Vineyard in Sicily, Italy
country flag

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

Dynamic pricing from $2,501

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.

View Custom Itinerary
Traditional assortment of the fish market of the island town, Sicily
Exquisite Tour of Sicily’s Culinary Culture

10 Day Custom Tour

Dynamic pricing from $3,575

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.

View Custom Itinerary
Harvested grapes in basket at Italian vineyard on Mount Etna, Sicily
Highlights of Sicily Wine Tour

9 Day Custom Tour

Dynamic pricing from $3,217

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.

View Custom Itinerary
Vineyards in Sicily, Italy
Sicily Itinerary for the Experienced Wine Connoisseur

8 Day Custom Tour

Dynamic pricing from $2,859

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.

View Custom Itinerary
Couple at a luxury resort pool surrounded by vineyards in Selinunte, Sicily
Romantic Sicily Wine Tour

9 Day Custom Tour

Dynamic pricing from $3,217

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.

View Custom Itinerary
Vineyards in Sicily with Mt. Etna in the background
Sicily Wine Tour: History & Culture Exploration

9 Day Custom Tour

Dynamic pricing from $3,217

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.

View Custom Itinerary

Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
Travel Worry-Free
Every Time
24/7 support and local assistance for every moment of your vacation.

We Work With the Best Travel Agents for Sicily Wine Tours

See all Agents

More About Sicily Wine Tours

Sicily Travel Guide
Coastal city of Cefalù in northern Sicily
Sicily Travel Guide

From the rumbling of Europe’s most active volcano to the golden shores that feed into three different seas, Sicily is a cultural marvel at the crossroads of Mediterranean heritage. Explore the delights of inviting local cuisine and embrace stunning views sweeping over Roman ruins and glowing coastline to a snowcapped volcanic peak. Whether visiting the largest Greek temples in Italy or embracing lavish Baroque architecture, Sicily is a breathtaking collection of beauty and charm. Our Sicily Travel Guide has plenty of information about what you can do during your trip, when to visit, and more.

Read More    >
Best Time to Visit Sicily
Taormina, Sicily, Italy
Best Time to Visit Sicily

Sicily is a welcoming island with a warmth that derives from the Mediterranean light and rich heritage. An eternal crossroads along the clear and colorful waters of the Tyrrhenian and Ionian seas, Sicily is imbued with cultural, culinary, and natural treasures any time of year that you choose to visit. From Byzantine churches to Baroque cathedrals, the fumes of Mt. Etna to the views of Taormina, Sicily brims with splendor no matter the time of year.

Read More    >
Italy Food & Wine Travel Guide
Coppa di Parma
Italy Food & Wine Travel Guide

Italy food and wine celebrates culture and heritage through fabulous flavors. By sipping celebrated vines in the north or learning world-renowned recipes in the south, indulging in intricate family favorites found in a small coastal village or basking in bold aromas that rise from vintages produced in medieval hillside towns, you can experience how food and wine in Italy is a transformative experience. Our travel guide gives you better insights into how to customize your trip to uncover ancient dishes or enjoy contemporary wine-productions. When you are ready to book, speak with a local travel specialist who understands how to craft your mouthwatering trip.

Read More    >
3 Best Cities to Explore the Food of Sicily
Catina, Italy
3 Best Cities to Explore the Food of Sicily

The three best cities of Sicily in which you can enjoy the customs of the Sicilian kitchen embody a tradition of expression and culinary artistry that is linked to the religious, historical, and cultural evolution of the island that you can find in the three best culinary cities across Sicily.  The closely linked events of Sicily’s history have developed famous dishes with regional and gastronomic cultures that reveal the contributions of the well-established civilizations throughout the island’s history that spans more than 2,000 years of settlers, merchants, and conquerors.

Read More    >
Best Sicilian Cheese and Street Food to Try on Vacation
Selection of Sicilian street foods on a table in Sicily, Itlay
Best Sicilian Cheese and Street Food to Try on Vacation

Sicily is a melting pot of gastronomic heritage, found in the best Sicilian cheese and street food that you can sample during your Italy vacation.

The exceptional cuisine of Sicily uses local ingredients to create flavors for a culinary adventure featured in surprising spices or indulgent textures. Whether enjoying authentic Sicilian cheese with wine or sampling street food at stalls in popular marketplaces, the cuisine represents the island’s eclectic heritage.

The following list focuses on the best cheese and street food you will discover as you wander the streets of Sicily to find cannoli, arancini, capers, ricotta cheese, and more.

Read More    >

Reviews of Zicasso's Referral Service

4.89 stars based on 4500 reviews.

Italy Luxury Group Travel Review: Sicily, Taormina, Wineries,...
"Alex did a wonderful job planning our very memorable 2...

Reviewed By Lauren R.

Italy Trip Review: Palermo, Segesta, Agrigento, Mt. Etna,...
"I can’t recommend this travel agency highly enough!"

Reviewed By Melanie S.

Italy Travel Review: Sicily, Palermo, Valley of the Temples,...
"We had a fabulous trip to Sicily, thanks to the travel...

Reviewed By Patty M.

Italy Tour Review: Sicily, Countryside, Local Cuisine, 10-Day...
"Excellent trip with everything working like clockwork."

Reviewed By Alan W.

Italy Anniversary Trip Review: Tuscany, Florence, San Gimignano,...
"Our first Tuscany experience was amazing and Luana at the...

Reviewed By Lisa P.

Italy Family Vacation Review: Sicily, Ortigia, Agrigento,...
"This was an excellent travel company."

Reviewed By Carol F.