Perfect One-Week Sicily Wine Tour

What to expect on this itinerary
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.
Customizable Itinerary
Taormina – Arrive in Sicily with a Tour of Gorgeous Taormina
The famous town of Taormina is perched on a mountaintop that overlooks the glistening waters of the Ionian Sea. The breathtaking setting will combine captivating views to Mount Etna, with a glamourous touch of Baroque architecture, and beautiful ruins from ancient civilizations that will emerge from the landscape. The sea breeze will carry semi-sweet aromas that blend with an herbaceous scent of wisteria, which dangles along the houses that line the old, cobbled lanes. Your flight will land at Catania-Fontanarossa Airport where your private transfer will meet you upon arrival.
You will have a chance to settle into the comforts of your luxurious hotel in the heart of Taormina, indulging in the fragrant scent of freshly baked cookies and pistachio torrone that will drift through the doors of the nearby pasticcerie. Your guide will greet you in the hotel lobby eager to introduce you to the vibrant ambiance of Taormina, immersing you in the ancient history that dates back to the fourth century BC.
You will see the silhouette of the ruins of Castello di Taormina that are perched on the peak of Monte Tauro at 1,305 above sea level. A belvedere that can be seen from Via Pirandello will offer a sensational view of rocky promontories, Byzantine rock-graves, and the funicular that leads to the small beach of Mazzarò. The wealth of history will come to life when you reach the Greek Theater, which is a famous landmark of the city that dates back to the third century BC and contains characteristics of both Greek and Roman architectural design. The impressive feat of ancient engineering used the natural grade of the hillside to shape the stadium seating, which offers a spectacular view of Mount Etna as it towers above the countryside in the distance.
What's Included:
Taormina – Visit a Winemaking Estate on the Slopes of Mount Etna
Taormina – Discover Mount Etna and Enjoy an In-Depth Wine Tour
Siracusa – Revel in Baroque Noto and Enjoy a Sweet, Tasty Lunch
Siracusa – Explore Historic and Culinary Charm in Ragusa and Modica
Siracusa – Visit the Incredible Ancient History of Agrigento’s Temples
Siracusa – Depart for Home
Trip Highlights
- Delight in the marvelous wines of a celebrated estate outside of the city of Ragusa that is perched on a secluded hilltop, overlooking lavish vineyards
- Indulge in a combination of sweet and savory flavors with a sampling of incredible desserts by an award-winning chef that is paired with elegant wines
- Discover the sensational history of ancient Greek temples that have been preserved in the Valley of the Temples and captured in the magnificent Temple of Concord
- Experience the ornate and friendly ambiance of Modica while wandering the streets and stairways, climbing the hillside that is crowned by San Giorgio Church
- Revel in the magnificent views of fumaroles and lava fields when touring the craters of Mount Etna
- Enjoy the pleasures of wines which harness complex flavors that are taken from the mineral-rich, volcanic soils of Mount Etna
- Bask in the lavish ambiance of Taormina, deriving from the enchanting coastal views and mixture of opulent baroque and ancient architecture
Detailed Description
The highlights of the Mediterranean world become the perfect picture for your 7-day Sicily wine tour which embodies the opulence of the ancient world, the splendor of the Baroque period, and the delights of celebrated flavors that are captured in the wine and cuisine. Your private tours will unveil the hidden tastes that are known to locals and the often-overlooked charms of towns that are spread between Taormina and Siracusa for a luxurious celebration of cultural heritage that can be found in the evolving tastes of chefs and winemakers within your atmospheric surroundings.
Your adventure into the wines of Sicily will begin with your arrival at the airport in Catania where your private transfer will greet you and escort you to Taormina. The gorgeous town will welcome you to Sicily with splendid views that lead from the Ionian Sea to the peak of Mount Etna. Revel in the beauty of the Baroque architecture, the treasured flavors of local bakeries, and antique ruins that decorate the edges of town. Follow your guide on a private tour of favored cellars and vineyards, which produce excellent wines that feature grapes and vines that are brought from other areas of the world. You will also venture to the top of Mount Etna for a thrilling experience along the crater of the most active volcano in Europe.
You will continue to Siracusa for three nights in which you can enjoy the unique ambiance of the largest, oldest, and best-preserved city in Sicily. Your guided tours will take you into the Baroque grandeur of towns like Ragusa, Modica, and Noto, which are known for their opulent facades, lavish piazzas, and delectable cuisines. Wine pairings will showcase the elegant flavors of locally produced wine and unique dishes that have been inspired by traditional recipes. From desserts to main courses, you will enjoy the depths of flavor that is born from simple ingredients. You will also have the opportunity to discover the ancient Greek world in Sicily with a guided tour of the Valley of the Temples at Agrigento, where several spectacular temples continue to decorate the landscape. Make sure your perfect Italian vacation is an unforgettable one by seeing additional Italy travel ideas.
Starting Price
$3,200 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 6141 reviews
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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I apologize for the delay in writing this review, but was very busy the last few months and wanted to dedicate the time it deserved. This review will address my wife and my trip to Italy from September 26, 2025, to October 6, 2025. Please feel free to share all or any portion of this review.
Trip Planning:
As a bucket-list event, I spent a great deal of time doing research, but would not have been able to put together the ideal vacation without the support of Zicasso and the travel company. Upon hearing my general interests, Zicasso provided two groups whom they thought would be able to plan and implement my trip. Both groups interviewed me and my wife about interests and price range, and then prepared an initial itinerary. Both groups would have done a fantastic job by their presentation, but it seemed I was slightly more in tune with the travel company and selected them. This proved to be a very wise choice, as the entire team at the travel company, particularly the travel specialists, were the absolute best and I would recommend their service without reservation. Fully responsive to my many questions before the trip, addressing all potential itinerary changes, and providing invaluable guidance throughout the entire process. Their response to inquiries while in the country was unbelievably prompt and thorough. At our request, the travel specialists made restaurant recommendations and reservations that were spot-on. I can’t say enough good things about these ladies.
Transportation and travel between locations:
Although not involved in the flights, the travel specialists provided great guidance concerning flights, trip insurance, and other logistics.
One key point that I fully expressed was that I did not want to flounder at the various transportation points and did not want to lug luggage in foreign areas on the way to and from lodging. The team took this to heart and provided me with either an escort or driver to and from every terminal. Everyone providing this task was friendly and provided information that made the travel much easier. Particularly valuable were our escorts, who adeptly negotiated our entrance and exit from Venice, and provided great insights into this historic city.
Venice:
Our hotel in Venice seemed to be right in the middle of everything, which allowed us to explore, and we have never had so much fun getting lost. At night, we opened our windows and fell off to sleep listening to nearby music; it was idyllic. The staff was professional and friendly. Breakfast was the best of all the hotels we stayed at in Italy.
The first full day in Venice, the travel company leveraged “skip the line” so we could make the very most of our time and is essential to any planning. Both guides were great and really good company. One guide’s knowledge of the Doge Palace really brought it to life for us. Another guide had a real insider’s view of Burano, as this was her family’s island. As private tours, we could go at our own pace, which we really liked. Probably the least enjoyable tour was the glass factory in Murano. We got the impression most of the tour beyond the initial exhibition was an attempt to sell their products. My wife succumbed and purchased a pair of earrings that broke the first time she wore them. Really disappointing, and I would advise you to spend more time in Burano.
Florence:
As with all the trains, the travel was very comfortable and we enjoyed watching the scenery. Our lodging in Florence was right on the Santa Maria square, superb for people watching. The staff was fine, nothing more. The hotel was near the world’s oldest pharmacy, famous as the world's oldest perfumery. Although there is a line to enter, it goes quickly and is historical, to say nothing of buying a scent more than 400 years old. I strongly recommend you go.
While knowledgeable, our tour guide for the Accademia and Uffizi Galleries was a little too technical for us, leaving us with the feeling that we were taking an art history class.
Dinner was based on the travel specialist's recommendation and it was delicious. A strong recommendation.
Day trip to Pisa:
The travel arrangements were perfect. The purpose of the trip was to take the obligatory picture holding up the tower—hokey, but we loved it.
The private cooking class with our instructor was a lot of fun. The view of the city from her window at sunset was beautiful. My wife and our instructor fell into a real rhythm cooking, and she was kind enough not to scoff at my ham-handed attempts. Her directions were simple enough for me to follow, theoretically. She followed up her lesson with an email containing detailed recipes. We have purchased all necessary utensils and are planning a pasta-making party soon. This was a fun change of pace.
Rome:
Our bed-and-breakfast in Rome was our least favorite lodging. Entry into the building was confusing and, as a B&B, the desk was not manned all the time, which made it difficult to secure a taxi early in the morning (we had to walk to a nearby hotel) or get assistance after 8pm or before 6am. When we came in, we attempted to coordinate laundry service with the person working the front desk, followed his instructions, but when we returned the next day, our dirty clothes were still where we were told to leave them. The initial response from the on-duty staff, who I believe was the owner, was that the individual was no longer an employee. Ultimately, the hotel comped and completed our laundry, which was nice. We would have preferred different lodging.
Our first afternoon, we took a four-hour golf cart tour, which was our favorite tour of the entire trip. Adding an extra hour to the traditional length and having only my wife and me allowed us to do everything we wanted to do. Our driver took us everywhere. He would drop us at the top of the Spanish Steps and meet us at the bottom, and would conveniently bring us closest to all other locations. I can’t believe how much we did in four hours. Our driver brought all these iconic sites to life with his marvelous insight and provided a great insider view of these monuments. This is a must-do for all first-time visitors to Rome. The only thing we were not able to do, due to no fault of our driver, was the Aventine Keyhole. When we got there in the afternoon, the line was 45 minutes and not a wise use of our time. If this is a strong interest, he recommends going early in the morning.
The travel specialists arranged tickets for the Papal general audience on Wednesday. Rising at sunrise was worth it to get the seats as close as we were able to secure. Most online sites suggest getting there an hour and a half before the start time, but I think that is much too late. I recommend you get there three to four hours ahead to get the best seats. The best seats are on the end near where the Pope drives by, ideally near an infant, and His Holiness will stop to personally bless these children. Facing the stage, the right side filled up quicker than the left side, so go directly to the left side of the audience. Being so close to the first American-born Pope was a memory I will never forget. His Holiness blesses all items in the audience's possession, so load up on rosary beads; they will make great Baptism and Communion gifts.
The afternoon was our first group tour at the Vatican Museums. It might be that we were spoiled with the previous private tours, but linking up with the group was chaotic and the quality of the tour was contingent on those in our group. Fortunately, all our groups were good, considerate, and friendly people. The main value was skipping the line for entrance. As with the Doge Palace, our guide was a little too academic and didn't really manage time well, potentially a victim of being in a group, but I would have rather spent more time in the Sistine Chapel and the Basilica. Taxis were extremely hard to get back to the hotel and I would arrange a ride if I were to do it again.
The Thursday tour of the Colosseum and Forum was also a group tour, but led by a guide who brought this ancient land to life. An archaeologist by trade, our guide seemed to know everything and also took a great picture.
The end of a very long but enjoyable day was another group tour of the catacombs and Santa Maria Maggiore. While the catacombs were the main attraction, the after-hours and behind-the-scenes access to Santa Maria Maggiore was an unexpected gem. Going through a second Holy Door, viewing the magnificent nighttime skyline from the roof, seeing the location of a relic from the baby Jesus’ manger, and being struck by the modesty of Bernini’s and Pope Francis’s tombs were all highlights. Unfortunately, taxis were again hard to come by.
Sorrento:
We took a train from Rome to Naples. While there was a national strike, it did not prove more than an inconvenience, no worse than New York City on a regular day. Our driver from Naples told us this simply provided us with a genuine Italian experience. I wish I could remember this driver’s name because he was the best of a very good group of drivers during this trip. En route to Sorrento, we stopped for a tour and meal at a winery and a private skip-the-line tour of Pompeii. We were so impressed with the quality of the winery that we made a large purchase of wines and olive oils that, thankfully, included free shipping.
During our drive to Sorrento, our driver took us through his hometown, which we really enjoyed. Going through the town, he pointed out the birthplace of Bruce Springsteen’s mother. Little did he know, we were from New Jersey and are HUGE Springsteen fans.
Our hotel in Sorrento was a nice place, close to the center of town. I would have preferred a hotel with a view of the coast.
On Saturday, we took a private tour up the coast. This was the most comfortable car I have ever ridden in, with heated and cooled seats, and a convenient icebox. The driver made clear he was at our disposal. The scenery was marvelous and it was a thrill to dip our toes in the Med. Our driver hooked us up with a restaurant on a cliff overlooking the water—beautiful and scrumptious.
Our last day was supposed to be the Gozzo tour of Capri, but was canceled due to weather. We refunded the canceled boat tour, but ate the driver and ferry fees. In hindsight, knowing this day was largely contingent on weather, I would have liked to have a contingency plan and would advise the travel company to plan this in the future.
Based on how smoothly things went, we will be contacting Zicasso to arrange a trip to Iceland and Ireland next fall, and hope they can refer a team as talented as this travel company.
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Thank you to Zicasso’s travel specialist and her amazing staff. The itinerary was fabulous. It was filled with food, wine, and highlights of the most important tourist places. Her guidance throughout the year-plus planning was the right amount of checking in and waiting. Thank you for the nudges to have reservations for all the holiday days. Things seemed to be pretty open overall, but it was nice not to worry.
All the restaurants set up for us were wonderful. The app was terrific to keep track of what we were doing when. All the drivers were very friendly, professional, and punctual.
Thank you for making our 35th wedding anniversary trip (December 22 2024 to January 6 2025) a most memorable one. We hope to return to Italy to enjoy the southern area and maybe some of the beaches and islands.
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We had an excellent itinerary and we really liked the accommodations provided, and their locations within walking distance of our must-see sites.
Excellent tour guides, drivers, and transportation were provided!
The Zicasso travel expert's recommended restaurants were also great and the guidelines were helpful!
My husband and I saw and enjoyed what we needed to see and experience!
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It was a great experience! Every activity was fun and interesting. The guides and drivers were wonderful. You made our trip so easy.
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