Polignano a Mare in Puglia, Southern Italy
country flag

Two Week Southern Italy Itineraries

Ratings of Zicasso's Service
<p>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.</p>

The charms of Southern Italy are ever-lasting. From the ancient Greek temples...

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.

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

Ratings of Zicasso's Service
Villa Rufolo in Ravello on the Amalfi Coast, Italy

Best of Southern Italy Tour

Places Visited: Rome, Vieste +6 more
Places Visited: Rome, Vieste, Alberobello, Matera, Positano +3 more

13 Day Custom Tour

From $5,900

Mondello beach near Palermo, Italy

Couple's Getaway: Two Weeks in Southern Italy

Places Visited: Naples, Pompeii +6 more
Places Visited: Naples, Pompeii, Sorrento, Amalfi, Positano +3 more

14 Day Custom Tour

From $6,300

Coastal view with rock formations at the Tonnara di Scopello, Province of Trapani, Sicily

Southern Italy Discovery in 2 Weeks

Places Visited: Sicily, Puglia +5 more
Places Visited: Sicily, Puglia, Scopello, Favara, Palermo (City) +2 more

14 Day Custom Tour

From $7,100

Ultimate Two-Week Family Vacation to Southern Italy

Places Visited: Naples, Pompeii +6 more
Places Visited: Naples, Pompeii, Sorrento, Amalfi, Positano +3 more

14 Day Custom Tour

From $6,300

Cathedral of Palermo in Italy

Two-Week Highlights of Southern Italy Tour

Places Visited: Naples, Pompeii +6 more
Places Visited: Naples, Pompeii, Sorrento, Amalfi, Positano +3 more

14 Day Custom Tour

From $6,300

View of Town in Sorrento, Italy

Wonders of Sunny Southern Italy & Sicily Itinerary

Places Visited: Sorrento, Ostuni +8 more
Places Visited: Sorrento, Ostuni, Alberobello, Matera, Tropea +5 more

14 Day Custom Tour

From $9,100

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

Places Visited: Rome,  Orvieto +18 more
Places Visited: Rome,  Orvieto, Deruta, Bevagna,  Assisi +15 more

15 Day Custom Tour

From $6,800

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

Featured Articles

Italy Travel Guide
Florence, Italy
Italy Travel Guide

From Roman ruins to the Tuscan countryside, there is something for every traveler in Italy.

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 tour.

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.

Read More    >
Top 7 Things to Do in Sicily
Ancient theatre of Taormina in Sicily with Mount Etna in the background at sunset
Top 7 Things to Do in Sicily

From cultural tours of Palermo to unique wine-tasting experiences, we share the top things to do in Sicily when traveling to Italy.

The island will captivate you with timeless ruins, classic culture, and mouthwatering gastronomy. From Mount Etna to the shoreline, its scenery has shaped its culture, with cities hiding touches of ancient wonder. From delicious food and wine to volcano trekking, reminders of the classical world, and a breathtaking coastline, these are the essential things to do when you visit Sicily.

Extraordinary travel begins with a human touch and our destination specialists design every journey with care, insight, and personal attention. As you consider a visit to Sicily, use the following information as a guide before connecting with our travel experts to ...

Read More    >

Reviews of Zicasso's Referral Service

4.9 stars based on 5806 reviews.

Italy Vacation Review: 9 Nights

Zicasso's travel agent helped to make our trip to Italy truly memorable. He listened to our interests and formulated a vacation that was unforgettable.

Reviewed By Barbara M.

Italy Tour Review: Amalfi Coast, Ischia, Capri, Positano,...

We booked an amazing trip with Zicasso's travel partner and his travel team, which, pleasantly, far exceeded our expectations. Every detail was perfectly planned out, from the moment we were greeted at the airport in Naples by our driver to the private tours, boat excursions, and Amalfi drive. Our accommodations were top-notch.

He made planning this trip stress-free, and we enjoyed every moment. It was first-class treatment all the way, without the hassle of trying to coordinate all of the logistics ourselves. Thanks to our agent for providing us with an amazing, personalized, trip of a lifetime!

Reviewed By Jeanine P.

Italy Tour Review: 10-Day Trip

Zicasso's tour partner helped put together the trip of a lifetime. She provided many great suggestions of things to do and places to visit in Italy. I was very pleased with her ability to coordinate the details of the trip, from hotel reservations to private transportation and excursions/tours. We were so busy that by the end of the day, we were worn out. When we plan our next trip, I am going to personally ask to work with her again, she became part of our family with her personalized service.

Reviewed By Robert C.

Italy Trip Review: Rome, Amalfi, Positano, 12 Days

The trip Zicasso's travel specialist arranged for us exceeded all our expectations. It was absolutely wonderful; not a single detail was overlooked. The hotels were excellent, the tours were great, and the drivers were always on time. I totally recommend Zicasso and the agency, and will undoubtedly use them for future travel plans.

Reviewed By Philip S.

Italy Travel Review: Lake Como, Ostuni, Private Boat Tour,...

Zicasso's travel designer did a terrific job. We had the initial phone consult, after which she delivered a first draft of the itinerary. From there, she helped guide us through a few revisions until we got the details smoothed out. We are experienced travelers and can appreciate a well-constructed trip, and that's what our experience with our agent reflected.

One crucial thing is that all the drivers who are engaged to move you around are prompt. Every one of them was right on time and friendly and helpful to boot. It was much appreciated.

To sum up our experience, I would do it all again with Zicasso and the agency and our agent. Our trip to Italy in the late summer of 2025 was something we will not soon forget!

Reviewed By tony B.

Italy Tour Review: Calabria, 11 Nights

Zicasso's travel partner is very thorough and makes sure the trip is tailored to your vision. They are flexible and very responsive. We would recommend them to anyone traveling.

Reviewed By Evan C.