Two Week Sicily Itineraries

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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.

How Zicasso Works

  1. Describe your dream tour.

  2. We match you with up to 3 top travel specialists. They compete to plan your trip.

  3. Book the trip when you are satisfied.

Ratings of Zicasso's Service

Sample Itineraries

Get inspired with our sample trips below. You can have any trip tailor made for your private travelAny number of days.
Any departure date. Any experience you want.

 Sicilian setting - wine glasses, olives, blue cheese, bocconcini and ciabatta.

Slow Food & Leisurely Wine Tour of Southern Italy and Sicily

14 Day Custom Tour

From $3,845

Through the beauty of the cuisine, you will discover endless passion, embrace unfamiliar flavors, and take pleasure in history and gastronomy while exploring Southern Italy. Olive trees captivate with produce ready for harvest and grapevines absorb vibrant minerals, adding depth to sophisticated wines; lemon trees offer fragrant hints of citrus and the coastline erupts with revitalizing aromas of the sea. Celebrate zesty sauces and inspiring seafood, mouthwatering stews and refreshing salads during your customizable Southern Italy itinerary connecting you to the villages, towns, and cities of the region, from Sicily to Puglia.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

traveling couple on the waterfront, Sicily


Unforgettable Romantic Getaway Tour to Sicily

14 Day Custom Tour

From $3,845

A romantic vacation should encompass exotic landscapes and transcendent experiences. Your custom-tailored romantic getaway to Sicily encompasses the lavish and the beautiful as well as natural wonders and ancient civilizations, combining for an unforgettable whirlwind of passion, history, and flavors. Share pastries in a celebrated bakery, with delectable treats crafted from inherited recipes. Sip wine on a secluded vineyard in view of Europe’s largest active volcano. Witness the magnificence of ancient temples up close. Swim in cobalt-blue waters and lounge on white sand beaches. Indulge in the otherworldly splendor of Sicily with your significant other, for a timeless memory.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Ragusa, ancient baroque city, Sicily

Discover Sicily Tour: A Feast for the Senses

14 Day Custom Tour

From $3,845

The discoveries of Sicily are endless on an island bursting with ancient wonders and vivacious culture, stunning landscape and iridescent beaches. Medieval towns crown towering mountains offering unparalleled views. Breathtaking Doric temples rise from valleys overlooking wild olive groves. Celebrated chocolate shops share with you their recipes passed down for hundreds of years. Cobblestone paths wind through antique buildings and into open elegant piazzas adorned with graceful churches. Your custom-tailored discover Sicily tour lets you explore Sicily like a local, relishing the thrill of adventure, the excitement of discovery, and the soothing calm of daily life.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Gorgeous view of the Calabria, Italy coastline

Best of Southern Italy & Sicily Tour

14 Day Custom Tour

From $3,845

Capture the essence of history, culture, and cuisine during your customizable, highlights tour of Southern Italy and Sicily. Indulge in the alluring splendor of Italian heritage that is featured in colorful towns around the Amalfi Coast and within the elegantly-preserved architecture of Palermo. The majesty of ancient Greek temples at Agrigento reveals the remarkable depths of heritage, which are emphasized by artifacts that are displayed in galleries like the National Archeological Museum of Naples. From walking the excavated streets of Pompeii to strolling beneath luxurious, Baroque adornments in Lecce, your Southern Italy and Sicily tour embraces grandeur and immerses you in unrivaled beauty.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

View of Palermo from the Cathedral of Santa Maria Aassunta, Sicily, Italy

Best of Sicily and Southern Italy Tour for Seniors

14 Day Custom Tour

From $3,845

Uncover the legends and immerse yourself in the history of Southern Italy. Spend a week in Sicily and a week on the mainland, hopping between three millennia of ruins, cultures, cities, and charms. Authentic local experiences mix with grand historical remains and plenty of coastlines, with just about every major European civilization having a role to play. Handcrafted for senior travelers who seek to both explore and experience, this is an in-depth tour full of fascinating details.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Skyline of Florence, Italy

Best of Italy and Sicily Tour

15 Day Custom Tour

From $4,120

Culture perpetually surrounds you, and the depths of history arise anew on your custom tailored Italy and Sicily tour. Gondolas float down the maze-like network of canals in Venice. The eclectic, historic cultures that once called Palermo home remain strong in the traditions of the marketplace. The summits of Mount Etna and Mount Vesuvius loom over cities both ancient and contemporary. Roman ruins and Doric temples, opulent beaches and Renaissance artwork combine for breathtaking vacation, showing you the unparalleled wonders of Italy expanding from north to south.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
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Every Time
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Helpful Content

Reviews of Zicasso's Referral Service

4.86 stars based on 219 reviews. See all our reviews.

Review photo submitted by Gerald H.
Luxury Italy Travel Review: Sicily, Siracuse, Greek Temples...

"Getting things done, arranging the best, and satisfying...

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"...we felt like VIP the entire time."

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"Our driver in Siracusa, went over and above to insure that...

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"We are so grateful to have worked with our travel planners...

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Review photo submitted by Brenda G.
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"While on our trip, the designer was in contact with me...making...

Reviewed By Brenda G.

Review photo submitted by Jennifer P.
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"I would say that the private tours that were arranged were...

Reviewed By Jennifer P.