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...
Customizable Itinerary
Day 1
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:
Day 2
Sicily – In the Lap of Luxury
Day 3
Sicily – The Footsteps of the Ancients
Day 4
Ragusa – The Journey Continues
Day 5
Ragusa – Keeping the Flavors in the Family
Day 6
Syracuse – Clear Remnants of the Past
Day 7
Taormina – Succulent Lava Soil
Day 8
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.
Reviews of Zicasso's Referral Service
4.9 stars based on 5887 reviews.
Zicasso's travel agent created an itinerary and experience that was simply perfect. Every hotel experience, guide, and driver was excellent. She was kind, patient, knowledgeable, and made the perfect suggestions. I loved working with her! Thank you to our agent, the tour operator, and Zicasso for a wonderful trip!
Reviewed By Anita L.
The trip was wonderful. Zicasso's travel agent and her staff planned the perfect 10-day trip. The accommodations, the drivers, the guides, and the restaurant recommendations were perfect. The communication was excellent and timely. They went above and beyond to make sure we were comfortable and happy. The staff were very attentive and flexible, even when we wanted some small changes, such as pick-up times for the drivers. They adapted and made it all work. This travel agent is absolutely terrific.
Reviewed By Marci M.
Our Italy trip with Zicasso’s travel partner was nothing short of spectacular! Referred by a friend who had an amazing experience, we decided to give it a try and were not disappointed. Our agent was fantastic, always ready with answers to our questions and providing excellent support throughout our journey.
In Tuscany, we visited beautiful wineries and enjoyed a delightful lunch with the vintners, who were incredibly warm and welcoming. Her attention to detail was evident when she adjusted our plans due to weather changes and even checked in on us when we were slightly delayed for a tour.
Siena was breathtaking and our hotel in Rome was perfectly located, allowing us to walk to all the major sites. One of the highlights was a small boat tour around Capri from Amalfi—perfect weather and stunning waters made it unforgettable. The cooking class on the Amalfi Coast, set on the side of a cliff, was exceptional and having personal tours just for the two of us was an unexpected and delightful bonus.
We can't express enough how much we enjoyed our Italy trip. The travel partner exceeded our expectations and we highly recommend them for a truly memorable experience!
Reviewed By Kent S.
Zicasso’s trip coordinator and her team did a fantastic job, not only in planning the trip to meet our needs and wants, but also in personalizing it as needed. They were also available as we needed them to adjust things, such as pickups, and even made some dinner reservations for us. With our budget, they set us up in excellent hotels that fit our desire for the trip to be a wonderful anniversary getaway. Her staff were also very helpful. We would strongly recommend them for a trip to Italy!
Reviewed By Rajesh J.
Zicasso's travel planner and her staff did a perfect job for our family of six. She made our trip seamless!
Everything she planned was perfect and no detail was left out. I would use them again and again for my travels to Italy.
Reviewed By Sally F.
My first solo trip was something I had dreamed about for years. I wanted it to be more than sightseeing. I wanted adventure, comfort, safety, and freedom without the stress of planning it all alone. Through Zicasso, I was connected to two specialists and Zicasso's travel consultant stood out immediately. She delivered an itinerary that gave me everything I asked for and more: maximum cities, maximum fun, and maximum value, all without compromise.
Before deciding, I researched and compared tours, packages, and individual prices online. The travel consultant’s proposal came out on top for value and content. While the other agent offered fewer cities and activities at a higher price, her plan was ambitious without being overwhelming. She booked my trains, arranged private transfers where needed, and selected boutique-style hotels that exceeded expectations. I was honestly surprised at how good they were. I stayed at hotels in Interlaken, Florence, and Sorrento. Each was clean, comfortable, and perfectly located for exploring. I had prepared myself for budget trade-offs, but instead, I found thoughtfully chosen hotels that balanced affordability with real quality.
Every document, train ticket, and activity confirmation was uploaded into the app. It became my lifeline throughout the trip, with every detail at my fingertips. The structure gave me confidence, while still leaving me free to explore.
Switzerland came first: Zurich, Lucerne, Interlaken, and Zermatt. Each city felt like stepping into a postcard. Interlaken gave me the adrenaline rush of skydiving, while Zermatt charmed me with its close-knit magic and alpine beauty. Italy unfolded with equal ease: Lake Como, Venice, Florence, Sorrento, Amalfi, and Rome. Every destination felt curated, yet natural, from gondola rides in Venice to boat tours on the Amalfi Coast.
What I loved most was the balance between structure and freedom. Pre-booked activities and restaurant reservations gave me a strong framework, but I could just as easily decide to spend an afternoon wandering Florence, eating gelato, or sitting in a piazza. The rhythm of the trip was perfect, structured enough to tick off bucket-list highlights, yet relaxed enough to feel like a real vacation.
Food was freestyle, but memorable. Highlights included a Japanese-Peruvian restaurant in Zurich with its elegant Japanese-Peruvian flavors, a different Japanese restaurant, a restaurant in Como with its modern fusion menu, an Indian restaurant for comforting classics, and international favorites like those in one of the restaurants in Rome. Between those meals and plenty of gelato and crepes, every stop added its own flavor to the journey.
As a solo traveler, safety mattered. I felt comfortable walking around in the evenings and was usually back in my hotel by 1am to stay rested for the next day. What really gave me peace of mind was the travel consultant’s constant support. Communication was fast and responsive. I never had to wait long for answers, whether through the app or email. There was a moment when I made a mistake with the trains and missed an activity. She immediately stepped in and worked to reschedule it or secure a refund that same day.
Earlier in the planning process, I also had a card issue due to an address error. Even though policy would not normally allow it, she and her team patiently waited until I received the refund before finalizing the booking, just weeks before my trip. That flexibility and care spoke volumes.
The difference was clear. She used my budget to its fullest potential, giving me more destinations, more experiences, and better hotels than the alternative option. She managed to combine the efficiency of a fully organized tour with the freedom of independent travel. Everything was planned, yet everything was still mine to shape.
This trip was everything I wanted: good food, beautiful views, safety, and absolute reliability. It was an organized journey with freestyle flexibility, which is exactly what solo travelers dream of. The travel consultant’s planning let me chase adventure while always knowing I had a safety net. Switzerland and Italy gave me memories I will never forget, but it was the behind-the-scenes planning that made it possible. If you want a trip that is your way, your budget, your pace, but without the endless hassle of managing it yourself, the travel consultant at this agency is the person who can make it happen. My first solo trip became my dream trip and that is the highest praise I can give.
Reviewed By tasmia S.