Polignano a Mare in Puglia, Southern Italy
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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

Dynamic pricing from $4,636

Your 13-day best of Southern Italy tour is tailored to show you the splendor of the seaside, countryside, and charming towns set across the historic landscape. See the zenith of Mount Vesuvius lingering in the distance at Pompeii. The Blue Grotto in Capri glows with a distinctive light. The ancient glories of Rome emanate from the Colosseum. A remodeled restaurant hides in an ancient cave. Experience how true luxury emerges from the diverse landscape and lavish history of Southern Italy. 

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Mondello beach near Palermo, Italy
Couple's Getaway: Two Weeks in Southern Italy

14 Day Custom Tour

Dynamic pricing from $5,007

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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Coastal view with rock formations at the Tonnara di Scopello, Province of Trapani, Sicily
Southern Italy Discovery in 2 Weeks

14 Day Custom Tour

Dynamic pricing from $5,637

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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Ultimate Two-Week Family Vacation to Southern Italy

14 Day Custom Tour

Dynamic pricing from $5,007

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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Cathedral of Palermo in Italy
Two-Week Highlights of Southern Italy Tour

14 Day Custom Tour

Dynamic pricing from $5,007

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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Beautiful view of town in Sorrento, Italy
Wonders of Sunny Southern Italy & Sicily Itinerary

14 Day Custom Tour

Dynamic pricing from $7,275

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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Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
Travel Worry-Free
Every Time
24/7 support and local assistance for every moment of your vacation.
The old part of Matera carved into the rock.
Hidden Jewels of Italy’s Southern Route Tour

15 Day Custom Tour

Dynamic pricing from $5,365

On this 15-day tour through the south, you will find the incredible hidden jewels that go far beyond the Amalfi Coast and Pompeii, where you venture down to the heel of Italy’s boot and find precious gems along the coastline and even remnants of Greek history, some hiding within the caves. The magnificence of Southern Italy goes beyond Naples and into a region that no longer needs to stay hidden.

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Our Italy Travel Guide provides helpful tips and inspiration from must-see destinations and top activities to the best time to visit. Discover traditional food and wine, inspirational culture, and amazing cities on a personalized vacation.

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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Top 7 Things to Do in Sicily
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Top 7 Things to Do in Sicily

Sicily is a treasure of Italy that captivates visitors with timeless ruins, classic culture, and mouthwatering gastronomy.  The scenery has shaped the culture from Mt. Etna to the shoreline, gorges to arid hills with cities hiding touches of ancient wonder. From captivating wines to delicious local recipes, volcano trekking to remainders of the Classical world and inspiring coastline, these are the essential things to do when you visit.

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Reviews of Zicasso's Referral Service

4.89 stars based on 4414 reviews.

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

Reviewed By Francesca P.

Southern Italy Vacation Review: Sicily, Pompeii, Lunch &...
"I was very impressed with our guides, they were well above...

Reviewed By Mary D.

Italy Family Trip Review: Rome, Sorrento, Food, Culture,...
"Our trip concierge, Renata, was responsive and friendly...

Reviewed By Danielle G.

Italy Family Trip Review: 2-Week Vacation
"From our first call to the last moment of our trip Cameron...

Reviewed By Stefani K.

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

Reviewed By Thomas F.

Italy Family Trip Review: 2-Week Tour
"Thanks to Cameron and her team, we didn't have to stress...

Reviewed By Elena S.