
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

13 Day Trip IdeaFrom $5,900
Best of Southern Italy Tour

14 Day Trip IdeaFrom $6,300
Couple's Getaway: Two Weeks in Southern Italy

14 Day Trip IdeaFrom $7,100
Southern Italy Discovery in 2 Weeks

14 Day Trip IdeaFrom $6,300
Ultimate Two-Week Family Vacation to Southern Italy

14 Day Trip IdeaFrom $6,300
Two-Week Highlights of Southern Italy Tour

14 Day Trip IdeaFrom $9,100
Wonders of Sunny Southern Italy & Sicily Itinerary
How Zicasso Works
Here's how we create life-enriching, luxury travel experiences
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.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.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.

15 Day Trip IdeaFrom $6,800
Hidden Jewels of Italy’s Southern Route Tour
Reviews of Zicasso's Two Week Southern Italy Itineraries
Based on 700 verified traveler reviews.
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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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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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