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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.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

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 5426 verified traveler reviews.

Grace B.
Italy, Greece Honeymoon Review: Culture, Cuisine, Snorkeling, Cooking Class, 12 Nights

My husband and I went through Zicasso to plan our honeymoon to Italy and Greece. This was the best decision ever! We worked closely with our travel specialist to plan our trip and she was absolutely phenomenal. This was our first international trip outside of the US, so we were a bit nervous at first! However, our specialist ensured every aspect of the trip was organized and that we were taken care of every step of the way.

The biggest relief was transportation. We did not have to give a second thought as to how we were getting places; we had drivers set up at every destination and for nearly every activity. Also, we had 24/7 support if anything were to go wrong, which gave us peace of mind.

If you are hesitant to use Zicasso for your next trip, I want you to know that I was too, but it was the best decision! We were able to personalize and tailor our trip to our needs without the hassle of dealing with the details.

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komal P.
Italy, Malta Trip Review: City Tour, 20 Days

I was very pleased with the entire planning of the trip. The communication with Zicasso's tour company was excellent. The meals that were pre-arranged by them were fantastic and we probably would not have found them on our own.

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Mitch A.
Italy, France Travel Review: Scenery, 10-Day Trip

The trip was amazing all around. Incredible. The service and itinerary were perfect. We highly recommend Zicasso's travel company.

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Helena H.
Greece, Italy Travel Review: Rome, Athens, Santorini, Local Cuisine, 14-Night Trip

Our trip was absolutely amazing! This was the trip of a lifetime. Zicasso and our trip planner were incredible. He was repeatedly helpful, offering personalized attention to our needs. He booked amazing tours for us and seemed to really grasp what we wanted. Everything was incredible.

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Robert K.
Italy Vacation Review: Ravenna, Padua, History, Art, Scrovegni Chapel, 13 Days

It was a great pleasure working with Zicasso's tour agency. Our travel designer and her staff were attentive to the kind of trip we wanted and planned a great itinerary. The hotels, restaurants, and drivers were all top-notch. For us, the acid test was the quality of the guides, and they excelled there as well. We would happily have them plan another trip for us.

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Danielle S.
Italy Tour Review: Ravenna, Verona, Rimini, Scrovegni Chapel, Private Tours, History, 12 Nights

My husband and I had a great time on our trip to the northeast Adriatic Coast of Italy. We have very specific tastes as far as where we like to stay and the private tours we like to have during the trip. Zicasso's travel company did a great job, giving us fantastic hotels, and all of our tour guides were top-notch.

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