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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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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 5921 verified traveler reviews.

Italy Travel Review: Sorrento, Taormina, Rome, Pompeii, Mount Etna, Wine Tasting, 2 Weeks

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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England, Italy Vacation Review: London, Rome, 3 Weeks

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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Italy Travel Review: Lake Como, Cinque Terre, Florence, Rome, Boat Ride, Hiking, Cooking Class, 10 Days

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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Italy Travel Review: Rome, Florence, Tuscany, Food Tour, Wine Tasting, 9-Day Trip

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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Italy Travel Review: Sicily, Taormina, Valley of the Temples, 5-Day Trip

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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Italy Vacation Review: Rome, Florence, Vatican, Colosseum, Roman Forum, Trastevere, Private Guide, Food Tour, 7-Day Trip

Zicasso’s travel company helped us plan a trip that exceeded our expectations. From the hotels to the guides to the scheduling of events, things could not have gone smoother. We visited all the sites and did all the things we wanted to do, and still had free time to roam on our own. This team is top-notch and we highly recommend them.

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