31,000+ Verified Traveler Reviews

Two Week Sicily Itineraries

The astounding island of Sicily welcomes visitors ready to display its many wonders. From the ancient Greek temples to the local seafood cuisine, a quintessential two-week Siciliy itinerary is best designed with the aid of one of Zicasso’s expert travel specialists that will immerse you in the island’s Mediterranean essence from cliffside views to sea infused wines.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

Olive grove in Sicily, Italy

14 Day Trip IdeaFrom $6,300

Slow Food & Leisurely Wine Tour of Southern Italy and Sicily

Catania, Tropea, Matera, Lecce, Benevento +11 more
Traveling couple on the waterfront, Sicily

14 Day Trip IdeaFrom $6,300

Unforgettable Romantic Getaway Tour to Sicily

Palermo, Erice, Agrigento, Modica, Valley of the Temples +6 more
Ragusa, ancient baroque city in Sicily, Italy

14 Day Trip IdeaFrom $6,300

Discover Sicily Tour: A Feast for the Senses

Palermo, Taormina, Erice, Syracuse, Ragusa +1 more
Gorgeous view of the Calabria, Italy coastline

14 Day Trip IdeaFrom $6,300

Best of Southern Italy & Sicily Tour

Rome, Tarquinia, Caserta, Naples, Pompeii +14 more
Ancient theater in Taormina, Sicily, Italy

14 Day Trip IdeaFrom $6,300

Best of Sicily and Southern Italy Tour for Seniors

Sicily, Palermo, Mount Etna, Il Capo, Segesta Erice +15 more
Skyline of Florence, Italy

15 Day Trip IdeaFrom $6,800

Best of Italy and Sicily Tour

Rome, Pisa, Florence, Venice, Assisi +6 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.

Learn More

4.9

Reviews of Zicasso's Two Week Sicily Itineraries

Based on 847 verified traveler reviews.

Sicily Vacation Review: Syracuse, Noto, Ragusa, Modica, Ortigia, 1 Week

We had a fabulous time in Sicily. It was our first visit and Zicasso’s travel company planned an excellent itinerary, with great recommendations on the cities and towns to visit that felt like a truly local experience. (Other agents focus on the big cities of Palermo and Taormina, but the travel company recommended we spend more time in Syracuse/Noto, Ragusa, and Modica.)

We loved our primary driver and the boutique hotels they selected for us. Communication and documents were all easy to follow.

The only piece we wish might have been curated a little more was the recommended dining options. There were too many and not necessarily great restaurants.

See more

Italy Trip Review: Taormina, Agrigento, Palermo, 8 Nights

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.

See more

Italy Vacation Review: Sicily, Temples, Cathedrals, Cooking Class, Boat Tour, 2 Weeks
"Zicasso’s travel agency planned the trip of a lifetime for us. They were attentive, communicated with us daily, and responded to any concerns."

See more

Italy Travel Review: Rome, Ortigia, Modica, Agrigento, Noto, Marzamemi, Taormina, Winery Visit, Food Tour, Mt Etna, 9 Nights

Overall, I loved all that was planned for me by the travel specialist. She did a great job planning the transfers, tours, and activities we discussed during our planning. In particular, I loved my tour of Modica, the winery visit, my visit to Agrigento, and my visit to Noto and Marzamemi. I also loved my hotel in Ortigia - the location, the architecture, the views. I wish I had requested a sea view for my Taormina hotel, as not having that felt like a miss. I did not like at all the hotel in Rome (in spite of its convenient location) - it was a miss after such a glorious trip.

Every single tour guide and driver was excellent, knowledgeable and reliable. The initial personal fast track transfer in Rome was also excellent, and I requested the same service when I was leaving.

I would have liked the food and wine tour in Taormina to be a bit more elevated, given I am a foodie with elevated tastes. The local Sicily organizer, was very responsive overall. I just found it strange that she did not follow through on her offer to pay for a dinner because I chose my own venue.

The reason I am not giving this trip a 5 is because of a few issues: the room in Taormina and the hotel in Rome. The trip started strong with the transfer support and I wish it had been included at the end - I paid an additional fee for it. I also paid a significant additional fee for a private tour to Mt. Etna, which was given by the same person who drove me there. I feel like I overpaid for that tour. I canceled the Etna Food and Wine tour and wish I had gotten some consideration for that.

Stepping back, I am grateful for the trip and all the detailed organizing that went into it. I will look more closely at hotels offered so I avoid being disappointed.

See more

Italy Vacation Review: Palermo, Ragusa Ibla, 20 Days

Zicasso’s travel agent and her team were very responsive when we needed assistance. We definitely didn't need three weeks in Sicily—there's not that much to see. Three of the hotels were great and two not so great, but again, the travel agent's team was quick to find us a better alternative. Thanks to the travel agent and her team.

See more

Italy, Greece Tour Review: Palermo, Messina, Mount Etna, Agrigento, Taormina, Rome, Cooking Class, Wine Tasting, 9 Days

Originally, we had booked a Turkey/Greece itinerary with a Zicasso affiliate. Due to the outbreak of Middle East hostilities, we canceled the Turkey portion of our trip and decided to replace it with Sicily/Rome. Zicasso’s travel specialist, with very little time to spare, developed an agenda that synced up with our remaining plans in Greece. The result was extraordinarily professional.

The detailed agenda, with descriptions, times, locations, and contact information, left nothing to chance, giving us great peace of mind. The drivers and tour guides were very professional. Most of our guides had PhDs! Foodie tours in Palermo, cooking classes in Messina, wine tasting on Mount Etna (with a five-course meal!), archaeological and historic sites with informed insights... amazing! Our hotels and restaurants were first class!

The travel specialist did a great job of involving us in the selection process. Kudos! Our airline ticketing was also handled seamlessly, with no glitches.

We would highly recommend this travel company!

See more