Wine Lovers Sicily Tour: History, Tasting & More

What to expect on this itinerary
Uncover the secrets to a perfect bottle of wine in the unparalleled landscape of Sicily. Follow the trail of an open-air museum dedicated to the different grapes of the island. Sip a sensual red or robust white in an antique farmhouse. Discover the ancient civilizations that settled the hillsides and shores. The subtle flavors of wine are influenced by the soil and elements, nurtured to absorb the qualities of its surroundings. Embark on a luxurious Sicily wine tasting experience that will introduce you to the Planeta estates and has you fall in love with the distinctive characteristic of each property’s wine and production.
Customizable Itinerary
Sicily – Surrounded by Vines
The history of the vineyards in Sicily spans thousands of years. In Palermo, remnants of an ancient lifestyle have combined with millennia of settlements from cultures around the world. The honey hue of the city glistens in the sunlight. The shimmering blue Tyrrhenian Sea brushes against the boats in the harbor. Women stroll along the paths of the marketplaces, listening to the shouts of the vendors vying for their patronage. The Cathedral has a 15th-century Gothic-Catalan portico. A single column contains an Arabic inscription connecting the structure to its former role as a mosque during the city’s Arab rule.
The bell tower was erected in the 12th century. The Baroque beauty of the city emanates from the Quattro Canti. The 17th-century plaza was erected with four mirroring corners rising three stories tall. A fountain decorates the lower floor, with sculpted figures adorning the upper floors, each flanked by elegant Greek columns. Your private transfer escorts you through the vibrant city and leads you to the town of Menfi. You settle into the comforts of your lavish resort, encircled by lush vines combing the hillside. The aroma of recently fried arancini, Sicilian stuffed rice balls, drifts from the kitchen. The elegance of the landscape and private accommodation is soothing. Consider reading some of our travelers' Sicily vacation reviews to further inspire and refine your perfect Sicily trip.
What's Included:
Sicily – In the Lap of Luxury
Sicily – The Footsteps of the Ancients
Ragusa – The Journey Continues
Ragusa – Keeping the Flavors in the Family
Syracuse – Clear Remnants of the Past
Taormina – Succulent Lava Soil
Taormina – After the Feast
Trip Highlights
- Explore the various family-owned vineyards of Sicily and enjoy sumptuous wine tastings
- Indulge in the unique properties of wine produced on the volcanic slopes of Mount Etna
- Follow the history of wine in Sicily on the Grapevine Route, which will introduce you to indigenous grapes along with varietals collected from around the world
- Discover the remarkable Doric ruins at the Valley of the Temples, where remnants of Greek settlement persist
- Witness the unique architectural properties of the Feudo di Mezzo Estate
- Traverse the ancient streets of Syracuse to find the largest ancient Greek theater in Sicily that remains intact
- Relax in luxurious wine resorts across Sicily, known for their comfort, seclusion, and unparalleled quality
Detailed Description
Your desire to explore the varieties of wines, from their unique properties to the quality of the soil, is a journey of discovery. Your 8-day Sicily wine tasting tour guides you through the ancient roots of the viticulture world that influence the wineries of today. Your Sicily vacation begins with your arrival in Palermo. Your private transfer guides you through the historic streets of the city, highlighting the distinct layers of the civilizations that have contributed to the growth of the region. Outside of the town of Menfi, you settle into your wine resort, surrounded by elegant waves of vineyards draping across the hillside.
The following morning, you venture to the Ulmo Estate for an introduction into Sicilian wine at Planeta’s first winery outside the town of Sambuca de Sicilia. After your tour, you take in the ancient ruins of Selinunte before returning to your resort for the evening. Your guide meets you at the hotel the next day, ready to lead you through the trails of the Valley of the Temples. The Doric structures have withstood the test of time and continue to inspire visitors from around the world. Tonight you find comforts in a wine resort outside of the undulating city of Ragusa.
Next, you explore the antique features of the Dorilli Estate and sample the fabulous flavors of the wine. In Ragusa, you travel along the streets, finding an alluring combination of Baroque buildings, medieval alleyways, and lavish churches. Travel to the Buonivini Estate to view the “Invisible Wine Cellar” and sample the wines produced on the distinctive grounds. Visit the Baroque city of Noto and relish the historical and architectural significance of the glowing city. In the evening, you can relax at your wine resort in the foothills of Mount Etna.
You’re free to discover the tremendous history of the Syracuse, discovering the Greek theater and fabled catacombs. You notice the stunning Feudo di Mezzo Estate blending into the landscape of Mount Etna. Tour the grounds and sample the wine before transferring to the enchanting seaside city of Taormina. On your final day, your private transfer escorts you to Catania. The city has an eclectic history noticeable in the culture of the people today. You make your way to the Catania airport for your flight home.
Starting Price
$3,600 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.
What's Included
- Accommodations
- 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.
Verified Traveler Reviews
Based on 4201 reviews
My husband and I went through Zicasso to plan our honeymoon to Italy and Greece. This was the best decision ever! We worked closely with our travel specialist to plan our trip and she was absolutely phenomenal. This was our first international trip outside of the US, so we were a bit nervous at first! However, our specialist ensured every aspect of the trip was organized and that we were taken care of every step of the way.
The biggest relief was transportation. We did not have to give a second thought as to how we were getting places; we had drivers set up at every destination and for nearly every activity. Also, we had 24/7 support if anything were to go wrong, which gave us peace of mind.
If you are hesitant to use Zicasso for your next trip, I want you to know that I was too, but it was the best decision! We were able to personalize and tailor our trip to our needs without the hassle of dealing with the details.
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I was very pleased with the entire planning of the trip. The communication with Zicasso's tour company was excellent. The meals that were pre-arranged by them were fantastic and we probably would not have found them on our own.
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It was a great pleasure working with Zicasso's tour agency. Our travel designer and her staff were attentive to the kind of trip we wanted and planned a great itinerary. The hotels, restaurants, and drivers were all top-notch. For us, the acid test was the quality of the guides, and they excelled there as well. We would happily have them plan another trip for us.
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My husband and I had a great time on our trip to the northeast Adriatic Coast of Italy. We have very specific tastes as far as where we like to stay and the private tours we like to have during the trip. Zicasso's travel company did a great job, giving us fantastic hotels, and all of our tour guides were top-notch.
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I am very happy that we chose this Zicasso travel agent. He was very responsive throughout the evaluation and planning process, as well as while we were traveling, with any questions we had. He checked in during our trip to ensure things were going smoothly and we asked his advice via WhatsApp a couple of times during our stay in Greece, to which he responded quickly and immediately researched our request.
Every transfer was on time and all of the tours were high quality. I really can't think of anything we weren't pleased with in terms of his service!
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The trip of a lifetime–thanks to Zicasso's travel company!
We recently had the absolute best travel experience of our lives, and it’s all thanks to the incredible team at this travel company. Words can hardly capture how grateful we are for the magic they created for our trip to Greece.
We were headed to a friend’s wedding on Paros and trying to plan the logistics ourselves quickly became overwhelming; figuring out how to get there, what to do, and where to stay felt impossible. That’s when my husband found this company and, from the very first interaction, we knew we were in good hands. They took the time to really get to know us, what we enjoy, our travel style, our budget, and how hands-on we wanted them to be.
After a few thoughtful conversations and a video call, they crafted multiple itinerary options tailored exactly to our preferences. In the end, we landed on a perfect blend of history, fun, and relaxation. They even helped us work everything around the wedding, ensuring we didn’t miss a thing.
We started our journey in Athens, landing early in the morning and diving straight into the day. Then came one of the highlights of the trip—meeting our travel agent in person. She met us with the warmest welcome, walked us through our itinerary, personally showed us around the city, and gave amazing recommendations for food and shopping. Her kindness, energy, and passion for hospitality were contagious.
But what truly set this company apart was their level of care and communication. Throughout our entire trip, they were just a WhatsApp message away. They proactively checked in before every activity, sent us all the necessary contacts for transport and tours, and made sure we felt supported every step of the way. Every place we stayed at was breathtaking. From Athens to Paros, Milos, and Naxos, each hotel was more stunning than the last. Immaculate rooms, beachfront views, and hosts that treated us like family. The breakfasts were absolutely mouthwatering and gave us the perfect start to each adventure-filled day.
Beyond the wedding festivities, our itinerary included food tours, temple visits, an unforgettable catamaran tour, and a dreamy sunset cruise. Every single moment felt like a dream. The islands are incredibly safe, perfect for solo travelers or a girls’ getaway, and the views? Just… wow!
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I’m already counting the seconds until we can go back. This trip exceeded every expectation we had and gave us memories we’ll treasure forever.
To top off this unforgettable trip, we decided to spend a few days in Rome—and the travel company helped with that too! It was the perfect ending to our adventure. We explored the Vatican, the Colosseum, the Roman Forum, and the Pantheon. Every site was awe-inspiring and the city’s energy was just electric. Rome was the cherry on top of a journey we will never forget.
To the entire team—thank you from the bottom of our hearts for the most unforgettable adventure of our lives. We wouldn’t dream of traveling to Greece again without you.
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