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.

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Tailor Made Itineraries

Get inspired with our sample trips below. Let our travel specialists customize a trip just for you.

Olive grove in Sicily, Italy

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.

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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.

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Ragusa, ancient baroque city in Sicily, Italy

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.

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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, 14-day highlights tour of Southern Italy and Sicily. Indulge in the alluring splendor of heritage featured in colorful towns around the Amalfi Coast and within the elegantly-preserved architecture of Palermo. 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.

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Ancient theater in Taormina, 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.

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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.

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Reviews of Zicasso's Referral Service

4.86 stars based on 228 reviews.

Italy Family Trip Review: Rome, Sorrento, Capri, Pompeii,...
"Marcella went above and beyond to answer my many questions...

Reviewed By Francesca P.

Italy Travel Review: Sicily, Ortigia, Taormina, Agrigento,...
"[Our travel agent] was excellent, delivering with no errors."

Reviewed By Thomas F.

Luxury Italy Vacation Review: Sicily, Palermo, Taormina,...
"[Our travel agents'] knowledge of the country as well as...

Reviewed By ANDrew C.

Luxury Italy Family Travel Review: Sicily, Amalfi Coast,...
"Everything about the trip was great."

Reviewed By James W.

Italy Vacation Review: Rome, Pompeii, Positano, Sorrento,...
"[Our travel agent] learned of our basic interests and took...

Reviewed By Bill T.

Southern Italy Tour Review: Puglia and Sicily, Art &...
"The trip was fantastic."

Reviewed By Deborah F.