Polignano a Mare in Puglia, Southern Italy
30,000+ 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.

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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 700 verified traveler reviews.

Italy Luxury Travel Review: Amalfi Coast, Puglia, Sicily, History, Local Cuisine, Bike Tour, Cooking Class, 2 Weeks
"We recently had an amazing trip in southern Italy, organized by a Zicasso tour company that I can't recommend enough!"

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Italy Trip Review: Amalfi Coast, Rome, Ravello, Sorrento, Wine Tasting, Cooking Class, Shopping, 1 Week
"We had a fabulous trip. Zicasso’s travel agent provided a very good itinerary and was very responsive."

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Italy Luxury Honeymoon Review: Amalfi Coast, Small Towns, Capri Boat Trip, Shopping, Cuisine, 1 Week
"I would send any of my friends who wanted to travel to Italy to Zicasso to plan a seamless trip. I could never have navigated this myself."

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Italy Trip Review: Taormina, Agrigento, Palermo, 8 Nights

Our Zicasso travel specialist did a fantastic job planning our family vacation for five adults.

Each hotel was top-notch. At the villa in Taormina, the rooms were luxurious, with unbelievable views of the bay and Mount Etna from private verandas. The staff were gracious and the restaurant's breakfast buffet delicious. Lunch and dinner were top-notch. The hotel in Agrigento was modern and the grounds were exceptional. It was close to the Valley of the Temples, with amazing views of the ruins from each room and the beautiful infinity pool. The hotel in Palermo was old-fashioned luxury with up-to-date facilities and close to the old town.

Our tour guides and drivers were excellent.

My only regret is that we only had 10 days to explore Sicily as there was so much more to see!

Our agent did a yeoman's job helping us plan this trip.

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Italy Trip Review: Naples, Apulia, Lecce, Otranto, 13-Day Trip

We had the good fortune to be introduced to Zicasso's travel consultant in 2024. She planned for us a perfect trip through Amalfi and Sicily. We were so impressed with her professionalism, attention to detail, and communication that we did not hesitate to seek her out for Naples and Apulia in June 2025. Her guides (who were always special) and drivers are dedicated to her.

Last year, I recall saying you should stay away from Google, tell her your vision, and let her do the rest. She will present every option. We did want to fine-tune a few small preferences this time, but overall, I would give the same advice. We find her to be exceptional and have told her so.

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Italy Vacation Review: Capri, Amalfi, Positano, Cooking Class, Wine Tasting, 1 Week
"I have been on many trips with several travel companies. This was among the most memorable. Zicasso’s agents were great communicators."

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