Text image with the phrase 'GEMS OF SICILY' in large, white capital letters on a black background.

Sicily is more than just postcard-perfect beaches and famous landmarks—it’s a land of untold stories, hidden villages, and centuries-old traditions waiting to be explored. Gems of Sicily Tours invites you to step beyond the ordinary and experience the island like a true insider.

At Gems of Sicily, we design intimate culinary and cultural journeys rooted in slow travel and real human connection. Our tours take you beyond the expected - into vineyards overlooking the sea, family-run kitchens, historic villages, and the stories of everyday Sicilians.

Every experience is crafted with intention, warmth, and local insight.

We offer three distinct ways to explore Sicily:

Boutique Sicily Tours for Travelers

Who Want More Than a Vacation

Family Tours

Playful, connected, stress-free journeys designed for kids, parents, and grandparents.

Think: beach days, gentle adventures, cooking together, and time to slow down.

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Signature Tours

Our most loved experiences — small-group, food-and-wine-focused journeys revealing Sicily’s culture, landscapes, and local producers.

Think: markets, vineyards, coastal towns, ancient sites, and hands-on cooking.

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Elite
Tours

Luxury itineraries featuring boutique hotels, private tastings, heritage estates, and curated once-in-a-lifetime experiences.

Think: exclusive access, high-end stays, private boats, premium wineries.

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Couple holding hands walking in front of historic building with statues and ornate architecture, sunny day.

why travel with

gems of sicily

Welcome! We’re Dara and Santi and we don’t just create tours, we build the Sicilian experience we have always wanted to share with the world.

As a Sicilian family, we share with you the Sicily we know and love. We combine Santi’s Sicilian roots and my American curiosity, bringing you a unique perspective you won’t find anywhere else. Santi, born and raised here, holds the deep, local knowledge of family traditions, secret spots, and timeless stories. I (Dara, short for Dorotea) arrived as an American with Sicilian roots, falling first for the island and then for Santi. I bring the fresh eyes and understanding of what fellow travelers seek and need.

Together, we’ve crafted Gems of Sicily to give you the perfect balance: the iconic sights you've dreamed of, paired with the tucked-away treasures and authentic moments that most visitors never find.

This is more than our business; it's our passion. We invite you to explore Sicily not as a tourist, but as our guest—to experience the rich history, the vibrant culture, and the warm connections that make this island so special.

Come, discover the Sicily we call home. We can’t wait to share it with you.

Group of people walking through a vineyard on a sunny day with a hill and blue sky in the background.

Exclusive Access

Step beyond closed doors into historic sites that remain untouched by mass tourism.

  • Walk through private estates and noble villas where generations of history come to life.

  • Experience ancient spaces and sacred places that few outsiders have ever seen.

  • Enter family-run vineyards and olive groves where the owners personally share their stories and techniques.

  • Unlock the secrets of Sicily’s past in hidden locations that aren’t on any map.

Two men working in a cheese-making facility, one stirring a large pot of curd using a wooden paddle, the other handling cheese molds, surrounded by containers and equipment.

Authentic Connections

Meet the local artisans who carry on Sicily’s rich traditions.Walk through private estates and noble villas where generations of history come to life.

  • Spend time with artisans who have dedicated their lives to preserving Sicily’s heritage.

  • Experience the daily life of fishermen, farmers, and craftsmen in remote villages.

  • Take part in long-standing traditions that most visitors never witness.

  • Step behind the scenes of Sicily’s cultural treasures.

Vineyard with rows of grapevines on a hillside, framed by palm trees against a blue sky with scattered clouds.

Undiscovered Beauty

Step beyond closed doors into historic sites that remain untouched by mass tourism.

  • Walk through private estates and noble villas where generations of history come to life.

  • Experience ancient spaces and sacred places that few outsiders have ever seen.

  • Enter family-run vineyards and olive groves where the owners personally share their stories and techniques.

  • Unlock the secrets of Sicily’s past in hidden locations that aren’t on any map.

Plate of spaghetti with tomato sauce topped with sliced almonds and garnished with an olive branch.

Flavors You’ll Never Forget

Taste Sicily the way it was meant to be enjoyed.

  • Savor meals prepared with ingredients harvested just steps from where you dine.

  • Taste wines crafted by families who have been making them for centuries.

  • Indulge in authentic recipes passed down through generations.

  • Dine in extraordinary settings where the atmosphere is just as memorable as the food.

A woman with long dark hair smiling while holding a woven basket filled with leafy green vegetables in an urban street scene.

Meet your hosts

Dara shahraki

Dara is an American marketing professional and digital creator who followed love to Sicily a decade ago. What began as a cross-cultural adventure with her husband, Santi, has grown into @Santindarainitaly, a lifestyle and travel brand that celebrates authentic Italian living.

As the Founder of Gems of Sicily, Dara noticed a growing desire among travelers (American & Canadian) for genuine, heart-filled experiences that go beyond the guidebooks. Together with Santi, they have created a series of boutique tours that invite guests to experience the island through its people, traditions, and stories.

Founder & your host

A woman with red hair wearing a blue dress and a beige sun hat, holding a woven basket, smiling against a plain light-colored wall.

Priscilla Stuart

Tour director & host

Priscilla Stuart is a seasoned chef and WSET sommelier, Level 3 candidate, from Montreal, Canada, who followed her heart to Sicily in 2022. Drawn by the island’s vibrant markets, soulful cuisine, and centuries-old winemaking traditions, she found in Sicily not just inspiration but a new way of life.

As Tour Director of Gems of Sicily, Priscilla curates intimate eno-gastronomic journeys that invite travelers to experience Sicily through its land, people, and table. Each itinerary reflects her passion for authentic connection, sharing meals with local chefs, tasting wines among the vines, and discovering the stories behind every dish and glass.

Blending her culinary background with a deep appreciation for Sicilian culture, Priscilla brings warmth, expertise, and a true sense of place to every tour, celebrating the simple, beautiful way of life that captured her heart.

What Our Guests Say

  • Lori

    “Taking a leap of faith for my first solo international trip was a tough one. The only other time I traveled outside of the USA was with my mother (rip). Thank you Dara and Santi for opening up your hearts and home and making the Gems of Scicily tour so magical. It was beautiful how 14 strangers came together and soon felt like traveling with family. Your attention to details and special touches were so thoughtful and kind. Don’t be surprise if you see me back in one of your future tours. I miss you already. Kisses to the girls.”

  • Cate

    “The Gems of Sicily experience was truly unforgettable. What made it so special was the chance to see, taste, and feel Sicily like a local—not just as a visitor. From quiet hilltop towns to hidden coastal towns, every moment felt authentic and personal. Dara brought the island to life with warmth, insight, and a deep love for the culture. I left feeling connected—not just to the place, but to the people.”

  • Susan

    “Gems of Sicily is a unique opportunity to travel with locals, providing access to experiences that are not necessarily available through other tour companies.

    The hosts and their travel partners are outgoing and very personable, resulting in a lively and fun experience.”

  • Steve

    “Santi. I just wanted to again thank you for everything. Lisa and I had a great time on the Gems of Sicily tour, thanks to you and Dara. It was an amazing experience.

    Lisa and I returned to the USA last night after visiting Parma, Lake Garda, the Dolomites and Milan. We Miss everyone on the tour.

    It was a pleasure meeting you and your entire family. Your daughters are beautiful and I know they are lucky to have you as their dad.

    You are a good friend and I hope to see you soon.”

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Intimate . Immersive

Unforgettable

Ancient Greek temple ruins with tall stone columns, blue sky, greenery, and the ocean in the background.
A pile of fresh yellow lemons, with one cut lemon showing the inside, displayed for sale at a market.
Three people smiling and enjoying outdoor scenery, wearing sunglasses, with trees and a clear blue sky in the background.
A group of tourists gathers by the water's edge in a seaside town with white and stone buildings and a hillside in the background on a sunny day.
Hands holding a wooden plate with fried croquettes on a decorated table set for dining.
A group of five friends enjoying desserts at an outdoor cafe with colorful murals of mythological figures on the wall behind them. They are smiling and taking a selfie.
A young girl and an adult man smiling during a cooking activity, with the girl kneading dough on a wooden table, set against a backdrop of a sunny outdoor area and a bar with various bottles.
A bowl of chopped red chili peppers with olive branches and green olives, surrounded by slices of grilled bread.
A woman with curly blonde hair leans on a ledge while overlooking a small Italian village with red tiled roofs, surrounded by green hills and mountains under a partly cloudy sky.
A close-up of numerous small, ripe cherry tomatoes on vine. The tomatoes are red, with some attached to green, hairy stems.
Group of people on a boat near a coastal town with rocky hills in the background, sunny weather, and clear blue water.
Group of women taking a selfie on a boat in the ocean, all wearing sunglasses and sun hats under clear blue sky.
Photo of a historic building with arched colonnades, multiple windows, and stone architecture, under a partly cloudy sky.
A close-up of a Margherita pizza topped with fresh basil leaves, cherry tomatoes, mozzarella cheese, and tomato sauce, inside a pizza box.
People sitting on a stone wall overlooking a landscape with ocean, mountains, and cloudy sky.
A large historic church with ornate architecture, statues, and bells, situated in a busy plaza with people and outdoor seating.
Colorful ceramic sun and moon wall decorations with smiling faces and expressive features, arranged on a textured background.
A display of various fresh fruits at an outdoor market, including apples, pears, blueberries, peaches, and melons.
Fresh green salad with herbs and shredded cheese on a white rectangular plate, placed on a tablecloth with lemon and orange patterns.
A woman in a black dress and a wide-brimmed hat walking up the steps of an ancient Greek or Roman style building with tall columns and decorative details at dusk or early evening.
A rectangular infinity pool overlooking a rural landscape with trees and rolling fields, under a partly cloudy sky.
A young girl with a big smile in a pink swimsuit is floating in the pool with a pool noodle, surrounded by three people swimming nearby in blue water.
A group of people on a boat enjoying a sunny day, holding drinks, with clear blue skies and water in the background.
A dining area with several round tables covered with white tablecloths, surrounded by vintage-style chairs, in a rustic restaurant with exposed brick walls, wooden ceiling beams, large windows, and decorative green plants on the walls, with hanging l

A journey like no other

Our tours are not just vacations but they are invitations into our world. Led by Santi & Dara, a Sicilian-American couple passionate about storytelling and adventure, each trip is crafted to be intimate, immersive, and unforgettable.

Whether you're exploring ancient ruins, learning traditional cooking methods, or sipping wine under the Sicilian sun, you’ll leave with more than memories - you’ll take home a piece of Sicily in your heart.

A woman and a young girl holding a peach in front of a fruit stand with fresh vegetables and fruits at a market with a green awning labeled "ALIMENTARI Prestianni".
Group of tourists posing in front of ancient Greek ruins with large stone columns in a sunny, outdoor setting.

Ready to taste

the real sicily?

We would be honored to welcome you.

Every tour is handcrafted with care, heart, and deep local knowledge.

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Get in touch

Whether you're ready to book or just dreaming about your Sicilian getaway, we're here to help. Send us a message, and we’ll get back to you as soon as possible!

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