Sicily Wine Tour: History & Culture Exploration

Vineyards in Sicily with Mt. Etna in the background

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.

Countries Visited

Italy

Places Visited

Catania, Siracusa, Vittoria, Caltanissetta, Mt. Etna

Suggested Duration

9 Days

Customizable Itinerary

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Day 1

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:

Transfer
Accommodation
Breakfast
Day 2

Caltanissetta – Explore Catania and Discover the Wines of Mt. Etna

Day 3

Caltanissetta – Enjoy an Immersive Tour of Cuisine and Culture

Day 4

Vittoria – Discover the Wines and History around Valledolmo

Day 5

Vittoria – Revel in a Delicious Wine Tasting in the Ragusa Province

Day 6

Siracusa – Tour the Sensational History in and Around Siracusa

Day 7

Siracusa – Traverse the History and Treasures of Modica and Scicli

Day 8

Siracusa – Delight in Olive Oils and Wines Made from Nero d’Avola

Day 9

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.

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Italy Travel Review: Sorrento, Taormina, Rome, Pompeii, Mount Etna, Wine Tasting, 2 Weeks

We had a fabulous trip to Italy, including to Sorrento, Taormina, and Rome. Zicasso’s travel specialist made sure every detail was taken care of, including stays in beautiful, well-located hotels and excursions that were interesting and fun for our family.

For example, she arranged for an airport host to assist us with our arrival to and departure from the Rome airport, and she was simply amazing, whisking us through the airport and eliminating stress for our family.

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Our recent trip to Rome, Florence, and Venice, planned by Zicasso’s travel specialist and her team, was nothing short of exceptional. Every detail was handled with care, precision, and an obvious commitment to excellence. The hotels were truly top rate, perfectly located, and impeccably chosen to enhance the experience of each city. The tour guides were extremely knowledgeable, engaging, and clearly passionate, adding depth and context that made each destination come alive.

What truly set this trip apart was the level of service. From seamless transfers to on-the-ground assistance, everything felt effortless. The recommendations and tips provided along the way were incredibly useful and allowed us to experience each city with confidence and ease. The assistants who helped guide us through logistics and navigation were attentive, professional, and reassuring, making the entire journey feel like true white-glove service from start to finish.

The travel specialist and her team exceeded every expectation. Their planning, responsiveness, and attention to detail transformed an already incredible itinerary into an unforgettable experience. I would recommend them without hesitation to anyone looking for a flawlessly executed, high-end travel experience.

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Zicasso’s travel company was amazing to work with! They really took care of every detail for a worry-free experience! They were very responsive during planning and the trip. All of the locations and accommodations were exactly what I wanted. I cannot recommend them enough!

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Italy Tour Review: Abruzzo, Pescara, Chieti, Venice, Verona, Lake Como, Milan, Turin, Cooking Class, Opera, Boat Ride, Food Tour, 12 Days

This was my third customized trip with Zicasso. I previously worked with Zicasso to plan and take mother-daughter trips to Iceland and Croatia. They are the perfect company to help your dreams for a personally unique adventure come true!

This time, I traveled with my daughter, son, and daughter-in-law to Italy. My hope was for my daughter and son to see the towns where their great-grandfather and great-grandmother emigrated from in the Abruzzo region, in the towns of Roccamontepiano and Bugnara. My research had an address for where their great-grandfather was born. Our driver found the address and we took photos of us standing in front of the house, which could now be considered a real fixer-upper. Just the same, it was a moment never to be forgotten. Thank you to our driver and his wealth of information!

Our home base was in Pescara, where we enjoyed a walk on the beach, excellent local cuisine at a local restaurant, and seafood at another local restaurant. These were recommended by our local travel agent and were clearly favorites of the locals.

We had a wonderful tour in Chieti, an historic and cultural gem, with our guide. She too was a gem of a guide!

We then traveled to Venice, which was far less crowded with tourists than in the high season. Upon arrival, a private gondola ride during dusk and at sunset was a surreal way to be welcomed to this beautiful city.

The next day we had a magnificent tour of St. Mark's Basilica and Doge's Palace. Our guide was so engaging and knowledgeable, and eager to share ideas about other things to see while in Venice. We followed our tour with lunch at a historic restaurant, home to the invention of the Bellini. Yum! After lunch, we took the elevator to the top of the tower across from the basilica, with its spectacular panoramic view of the city and surrounding islands. Then our group splintered off—two of us did a Grand Canal boat ride and the other two headed to the isle of Murano to search for glass souvenir treasures.

Our next stop was Lake Como, with a one-hour unexpected stop in Verona. Thank you to our driver for suggesting the stop! Who knew there was a Roman arena and some to-die-for hot chocolate in Verona!

Then off to Lake Como. We had time before we could check in to our hotel, so we did a walkabout to acquaint ourselves with the city. We took a ride on the funicular for another delightful panoramic view and enjoyed cocktails while surveying the lake and city below. That evening, we traveled up into the mountains and had a marvelous meal at a mountain trattoria. We were just us and one other couple in the restaurant, and we watched the chef prepare our local food specialties from our table in front of the wood-burning fireplace. The mantel was adorned with trophies and photos of the local bocce teams over the decades. Again, if you want to travel for cibo delizioso, go to Italy!

The next day, we had a three-hour boat ride on Lake Como. Our skipper and guide made certain to point out and give some history on the villages dotting the coastline and the famous villas.

The following day we traveled north to Domaso for an afternoon at a family-run vineyard and restaurant with views of Lake Como and the Alps! Bellissimo! A family member gave us a wonderful tour of the history and the winemaking facility, as well as the many wines we sampled. We were treated to local charcuterie and ravioli that was made fresh while we were busy sampling. When we received the wine we ordered and shipped back home, they threw in extra gifts for us, with wishes for a Merry Christmas and Happy New Year!

Then we were off to Milan for a chance to try our luck at making our own pasta, sauces, and gelato at a cooking school. Our chef instructor guided us as we made tagliatelle with a pesto sauce and pumpkin ravioli with a cream sauce. Of course, there were wine pairings! He made certain our creations were delicious!

That evening, we donned our fancy apparel and headed to La Scala to take in the opera, "Così fan tutte." The modern take on the comedy was refreshing and the venue was a must-see!

The next day, we were met by our guide, who shared the history of the UNESCO site of Santa Maria delle Grazie and Leonardo da Vinci’s "Last Supper" with expertise and reverence, while keeping us engaged. She likewise inspired us as we toured the Duomo di Milano, San Maurizio al Monastero Maggiore, and the controversial Il Dito sculpture outside the city’s stock exchange.

That evening, we experienced a delightful meal at a Michelin-starred restaurant. The chef, from Naples, created and explained a never-to-be-forgotten bite-sized sampling plate highlighting the tastes of Naples on a plate shaped like the region, with its various borders.

Before leaving Milan, we had a tour of La Scala and its adjacent museum with our guide. She provided us with a history lesson that was quite interesting. That night, we dined at a local seafood restaurant, another treasure clearly favored by the locals. Our waiter was a gem and sent us off with the gift of a bottle of wine.

Our final stop was Turin. Once again, we divided—two of us visited the National Museum of Cinema and the panoramic lift housed in the museum. At the top, we gained a wonderful sense of the city,and the cinema museum was a fun surprise! Our other two toured the Juventus Museum and Stadium, and they thoroughly enjoyed their experience as well.

Our final day, we met our guide, who spent the entire day with us, with only a short break, beginning with a gourmet food tour of traditional Piedmont dishes. Along the way, she shared insights into the history and cultural significance of the foods. Later in the day, she guided us through the Royal Palace of Turin, including the Holy Shroud Chapel, Armory, and Museum. Once again, we were treated to a knowledgeable and entertaining guide.

We departed the next day, leaving with priceless memories of our Italy adventure.

Thank you so much to Zicasso’s travel agent. You helped make our trip come true with such care. Grazie mille!

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Our trip to Italy was absolutely amazing. Zicasso’s travel company provided exceptional service and attention to detail. We had never used a travel company for arrangements prior to this trip and we are so glad we did. It made the trip stress-free and truly over-the-top.

Our favorite time on the trip was at a location recommended by our travel agent in a very small area called Ciociaria. We loved this location and our resort in Ciociaria. The staff was incredible and we felt so relaxed.

I have been telling all my family and friends about the travel company’s services and that I will use them for future trips. I am so thankful to Zicasso for connecting me to an incredible experience with our travel company.

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This was our first time using a travel agency for a trip like this and Zicasso’s travel company completely exceeded our expectations. Traveling internationally with pre-teen children can be stressful, but from the very beginning, this travel company removed every bit of that anxiety. Every detail was thoughtfully planned, clearly communicated, and flawlessly executed.

From airport transfers to hotels, tours, trains, guides, and daily logistics, everything worked seamlessly. We never once felt lost, rushed, or unsure of what was next. Instead of worrying about schedules or navigating a foreign country, we were able to fully focus on our family and enjoy the experience. That peace of mind alone was invaluable.

What really stood out was how well the trip was tailored to our family. The pacing was perfect, the experiences were engaging for adults and kids, and every guide we worked with was knowledgeable, friendly, and professional. It truly felt like a curated, high-quality experience rather than a generic itinerary.

We came home with incredible memories and zero travel stress, something I didn’t think was possible with kids that age. This travel company was phenomenal and we would absolutely use them again, and recommend them without hesitation to anyone considering international travel, especially families.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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