This luxurious 14-day Southern Italy tour has you traveling through revered regions and back-country villages to uncover tales of ancient cultures and modern delicacies. Luxuriate on the beaches in Sicily after sipping homemade wines, marvel at spectacular views from a Norman Castle, admire art and architecture in magnificent cathedrals, witness active volcanoes, and learn how to make cannoli during your majestic experience of Southern Italy.
Customizable Itinerary
Day 1
Taormina – Attend a Performance at the Greek Theater
The transparent waters of the Ionian Sea will welcome you as your plane touches down at Catania Fontanarossa Airport. Your private driver will be waiting for you and will promptly usher you to your luxurious accommodation, which will be located in the heart of Taormina. You will meet your guide at your hotel after you check-in to explore the fascinating town by foot. In the evening, you will travel back in time by visiting Teatro Greco, which is the Greek Theater. Here, you can walk in the footsteps of the ancient Greeks and learn about the history of their settlement in Sicily.
What's Included:
Day 2
Taormina – Indulge in a Food and Wine Tour
Day 3
Taormina – Hike along Dried Lava Beds
Day 4
Cefalu – Admire Byzantine Mosaics and Castle Ruins
Day 5
Cefalu – Delight in a Wine and Cheese Tasting
Day 6
Cefalu – Watch a Volcanic Eruption on Stromboli
Day 7
Ostuni – Soar through the Skies on a Private Jet
Day 8
Ostuni – Partake in the Art of Crafting Olive Oil
Day 9
Ostuni – Wander through a Maze of Trulli
Day 10
Positano – Tour the Ancient Civilizations in Matera
Day 11
Positano – Sip Homemade Limoncello
Day 12
Positano – Splash in the Blue Grotto
Day 13
Naples – Venture through the Ruins of Pompeii
Day 14
Naples – Depart for Home
Trip Highlights
- Stroll through town and learn about the history of Taormina, which will be followed by an open-air performance at a Greek Theater that was built in the 3rd Century BC
- Explore phenomenal scenery from the remote village of Castelmola while enjoying a uniquely flavorful almond wine
- Indulge in a thrilling hike to the summit of Mt. Etna for a Sicilian picnic that will be complete with spectacular views
- Admire Byzantine mosaics and ancient Norman architecture as you immerse yourself in the dynamic history of Cefalu
- Learn the art of producing traditional Madonie Provola cheese, which will be followed with a local Sommelier who pairs these cheeses with Sicilian wines
- Island-hop through the remote Aeolian Islands to enjoy a wine tasting in Salina and to watch Stromboli’s volcano erupt against the dark night sky
- Craft your own cannoli in Palermo before jetting off to the sun-soaked Puglia Region in a private jet
- Wander through the whimsical town of Alberobello as you curiously admire the unique design of a trullo
- Uncover centuries worth of history and culture as you venture through the pre-historic streets of Matera
- Appreciate the fine art of production of homemade Limoncello as you sip the sweet and tangy delicacy in the shade of a family-owned lemon grove
- Cruise to the luxurious island of Capri in a privately chartered boat and explore the hilltop village of Anacapri
- Meander through the wide streets of Pompeii to learn about ancient culture and life in the shadow of Mt. Vesuvius
Starting Price
$6,300 per person (excluding international flights)
What's Included
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Reviews of Zicasso's Referral Service
4.9 stars based on 5976 reviews.
Zicasso's travel agent created an itinerary and experience that was simply perfect. Every hotel experience, guide, and driver was excellent. She was kind, patient, knowledgeable, and made the perfect suggestions. I loved working with her! Thank you to our agent, the tour operator, and Zicasso for a wonderful trip!
Reviewed By Anita L.
The trip was wonderful. Zicasso's travel agent and her staff planned the perfect 10-day trip. The accommodations, the drivers, the guides, and the restaurant recommendations were perfect. The communication was excellent and timely. They went above and beyond to make sure we were comfortable and happy. The staff were very attentive and flexible, even when we wanted some small changes, such as pick-up times for the drivers. They adapted and made it all work. This travel agent is absolutely terrific.
Reviewed By Marci M.
Our Italy trip with Zicasso’s travel partner was nothing short of spectacular! Referred by a friend who had an amazing experience, we decided to give it a try and were not disappointed. Our agent was fantastic, always ready with answers to our questions and providing excellent support throughout our journey.
In Tuscany, we visited beautiful wineries and enjoyed a delightful lunch with the vintners, who were incredibly warm and welcoming. Her attention to detail was evident when she adjusted our plans due to weather changes and even checked in on us when we were slightly delayed for a tour.
Siena was breathtaking and our hotel in Rome was perfectly located, allowing us to walk to all the major sites. One of the highlights was a small boat tour around Capri from Amalfi—perfect weather and stunning waters made it unforgettable. The cooking class on the Amalfi Coast, set on the side of a cliff, was exceptional and having personal tours just for the two of us was an unexpected and delightful bonus.
We can't express enough how much we enjoyed our Italy trip. The travel partner exceeded our expectations and we highly recommend them for a truly memorable experience!
Reviewed By Kent S.
Zicasso’s trip coordinator and her team did a fantastic job, not only in planning the trip to meet our needs and wants, but also in personalizing it as needed. They were also available as we needed them to adjust things, such as pickups, and even made some dinner reservations for us. With our budget, they set us up in excellent hotels that fit our desire for the trip to be a wonderful anniversary getaway. Her staff were also very helpful. We would strongly recommend them for a trip to Italy!
Reviewed By Rajesh J.
Zicasso's travel planner and her staff did a perfect job for our family of six. She made our trip seamless!
Everything she planned was perfect and no detail was left out. I would use them again and again for my travels to Italy.
Reviewed By Sally F.
My first solo trip was something I had dreamed about for years. I wanted it to be more than sightseeing. I wanted adventure, comfort, safety, and freedom without the stress of planning it all alone. Through Zicasso, I was connected to two specialists and Zicasso's travel consultant stood out immediately. She delivered an itinerary that gave me everything I asked for and more: maximum cities, maximum fun, and maximum value, all without compromise.
Before deciding, I researched and compared tours, packages, and individual prices online. The travel consultant’s proposal came out on top for value and content. While the other agent offered fewer cities and activities at a higher price, her plan was ambitious without being overwhelming. She booked my trains, arranged private transfers where needed, and selected boutique-style hotels that exceeded expectations. I was honestly surprised at how good they were. I stayed at hotels in Interlaken, Florence, and Sorrento. Each was clean, comfortable, and perfectly located for exploring. I had prepared myself for budget trade-offs, but instead, I found thoughtfully chosen hotels that balanced affordability with real quality.
Every document, train ticket, and activity confirmation was uploaded into the app. It became my lifeline throughout the trip, with every detail at my fingertips. The structure gave me confidence, while still leaving me free to explore.
Switzerland came first: Zurich, Lucerne, Interlaken, and Zermatt. Each city felt like stepping into a postcard. Interlaken gave me the adrenaline rush of skydiving, while Zermatt charmed me with its close-knit magic and alpine beauty. Italy unfolded with equal ease: Lake Como, Venice, Florence, Sorrento, Amalfi, and Rome. Every destination felt curated, yet natural, from gondola rides in Venice to boat tours on the Amalfi Coast.
What I loved most was the balance between structure and freedom. Pre-booked activities and restaurant reservations gave me a strong framework, but I could just as easily decide to spend an afternoon wandering Florence, eating gelato, or sitting in a piazza. The rhythm of the trip was perfect, structured enough to tick off bucket-list highlights, yet relaxed enough to feel like a real vacation.
Food was freestyle, but memorable. Highlights included a Japanese-Peruvian restaurant in Zurich with its elegant Japanese-Peruvian flavors, a different Japanese restaurant, a restaurant in Como with its modern fusion menu, an Indian restaurant for comforting classics, and international favorites like those in one of the restaurants in Rome. Between those meals and plenty of gelato and crepes, every stop added its own flavor to the journey.
As a solo traveler, safety mattered. I felt comfortable walking around in the evenings and was usually back in my hotel by 1am to stay rested for the next day. What really gave me peace of mind was the travel consultant’s constant support. Communication was fast and responsive. I never had to wait long for answers, whether through the app or email. There was a moment when I made a mistake with the trains and missed an activity. She immediately stepped in and worked to reschedule it or secure a refund that same day.
Earlier in the planning process, I also had a card issue due to an address error. Even though policy would not normally allow it, she and her team patiently waited until I received the refund before finalizing the booking, just weeks before my trip. That flexibility and care spoke volumes.
The difference was clear. She used my budget to its fullest potential, giving me more destinations, more experiences, and better hotels than the alternative option. She managed to combine the efficiency of a fully organized tour with the freedom of independent travel. Everything was planned, yet everything was still mine to shape.
This trip was everything I wanted: good food, beautiful views, safety, and absolute reliability. It was an organized journey with freestyle flexibility, which is exactly what solo travelers dream of. The travel consultant’s planning let me chase adventure while always knowing I had a safety net. Switzerland and Italy gave me memories I will never forget, but it was the behind-the-scenes planning that made it possible. If you want a trip that is your way, your budget, your pace, but without the endless hassle of managing it yourself, the travel consultant at this agency is the person who can make it happen. My first solo trip became my dream trip and that is the highest praise I can give.
Reviewed By tasmia S.
