
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 966 verified traveler reviews.
We had a lovely tour of Sicily and we thoroughly enjoyed the scenic villages, mountains and coastal areas, the delicious food, the history and culture of the region, and, of course, the many lovely Sicilians we met on our journey! This was made possible by the travel company we went with when we first engaged Zicasso. They met with us (online) and developed a great tour, for which a few highlights are summarized below. They were also very helpful during the trip to offer us assistance if we needed it. In short, they made our trip truly memorable!
On our visit to Palermo, we experienced its ancient history and fine cuisine. Touring some of the smaller towns and villages, such as Cefalù, Modica, Scicli, Marzamemi and Noto, we enjoyed many scenic streets and alleys with their many shops and restaurants, and also seeing some beautiful artwork in their ancient cathedrals. The countryside of Sicily is also lovely to see and on our tour, we were privileged to visit some farms and talk with some locals who make their living off the land.
We were captivated by the rich historical underpinnings of Sicily, as we saw when we toured Agrigento to visit the Valley of the Temples. In other larger towns/cities we visited, such as Ragusa, Syracuse and Taormina, we had many opportunities to tour food markets and taste (and to learn to prepare) some specialty dishes of the local area.
Having a walking tour around Mount Etna with a local guide provided us with a refreshing outdoor nature hike that was a great way to learn about the area. Capping off our nature walk with a gastro/wine tour at a local winery was a great finale to our two-week vacation! In the end, our only regret was that we didn't want the vacation to end!
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We had a fabulous time in Sicily. It was our first visit and Zicasso’s travel company planned an excellent itinerary, with great recommendations on the cities and towns to visit that felt like a truly local experience. (Other agents focus on the big cities of Palermo and Taormina, but the travel company recommended we spend more time in Syracuse/Noto, Ragusa, and Modica.)
We loved our primary driver and the boutique hotels they selected for us. Communication and documents were all easy to follow.
The only piece we wish might have been curated a little more was the recommended dining options. There were too many and not necessarily great restaurants.
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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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Overall, a very good trip; we enjoyed it very much. There were, however, a few glitches. On our first tour day, our guide was late, and we ended up picking her up from the train station, which started the tour late. Then, the transportation company wanted to charge us extra because the tour ran over time. Zicasso's travel company intervened, and we were not charged. On our second tour day at the Borghese Gallery, the guide was a no-show, and we were notified at 2 p.m. when we were scheduled to meet the guide at the gallery. Our tour of Stabiae was scheduled on a day when the facility was regularly closed and the travel company arranged for us to visit two sites in Pompeii as a substitute.
We wish the travel company had provided more information on two of our hotels. Our room at the hotel in Palermo, while spacious, was sparsely furnished and didn't seem like a 5-star hotel room. The hotel informed us that the room is scheduled to be refurbished next year. At our hotel in Syracuse, we had a two-story room with a beautiful view, but there was no room for bags on the second floor, where the bed was located, which would have entailed dressing on the first floor and many uses of the stairs. We declined that room and ended up in a small downgraded room for two nights until another room was available. Additionally, the breakfast room was very cold and even the staff complained about the temperature. When I asked a staff member about the temperature, I was told they were "between cycles" - it was not clear what that meant. To be fair, I was involved with the choice of hotels, but perhaps the travel company could have alerted me to these potential difficulties.
On a positive note, all of our drivers were on time and exceptionally polite. Additionally, the app, worked very nicely, was easy to read and helpful. Finally, the WhatsApp communication with the travel company was always available and worked well.
It should be emphasized that we enjoyed the trip and have many fond memories, especially regarding the amazing archeological sites.
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My wife and I spent two weeks in Sicily and four more days in Rome. The trip was seamless: no glitches and no problems. Zicasso's travel specialist and others were promptly responsive, friendly, and cooperative. They made excellent suggestions and respected our preferences.
The transportation and the guides were all very good. The hotels were appropriate for our desires and budget. They provided wonderful sunset cruises in Palermo and Taormina, and they got us restaurant reservations for dinner each night at non-touristy places.
Surprisingly to us since we have been there before, Rome was especially enjoyable. The art in the Borghese Gallery and in the Pope's museum at the Vatican was overwhelming.
My wife and I have traveled extensively, particularly with agents obtained through Zicasso. They have all been good, and this one was one of the best. I can recommend our travel company without reservation.
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We thoroughly enjoyed our two-week stay in southern Italy that Zicasso's travel specialist and the team at our travel company prepared for us. Our group included two couples traveling along the Amalfi Coast, across Italy through Matera to the Puglia region. Planning, execution, and follow-up were all very well thought out and professional.
Our travel company was also readily available to address concerns during our stay. For example, we needed to reschedule a planned boat tour due to bad weather, and they were able to reschedule a few days' worth of activities to accommodate us.
Hotel selections were excellent, especially the hotel in Sorrento with an incredible view of Mt. Vesuvius, an easy walk to town, and access to other attractions. Our hotel in Ostuni was similarly situated with incredible views and easy access to shopping, restaurants, and activities.
The travel company's team booked several tours for us ranging from a few hours to all-day events. The tour guides were professional and very knowledgeable, and the drivers were excellent, especially along the Amalfi Coast where driving is very challenging. We would definitely recommend Zicasso's travel company again.
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