What I See From the Other Side of the Table during our Gems of Sicily Journeys
What hosting our guests has taught me, and how it shaped our Gems of Sicily journeys for 2027.
I have the best seat on every Gems of Sicily journey, and it is rarely the one with the best view.
From my side of the table, I watch a group of strangers figure each other out. I notice who asks the questions no one else thought to ask, who is already planning to return and when the person who arrived worried about travelling alone realizes they are no longer alone.
I also see Sicily through their reactions. The famous places impress them, of course. But often it is the winemaker’s story, an unexpected conversation or a place they had never heard of before arriving that they talk about at the end of the journey.
Watching this happen has taught me a great deal about how people experience Sicily and how we should design our tours.
For 2027, we have made some important changes. There are more opportunities to travel with us, a clearer choice between journeys hosted by Santi and Dara and those hosted by me, and the option to experience Eastern and Western Sicily back-to-back.
But before deciding what to add, we were very clear about what we would not change.
More journeys and a clearer way to choose
As Gems of Sicily has grown, so has the number of people asking to travel with us. Some are drawn to a particular part of the island. Others choose according to the time of year. Many want the opportunity to experience Sicily specifically with Santi and Dara.
For 2027, there are two clear ways to travel with us: Santi & Dara’s Sicily and our Eastern and Western Sicily Journeys, hosted by yours truly as the Gems of Sicily Tour Director.
This isn’t a division based on quality, group size or pace. Those standards remain consistent across every departure. The choice comes down to when you want to travel, where you want to go and who you want to experience Sicily with.
More opportunities to travel with Santi and Dara
For years, guests have followed Santi and Dara as they renovate homes, raise their family, navigate Sicilian bureaucracy and share the honest, sometimes chaotic reality of building a life here.
In 2027, there will be three opportunities to experience Sicily exclusively with them.
Santi & Dara’s Sicily has been shaped around the Sicily they personally want to share, bringing together different parts of the island with people, traditions and places connected to their story.
They will host one journey in May and another in October. They will also host our Family Journey at the end of June, designed for parents, grandparents and children who want to experience Sicily together without asking the adults to compromise on their own trip.
These are not existing tours with Santi and Dara added as hosts. Their involvement determines the itinerary and the experiences within it.
Eastern and Western Sicily, separately or together
In 2027, I will host two Western Sicily Journeys and two Eastern Sicily Journeys, with departures in late spring and again in early autumn.
Western Sicily is the part of the island I have come to know most intimately since making Palermo my home. It is layered, intense and often misunderstood. Its identity has been shaped by the sea, agriculture, centuries of outside influence and a strong sense of independence. Palermo, Marsala and the surrounding countryside each tell a different part of that story.
Eastern Sicily has its own character. Its baroque towns, markets, vineyards, coastline and volcanic landscape create an experience that feels entirely different from the west. It may appear more polished in places, but it is just as complex and certainly cannot be reduced to Taormina alone.
Keeping these as two distinct journeys allows us to spend meaningful time in each region without rushing across the island just to include more names on an itinerary.
But we also know that many guests do not want to choose one or the other.
That is why the Eastern and Western Journeys will run back-to-back in both spring and autumn. You can join one journey on its own or combine the two for a fuller experience of Sicily. The itineraries work together without repeating the same places or experiences, making it easy to continue from one side of the island to the other.
I will personally host each of these departures from beginning to end. My role goes well beyond managing logistics. I’m there to bring context to what we experience, look after the group and make sure each day runs as it should. Santi, Dara and I also remain closely involved in the design and operation of every journey.
What we are not changing
Growth often creates pressure to make things bigger. We have chosen to add more departures while keeping the groups small.
That decision is important.
I can see when a local host has learned everyone’s name. I notice when a guest feels comfortable enough to ask another question instead of quietly following the group. I know when the timing of a day gives people the chance to enjoy where they are without worrying about the next departure.
Those things become much harder to protect when a group gets too large.
Our approach to the people and places included in the journeys also remains the same. We work with hoteliers, chefs, winemakers, farmers, guides, drivers and families who understand what we want our guests to experience.
Some have worked with us for years. Others are newer relationships that have developed as we continue to explore Sicily ourselves. Either way, every inclusion is deliberate. A place has to offer more than a beautiful setting, and an experience has to add more than another activity to the itinerary.
What I hope you take home
I visited Sicily three times in four months before deciding to move here, so clearly the island had gotten under my skin.
I see a version of that happen with our guests. They arrive excited about the places on the itinerary, but when they write to us after the tour, they often talk about something else: a person they met, a meal they are trying to recreate or an experience that made them feel part of life here.
The group chats continue. Friendships continue. And yes, many start talking about coming back.
Of course, we want you to love the hotels, the food and everything we have planned. But more than that, we want you to form a genuine connection with Sicily.
It doesn’t have to make you move here. I may have taken things a little further than most.
But if a small part of Sicily comes home with you, then we have accomplished our goal..
Warmly from Sicily,
Priscilla
Tour Director, Gems of Sicily
P.S. We have just a few places remaining on our 2026 October Eastern Sicily Journey. If you've been dreaming about Sicily, we'd love nothing more than to welcome you .
Comments