
Eight Day Sicily Itineraries
Eight-day Sicily itineraries bring the Mediterranean’s crossroads to life by immersing you in the seductive coastline and remarkable cultural heritage. Sicily is timeless and endlessly alluring, with a collection of ancient Greek ruins and flavors influenced by the historic connections to surrounding civilizations, shimmering seas, and rugged mountains. Zicasso travel specialists have planned thousands of custom Italy tours and vacations, providing travelers with unique experiences based on local knowledge and expertise. Find inspiration with our sample itineraries before speaking with the right Zicasso travel specialist for you.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

8 Day Trip IdeaFrom $3,600
Immersive Southern Italy and Sicily Tour: Food, Culture, and History

8 Day Trip IdeaFrom $3,600
Custom Tailored Sicily Wine Tour

8 Day Trip IdeaFrom $3,600
Wine Lovers Sicily Tour: History, Tasting & More

8 Day Trip IdeaFrom $3,600
A Perfect Sicily Culinary Tour

8 Day Trip IdeaFrom $3,600
Sicily Itinerary for the Experienced Wine Connoisseur
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 Eight Day Sicily Itineraries
Based on 5725 verified traveler reviews.
We had a fabulous trip to Italy, including to Sorrento, Taormina, and Rome. Zicasso’s travel specialist made sure every detail was taken care of, including stays in beautiful, well-located hotels and excursions that were interesting and fun for our family.
For example, she arranged for an airport host to assist us with our arrival to and departure from the Rome airport, and she was simply amazing, whisking us through the airport and eliminating stress for our family.
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In all respects, a well-planned and well-executed trip to London and Rome. The guides were exceptional in knowledge, kindness, and sense of humor. The best restaurant recommendation was the one in London.
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Amazing!! Everything from start to finish was simply amazing! The process, from the beginning with Zicasso to the end with Zicasso’s travel consultant, was flawless. She was in touch throughout the whole process. In preparation, she was very responsive and, once we were there, every little detail was thought through.
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Zicasso’s travel specialist put together a perfect trip for us. We were a large group, with large age and ability ranges—in addition to traveling over the holidays, so places being closed for the holidays was also a challenge. She made magic happen and, honestly, our trip could not have been more seamless.
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Zicasso’s travel company did a great job and was very responsive. The guides and drivers were excellent. It was a wonderful family trip.
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Aside from the delay because of the time change, working with Zicasso’s travel specialist was great. She took care of all arrangements in Sicily once our decisions were made. She confirmed with every hotel, driver, and guide, making sure our travel was effortless.
The guides were great, adding so much historical information to our attractions. Our drivers were friendly, providing us with clean, comfortable vehicles, safe driving, and interesting conversation about modern life in Italy. Our hotels were high-end, in city centers, with amazing breakfast buffets and professional, kind staff.
We used a reputable tour group for our first week of mainland Italy travel, but our experience with this travel specialist far surpassed the tour group experience and our expectations. I would not hesitate to use her again for any travel plans in Italy. She checked in with us pre-, mid-, and post-travel. There wasn’t one hiccup with the plans she made for us.
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