Hosted by
PRISCILLA
Dates
May 29 - June 7, 2027
Maximum Group Size
14 guests
This spring journey travels from Taormina’s Ionian coastline through the countryside and baroque towns of the southeast, finishing amid the markets and sea light of Ortigia. Each region offers a different way into Eastern Sicily.
The moments that stay with you...
Taste almond wine above Taormina and see the Greek Theatre in the softer light of evening.
Spend a day shaped by Etna: granita craft, volcanic wine, and lunch in the landscape that produces it.
Walk through olive country before dinner in the Ragusa countryside.
Meet artisans in Modica and experience chocolate as part of the city’s living tradition.
Arrive in Ortigia through its market, then see the coast from the water.
Your hosts
As Gems of Sicily’s Tour Director, Priscilla travels with the group throughout the journey. Her expertise in Sicilian food, wine and culture brings context, calm and care to each day. Santi and Dara join the group for selected experiences, giving every guest time to meet them and share part of the journey together.
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
TAORMINA & ETNA
Castelmola, almond wine, the Greek Theatre, granita, volcanic vineyards, and free time by the sea.
RAGUSA & MODICA
Olive country, baroque streets, Donnafugata, local artisans, chocolate, and farm-to-table hospitality.
ORTIGIA
A lively market, coastal light, ancient Syracuse, a boat experience, 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 the places you visit
✔ Visits to vibrant local markets and immersive culinary moments
✔ Private boat activity
✔ Guided explorations of baroque towns and historic villages
✔ Castle visit with garden walk
✔ Artisan chocolate experience and tasting
✔ Mount Etna day with winery visit and tasting
✔ Hands-on granita workshop
✔ Cultural highlights including a historic theatre visit
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
Elegant Seaside Boutique Hotel
A refined 5-star hotel blending contemporary elegance with historic charm, just steps from the sea and Ortigia’s ancient streets.
Countryside Resort Retreat
A peaceful countryside retreat surrounded by olive groves, offering spacious rooms, gardens, and a serene atmosphere.
Cliffside Boutique Hotel in Taormina
A cliffside boutique stay overlooking the Ionian Sea, combining understated luxury with sweeping coastal views.
Sample Itinerary
Over ten days, the journey unfolds from Taormina’s Ionian coastline and the volcanic landscapes surrounding Mount Etna to the countryside and baroque towns of Ragusa, ending beside the water in Ortigia.
Day 1
Arrival in Taormina
Taormina welcomes you with sea air, elegant streets, and the unmistakable presence of Mount Etna. Settle in, then let the journey begin over dinner together.
Day 2
Hilltop Views & Ancient Beauty
Above Taormina, Castelmola pairs sweeping views with lunch and a taste of almond wine. Later, the ancient Greek Theatre is at its most evocative, framed by the softer light of evening.
Day 3
Mount Etna & Wine Country
The day begins with one of Sicily’s sweetest rituals before turning toward Etna’s volcanic vineyards. Wine and lunch are shared in the landscape that created them, with the evening left open for Taormina.
Day 4
From Coast to Countryside
Leaving the coast behind, the road bends south toward Ragusa. An olive-grove walk and relaxed apericena ease you into the quiet rhythms of the countryside.
Day 5
Modica’s Flavours & Traditions
Modica’s baroque beauty is inseparable from its food traditions. Time with local artisans, and the city’s distinctive chocolate, leads into a farm dinner rooted in the surrounding land.
Day 6
Castles & Baroque Streets
Donnafugata’s rooms and gardens offer a glimpse into another era. As evening falls, Ragusa Ibla glows in honey-coloured stone, inviting a slow walk through the old town.
Day 7
Toward Ortigia
Ortigia announces itself through colour, scent, and conversation at the morning market. Once settled on the island, the day drifts toward a seaside aperitivo.
Day 8
Ortigia from the Sea
Seen from the sea, Ortigia takes on an entirely different beauty. The remaining hours leave space to wander, pause, and return to the places that have already caught your eye before dinner together.
Day 9
Ancient Syracuse & Celebration
Ancient Syracuse gives the journey one final sweep of history. The evening belongs to celebration, with a memorable closing dinner shared around the table.
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 coast, baroque towns, food traditions, and Mount Etna in one thoughtfully paced Eastern Sicily journey.
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 Eastern 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
