Our Approach To Experiencing Sicily
Personal by Nature. Professional by Design.
Gems of Sicily brings together the warmth and flexibility of personal hosting, and the organization, accountability and consistency of a professional tour operator.
Each itinerary is developed as a complete journey rather than a collection of bookings. Our Sicily-based team coordinates the route, accommodation, transportation, reservations, local specialists, meals and experiences so that timing is realistic, transitions feel natural and guests are supported from arrival through departure.
Your dedicated host remains with the group throughout, becoming the familiar point of contact for the entire experience. They are backed by an established network of trusted partners and the operating standards of a fully licensed Sicilian tour operator, allowing personal attention and professional delivery to work together every day.
Designed for Travelers
Who Value Depth
The best journeys begin with the right fit.
You will likely feel at home with us if you:
✓ Love food, wine and culture, and want to understand Sicily beyond the surface
✓ Appreciate comfort, thoughtful organization and an unhurried pace
✓ Prefer the warmth of a small group and the ease of a dedicated host
✓ Want the important details handled, with time to explore and recharge
A different style of travel may suit you better if you:
✕ Want to cover the maximum number of sights in the shortest time
✕ Are looking for a nightlife-led holiday
✕ Prefer to plan and control every detail of each day yourself
We focus on the kind of journey we do best: personal, generous and deeply connected to Sicily.
Personally Hosted
The person who welcomes you on the first day is still there at the final breakfast. Your host travels with the group, shares meals, answers the questions that arise between stops and handles changes without turning them into your problem. As the days unfold, they learn how the group moves and what each guest needs.
On Santi & Dara’s Sicily and Sicily for Families, Santi and Dara host the group from beginning to end. On our Eastern and Western journeys, Priscilla is your host throughout, with Santi and Dara joining for selected experiences.
Archaeologists, local guides, winemakers and artisans join us when their specialist knowledge belongs in the conversation. Your Gems of Sicily host remains the familiar presence connecting those encounters into one coherent journey.
Food, Wine & the Everyday
In Sicily, food and wine carry the story of the island. Markets reveal the season. Vineyards explain the landscape. Family recipes hold generations of memory, and the table is where strangers so often become friends.
These moments are woven naturally through every journey: a conversation with a winemaker, lunch where the ingredients were grown, a familiar dish understood in a completely new way. They offer a sense of place that no list of landmarks could ever provide.
Your Hosts
Gems of Sicily is hosted by people who live here, know the island deeply and care about how it is shared. Each brings a different perspective; all share the same commitment to making guests feel welcomed, comfortable and connected.
Santi & Dara
Santi was born and raised in Sicily, surrounded by the family traditions and everyday rituals that continue to shape his understanding of the island. He shares the meaning behind the things visitors often see but rarely have the chance to truly understand.
Dara, a Sicilian-American, brings the warmth and ease that make people feel immediately part of the experience. Together, they share Sicily through stories, humour, food and the relationships that have grown around them.
They host Santi & Dara’s Sicily and Sicily for Families from beginning to end, and join selected experiences on the Eastern and Western journeys.
Priscilla
Priscilla is Gems of Sicily’s Tour Director, a Canadian chef and food-and-wine expert who made Sicily home. Her understanding of the island has been shaped through its kitchens, vineyards, producers and the life she has built here.
She hosts every Eastern and Western journey throughout, bringing warmth, calm direction and a deeper appreciation of Sicily’s food, wine and culture. Her role is to make each day flow naturally, help guests feel at ease and bring meaning to the places and experiences along the way.
For Priscilla, hosting is personal. Sicily changed her life, and sharing it thoughtfully is at the heart of everything she does.
The Gems of Sicily Standard
The route and host may change, but every departure is built and delivered according to the same promises.
• Small groups, personally hosted from beginning to end
• Exceptional stays chosen for comfort, atmosphere and a genuine sense of place
• Food and wine selected for quality, context and connection
• People we know and work with personally, so encounters feel generous rather than staged
• Thoughtful pacing that leaves room to enjoy where you are
• Transfers, reservations, timing and day-to-day changes handled by the team traveling with you
