
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 $5,100
Couple's Getaway: Two Weeks in Southern Italy

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

14 Day Trip IdeaFrom $5,100
Ultimate Two-Week Family Vacation to Southern Italy

14 Day Trip IdeaFrom $5,100
Two-Week Highlights of Southern Italy Tour

14 Day Trip IdeaFrom $7,300
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 2287 verified traveler reviews.
We (family of 4 including two teenagers) had a wonderful trip to southern Italy the last two weeks of June: Sorrento, Naples, Matera, Polignano a Mare (Puglia region). With Sorrento as our base we saw Positano/Amalfi Coast, Capri and Pompeii. In Puglia we visited Ostuni, Alberobello and Lecce, went to a wine tasting (with great wine!), and visited two masserias: one for an olive oil tasting, and another with a pasta-making class. Our travel agent at at this company helped us to plan a great itinerary. She was very flexible and helped us keep within our budget, and the logistics she put together were flawless. I also felt she truly listened to what we wanted - even her first draft itinerary was very close to the mark. Highly recommended.
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My wife and I have wanted to travel to Italy for almost a decade, so picking the right travel agent was a very important step for us. Zicasso connected us with several agencies. We ultimately selected this company and worked with this travel agent to plan our trip. We could not have been more pleased with our experience.
One of the reasons we selected this travel agent was because she was based out of Italy. We felt more comfortable with someone living in the country as opposed to a travel agent who had simply visited Italy. Her expertise definitely improved many aspects of our trip. Our must-haves included a multi-night stay in Rome and Pompeii. Our agent crafted a 11-day vacation for us that included Rome, Pompeii, Sorrento, Matera, and Puglia. Each detail of our trip was planned perfectly.
We were picked up by private automobile transport at the airport and had private tours through almost our entire trip. Our tour groups ranged in size from just us to 10 people. The tour guides that our agent selected were incredibly knowledgeable and personable. They were enthusiastic and clearly very passionate about their tours. She also recommended a variety of restaurants and made reservations for us for every evening we were in Italy. She offered options for each day and we were able to select the tours that best suited our interests (Roman Catacombs, Food tour, Jewish Ghetto, etc.). We had 4-star accommodations throughout the trip. Not only were all the hotels great, they were in perfect locations in the center of the cities we visited.
When it was time to travel to Sorrento, our agent arranged travel by train and then private automobile pickup to our final destinations. We spent a day in Sorrento, another day in Capri, and our last day touring the Amalfi coast. We were able to take a boat tour around Capri and visit multiple cities along Amalfi. We tried our first ever Michelin rated restaurant and it was delicious. We couldn't believe that she arranged for a private driver to spend 12 hours with us along the Amalfi Coast (he dropped us off at designated cities and picked us up an hour or two later).
For our next step, our agent took us off the common tourist path and had us visit Matera and Puglia. It was a great cultural contrast to Rome and Sorrento. We slept in a Grotto (hotel) in Matera and had splendid views of the country and old city. In Puglia, we visited a winery and dined along the Adriatic Sea.
It was a memorable trip that we could not have been more thankful for. During multiple times on the trip, my wife and I remarked how lucky we were to have a travel agent so knowledgeable.
Our agent called us several times to check-in on us and immediately remedied a situation where our itinerary was forced to change. We had her number 24-7 for any needs. We had a stress-free trip. We could not have planned this trip on our own, so we are grateful to have had our agent's wisdom. We had contemplated doing our own research, but we could not have recreated the magic of this trip.
When we travel to Italy again, we will definitely be using this travel company!
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We just returned from a two week trip to Italy. We spent a week on the Amalfi Coast staying in Positano for five nights and Ischia for two nights. We then traveled to Sicily for a week staying in Palermo for two nights, Siracusa for three nights and Taormina for two nights. Our travel agent planned a detailed and well thought out itinerary for us. We saw and experienced Italy in a way that would not have been possible on our own. In particular in Sicily we did several private walking tours of the cities and the ruins and we learned so much about the history of this island and about the people who live there. All the hotels our travel agent booked for us were terrific. Every transition from place to place went off perfectly. All the drivers were always on time and very pleasant as were the guides we had on our tours. We did have one glitch when leaving Ischia when our ferry boat was cancelled due to rough seas. Our agent had provided us with a phone to reach her should a need arise. When I called about the ferry she was already working on this problem for us. We did get on a larger boat and our vacation continued without a problem. We really had a wonderful trip! If we return to Italy for another visit we would not hesitate to call this agent for help in planning our next trip.
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