`Gems of Sicily October 18 - October 26

Your Sicilian adventure begins!

Your adventure begins with a private transfer from Palermo Airport to our boutique seaside resort in Cefalu. With its stunning beaches, medieval charm, and scenic streets, Cefalù invites you to relax and unwind. Upon arrival, you’ll check into our hotel, where you can settle in and enjoy the seaside views. The magic of the coast will be yours to experience. That evening, we gather for a special Welcome Dinner  — a moment to savor local flavors, meet your fellow travelers, and begin uncovering the magic of Sicily. The dinner will be a mix of fish, meat and vegetarian, so it is something for everyone!

Take time to explore the seaside charm of Cefalù at your own rhythm. Wander the cobblestone streets of the historic center, discover hidden artisan shops, or climb to the top of La Rocca for sweeping views of the coastline. You might choose to bask on the golden beach, visit the stunning Norman Cathedral, or simply linger at a café with a gelato in hand, watching the world go by. However you spend it, this is your moment to soak in the effortless beauty and laid-back spirit of one of Sicily’s most beloved coastal towns.

After a leisurely day in Cefalù, we reunite for a sunset rooftop pasta making class with Priscilla — crafting Sicilian dishes and toasting our adventures with a festive aperitivo and pasta dinner under the stars.

Our journey takes us into the heart of the Madonie Mountains, where we arrive at the enchanting village of Castelbuono. Castelbuono is home to Santi and Dara! Nestled amidst breathtaking landscapes, this medieval town offers a glimpse into Sicily’s rich history and culture. We’ll enjoy a private tour, wandering through its charming streets, ancient churches, and local landmarks, uncovering the stories that have shaped this picturesque village over the centuries.

Next, we dive into one of Sicily’s most cherished traditions with an authentic caseificio experience. Here, you’ll witness firsthand the art of traditional Sicilian cheesemaking. From the careful selection of ingredients to the meticulous process of crafting cheeses like ricotta and caciocavallo, this experience will give you a deeper appreciation for the skill and passion that goes into every bite of Sicilian cheese.

As the sun begins to dip below the horizon, we’ll set sail from the charming port of Cefalù for an unforgettable sunset boat excursion. With the golden light dancing on the water and the dramatic coastline unfolding around us, this experience offers a new perspective on Sicily’s coastal beauty. Relax aboard as we cruise along the bay, sipping a chilled aperitivo and enjoying a selection of light Sicilian snacks. The mood is unhurried, the views are cinematic, and the moment is one you’ll want to savor—just you, the sea, and the glow of a Sicilian sunset.

A Day in Taormina — Sicily’s Crown Jewel

Today, we arrive in Taormina, a cliffside haven overlooking the sparkling Ionian Sea. With its mix of ancient history, coastal glamour, and effortless charm, Taormina invites you to explore at your own pace.

Wander the elegant Corso Umberto, lined with chic boutiques, artisan shops, and sunlit cafés. Step back in time at the breathtaking Greek Theatre, where sweeping views of the sea and Mount Etna create an unforgettable backdrop. Be sure to stop at the iconic Bam Bar for what many say is the best granita in all of Sicily—a refreshing local treat that’s as vibrant as the town itself.

Linger over lunch in the piazza, dip your toes in the turquoise waters of Isola Bella, or simply lose yourself in the timeless beauty of this enchanting town.

As golden hour approaches, we’ll gather together at Atlantis Bay—a luxurious seaside setting—for a sunset moment to remember. The sea glows, the air softens, and the beauty of Sicily comes alive in the light of day’s end.

Today is yours—to unwind, to discover, and to fall a little more in love with Sicily.

Immerse yourself in the heart of Sicily with a private street food tour of Palermo, guided by the passionate and charismatic Priscilla. As you stroll through the bustling streets, Priscilla will introduce you to the hidden culinary treasures that lie off the beaten path—flavors that few travelers get the chance to experience. Along the way, she’ll share fascinating stories and historical insights that bring the city’s vibrant food culture to life, from its bustling markets to its centuries-old traditions. This isn’t just a tour—it’s a journey through the soul of Palermo, where every corner has a story and every bite tells a tale of Sicily’s rich, diverse heritage.

After indulging in Palermo’s mouthwatering street food, we’ll venture into the heart of the city for a market tour, where you can browse the colorful stalls of local vendors selling everything from fresh produce to handmade goods. This is your chance to experience the pulse of Palermo’s everyday life, as locals barter and share in the lively atmosphere. Following this, you’ll embark on a historical tour, uncovering the layers of Palermo’s fascinating past, from its Arab influences to its Norman architecture, all while soaking in the city’s captivating sights.

Later, we make our way to the countryside resort—a true Sicilian gem. Nestled among centuries-old olive groves in the Selinunte countryside, Momentum Resort offers a peaceful retreat that blends modern comfort with natural beauty. This elegant eco-resort is thoughtfully designed to reflect the rhythms of the land—where earthy textures, open-air lounges, and a serene pool create an atmosphere of total relaxation. Each room is a calming space with minimalist style and soft, natural tones, inviting you to unwind between adventures. Whether you're sipping a glass of local wine on the terrace or enjoying the stillness of the Sicilian landscape, Momentum feels like a gentle exhale—a perfect home base for our journey.

The day begins with a relaxed morning, offering the perfect opportunity to either join a leisurely eBike ride through the Sicilian countryside or simply enjoy some free time to soak in the peaceful surroundings.

Our journey then takes us to the esteemed Planeta Winery, where you’ll experience an exclusive wine tasting set against the backdrop of rolling vineyards. Learn about the history and passion behind the wines, while savoring the rich flavors that have made Planeta a name synonymous with Sicilian excellence.

After indulging in the winery’s offerings, we travel back in time at Molini del Ponte, an ancient mill that offers a hands-on experience in the art of couscous making—an integral part of Sicilian culinary tradition.

Next, we take a leisurely walk with a certified tour guide through the colorful and historic city of Mazara del Vallo. As we wander the lively streets, you’ll have the chance to admire the city’s blend of ancient architecture, vibrant markets, and Mediterranean charm, all while learning about its rich cultural heritage.

The day concludes with a special seaside dinner that celebrates Sicily’s long-standing fishing traditions. Gathered at a local restaurant, we’ll indulge in a traditional seafood couscous feast, where the freshest catch of the day is paired with perfectly prepared couscous. It’s a meal that encapsulates the heart of Sicilian coastal cuisine, offering a fitting end to a day filled with culture, history, and unforgettable experiences.

Ease into the Sicilian rhythm with a slow morning at the resort, or set out on an eBike ride to explore the majestic ruins of Selinunte, one of Sicily’s hidden archaeological treasures.  
 

As midday approaches, we’ll head to the heart of the Sicilian countryside, where generations of tradition await. At a rustic family-run olive farm, we’ll be greeted by the warm embrace of Nanna Vita, the matriarch of the estate. Gather around her table for a heartfelt, farm-to-table lunch featuring estate-pressed olive oil, heirloom vegetables, handmade pastas, and other seasonal specialties. It's a glimpse into the true spirit of Sicilian hospitality—simple, soulful, and unforgettable.

Immerse yourself in the rich and storied history of Marsala with an exclusive private wine tasting and guided tour at the iconic Florio Winery—an esteemed establishment renowned for its centuries-old winemaking tradition and breathtaking coastal cellars. Following this unforgettable experience, enjoy leisurely free time to explore the charming streets of Marsala at your own pace, where colorful markets, historic architecture, and a lively Sicilian atmosphere await discovery.

Start your day with a rejuvenating soak in the natural hot springs of Segesta, where you’ll be surrounded by the tranquil beauty of the Sicilian countryside. The warm, mineral-rich waters offer a peaceful escape, allowing you to unwind in the midst of lush landscapes. After your soak, enjoy a leisurely countryside picnic, savoring fresh, local ingredients as you take in the sights and sounds of this serene environment.

In the afternoon, we make our way to the medieval hilltop town of Erice, a place where time seems to stand still. With its narrow cobblestone streets, ancient stone walls, and panoramic views of the surrounding countryside, Erice feels like a step back in history. A guided tour will reveal the town’s fascinating past, from its medieval roots to its rich cultural heritage. Before we leave, make sure to stop at one of the town’s quaint bakeries for a taste of Erice’s famous pastries, made with centuries-old recipes and local ingredients.

Next, we head to the ethereal Salt Flats of Trapani, a place where the shimmering white plains meet the blue sky in an almost otherworldly landscape. Here, you’ll explore the Salt Flats and the informative museum, learning about the region’s ancient salt production and the vital role it has played in Sicily’s economy and culture for centuries.

The day wraps up with a relaxed pizza dinner by the sea, where you can unwind with a delicious meal. It’s the perfect way to end a day of exploration and discovery in this beautiful corner of Sicily.

Enjoy a relaxed morning before private transfers to Palermo Airport.

You’ll leave not just with souvenirs, but with Sicily in your heart — the flavors, the friendships, and the timeless stories of the Gems of Sicily.

We’ve taken care of the details so you can relax, explore, and fully immerse yourself in the beauty of Sicily. Here's what you can expect on your journey:

✅ Included:

• 8 nights of curated accommodations with a focus on comfort and ambiance
• Almost all meals. Enjoy delicious, authentic Sicilian cuisine throughout the trip. Just 4 meals are left open for personal exploration.
• Group experiences tailored to help bring you closer to local culture
• Professional photographer to capture your key moments 

❌ Not Included:

• Flights to/from Sicily - You’ll book your own travel to and from Palermo (PMO).
• Personal Spending - This includes souvenirs, additional snacks, and any extra drinks outside our group meals. 
• Travel Insurance (Recommended)  For peace of mind, we recommend coverage through trusted providers like Wanderwell. 

Highlights:

• Breakfast daily
• 6 dinners, 5 lunches 
• A warm Sicilian welcome with apericena at a serene countryside resort in Selinunte
• Two wine tastings among the vines at a historic estates
• Decadent caseificio experience (cheese making)
• Professional photographer on select days to capture the essence of your experience in Sicily
• Olive oil tasting 
• Mill experience where you'll see the finest Sicilian grains transformed into flour for pasta, bread and couscous
• Sicilian pasta making class
• Palermo Street food tour
• Sunset stroll and seaside dinner in Mazara del Vallo
• Leisure time in towns Marsala and Cefalu
• Greek ruins at Archaeological Park of Selinunte
• A boat excursion along Cefalu's coast, complete with lunch and scenic swim stops
• Closing gala dinner at a vineyard
• Private transportation between all destinations
• Guided tours with certified tour guides of hidden gems, artisan visits, and cultural sites
• All Activity & Site Entry Fees. No hidden costs. If it’s on the itinerary, it’s covered.
• Airport Transfers at Palermo Airport (PMO) are included for a smooth arrival and departure. Airport transfers are only on days of arrivals and departure. If you arrive earlier or depart later than the tour date, you are responsible for your own transportation to and from airport.

Sicily You Won’t Find in the Guidebooks

At Gems of Sicily, Santi and Dara take you past the postcard-perfect views and into the beating heart of the island—the places only locals know, the stories that never make it into guidebooks, the flavors you won’t find in any restaurant.

⟡ Wander Hidden Villages – Step into forgotten towns where time stands still, where grandmothers still bake bread in ancient wood-fired ovens, and life moves to the rhythm of tradition.

⟡ Eat Like a True Sicilian – Forget tourist menus. We take you to places where you will eat like a local.

⟡ Meet the Real Keepers of Sicilian Culture – Wine is better when shared with the winemaker, stories are richer when told by the families who lived them, and food is unforgettable when made by hands that have perfected it for generations.

⟡ Travel Like Family, Not Like a Tourist – This isn’t a tour. It’s an invitation. We don’t just show you Sicily—we welcome you into our world, sharing the places, people, and traditions we love most.

Get to see the side of Sicily that most don't see!

Our exclusive small-group experiences are limited. We keep them intimate so every moment feels personal, every story feels real, and every encounter is unforgettable.

What You Will Experience

Welcome to an intimate, soul-stirring journey through Sicily’s western coast, where ancient landscapes, timeless traditions, and heartfelt hospitality converge. This is not a tour—it’s an invitation. A warm, sun-drenched welcome into the rhythms of real Sicilian life, curated by those who live it.

Your adventure begins at a countryside estate nestled among olive groves and vineyards, where you’ll be embraced by the serenity of nature and the charm of rural Sicily. A candlelit welcome dinner sets the tone—abundant, joyful, and brimming with local flavor.

As the days unfold, you’ll sip world-class wines at family-run estates, tour a working flour mill that preserves ancient grains and traditions, and explore the seaside town of Mazara del Vallo, where Arabic and Sicilian influences merge into one vibrant cultural mosaic.

Wander the medieval streets of Erice perched high above the sea, and marvel at the salt flats of Trapani—a stunning pink-and-white dreamscape. Evenings are filled with rustic dinners, folk music, and the kind of laughter that lingers long after the sun goes down.

Ride through the ruins of ancient Selinunte by bike, picnic under the Sicilian sun, and savor golden olive oil pressed from trees older than most empires. In Marsala, you’ll taste the namesake wine where it’s born, and wander the baroque streets that echo with history.

From there, the island reveals even more: Palermo’s electrifying street food, Cefalù’s romantic coastlines, rooftop cooking classes where pasta is made by hand and shared like a story, and afternoons with nothing to do but live slowly.

You’ll explore the dramatic beauty of Taormina, discover Castelbuono’s medieval charm, and step into a local caseificio for an unforgettable cheese-making experience. And on your final night, you’ll come together for a celebratory dinner under the Sicilian sky—one last gathering to toast a week of memories, connection, and transformation.

The History of Sicily: A Crossroads of Civilizations

Sicily is not just Italy’s largest island—it’s one of the most historically layered and culturally rich places in the world. Sitting at the heart of the Mediterranean, it has been a crossroads of civilizations for over 3,000 years, shaped by a powerful blend of cultures, conquests, and creativity.

Ancient Beginnings

Sicily’s story begins with the indigenous Sicani, Elymians, and Sicels, but it entered recorded history with the arrival of the Greeks in the 8th century BCE. They founded cities like Syracuse and Agrigento, transforming the island into a flourishing center of art, philosophy, and architecture. You can still walk among their temple ruins today.

The Romans and Byzantines

After centuries of rivalry with Carthage (including the famous Punic Wars), Sicily became Rome’s first province. Under Roman rule, it was known as the “breadbasket of the empire.” When the Western Roman Empire fell, the island came under Byzantine control, marking a shift toward Eastern Christian influence.

Arab Golden Age

In the 9th century, Arab (Muslim) rulers from North Africa took control, ushering in a golden age of agriculture, science, poetry, and architecture. They introduced citrus trees, irrigation systems, and a refined culinary culture that still influences Sicilian food today. You’ll feel their legacy most in towns like Mazara del Vallo and Palermo, where Arabic domes and street names remain.

Normans, Swabians, and a Royal Fusion

In the 11th century, Norman knights from Northern France conquered the island, blending Roman Catholic, Arab-Islamic, and Byzantine influences into one of Europe’s most unique medieval cultures. The result? A dazzling mosaic of cathedrals, palaces, and mosaics that reflect multiple faiths and styles—especially visible in places like Monreale and Cefalù.

Over the next few centuries, Sicily passed through the hands of various European dynasties, including the Swabians, Angevins, and Spanish Bourbons, each leaving their mark on the island’s language, architecture, and governance.

Modern Sicily

In the 19th century, Sicily joined the newly unified Kingdom of Italy, but the transition was not without struggle. Waves of emigration followed, especially to the United States, as Sicilians sought better opportunities abroad. Despite hardship, the island preserved its fierce identity and traditions.

Today, Sicily is a living tapestry—Greek temples beside Arab markets, Norman cathedrals above Roman roads. Its food, language, and rhythms still carry echoes of every civilization that ever called it home.

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