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Two Week Southern Italy Itineraries

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The charms of Southern Italy are ever-lasting. From the ancient Greek temples on Sicily to the whitewashed villages of Puglia, traditions persist throughout. Your two-week itinerary to Southern Italy will encompass everything you want in a personalized vacation. Immerse yourself in the Mediterranean lifestyle when you plan with a local expert.

How Zicasso Works In 3 Simple Steps

  1. 1

    Describe your dream two-week Southern Italy vacation.

  2. 2

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

  3. 3

    Book the trip when you are satisfied.

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Tailor Made Itineraries

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

Villa Rufolo in Ravello on the Amalfi Coast, Italy


Best of Southern Italy Tour

13 Day Custom Tour

From $3,557

Your 
best of Southern Italy 13-day tour is tailored to show you the splendor of the seaside, countryside, and charming towns set across the historic landscape. From the quiet streets of Pompeii, you can still see the zenith of Mount Vesuvius lingering in the distance. The Blue Grotto in Capri glows with a distinctive light shining beneath the water. The ancient glories of Rome emanate from the Colosseum, and the villas decorate the countryside that once belonged to celebrated emperors. A remodeled restaurant hides in an ancient cave, where locals have resided for thousands of years.

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Mondello beach near Palermo, Italy

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.

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Immerse yourself in the beauty of the land and sea on the coast of Scopello, Sicily.

Southern Italy Discovery in 2 Weeks

14 Day Custom Tour

From $4,335

A soulful ambiance with ancient splendor, sun-bleached coastline, and enticing cultural cuisine immerse you in the beauty of land, sea, and heritage during your luxury two-week Southern Italy tour. Explore gripping history from Greek settlements to Arab traders. Savor the culinary prowess at the Crossroads of the Mediterranean. Enjoy the natural beauty that accentuates established cities as you discover the grandeur of Sicily and Puglia at your pace.

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Discover Sicily and its bustling capital, Palermo.

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.

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Skyline and Bay in Naples, Italy.

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.

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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.

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Benefits of Using Zicasso

Plan Your Trip with
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Your Itinerary Tailor-Made
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For more information on how to make your dream journey a reality, get connected with a top travel specialist by filling out a Trip Request.

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Reviews of Zicasso's Referral Service

4.89 stars based on 4232 reviews.

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

Reviewed By Bill T.

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

Reviewed By Gerald N.

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

Reviewed By Christopher S.

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

Reviewed By ANDrew C.

Italy Trip Review: 2-Week Tour
"Having our own "tour specialist" to help with unexpected...

Reviewed By Mike P.

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

Reviewed By Deborah F.