Hosted by
SANTI & DARA
Dates
October 15-24, 2027
Maximum Group Size
14 guests
The journey at the heart of Gems of Sicily, shaped by the places, people, and traditions that tell Santi and Dara’s story. It follows Sicily from energetic Palermo to the open landscapes of Marsala, then finishes beside the sea in Cefalù.
Because Santi and Dara host the journey throughout, Sicily is shared personally: through conversation, introductions, meals, and the everyday moments that rarely appear in an itinerary.
The moments that stay with you
Settle into Cefalù before spending a day among the villages and traditions of the Madonie.
Keep a full day open for the sea, a long lunch, or simply enjoying where you are.
Visit Segesta and local cheesemakers on the way to Marsala.
Cross the salt lagoon to Mozia and dine with winemakers.
Experience Palermo through its food and history before cooking and celebrating together.
Your hosts
Santi and Dara travel with the group from beginning to end. Their presence brings the journey to life through lived knowledge, warm introductions, shared meals, conversation, and the everyday moments that make Sicily feel personal.
Select Your Room Type
Please select Single or Double Occupancy
Reserve your spot now by paying a deposit - the balance is due 60 days before your journey starts
What Happens Next
Once your reservation is confirmed, a member of our team will be in touch to guide you through the next steps and answer any questions you may have.
Journey Overview
CEFALÙ & THE MADONIE
A seaside welcome, historic streets, mountain villages, agriturismo traditions, and a free day.
MARSALA
Segesta, cheesemaking, salt landscapes, Mozia, winemakers, and Nanna Vita.
PALERMO
Markets, street food, free time, hands-on cooking, and a final dinner together.
What's Included
✔ Carefully selected hotels and countryside properties chosen for comfort, location, atmosphere, and warm Sicilian hospitality.
✔ Private transportation and airport transfers for effortless movement between destinations
✔ Thoughtfully planned meals, allowing you to simply relax and savor each bite (Select meals are intentionally left open for your own discovery and personal dining experiences)
✔ A collection of elevated and immersive, hand-selected experiences curated exclusively for your journey
✔ All site entries and activity fees
✔ Private local guides who bring depth and meaning to every place you visit
✔ Visits to vibrant local markets and immersive culinary moments
✔ Marsala salt pans, windmills, and private boat experience
✔ Guided visit to an archaeological park with a live sunset concert among the temples
✔ Historic town explorations and guided cultural tours
✔ Artisan cheese-making experience with tasting
✔ Winery visits with cellar tastings and intimate dinners with local winemakers
✔ Charming village visit and cultural immersion in the Sicilian mountains
✔ Farm-to-table countryside experiences
What's Not
Airfare to and from Sicily
Gratuities, offered at your discretion
Personal expenses and individual purchases
Four meals left open for your own discovery, giving you the freedom to explore and dine as you choose
Hotels
Vineyard Estate Stay
A charming historic wine resort set among vineyards overlooking the sea and the Egadi Islands, where classic Sicilian character meets warm hospitality and sweeping sunset views.
Countryside Resort Retreat
A tranquil countryside retreat surrounded by olive groves and Mediterranean landscapes, featuring stylish rooms, spa facilities, and a peaceful atmosphere designed for true relaxation.
Chic Boutique Palermo City Hotel
A refined, centrally located hotel overlooking one of Palermo’s most elegant squares, offering comfortable modern rooms and easy access to the city’s historic streets, markets, and vibrant local life.
Sample Itinerary
Over ten days, the journey unfolds from Cefalù’s Ionian coastline and the mountain villages of the Madonie to Marsala’s wine country and salt landscapes, ending in the markets and historic streets of Palermo.
Day 1
Arrival in Cefalù
Cefalù offers a gentle beginning: sea air, golden stone, and time to settle in. That evening, the journey formally opens over a warm welcome dinner together.
Day 2
Cefalù & Coastal Life
Cefalù is a place to notice slowly, the curve of the bay, the life of its narrow streets, and stories held in stone. With context and conversation along the way, the town begins to feel familiar.
Day 3
The Villages of the Madonie
The Madonie reveals a more intimate Sicily of mountain villages and enduring traditions. An agriturismo lunch anchors the day, which closes in the relaxed spirit of apericena.
Day 4
Cefalù at Leisure
A whole day is left beautifully open: the beach, a favourite café, a walk through town, or lunch with nowhere else to be.
Day 5
Ancient Sicily & Cheesemaking
The road west leads first to Segesta, where an ancient temple stands alone above the hills. Time with local cheesemakers brings the landscape into the present before Marsala welcomes you into wine country.
Day 6
Salt, Mozia & Winemakers
Salt, sea, and centuries of history shape the day. Cross the lagoon to Mozia, then return to the mainland for an intimate evening with winemakers whose family story is inseparable from this place.
Day 7
From Farm to Table
At Nanna Vita, the countryside sets the table. A generous farm lunch celebrates what is grown and made here, leaving the afternoon open for the unhurried pleasure of the hotel.
Day 8
Toward Palermo
Palermo arrives with energy. Its markets, food, and layered culture offer an immediate contrast to the quiet landscapes behind you, and a vivid final chapter to the journey.
Day 9
Palermo at Leisure & Celebration
The morning is yours for one last encounter with Palermo. Later, everyone gathers in the kitchen before a final dinner filled with good food, shared stories, and the warmth of travelling together.
Day 10
Departure
One last breakfast together, followed by farewells and your private departure transfer.
Is this journey right for you?
Travelers who want the founders’ most personal expression of Sicily, with food, wine, conversation, and time to experience each place fully.
Good To Know
PHYSICAL EXPECTATIONS
Expect regular walking through historic towns and cultural sites, often on uneven stone streets, with stairs and periods of standing. Some days include boats, rural properties, or archaeological areas.
DIETARY RESTRICTIONS
Sicily’s cuisine is diverse and naturally accommodates various dietary requirements. Should you have specific needs, we are happy to accommodate you. Upon booking you will be prompted to inform us in advance regarding any dietary restrictions and food allergies.
WHAT TO PACK
When packing for your trip to Sicily, consider the time of year and expected weather, which can be temperate and unpredictable. Dress for comfort with versatile layers and lightweight cotton for daytime and a sweater or jacket for cooler evenings or higher elevations. A detailed packing list will be provided upon booking.
The Benefits of Small Group Travel
Traveling in a small group allows for a more relaxed pace, easier access to local places, and genuine connection — both with the destination and with fellow travelers.
It means quieter moments, shared tables, and the flexibility to adapt when something unexpected appears. For Sicily, this way of traveling makes all the difference.
What Guests Say...
Ready to experience Santi & Dara’s Sicily?
Booking & Payment
Secure your place on this journey with a deposit. It is fully refundable within the first 14 days. The remaining balance is due in two parts,120 and 60 days prior to departure.
Select Your Room Type
Please select Single or Double Occupancy
What Happens Next
Once your reservation is confirmed, a member of our team will be in touch to guide you through the next steps and answer any questions you may have.
Booking & Payment
Secure your place on the journey with a deposit.
The remaining balance is due 60 days prior to departure.
What Happens Next
Once your reservation is confirmed, a member of our team will be in touch to guide you through the next steps and answer any questions you may have.
Blog Journals
