Sicily Wine Tour: History & Culture Exploration

What to expect on this itinerary
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.
Customizable Itinerary
Catania – Arrive in the Bustling City of Catania with the Day at Leisure
As Sicily’s second-largest city, the city of Catania bustles with activity throughout the day. The picturesque countryside sweeps to the slopes of Mount Etna in the distance while the Baroque architecture shines with a subtle gold hue across the city. Your flight will land at Catania-Fontanarossa International Airport, where your private transfer will greet you upon arrival. The remainder of the day will be yours to enjoy the charms of Catania at your preferred pace, and you might want to begin by indulging as the sensational aromas draw you in. The surrounding restaurants serve mouthwatering classic dishes like pasta cooked in squid ink, indulgent grilled meats, and the traditional flavors of pasta served with tomato sauce, eggplant, and ricotta cheese in a dish known as pasta alla norma.
The enticing aroma of pistachios usually drifts through the streets, but often fade beneath the fragrant pastries of Sant’Agata, which contain goat milk ricotta, candied fruit, and dark chocolate. When strolling through the city, you will find the Teatro Romano, an ancient Greek theater built in the second century BC. The fascinating structure contains steps made from dried lava and stadium seating covered in marble. The narrow lanes leading to the theater possess an iconic image of laundry dangling from lines and the sounds of the radio shaping the welcoming ambiance that combines the ancient and the contemporary life of the city.
What's Included:
Caltanissetta – Explore Catania and Discover the Wines of Mt. Etna
Caltanissetta – Enjoy an Immersive Tour of Cuisine and Culture
Vittoria – Discover the Wines and History around Valledolmo
Vittoria – Revel in a Delicious Wine Tasting in the Ragusa Province
Siracusa – Tour the Sensational History in and Around Siracusa
Siracusa – Traverse the History and Treasures of Modica and Scicli
Siracusa – Delight in Olive Oils and Wines Made from Nero d’Avola
Siracusa – Depart for Home
Trip Highlights
- Revel in the delightful flavors of wines produced on the volcanic slopes of Mount Etna during a private wine tour
- Bask in the remarkable authentic ambiance of the famous fish market of Catania during a morning walking tour
- Sample the delectable traditional cuisine of Sicily with a private cooking class led by a private chef offering insight into the ancient grains of the island
- Indulge in the magnificent flavors of Nero d’Avola wines with a special tasting designed around the different uses of the grape in a variety of wines
- Discover the charm and opulence of the Baroque architecture in Modica captured in the pristine Church of San Giorgio
- Explore the fascinating ancient history of Siracusa with a guided tour through the Archeological Park and Baroque city center
- Enjoy the authentic culture of Sicilian cuisine and wine by visiting charming towns and vineyards in the Ragusa province
Detailed Description
You will indulge in the specialties of the Mediterranean during your 9-day wine, history, and culture tour of Sicily and uncover the captivating heritage and alluring culture connected by thousands of years of trade and cultivation. From the ancient streets of Siracusa to the Baroque architecture of Modica, the wines produced in the Ragusa province to the elaborate flavors found on Mount Etna, your wine tour of Sicily will celebrate the quintessential culinary spirit of the island where you can savor the delights of both sweet and savory, aromatic and acidic.
Your elaborate wine tour of Sicily will begin with your arrival in Catania, where your private transfer will greet you at the airport. Enjoy one night in the vibrant city known for an eclectic culture from millennia of trade featuring brilliant Baroque architecture and the bustling La Pescheriafish market. You will travel to Caltanissetta for two nights after enjoying a private tour of the cultural history of Catania. With lavish architectural styles and a lively morning market, you will also be drawn to the alluring flavors of both the historical and the contemporary wines produced on Mount Etna. After a full day in the charming town of Caltanissetta, dive into the beauty and the charm of the local heritage with a private cooking class that will introduce you to the gastronomic history in the form of both the ancient and the contemporary grains grown in the province.
Travel to Vittoria next for two nights and discover the wines of the Ragusa province with guided tours. Designed around authentic tastings, cooking experiences, and elegant wines found both in the town of Valledolmo, as well as other villages from around the surrounding province. You will then transfer to the ancient city of Siracusa for three nights in the luxurious ambiance accentuated by the seaside location. Explore the city’s blend of ancient, Baroque, and contemporary life as well as the gorgeous Baroque majesty of nearby destinations such as Modica and Scicli. Sample olive oils and wines around the province celebrated for the specific properties and endemic histories when visiting inviting family-owned estates.
Starting Price
$4,100 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
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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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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.
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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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The entire experience was nothing short of exceptional. From the very beginning, we had the pleasure of working with Zicasso travel agents, who went above and beyond to make sure every detail was accounted for. They were incredibly accommodating, adjusting our itinerary to fit the needs of everyone in our family.
Every tour guide and driver we had along the way was phenomenal in their own unique way. They each added something special to our trip. The activities were well thought out, engaging, and perfectly paced, and we especially appreciated the excellent food recommendations. We did not experience one bad meal.
This was truly a stress-free, memorable journey, thanks to the thoughtful planning and dedication of our travel company. We would highly recommend them for anyone looking for a smooth and enjoyable travel experience.
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My husband and I had utilized the services of Zicasso for prior journeys to Italy, Southeast Asia, and Australia/New Zealand. For our recent trip to Matera and Puglia, I requested an agency located in Italy that specializes in travel to Italy. We selected a company that was on a magazine’s A-list of travel advisors.
Our travel consultant listened to and respected my requests for certain activities (private food, historical and boat tours, wine tastings, cheese making) and types of accommodations (properties that offered a shaded area to relax and read). She also emailed answers to my numerous detail-oriented questions (the curse of having personally worked as a tour guide). She sent a lovely gift to our first hotel and called halfway through our vacation to check in with us. Communication via text with WhatsApp was convenient and used frequently. Most importantly, when we had a problem with one of our accommodations, she followed up (even after our trip had ended) and graciously offered some compensation.
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Italy’s beauty is legendary—its rolling landscapes, vibrant culture, incredible cuisine, and deep history are truly one of a kind. But what made our trip truly extraordinary was the care, creativity, and attention to detail that the Zicasso travel company team brought to every part of our journey.
Our 12-day family adventure—with three teenagers!—was the perfect balance of guided exploration, fun hands-on experiences, and thoughtfully chosen hidden gems. Every stop offered something special for each of us, which is no small feat when traveling with a group of different interests.
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And the hotels—just wow. Every property was not only comfortable and welcoming, but also perfectly located, making it easy for us to explore and enjoy each destination to the fullest.
A heartfelt thank you to the entire travel company team for creating such a seamless and memorable experience. We can’t wait to plan our next adventure with you.
Grazie mille and arrivederci for now!
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Zicasso's travel experts made this trip effortless for us! They were responsive to my many questions and created a memorable trip for my daughter and me that included all of our favorite things, addressed any concerns I had, and stayed within our budget. Every detail was planned and communicated flawlessly. My daughter and I only had to pack our bags and enjoy every minute of this trip of a lifetime. I highly recommend Zicasso and their travel company!
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