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Sicily Wine Tours & Vacations

Ratings of Zicasso's Service

Sicily offers a unique experience for wine novices and aficionados alike. Explore an island immersed in ancient traditions, covered with timeless landscapes and prevalent with delectable food and wine. Introduce your palate to whole new flavors with a private Sicily wine tour handcrafted just for you by Zicasso’s experts.

How Zicasso Works In 3 Simple Steps

  1. 1

    Describe your dream Sicily wine tour vacation.

  2. 2

    We match you with up to 3 top travel specialists (travel agencies). They compete to plan your tour.

  3. 3

    Book the trip when you are satisfied.

Ratings of Zicasso's Service

Tailor Made Itineraries

Get inspired with our sample trips below. Let our travel specialists customize a trip just for you.

Medieval church of the city of Taormina. Sicily, Italy

Perfect One-Week Sicily Wine Tour

7 Day Custom Tour

From $1,920

Discover corners that are filled with magic and flavors as they support greatness during your customizable wine tour of Sicily, immersing you in the soul of the landscape and passion of this historic culture. Experience the perfect trip for real oenophiles that accentuates the complexities of the regional microclimates and the pleasures that are brought about by a brilliant pairing between the right glass of wine and a treasured, local recipe. Uncover the deep-rooted oenological history and the enchanting splendor of Baroque cities, the marvels of secluded estates, and the grandeur of the ancient world during your exclusive Sicily wine tour.

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Traditional assortment of the fish market of the island town, Sicily

Exquisite Tour of Sicily’s Culinary Culture

10 Day Custom Tour

From $2,745

While the reputation of Italian wine and food is legendary, the true art of the vinicultural and culinary spirit will shine during you custom-tailored wine and food tour of Sicily. Over the course of nearly three millennia, Sicily has acted as the center of Mediterranean trade, bringing vibrant culture and sensational flavor to the rugged mountains, fertile plains, and golden coastline. You will experience the majestic mixture of customs and the alluring continuation of tradition within the context of modern luxury that unveils the beauty of the vines, the splendors of the seasonal ingredients, and the preservation of cultural heritage.

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Harvested grapes in basket at Italian vineyard on Mount Etna, Sicily

Highlights of Sicily Wine Tour

9 Day Custom Tour

From $2,470

The incredible diversity of flavor and the captivating complexity of history will keep you engaged during your exclusive wine and highlights tour of Sicily that will unveil the distinctive characteristics of the local grapes and the undeniable charm of the unique culture. The cities possess a quintessential Mediterranean ambiance while the smaller towns reflect a sense of ancient history that dates back to the Greek settlements and the Arab traders. An incredible diversity of varietals embodies the long heritage of winemaking on the island that binds together the past and the present while the scenery is an incredible setting where you will discover transcendent beauty.

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Cultivated land and majestic snow-capped Mount Etna, Sicily

Sicily Itinerary for the Experienced Wine Connoisseur

8 Day Custom Tour

From $2,195

Combine traditional flavor with ancient history, and Baroque charm with rich landscapes during your custom-tailored wine tour of Sicily for seniors. The indelible marks of ancient settlers gave rise to stunning culinary delights while elegant towns capture the grandeur of former kingdoms. Your immersive tour will highlight the treasured sunsets in Noto and luxurious coastline at Marzamemi, as well as the bountiful vineyards that spread across the foothills of Mount Etna. You will capture the spirit of the local markets that reveal customary recipes and explore the isolated islands that overflow with hidden splendors to shape your perfect blend of the past and present of Sicily.

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Couple at a luxury resort pool surrounded by vineyards in Selinunte, Sicily

Romantic Sicily Wine Tour

9 Day Custom Tour

From $2,470

Capture the romance of Italy during your custom-tailored Sicily wine tour for couples. Revel in the perfect mixture of seductive history and enchanting flavors with private tours that offer exclusive access to boutique vineyards from Palermo to Marsala. The art and artistry of tradition bring a deep well of heritage that spans the millennia and shapes the captivating ambiance in which you will find Byzantine mosaics, ancient Greek architecture, delicate olive oil, and complex wines. Relax in the beauty of seaside towns, indulge in the splendor of golden architecture, and embrace the immersive panoramas seen during your luxurious wine tour of Sicily.

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Vineyards in Sicily with Mt. Etna in the background

Sicily Wine Tour: History & Culture Exploration

9 Day Custom Tour

From $2,470

Italy is famous for its wine and its cuisine but beyond the mainland the gastronomic traditions and ancient marvels the best of Italian heritage will be yours to enjoy during your customizable wine, culture, and history tour of Sicily. The vines on the island have become legendary for the rocky plateaus, the fertile valleys, and the vineyards found along the slopes of soaring Mount Etna. With culinary and oenological traditions dating back to Phoenicians and Greeks with hints of Arab and Norman customs, your tour of Sicily will be an incredible immersion into a cornerstone of the Mediterranean filled with ancient wonder, Baroque opulence, and endless mouthwatering delights.

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Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
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Just for You
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Reviews of Zicasso's Referral Service

4.89 stars based on 4412 reviews.

Luxury Italy Vacation Review: Sicily, Palermo, Taormina,...
"[Our travel agents'] knowledge of the country as well as...

Reviewed By ANDrew C.

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"Ben shaped the itinerary so that we were able to experience...

Reviewed By Micayla B.

Sicily Travel Review: Luxury Trip to Italy, History &...
"All of the guides were friendly, knowledgeable, and professional..."

Reviewed By Lisa C.

Luxury Italy Travel Agent Review: Pompeii, VIP Cheese Making...
"Our travel company helped plan the itinerary and everything...

Reviewed By Ray M.

Italy Vacation Review: Rome, Pompeii, Positano, Sorrento,...
"[Our travel agent] learned of our basic interests and took...

Reviewed By Bill T.

Italy Travel Review: Umbria, Abruzzo, Basilicata, Puglia,...
"Zicasso recommended two agents to assist with the trip...

Reviewed By Heidi B.