
Two Week Sicily Itineraries
The astounding island of Sicily welcomes visitors ready to display its many wonders. From the ancient Greek temples to the local seafood cuisine, a quintessential two-week Siciliy itinerary is best designed with the aid of one of Zicasso’s expert travel specialists that will immerse you in the island’s Mediterranean essence from cliffside views to sea infused wines.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

14 Day Trip IdeaFrom $6,300
Slow Food & Leisurely Wine Tour of Southern Italy and Sicily

14 Day Trip IdeaFrom $6,300
Unforgettable Romantic Getaway Tour to Sicily

14 Day Trip IdeaFrom $6,300
Discover Sicily Tour: A Feast for the Senses

14 Day Trip IdeaFrom $5,100
Best of Southern Italy & Sicily Tour

14 Day Trip IdeaFrom $5,100
Best of Sicily and Southern Italy Tour for Seniors

15 Day Trip IdeaFrom $6,800
Best of Italy and Sicily Tour
How Zicasso Works
Here's how we create life-enriching, luxury travel experiences
1.Share Your Travel Dreams
Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.
2.Meet Your Travel Specialists
To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.
3.Design Your Perfect Journey
Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.
Reviews of Zicasso's Two Week Sicily Itineraries
Based on 1492 verified traveler reviews.
Zicasso’s travel professional crafted an unforgettable Sicily trip for our group of seven. After discussing our preferences, she designed a flawless itinerary, incorporating unique experiences that became trip highlights. Her communication was exceptional, with prompt responses to our questions before the trip and daily updates for the next day's activities, including driver and guide details, which were incredibly helpful.
We stayed at superb hotels in Taormina, Agrigento, Palermo, and Cefalù, each with stunning views and private tours. Sicily’s warm, hospitable people stood out compared to other European destinations. At our hotel on Via Leonardo da Vinci in Taormina, the staff greeted us warmly, setting a perfect tone. Other stops included Mount Etna, Erice, Castelbuono, and Savoca. All of these locations were great, but don't miss Castelbuono!
Two standout experiences were private meals with families. Near Erice, a chef and his family welcomed us into their sea-view home, preparing amazing Sicilian meals that felt like dining with family. In Palermo, another home chef and her husband created a similarly memorable evening, with lots of great conversation and stories.
Every driver was professional, friendly, and informative, while our guides — often archaeologists or historians — were engaging and knowledgeable.
Highlights included a welcome dinner in Taormina, a farm cooking class, two wine tours with lunch, a Mount Etna hike, a Valley of the Greek Temples tour, town and village tours, cheese and pastry tastings near Cefalù, and a farewell dinner. The Godfather tour in Savoca was special, with our guide introducing us to a local who played Apollonia’s mother, waving from her balcony.
Our travel professional's meticulous planning and personal touches made this trip extraordinary. Thanks to Zicasso for matching us with the tour company and we highly recommend them for a perfect Sicilian/Italian adventure!
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This was a superb trip that allowed us to combine personal visits to Taormina and Syracuse with a pre-planned group meeting in Catania. Planning and communication were excellent, supported by an app that let us easily view our itinerary, complete with phone numbers for the drivers, hotels, and the tour operator contacts.
The hotels were perfect! They were wonderfully located, with impeccable service in Taormina and Syracuse. Our excursions were private and diverse, and allowed us to combine culture, foodie interests, and free time. The guides were top-notch, knowledgeable, and flexible.
We especially loved seeing the smaller towns of Sicily; Militello, Ragusa, Aci Castello, and Modica. We even arrived in one small town during their annual festival.
We had a dedicated driver for our trip who was, himself, a treasure; always on time, always ready to adjust to changes, and a delightful personality.
This was such a good experience that we have selected Zicasso's tour operator to book another Italy trip next year.
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Our Zicasso travel specialist did a fantastic job planning our family vacation for five adults.
Each hotel was top-notch. At the villa in Taormina, the rooms were luxurious, with unbelievable views of the bay and Mount Etna from private verandas. The staff were gracious and the restaurant's breakfast buffet delicious. Lunch and dinner were top-notch. The hotel in Agrigento was modern and the grounds were exceptional. It was close to the Valley of the Temples, with amazing views of the ruins from each room and the beautiful infinity pool. The hotel in Palermo was old-fashioned luxury with up-to-date facilities and close to the old town.
Our tour guides and drivers were excellent.
My only regret is that we only had 10 days to explore Sicily as there was so much more to see!
Our agent did a yeoman's job helping us plan this trip.
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Zicasso's travel designer did an excellent job planning a three-week trip for us in Naples, the Amalfi Coast, Capri, and several cities in Sicily. We appreciate that she met with us by Zoom on two occasions to tweak the draft itinerary to be sure it was the trip we were looking for. She listened to us and created an itinerary that met all of our needs.
The guides, drivers, and accommodations were excellent. The guides all spoke excellent English, were easy to understand, and obviously well educated and informed about the details of the history, architecture, art, and culture of each site we visited. The experience was educational, in addition to just enjoying the beauty of Southern Italy and Sicily.
We had one potentially disruptive event when a labor strike caused a cancellation of our flight from Naples to Sicily. Her team did an amazing job of creating an alternative, involving going by train to Rome, then catching a plane from Rome to Catania, and our arrival was only a few hours later than the original itinerary. Our word to describe their creative plan is "Brilliant."
Overall it was a great and memorable experience, thanks to the excellent recommendations, planning, and making all of the arrangements for our visit.
We will have no hesitation to recommend her and her team to our friends and family. Thank you for arranging for us to benefit from their incredible services.
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The travel company and staff were excellent. The trip coordinators accompanied us through the trip via WhatsApp. They were terrific. The service was top-notch, including the drivers, tour guides, and accommodations.
The one thing I would change about the trip is to have longer stays in each city visited. Moving to a new hotel every two nights prevented us from really enjoying each city we visited. I would also forgo Palermo and substitute a smaller city like Noto or Agrigento. But again, the itinerary was based on my interests and time. It is not an indication of the tour company's abilities. However, it may be good for the agency to suggest longer stays to other customers. Otherwise, we had a great trip and once again, I have recommended Zicasso and the tour company to family and friends.
Thank you again for a great time!
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