The majesty of Sicily will enrapture you with mythical tales, vibrant culture, indulgent cuisine, and ineffable history. Architecture seamlessly blends Arab and Norman influence. Markets present an atmosphere similar to a North African bazaar. The seaside glistens multiple shades of indescribable blue. The beauty of Greek ruins shares the spotlight alongside Baroque palaces. The wonderment of Mount Etna’s towering peak complements the five-star luxuries of your unforgettable accommodations. Your...
Customizable Itinerary
Day 1
Palermo - Passionate Palermo
Palermo is a city of splendor that encapsulates the history of Sicily. Vibrant cultures have influenced the city and the traditions of the locals for millennia. Historic structures glint gold in the sunlight. The city is draped in adventure, from the narrow medieval streets to the wide, proud boulevards. Your private transfer meets you at the airport and escorts you to your lavish accommodation located in the heart of the historic center. The vibrant markets showcase the melting pot past of the city. Tarps cover the stalls. Vendors call out to passersby. The bright colors of fresh produce, from bananas to pomegranates, burst from the stands.
When walking between the antique buildings it feels as though you have wandered into North Africa rather than strolling along a European cobblestone lane. Graceful architecture and imposing churches encircle the Piazza Pretoria. However it’s the Fontana Pretoria that is the center of attention in the square, a fountain with tiered concentric circles forming the base. Statues of nymphs, tritons, and leaping river gods decorate the elegant 16th-century structure. The neoclassical décor adds to the illustrious figureheads decorating the fountain and speaks to the ancient Greek history spanning the island. It now adorns the façade of Municipal Hall.
What's Included:
Day 2
Palermo - Mediterranean Bridge
Day 3
Palermo - High on the Medieval Hill
Day 4
Ragusa - Captivating Ancient Artwork
Day 5
Ragusa - A Brief History of Chocolate
Day 6
Ragusa - Where Modern and Ancient Life Mingle
Day 7
Taormina - Encircling the Peak
Day 8
Taormina - The Edges of Mainland Italy
Day 9
Taormina - Waving Farewell to the Sea
Trip Highlights
- Bask in the seaside splendor of Taormina, a picturesque resort city overlooking the marvelous waters of the Bay of Naxos
- Trek to the breathtaking summit of Mount Etna, the tallest volcanic peak in Europe, to see numerous active craters
- Indulge in sweet treats, with private confectionary lessons to learn the art of making traditional cannoli and celebrated Sicilian chocolate
- Delight in a wine tasting on an organic family owned and operated vineyard, which produces some of the most famous wine in Sicily
- Discover the Baroque beauty of historic towns across the island landscape
- Stroll alongside marvelous ancient Greek temples at the Valley of the Temples
- Enjoy a scenic gondola ride to the top of a mountain to explore the medieval streets of the charming town of Erice
Detailed Description
Ancient springs and gilded Byzantine mosaics, exceptional vineyards and charming citrus orchards, your 9-day best of Sicily tour encompasses the pleasures of the Italian island ranging from historic charms to natural majesty. You arrive in Palermo where your private transfer greets you at the airport. The city has a vibrant atmosphere meandering along the cobblestone streets of the historic city center. Your guide leads you on a private tour of the city to introduce you to the marvelous medley of Mediterranean life that has inhabited the island for millennia.
You continue to Monreale to visit the celebrated cathedral atop Mount Caputo. Your private transfer meets you in the lobby and escorts you to the fabulous hilltop town of Erice to explore the medieval streets. In Segesta, you step back in time to witness the magnificent Doric temple, one of the best-preserved Hellenistic temples on earth. The following day takes you along the paths routing to the remarkable Valley of the Temples to see the ancient Greek ruins.
Outside of Piazza Armerina, you witness the Roman estate of Villa Romana del Casale, which is filled with spectacular mosaics. Your guide leads you on the best Sicily tours of the ancient streets of Ragusa. Enjoy lunch at a Michelin-star restaurant before continuing to the Baroque town of Modica, where you can indulge in a chocolate tour, learning about the centuries-old traditions of the city’s celebrated sweet delectable. The next day brings you to Syracuse, a city that balances its ancient past with contemporary life. After your tour, you continue to the magnificent seaside city of Taormina.
You venture to the foothills of Mount Etna, trekking along the landscape on a guided tour to explore the craters. Your guide leads you across the Strait of Messina to visit the marvels of the National Archeological Museum of Reggio Calabria, which is filled with ancient Greek and Roman artifacts. On your last day in Sicily, your guide meets you at the hotel and escorts you to the airport. Instead of making your way home, you could extend your vacation with a visit to the Renaissance charms of Florence or the graceful remains of the Venetian Republic in Venice.
Starting Price
$4,100 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
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 5811 reviews.
The trip Zicasso's travel specialist arranged for us exceeded all our expectations. It was absolutely wonderful; not a single detail was overlooked. The hotels were excellent, the tours were great, and the drivers were always on time. I totally recommend Zicasso and the agency, and will undoubtedly use them for future travel plans.
Reviewed By Philip S.
Zicasso's travel designer did a terrific job. We had the initial phone consult, after which she delivered a first draft of the itinerary. From there, she helped guide us through a few revisions until we got the details smoothed out. We are experienced travelers and can appreciate a well-constructed trip, and that's what our experience with our agent reflected.
One crucial thing is that all the drivers who are engaged to move you around are prompt. Every one of them was right on time and friendly and helpful to boot. It was much appreciated.
To sum up our experience, I would do it all again with Zicasso and the agency and our agent. Our trip to Italy in the late summer of 2025 was something we will not soon forget!
Reviewed By tony B.
Zicasso's travel partner is very thorough and makes sure the trip is tailored to your vision. They are flexible and very responsive. We would recommend them to anyone traveling.
Reviewed By Evan C.
Zicasso's travel agency far exceeded our expectations. We had our five-year-old and 11-year-old children with us, so the tour guides and walking needed to be kid-friendly.
Our hotel in Rome was wonderful, the location was perfect, and they had good A/C and a breakfast buffet. There were plenty of great restaurants within easy walking distance, as well as the Vatican.
Our tour guide for the Colosseum and Roman Forum was great. Pompeii was amazing. Our tour guide was basically a celebrity down there and knew exactly how to take us around the ruins without ever waiting.
Tuscany was our favorite by far. We did a cheese-making experience and lunch that was super-cool. The kids got to play with the farm animals and the owners were so attentive and interesting. We did a cooking class with a chef that was the kids' favorite thing on the entire trip. I would make a point to book this experience; the kids still talk about it and wear the aprons around the house. The resort in Tuscany was nice. We had our own private pool, plus the resort pool, and could easily walk to a small local town with some great food.
Venice was good, but probably our least favorite on the trip. You have to walk a ton, which was difficult for the kids, but it's still worth experiencing.
We travel a bunch and I would highly recommend using Zicasso's travel partner.
Reviewed By Kevin S.
This was the best trip ever!!! I am so grateful Zicasso introduced us to our tour operator. This team was amazing! They set up a call to learn more about us and jumped into action. Within a short time, they came back to us with a presentation on ideas, with recommendations. There is no chance our trip would have been half as good without them. They even had a text group on standby while we were here in case we needed anything.
Reviewed By Linda C.
Zicasso's travel partner organized a fabulous trip for us to Italy. Everything from the minute we arrived in Venice to when we departed from Rome was perfectly arranged and seamless. Our hotels were superb! We so enjoyed all of the excursions/day trips.
We had been referred to Zicasso by a friend and we have passed the word on to other friends.
Reviewed By Janiece P.