
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 $6,300
Best of Southern Italy & Sicily Tour

14 Day Trip IdeaFrom $6,300
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 746 verified traveler reviews.
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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The trip itself was OK. We loved getting to know Sicily and the itinerary provided by Zicasso's travel company was very interesting. The suggestion I would make for new travelers to this region is that they choose another time, instead of May. We expected warmer weather.
Another suggestion is that if you are going to rent a car, choose a small one. The cities are really small (downtown), so the streets are very narrow. You have to be very careful when driving. In Ragusa, a parking lot near the best part of the city should be recommended (I have already told the travel consultant about that).
As for the rest, everything went just fine and I would recommend visiting Sicily.
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It was a pleasure working with Zicasso’s travel specialist and her team for our recent trip to Italy, including Rome and Sicily. The travel specialist was thoughtful throughout and demonstrated exceptional local knowledge when crafting our itinerary, particularly for Sicily, where we spent seven to eight days exploring the northwest, east, and southeast regions.
The itinerary beautifully blended visits to charming fishing villages with well-paced day tours, allowing for meaningful free time in between. In fact, she strongly encouraged us to include a free day to explore on our own, which made a noticeable difference, as we never felt rushed or exhausted. The hotels were impeccably selected and added greatly to the overall experience.
This was a truly memorable trip that we enjoyed every step of the way.
Thank you to the travel specialist and the travel company for creating such a wonderful experience. We will absolutely turn to them again for our next visit to Italy.
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We loved Sicily! Zicasso's travel operator provided us with an amazing trip! Every guide and activity surpassed our expectations. From the archaeological parks to the cooking class at the palace, the art class, the Jeep tour of Mount Etna, the olive oil and lemon farm, but especially the guides she selected for us, it was pure joy! The history of that country is mind-boggling and fascinating to learn about.
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We had an amazing 2 weeks in Italy, from Rome, to Bari, Positano, Sorrento, and Naples. The planning and execution of our trip through Zicasso’s tour operator was flawless! They worked with me quite a bit in the planning phase to make sure this was going to be our dream trip.
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