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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.

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Olive grove in Sicily, Italy

14 Day Trip IdeaFrom $6,300

Slow Food & Leisurely Wine Tour of Southern Italy and Sicily

Catania, Tropea, Matera, Lecce, Benevento +11 more
Traveling couple on the waterfront, Sicily

14 Day Trip IdeaFrom $6,300

Unforgettable Romantic Getaway Tour to Sicily

Palermo, Erice, Agrigento, Modica, Valley of the Temples +6 more
Ragusa, ancient baroque city in Sicily, Italy

14 Day Trip IdeaFrom $6,300

Discover Sicily Tour: A Feast for the Senses

Palermo, Taormina, Erice, Syracuse, Ragusa +1 more
Gorgeous view of the Calabria, Italy coastline

14 Day Trip IdeaFrom $6,300

Best of Southern Italy & Sicily Tour

Rome, Tarquinia, Caserta, Naples, Pompeii +14 more
Ancient theater in Taormina, Sicily, Italy

14 Day Trip IdeaFrom $6,300

Best of Sicily and Southern Italy Tour for Seniors

Sicily, Palermo, Mount Etna, Il Capo, Segesta Erice +15 more
Skyline of Florence, Italy

15 Day Trip IdeaFrom $6,800

Best of Italy and Sicily Tour

Rome, Pisa, Florence, Venice, Assisi +6 more

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  1. 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. 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. 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.

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4.9

Reviews of Zicasso's Two Week Sicily Itineraries

Based on 746 verified traveler reviews.

Italy Trip Review: Taormina, Agrigento, Palermo, 8 Nights

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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Italy Vacation Review: Sicily, Temples, Cathedrals, Cooking Class, Boat Tour, 2 Weeks
"Zicasso’s travel agency planned the trip of a lifetime for us. They were attentive, communicated with us daily, and responded to any concerns."

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Italy Travel Review: Sicily, Ragusa, Cefalu, Siracusa, Taormina, Wine, Local Cuisine, 13 Days

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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Italy Trip Review: Rome, Sicily, 12 Days

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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Italy Tour Review: Sicily, Archaeology, Cooking Class, Mount Etna, Art Class, Olive Oil and Lemon Farm, History, Guides, 1 Week

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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Italy Tour Review: Rome, Bari, Positano, Sorrento, Naples, Amalfi Coast, 2-Week Trip

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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