Ischia Island in Sicily, Italy
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Eight Day Sicily Itineraries

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Eight-day Sicily itineraries bring the Mediterranean’s crossroads to life by immersing you in the seductive coastline and remarkable cultural heritage. Sicily is timeless and endlessly alluring, with a collection of ancient Greek ruins and flavors influenced by the historic connections to surrounding civilizations, shimmering seas, and rugged mountains. Zicasso travel specialists have planned thousands of custom Italy tours and vacations, providing travelers with unique experiences based on local knowledge and expertise. Find inspiration with our sample itineraries before speaking with the right Zicasso travel specialist for you.

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Tailor Made Itineraries

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

Discover the famous Colosseum, which takes you back in time to Ancient Rome.

Immersive Southern Italy and Sicily Tour: Food, Culture, and History

8 Day Custom Tour

From $2,195

During this immersive 8-day vacation, you will discover the rich history, lively culture, and delicious cuisine of the area. Picturesque towns and stunning landscapes can be found throughout southern Italy and Sicily. Exclusive tours and private tastings will be enjoyed at every destination as you indulge in la dolce vita during this unforgettable vacation.

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Enjoy a relaxing morning boat ride along the bay in Mondello, Mediterranean, Palermo

Taste of Sicily: VIP Food & Wine Tour

8 Day Custom Tour

From $4,795

On this VIP culinary Italy itinerary, experience life beyond the mainland with a gourmet taste of Sicily’s rich history of cuisines. Sample fine wines on premier estates. Wander the vibrant open-air markets in Palermo, passing colorful produce and fresh seafood. Witness the golden stones of Arab-Norman palaces. Discover the largest ancient temple on the island rising out of the blossoming wildflowers. Discuss ideal wine pairings with an experienced sommelier and enjoy an unparalleled panorama of the beach on a secluded cruise of a gorgeous bay. Bask in the beauty, luxury, and flavor of Sicily on this unforgettable Italy vacation.

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Sunset on the famous vineyards of Sicily, Italy

Custom Tailored Sicily Wine Tour

8 Day Custom Tour

From $2,195

Your private tailored Sicily wine tour allows you to settle into the captivating life of Sicily, a destination where you can slow down, sample the best varieties of local wine, and explore the depths of ancient cultures that have evolved in the undulating hillsides. Indulge in a sweet confection inside a chocolate shop that has spent centuries perfecting its craft. Grab a handful of the earth that nourishes the lush flavors of the timeless cuisine. Sensational trips to Sicily can be tasted, touched, and experienced; experience it all in this handcrafted tour of a lifetime.

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The grapes are ripe and ready to harvest. Variety quot uva Italia quot. September, near the city of Agrigento.

Wine Lovers Sicily Tour: History, Tasting & More

8 Day Custom Tour

From $2,195

Uncover the secrets to a perfect bottle of wine in the unparalleled landscape of Sicily. Follow the trail of an open-air museum dedicated to the different grapes of the island. Sip a sensual red or robust white in an antique farmhouse. Discover the ancient civilizations that settled the hillsides and shores. The subtle flavors of wine are influenced by the soil and elements, nurtured to absorb the qualities of its surroundings. Embark on a luxurious Sicily wine tasting experience that will introduce you to the Planeta estates and has you fall in love with the distinctive characteristic of each property’s wine and production.

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Taste real chocolate on a guided tour of Modica, Italy.


 A Perfect Sicily Culinary Tour

8 Day Custom Tour

From $2,195

Bask in the simultaneously simple and complex flavors of Sicily in a paradise that you never knew existed. The Mediterranean Sea sparkles along the golden sandy beaches. Greek ruins adorn hilltops and overlook the surrounding valleys. Citrus orchards and olive groves provide ample tastes of the island’s natural flavors. Wineries blanket the undulating landscape and chocolateries fill the streets with indulgent rich aromas. Your Sicily culinary tour is custom tailored to your desires, allowing you to immerse yourself in the cuisine of Sicily that can be rustic or refined, sweet or savory, and is never less than scintillating.

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Cultivated land and majestic snow-capped Mount Etna, Sicily

Sicily Itinerary for the Experienced Wine Connoisseur

8 Day Custom Tour

From $2,195

Combine traditional flavor with ancient history, and Baroque charm with rich landscapes during your custom-tailored wine tour of Sicily for seniors. The indelible marks of ancient settlers gave rise to stunning culinary delights while elegant towns capture the grandeur of former kingdoms. Your immersive tour will highlight the treasured sunsets in Noto and luxurious coastline at Marzamemi, as well as the bountiful vineyards that spread across the foothills of Mount Etna. You will capture the spirit of the local markets that reveal customary recipes and explore the isolated islands that overflow with hidden splendors to shape your perfect blend of the past and present of Sicily.

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Reviews of Zicasso's Referral Service

4.86 stars based on 222 reviews.

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

Reviewed By ANDrew C.

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

Reviewed By Deborah F.

Sicily Travel Review: Luxury Couples' Trip to Italy, Palermo,...
"Our travel planner was gracious, accommodating, creative,...

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Sicily Travel Review: Luxury Trip to Italy, History &...
"All of the guides were friendly, knowledgeable, and professional..."

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Travel Review: Italy Family Vacation, Sicily, Siracusa,...
"Daniela was a pleasure to work with as she helped us tailor...

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Italy Anniversary Travel Review: Naples, Pompeii, Sorrento,...
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