Polignano a Mare in Puglia, Southern Italy
29,000+ Verified Traveler Reviews

Two Week Southern Italy Itineraries

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.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

Villa Rufolo in Ravello on the Amalfi Coast, Italy

13 Day Trip IdeaFrom $5,900

Best of Southern Italy Tour

Rome, Vieste, Alberobello, Matera, Positano +3 more
Mondello beach near Palermo, Italy

14 Day Trip IdeaFrom $6,300

Couple's Getaway: Two Weeks in Southern Italy

Naples, Pompeii, Sorrento, Amalfi, Positano +3 more
Coastal view with rock formations at the Tonnara di Scopello, Province of Trapani, Sicily

14 Day Trip IdeaFrom $7,100

Southern Italy Discovery in 2 Weeks

Sicily, Puglia, Scopello, Favara, Palermo (City) +2 more

14 Day Trip IdeaFrom $6,300

Ultimate Two-Week Family Vacation to Southern Italy

Naples, Pompeii, Sorrento, Amalfi, Positano +3 more
Cathedral of Palermo in Italy

14 Day Trip IdeaFrom $6,300

Two-Week Highlights of Southern Italy Tour

Naples, Pompeii, Sorrento, Amalfi, Positano +3 more
View of Town in Sorrento, Italy

14 Day Trip IdeaFrom $9,100

Wonders of Sunny Southern Italy & Sicily Itinerary

Sorrento, Ostuni, Alberobello, Matera, Tropea +5 more

How Zicasso Works

Here's how we create life-enriching, luxury travel experiences

  1. 1.Share Your Travel Dreams

    Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.

  2. 2.Meet Your Travel Specialists

    To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.

  3. 3.Design Your Perfect Journey

    Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

Learn More
The old part of Matera carved into the rock.

15 Day Trip IdeaFrom $6,800

Hidden Jewels of Italy’s Southern Route Tour

Rome,  Orvieto, Deruta, Bevagna,  Assisi +15 more

4.9

Reviews of Zicasso's Two Week Southern Italy Itineraries

Based on 6038 verified traveler reviews.

Tracy S.
Italy Trip Review: Bike Tour, 5 Nights

It was a great experience! Every activity was fun and interesting. The guides and drivers were wonderful. You made our trip so easy.

See more

Judy B.
Italy Trip Review: Rome, Milan, Venice, Lake Como, 1 Week

Everything went perfectly. We had such a good time. All our tour guides were expert historians. All the car pick-ups and trains went smoothly. We added a last-minute tour in another city and Zicasso's travel specialists were so accommodating. I highly recommend them.

See more

Michael W.
Italy Vacation Review: Florence, Tuscany, Umbria, Local Cuisine, Museums, 14-Day Trip

My wife and I recently returned from our first trip to Italy and want to highly recommend Zicasso's travel specialist and her company for creating the perfect vacation for us. It was a two-month process of back and forth, but no matter what we asked of her, she delivered several options.

We had a perfect mix of historical Florence and its museums, and wonderful restaurants, and the Tuscany and Umbria countryside experience. And on our first day, when our flight into Florence got diverted to Milan, we had the peace of mind that our travel specialist was there to help with her much appreciated support.

See more

Jess G.
Italy Tour Review: Mount Etna, Ravello, Wine Tasting, ATV Tour, Local Cuisine, 1 Week

Working with Zicasso’s travel specialist and the team was easy and wonderful. Our group enjoyed all of our excursions and tours. The drivers and guides were all wonderful, kind, and informative. Our arrangements for staying were clean, accessible, in great locations, and with incredibly friendly staff. The daily reminders were perfect and the few times we had questions, the response was timely and helpful.

See more

Richard S.
Italy Tour Review: Florence, Montepulciano, Tuscany, Pompeii, Cooking Class, Wine Tasting, Olive Oil Experience, 11 Nights

From start to finish, this was an amazing trip! All the accommodations were excellent, the tour guides were knowledgeable and engaging, our drivers were friendly and helpful, and the experiences (walking food tours, cooking class, wine tastings) were just what we wanted! We are extremely happy with the help we received from Zicasso's travel specialists, all the arrangements that were made, the communication throughout our stay—the entire trip!

See more

Sarah K.
Italy Travel Review: Local Cuisine, 3 Weeks

We loved our itinerary! We gave the locations we wanted to visit to Zicasso’s tour operator and they fit everything in. They were with us every step of the way and listened to feedback about any adjustments, and stayed within budget.

See more