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Two Week Southern Italy Itineraries

Each region of Italy is defined by local traditions and experiences, and Italy is a place where excellent food & wine will surely accompany you on your journey. Discover Southern Italy & Sicily, from the colorful, seaside villages of Amalfi and the authentic culture in Puglia to the ancient history of the Valley of the Kings on Sicily, with a customized tour from Zicasso.

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Sample Itineraries

You can have any trip tailor made for your private travel.

Couples Getaway: Two-Weeks in Southern Italy

14 Day Custom Tour

From $3,845

Fourteen days will give you and your partner ample opportunities to explore the rich heritage of Southern Italy. From the crumbling cliffs of Capri to the rustic charm of Naples’ old city center, every aspect of this itinerary is best paired with your companion and has been custom-tailored to those couples that enjoy a blend of both comfort and excitement during their international travels. As you witness the class of the past and present that is this region, it is best to leave plenty of space on your camera’s digital memory because each stunning view will be replaced by another stunning view.
Ultimate Two-Week Family Vacation to Southern Italy...

14 Day Custom Tour

From $3,845

From scaling the heights of a dormant volcano to exploring the depths of a royal escape route, this luxurious, 14-day tour of Southern Italy provides destinations and activities that will be treasured by your whole family. Across three major regions, this journey focuses on providing a balanced approach to travel with curated tours and activities that have been combined with plenty of time to relax on a beach with a good book. No matter what your family’s travel style is, the city of Naples, the Sorrentine Peninsula, and the exotic city of Palermo will bring you closer together and provide memories to last a lifetime.
Two-Week Highlights of Southern Italy Tour

14 Day Custom Tour

From $3,845

Southern Italy offers a genuine contrast to the icy elegance of the North as this is a land that has no time for the inauthentic. This luxurious, 14-day tour of the Bay of Naples, the Amalfi Coast, and Sicily’s capital is handcrafted to reveal what is unique about the South while offering all the sights, sounds, and flavors that have made Italy one of the most sought after destinations in Europe. From the heights of Mount Vesuvius to the depths of the Grotta Azzurra, this adventure will ensure that there is nothing to distract you from the rich heritage and cultural legacy that are waiting for you.  
Wonders of Sunny Southern Italy & Sicily Itinerary...

14 Day Custom Tour

From $5,595

Sun-swept valleys and glistening azure waters warmly greet you on your luxurious, 14-day adventure through Southern Italy. Journey through the soul-stirring Amalfi Coast, delight in the tantalizing natural beauty of the luxurious coastline, and explore candy-colored villages that cling to rugged cliffs and drop dramatically into the Adriatic Sea. Your dynamic two weeks in Italy will lead you to the heartbeat of the Roman civilization while simultaneously dazzling you with awe-inspiring landscapes.

Reviews of Zicasso's Referral Service

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4.88 stars based on 4493 reviews. See all our reviews.

Italy Review, Rome, Cinque Terre, Florence, Two-Week Trip...
5 Stars for this travel team! Our trip planner and his team

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Reviewed By Jan T.

Southern Italy Vacation Review: Sicily, Taormina, Positano,...
Our travel planner was very attentive and scheduled all

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Reviewed By Sally T.

Southern Italy Solo Tour Review: Amalfi Coast, Sorrento,...
I just returned from one of my best vacations ever! 

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Reviewed By Karen A.

Travel Review: Luxury Italy Vacation, Amalfi Coast, Puglia,...
As mentioned on the Zicasso website, they connected me to

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Reviewed By Marilou P.

Southern Italy Couple's Vacation Review: Sicily & Puglia...
My husband and I recently took a trip to southern Italy.

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Reviewed By Lauren B.

Northern Italy Travel Agent Review: Venice, Florence, Two-Week...
May 8, 2019This travel team planned a two-week trip for

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Reviewed By Dan &.

Southern Italy Luxury Tour Review: Amalfi Coast Journey,...
Our travel agent was fabulous. She developed a two week

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Reviewed By Thomas R.

Honeymoon to Italy Review: Positano Private Sunset Coastal...
I started working with the travel designer in April to plan

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Reviewed By Megan H.

Luxury Italy Honeymoon Review: Puglia, Matera, Coastline...
We used this travel company to plan and book our honeymoon

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Reviewed By Abby G.

Two-Week Italy Trip & Travel Agent Review
Completely top notch!  Completely happy that chose

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Reviewed By DOREEN C.

Italy Two-Week Trip Review
I would recommend this trip in a heartbeat! This trip planner

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Reviewed By Katerina T.

Travel Review: Italy Vacation, Venice, Rome, Naples, 2-Week...
We're senior citizens with mobility walking issues so we

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Reviewed By Cynthia I.