HomeEuropean ToursItaly Tours2 Week Sicily Itineraries
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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

How Zicasso Works

Here's how we create life-enriching, luxury travel experiences

  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 2185 verified traveler reviews.

Travel Review: Italy Tour, Sicily, Palermo, Agrigento, Catania, Ragusa, Syracuse, Modica, Chocolate Making, Olive Oil Factory
"All the arrangements made by the travel company worked flawlessly."

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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 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 Travel Review: Palermo, Trapani, Erice, Mazara del Vallo, Marsala, Taormina, Zingaro Reserve, Historic Sites, Wine Tasting
"The trip planning and organization done by the travel agency were amazing."

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Southern Italy Luxury Vacation Review: Hilltop Town of Taormina, Greek Ruins of Agrigento, Marsala Wine Tasting, History & Food
"This travel team is an excellent agency, with an emphasis on service."

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Luxury Italy Travel Review: Sicily, Palermo, Catania, Ortigia, Taormina, Mount Etna

"Matteo provided exactly the trip we wanted...He provided us with a cellphone upon arrival and checked in from time to time."

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