the sea lapping on the beach. The aroma of fresh espresso refreshes your senses. The luxuries of your resort have cradled you throughout the night, and the wonders around Marsala have kept you intrigued during the day. The majesty of Sicily continues with your private transfer to a wonderful vineyard in the province of Sambuca di Sicilia. The landscape rises to an altitude of 1,148 feet. Arab settlers founded the area in the 9th century, but archeological evidence suggests people have populated the area since prehistoric times.

Low houses and courtyards decorate the Saracen quarter of the town. Oak and maple trees create forests inside the lava landscape. Vineyards stretch across the hills, casting a verdant glow. It is here where you find the local winery encompassing 229 acres, yielding numerous grape varieties. The estate was constructed in the mid-1990s, with a wine cellar erected near a charming 16th-century farmhouse. The calm waters of the lake reflect the surrounding greenery. In the tasting room, you find a white wine with exuberant youthfulness. Mineral essences from the volcanic soil enrich the earthy notes and citrus tones. The fascinating flavor balances the delicate with the strong.

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

Day 5: Indulging in Tradition

The medieval center of Agrigento buzzes with energy. Boutique shops and cafes line Via Atenea. Narrow alleyways meander away from the main street and into the historic landscape of the city. In the morning, you visit an exclusive winery near the city before continuing to a famous culinary school known for educating chefs in the traditional flavors of Sicily and the importance of connecting with your food. The landscape around the culinary school is lush, filled with vineyards rolling along the hills and sporadic trees decorating mountains on the horizon. The country ambiance is comforting. The chef welcomes you into her way of life, happy to use the seasonings to inspire the timeless combinations of flavors that have lasted for centuries.

Pistachio, lemon, and mulberry orchards provide shade in a garden blossoming with tomatoes, artichokes, and eggplants. You follow the Chef through her garden, noting the types of vegetables she chooses and her reasons for doing so. The country house has a Sicilian charm that you have noticed during your time on the island, encompassing 1,200 acres. You prefer to attempt a challenging dish, mixing flour and eggs to create a fresh pasta dough. Knead the dough, ensuring its quality, and round it into the perfect ravioli that you stuff with ricotta and mint. When you finish the dish, the aromas of mint and almond are enticing. A stunning dish drizzled with sage-almond pesto sits before you, turning curious and enchanted heads and noses.

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

Day 6: The Beauty of Baroque 

In the morning, you leave behind the central medieval character of Agrigento for the Spanish Baroque qualities of the towns of Ragusa and Modica. In the afternoon, you arrive in Modica, a town known for its architecture, food-loving locals, and exceptional chocolate. Buildings rise along the steep hillside overlooking the valley. The main street of Corso Umberto I meanders along the banks of one of the three main rivers in the valley. One of the treasures of Modica is the thrill of discovery. The historic buildings are peppered around town, necessitating your exploration of the streets and piazzas.

On the upper reaches of the town, known as Modica Alta, is Chiesa di San Giorgio. The church is secluded atop a 250-step staircase. Medieval alleyways wind beneath a three-tiered façade. Sunlight pours through the windows to shine some natural light on the silver, gold, and blue colors of the interior, producing a kaleidoscope of Baroque art. Your guide continues to lead you through the streets following the aroma of chocolate, chili pepper, and hints of cinnamon or vanilla. You find Dolceria Bonajuto and settle into the quaint café that produces some of the most luxurious chocolates in the region.

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

Day 7: Wine and Dine and Differentiation

The Old Town of Ragusa is a quiet neighborhood filled with narrow streets that twist and turn among the Baroque architecture. A mixture of 18th-century buildings is scattered amongst the pre-17th-century structures that survived the earthquake of the late 1600s. After breakfast, your private transfer greets you at the hotel and escorts you to the southeastern corner of Sicily. Carob and almond groves rise over the expansive vineyards on the property. The landscape fills with red and yellow hues emanating from the rocks and flora. The boutique vineyard uses well-preserved techniques to produce various types of wines.

Your guide tours you along the property. You enter a room filled with terracotta jars. Your guide explains that the simple method accentuates the humble ingredients, but allows the mixture to ferment, grow, and establish itself as a classic wine. The boutique vineyard produces wines that mirror the landscape, ranging from floral and vibrant to rugged and earthy. Your guide pours you a sample of the Pithos Rosso, a red wine produced with the age-old methods you had seen earlier. A cherry nose entices you to sip your tasting.  The wine has an elegant spice with earth notes and a complex tannic structure.

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

Day 8: Tremendous Taormina

In the morning, you venture away from the hilly borders of Ragusa to the towering cliffs of Taormina. The waterside city overlooks the Ionian Sea, reaching an elevation of 669 feet. Cacti sprout from the cliffs. The water is clear and crisp below, splashing against the rocky base of the landscape. In the distance, you can spot the looming peak of Mount Etna. White puffs of smoke rise out of the volcano’s summit. Your guide leads you on an encompassing tour of the city, taking in the quaint lifestyle of locals lingering in the piazzas and enjoying the narrow shady lanes.

Greek settlers founded the town in the 6th century BC. The Greek Theater was erected in the 3rd century BC and offers a dramatic view of the sea, sky, and Mount Etna’s stunning peak. It is the second largest Greek theater in Sicily, behind Syracuse. The edifice was built from brick and carved into the sloping mountainside. The horseshoe configuration arches around the stage with a diameter of more than 357 feet. During the summer, the community still shows movies and offers opera performances inside the theater.

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

Day 9: Remembering the Flavor

When morning washes over Taormina, the romantic buildings and lavish terraces come into view. Via Pirandello winds up the mountainside, passing Byzantine monuments. Gondolas ascend and descend the funicular to Mazzarò. Locals sit at open-air cafes and bask in the early morning sea breeze. The ambiance is refreshing and relaxed. After breakfast, your private transfer greets you at the hotel. Soon you will venture to Catania-Fontanarossa Airport for your flight home. For the moment, you prefer to do as the locals do and indulge in the sights and sounds of a perfect Sicilian morning.

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.