Sicily Wine Tours & Vacations

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How Zicasso WorksCustom Italy Tours

  1. Describe your dream Sicily wine tour vacation.

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

  3. Book the trip when you are satisfied.

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.

Sample Itineraries

Get inspired with our sample trips below. You can have any trip tailor made for your private travel. Any number of days.
Any departure date. Any experience you want.

Perfect One-Week Sicily Wine Tour

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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Exquisite Tour of Sicily’s Culinary Culture

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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Highlights of Sicily Wine Tour

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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Sicily Itinerary for the Experienced Wine Connoisseur

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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Romantic Sicily Wine Tour

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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Sicily Wine Tour: History & Culture Exploration

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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Reviews of Zicasso's Referral Service

4.88 stars based on 4471 reviews. See all our reviews.

Luxury Italy Travel Review: Sicily, Siracuse, Greek Temples...
"Getting things done, arranging the best, and satisfying

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Reviewed By Gerald H.

Luxury Italy Travel Review: Siena, Florence, Chianti, Fiat...
"[Our travel agency] made the entire trip effortless, so

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Reviewed By Nicholas W.

Italy Honeymoon Trip, Florence, Rome, Truffle Hunting, Food...
"[The travel planners] did a great job gauging our tastes

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Reviewed By Amelia J.

Italy & Sicily Family Travel Review: Mozzarella Making...
"...we felt like VIP the entire time."

Reviewed By Christina M.

Italy Sisters Travel: Tuscany Countryside, Tours of Balsamic...
"...absolutely loved our excursions out of the city and

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Reviewed By Chelsey A.

Travel Review: Luxury Italy Vacation, Naples, Bari, Apulia,...
"The overall trip was superb and the services provided professional

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Reviewed By Angelia L.