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Two Week Sicily Itineraries

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<p>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.</p>

The astounding island of Sicily welcomes visitors ready to display its many wonders....

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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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    Trips curated by the world’s top destination experts

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    Concierge-level service leading up to and during your trip

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    Unique, exclusive experiences and insider access

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Ratings of Zicasso's Service
Olive grove in Sicily, Italy

Slow Food & Leisurely Wine Tour of Southern Italy and Sicily

Places Visited: Catania, Tropea +14 more
Places Visited: Catania, Tropea, Matera, Lecce, Benevento +11 more

14 Day Custom Tour

From $6,300

Traveling couple on the waterfront, Sicily

Unforgettable Romantic Getaway Tour to Sicily

Places Visited: Palermo, Erice +9 more
Places Visited: Palermo, Erice, Agrigento, Modica, Valley of the Temples +6 more

14 Day Custom Tour

From $6,300

Ragusa, ancient baroque city in Sicily, Italy

Discover Sicily Tour: A Feast for the Senses

Places Visited: Palermo, Taormina +4 more
Places Visited: Palermo, Taormina, Erice, Syracuse, Ragusa +1 more

14 Day Custom Tour

From $6,300

Gorgeous view of the Calabria, Italy coastline

Best of Southern Italy & Sicily Tour

Places Visited: Rome, Tarquinia +17 more
Places Visited: Rome, Tarquinia, Caserta, Naples, Pompeii +14 more

14 Day Custom Tour

From $6,300

Ancient theater in Taormina, Sicily, Italy

Best of Sicily and Southern Italy Tour for Seniors

Places Visited: Sicily, Palermo +18 more
Places Visited: Sicily, Palermo, Mount Etna, Il Capo, Segesta Erice +15 more

14 Day Custom Tour

From $6,300

Skyline of Florence, Italy

Best of Italy and Sicily Tour

Places Visited: Rome, Pisa +9 more
Places Visited: Rome, Pisa, Florence, Venice, Assisi +6 more

15 Day Custom Tour

From $6,800

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Help Me Plan My Trip

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Help Me Plan My Trip

Zicasso in the News

New York TimesWall Street JournalTravel + LeisureCNN

Reviews of Zicasso's Referral Service

4.9 stars based on 267 reviews.

Italy Travel Review: Sicily, Two-Week Trip
"We felt supported throughout the trip by our agent's availability...
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Reviewed By Diane K.

Italy Luxury Tour Review: Sicily, Culture, Local Cuisine,...
"Our trip was amazing. We are already planning our next...
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Reviewed By Cathy B.

Italy Luxury Travel Review: Amalfi Coast, Puglia, Sicily,...
"We recently had an amazing trip in southern Italy, organized...
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Reviewed By Stephen S.

Italy Luxury Vacation Review: Rome, Capri, Mount Etna, Taormina,...
"Our Zicasso travel agent did a wonderful job planning and...
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Reviewed By Paul G.

Italy Luxury Vacation Review: Milan, Puglia, Sicily, Sardinia,...
"Our agent put together a great itinerary and was extremely...
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Reviewed By Maria M.

Italy Vacation Review: Sicily, Local Cuisine and Wine, 3-Week...
"It was a wonderful trip. The Zicasso travel agency's attention...
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Reviewed By Linda T.

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