Polignano a Mare in Puglia, Southern Italy
31,000+ 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.

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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 1024 verified traveler reviews.

Italy Tour Review: Venice, Florence, San Gimignano, Siena, Rome, Vatican, Amalfi Coast, Capri, Sorrento, Positano, Doge's Palace, Colosseum, Palatine Hill, Boat Ride, 12 Days

This was possibly the best trip of my life!

Once I arrived in Venice and put myself in the hands of Zicasso’s tour company, I was supremely well taken care of.

I left my passport on the plane, so I was held up in the airport for probably two hours. This was the first time I used the emergency number (or the chat app). The communication was answered immediately and we were able to let my first guide know I was being held up. I thought the first person who helped me was just someone to get me to the hotel, but she was also a guide in the sense that she described many of the things we saw on the way to the hotel. A very pleasant and gracious guide who made sure also that I was prepared for where to be the next day. It was a very great first experience of the tour company’s service.

Throughout this adventure, the guides were outstanding, the hotels were located practically on top of the interesting sites (especially in Rome) and very pleasant to be in.

Also, I continued to use the emergency number or the chat app multiple times. They were very responsive, very pleasant, and perfectly helpful each time. I don't know if I was high-maintenance compared to other clients the tour company has had, but though I felt like it in my mind, I was treated completely graciously each time.

I loved every destination and I loved having a structured tour, combined with a good portion of free time to explore on my own. Perfect.

I was very well guided on each travel day, being met by drivers to drop me off and to pick me up, and the train travel was very fun.

I think there was only one guide who I thought was just going through the motions, but all the other guides were the height of professionalism. I loved being met by our guides at Doge's Palace, which was absolutely outstanding. Walking around old Florence was great fun! The drive out to San Gimignano and Siena was well-planned and well-guided! In Rome, the guide who took us to the Colosseum and Palatine Hill was outstanding, and it was a great outing. (I had also already pretty much visited all the sights since my hotel was practically in the middle of it all.)

The trip to the Vatican was a whole other story. Unfortunately, I forget that guide's name. This guide was also excellent—entertaining, informative, approachable, and professional. The trip to the Amalfi Coast was a long train ride, followed by a very long car ride, but it was worth it. What a beautiful setting! My trip to Capri was absolutely fulfilling and I was a little sad to say goodbye to the guide—we connected with him so well. The next day was our boat tour from Sorrento to Amalfi and Positano. I absolutely enjoyed being guided by our guides! On the way back after that beautiful excursion, we were just cruising along the water, 1970s music playing, wind rushing by and I had a peak moment of happiness. Truly.

This trip was as if the tour company had read my mind and provided even more than I had imagined. I come away deeply grateful.

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Italy Trip Review: Sorrento, Positano, Amalfi, Ravello, Pompeii, Herculaneum, Naples, 5 Days

Zicasso’s travel company helped us plan and execute a vacation to the Amalfi Coast. The travel specialists suggested sites and arranged hotels, ground transport, and guides. It was all accomplished flawlessly; we had a perfectly paced itinerary.

Not only were the drivers well experienced with the incredible labyrinth of roads along the coast and in Sorrento and Positano, where we stayed, but they were also great sources of local colorhighly experienced with the incredible labyrinth of roads along the coast and in Sorrento and Positano, where we stayed, but they were also great sources of local color and conversation, and, above all, they conversation, and, above all, showed their love for the country and region.

We had several guides who were spot-on, including an archaeology graduate for Pompeii and Herculaneum, and an incredible historian on a walking tour of Naples.

The hotels were wonderful, with experience and professionalism throughout.

The drive along the coast to Amalfi and Ravello was spectacular!

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Italy Travel Review: Rome, Ravello, Amalfi Coast, Positano, Sorrento, Naples, Pompeii, Capri, Mount Vesuvius, Cooking Class, Local Cuisine, 20 Days

My husband and I were thrilled with our recent trip to Italy that Zicasso’s travel designer put together. We began by attending a family friend’s wedding, held in Ravello, on the Amalfi Coast. Due to my husband’s mobility issues, we were met by a driver and headed to the Amalfi Coast. The driver was first class and the trip was very comfortable.

After the wedding festivities, we were able to have the most wonderful experiences visiting the towns of Amalfi and Positano, and our base for one week was in beautiful Sorrento. We attended a cooking class and enjoyed eating what we prepared. We had in-depth learning opportunities in Naples and Sorrento. Every guide we had spoke excellent English and was so knowledgeable. We especially enjoyed Pompeii! A super-fun day was had on the small group tour of Capri. The crew was fantastic and very accommodating in consideration of my husband’s mobility issues.

From beginning to end everything went well. The use of a messaging app was great for making sure everyone was on the same page.

The only thing that was a disappointment was the pizza in Naples. It wasn’t the best.

The hotel in Sorrento was phenomenal - it couldn’t have been better. The view of Mt. Vesuvius from our balcony helped create memories we will have forever. The hotel in Rome was also very nice. It was right in the middle of the main attractions.

We are very happy with our experience with this travel company and would not hesitate to recommend it!

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Italy Tour Review: Rome, Bari, Positano, Sorrento, Naples, Amalfi Coast, 2-Week Trip

We had an amazing 2 weeks in Italy, from Rome, to Bari, Positano, Sorrento, and Naples. The planning and execution of our trip through Zicasso’s tour operator was flawless! They worked with me quite a bit in the planning phase to make sure this was going to be our dream trip.

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Italy Birthday Travel Review: Amalfi Coast, Rome, Pompeii, Mount Vesuvius, Capri, Ischia, Sorrento, Minori, Cooking Class, Winery, 10 Nights

Our trip to the Amalfi Coast, arranged by Zicasso's travel specialist, could not have been more perfect! All our travel ran so smoothly. It was so nice not to worry about arranging pick-up and transportation. We were even met right as we got off the plane in Rome! All the drivers and guides were excellent, sharing helpful tips that ensured we used our time wisely to see the most interesting sites.

The hotels were all wonderful, with perfect locations, beautiful and spacious rooms, and breathtaking views. Our food journey was inspiring, with lots of fish, buffalo mozzarella cheese, pasta, and even a wonderful cooking class at an organic farm for my birthday! A team member made sure all our restaurant reservations were secured and even tipped us off to a transit strike in Italy so we could arrive early at the airport.

The travel specialist's suggestion that we visit a winery on Mount Vesuvius and visit Pompeii was excellent, so fascinating! The travel specialist and her team also arranged boat rides for us in Capri and in Sorrento to Ischia, which were extra-special. Our Sorrento boat captain even brought a delicious chocolate cake to celebrate my birthday!

Thank you so much for arranging such a special birthday trip and for making our travel so effortless, a truly relaxing retreat!

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Italy Trip Review: Naples, Capri, Pompeii, Amalfi Coast, Ischia, Cooking Class, Boat Tour, 12-Day Tour

On the whole, we enjoyed our trip. However, we want to make note of a few things that could have been done better. When we landed in Naples, our driver was waiting for us. But instead of bringing the car to where we were, the 4 senior adults had to walk with luggage in the heat to get to his car. On our first full day in Naples, we were picked up for our cooking class. The driver did not speak any English, and when we arrived at the address, he expected us to get out of the car. We did not know where to go, and he was not able to assist us. Lucky for us, we met a nice lady who spoke English and was able to help us. The cooking class was wonderful. One of the highlights of the trip. The Capri boat tour was enjoyable. The tour of Pompeii was fascinating. The day we were taken to the Amalfi Coast was a holiday, and we mostly sat in traffic. Not anyone's fault but not very pleasant. On June 3 we were picked up very early to go to the port for the Hydrofoil to Ischia. At the port, we had to wait around for almost 2 hours. We were not sure why we were picked up so early. On June 6 we checked into our hotel in Naples, looking forward to our Jewish Heritage tour the following day. Our tour guide was lovely - 4 stars for her - but we learned there is no Jewish heritage in Naples, so that was quite disappointing. It would have been nice to establish realistic expectations.

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