Hosted by
PRISCILLA
Dates
September 20-29, 2027
Maximum Group Size
14 guests
Early autumn gives Eastern Sicily a beautiful balance: the sea is still inviting, markets remain abundant, and the light softens across baroque towns and volcanic landscapes.
The journey begins in Ortigia, moves into the Ragusa countryside, and finishes in Taormina beneath Mount Etna. Priscilla hosts throughout, bringing context and care to every day. Santi and Dara join selected experiences.
The moments that stay with you...
Ortigia’s market and charming baroque architecture.
Beach day with the coastal village of Marzamemi and baroque Noto.
Explore Donnafugata’s castle and gardens and an evening in Ragusa Ibla.
Meet Modica artisans and understand the city through its chocolate and food traditions.
Etna winery tour and lunch
Master granita workshop and tasting.
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
ORTIGIA
Golden-hour streets, markets, Borderi, the coast by boat, Marzamemi, Noto, and time by the sea.
RAGUSA & MODICA
Country hospitality, Donnafugata, Ragusa Ibla, artisans, chocolate, and a slower afternoon.
TAORMINA & ETNA
Castelmola, volcanic wine country, granita, the Greek Theatre, pool time, and a chef’s-table finale.
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
✔ 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 the countryside of Ragusa to the historic streets of Ortigia and the dramatic landscapes surrounding Mount Etna, ending along Taormina’s Ionian coastline.
Day 1
Arrival in Sicily
A private transfer carries you from Catania into the Ragusa countryside, where the pace immediately begins to soften. There is time to settle before the journey opens over a generous welcome dinner.
Day 2
History & Hilltop Towns
A grand 19th-century castle and its gardens set the tone for a day rich in history and beauty. By evening, Ragusa Ibla’s golden streets lead to a traditional dinner in the heart of the old town.
Day 3
Chocolate & Leisure
In Modica, chocolate is a centuries-old craft rather than a simple indulgence. Time with local makers reveals the techniques and stories behind it, followed by lunch and an afternoon left entirely your own.
Day 4
From Countryside to Coast
A final taste of the Ragusa coast precedes the journey to Ortigia. The island’s sea-washed atmosphere offers an immediate change of mood, best welcomed over a quiet dinner of coastal flavours.
Day 5
Markets & Ancient Beauty
Ortigia begins in its market, alive with colour, voices, and the morning’s catch. Ancient Syracuse adds a deeper layer of history before sunset draws everyone back toward the marina for aperitivo.
Day 6
Seaside Villages & Baroque Beauty
A colourful fishing village, lunch beside the water, and the theatrical beauty of a baroque town create a day of striking contrasts. Dinner is waiting at a family-run trattoria loved for all the right reasons.
Day 7
Toward Taormina
The road to Taormina pauses high above the coast for lunch and a taste of almond wine. By evening, elegant streets and the ancient Greek Theatre reveal themselves in the warmth of sunset.
Day 8
Mount Etna & Wine Country
Etna dominates the horizon and defines the day. A private winery lunch among the vines brings the mountain’s wines and landscape together, while the evening in Taormina is yours to enjoy slowly.
Day 9
Taormina at Leisure
Morning begins as Sicilian mornings should, with granita at a renowned café. The hours that follow are left open for Taormina, before an intimate chef’s table gathers everyone for exceptional food, wine, and a heartfelt final celebration.
Day 10
Departure
A farewell breakfast together, followed by private transfers to the airport.
Is this journey right for you?
Travelers who value food and wine, coastal time, cultural context, and an active but thoughtful pace with room to pause.
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
