Capturing a dramatic view of Mount Etna volcano on a summer day seen from the Ancient Greek Theater of Taormina, Sicily, Italy

Exclusive Sicily Travel Experiences

Sicily, an island steeped in history, culture, and natural beauty, invites you to explore its treasures through bespoke, luxury experiences.

At our Italy-based agency, we specialize in creating personalized Sicily itineraries tailored to your unique interests. Whether you’re visiting iconic landmarks like the Valley of the Temples or enjoying private wine tastings in sun-drenched vineyards, every aspect of your trip is designed to provide you with an unforgettable experience.

Discover Sicily Beyond the Ordinary with a Private Trip Tailored Just for You 

Sicily’s beauty is unparalleled, but this captivating island holds even more than meets the eye. With our in-depth local knowledge and strong relationships with trusted partners, we offer you exclusive access to Sicily’s hidden gems, going far beyond typical tourist attractions. Indulge in authentic culinary experiences, explore ancient traditions, and enjoy the luxury of handpicked accommodations that reflect Sicily’s charm. From historical tours to bespoke leisure experiences, every detail of your journey is crafted to match your unique interests, ensuring your Sicilian escape is truly remarkable.

Uncover Sicily’s rich history, vibrant culture, and extraordinary flavors with a bespoke journey, designed by our experts with private guides and curated stays.

Our Italian Difference

At Nancy Aiello Tours, we don’t just travel across Sicily—we unveil the island’s ancient soul through the eyes of those who have inherited its rich tapestry of cultures. As Sicilians ourselves, we invite you into a world where Greek temples, Arab gardens, Norman palaces, and Baroque towns create an experience unlike anywhere else in Italy, allowing you to discover our homeland’s passionate spirit and timeless traditions.

  • Sicilian Heritage Keepers: Our local team shares insights cultivated through generations on this island crossroads, transforming standard sightseeing into revelatory journeys across landscapes shaped by millennia of Mediterranean civilizations.
  • Island Connections: Enter our community of olive farmers, ceramic masters, and culinary families whose ancestral techniques have been preserved through centuries, welcoming you into countryside estates and workshop kitchens where Sicily’s true character flourishes.
  • Hidden Trinacria: Experience the island beyond Taormina—dawn fishing rituals in ancient ports, hillside vineyards cultivated on volcanic soil since Roman times, and evening passeggiatas where village elders share tales of Sicilian history that textbooks never captured.
  • Authentic Luxury: Navigate Sicily’s diverse landscapes with local confidence while our meticulous coordination transforms the island’s complexity into effortless elegance, allowing you to surrender completely to the seductive blend of cultures that makes Sicily an empire of the senses.

Italy Trips to Inspire

Explore our curated sample itineraries, then let our experts craft a bespoke journey tailored to your desires with luxury and insider access.

Exclusive Luxury Stays in Sicily

Indulge in comfort with our handpicked selection of luxury accommodations, each offering unique charm and service.

Indulge in Italy’s Richness, Handcrafted for You

Explore authentic, private encounters that seamlessly integrate into your bespoke itinerary, creating unforgettable moments tailored to you.

Our Travel Advisory Services

BESPOKE ITINERARIES

Whether you are planning your honeymoon, your first family trip or your 50th wedding anniversary, we curate creative, tailor-made Italy trips that enrich your life.

INSIDER ACCESS

We know a thing or two about Italy travel. Our local access to exceptional experiences, insiders, and accommodations, result in memories that last a lifetime.

COMPLETE SUPPORT

Before, during, and after your trip. From start to finish, we keep close tabs on your journey and are here to make everything as enjoyable and effortless as possible.

Ask Our Italian Advisors

Sicily is a beautiful place to visit year-round, but the best time to visit is in the late spring and autumn months. Go from May to the beginning of June, and from September to the beginning of October, when the island looks lush and the water is warm enough to swim in. If you’re planning to visit during the peak summer months (July and August) the region can get very busy. You can also consider traveling in November and December as the weather is pretty mild and you can enjoy the festive Christmas season with few tourists around. Not all luxury hotels might be open during the winter months, though.

Absolutely, Sicily is worth visiting! This largest island in the Mediterranean Sea offers a captivating blend of historical significance, natural beauty, and cultural richness, making it a truly unforgettable destination for any type of holiday and for every type of traveler. And if that wasn’t enough to tempt you the food in Sicily is some of the best in the country. Expect fresh cannoli, incredible seafood, and a symphony of flavors. See our Palermo, Sicily Travel Guide.

If you want to see the highlights and get a taste of the island, yes, 10 days is a good amount of time. With ten days you can encounter a slice of Sicily and its wonderful coastlines, culture, and ancient ruins. We have brought together two sample itineraries on our website that show off these highlights and more, but these are primarily meant to spark inspiration. We will design your trip from scratch mapping your time frame, personal interests, priorities, and travel style onto our deep regional expertise.

Sicily can be a fantastic vacation destination for families offering a delightful mix of beautiful beaches, rich history, delicious food, and family-friendly activities. On top of that Sicilians are known for their warm hospitality and love for children. For inspiration see our ultimate itinerary for experiencing the best of Sicily with kids. With expert planning this ancient island can be the perfect place to relax and create lasting family memories.

As expected, most travelers come to Sicily by air. You can flight nonstop from the U.S. to Palermo. You can also flight from Europe to Catania. Throughout the process, we’ll advise on the best way to travel in and out of Sicily.

Ready to Uncover Sicily’s Hidden Gems?

Explore Italy’s Iconic Destinations, Tailored for You

Why Nancy Aiello Tours?

Destination Experts

  • At Nancy Aiello Tours, we live, breathe, eat, and sleep Italy, the country we are proud to call home.
  • We use our insider knowledge, relationships, and expertise to create one-of-a-kind journeys and experiences that you will cherish for a lifetime.
  • Whether you’re planning a family vacation, honeymoon, or romantic escape, we’re here to create an authentic luxury travel experience that will stay with you forever.

Unique to You

  • You won’t find packaged trips here, or any set dates either. That’s because every one of our trips is specifically designed and scheduled around your interests and needs.
  • From honeymooners to baby boomers, millennials to multi-generational families, every itinerary we design is unique to each client's travel style.
  • We want to give you the most memorable and rewarding luxury vacation possible, and we’ll work closely with you to create an itinerary that exceeds your hopes and expectations.

Carefully Curated

  • With 16+ years of success, we’ve built a coveted collection of top-notch properties, immersive experiences, and local experts.
  • Our insider connections mean that these extraordinary luxury travel opportunities are always a part of our itineraries no matter where you decide to go.
  • Wherever you go, we can connect you with some incredible people, including artists, art historians, chefs, and many more so you have a truly personalized and enriching luxury travel experience.