Hosted by
PRISCILLA
Dates
October 15-24, 2026
Maximum Group Size
12 guests
Eastern Sicily is a place of contrast and beauty — volcanic landscapes beside the sea, golden baroque towns, lively markets, and quiet countryside shaped by tradition and time.
This journey was designed to experience the eastern side of the island as it’s truly lived. Through food, local artisans, historic towns, and time spent simply being present, you’ll move beyond sightseeing into a deeper understanding of place.
Along the way, you’ll share meals, stories, and everyday moments with people we know personally — farmers, chocolatiers, winemakers, guides, and hosts who open their doors generously. The pace is relaxed, the experiences meaningful, and the atmosphere warm and welcoming.
This is Sicily with substance, rich in culture, flavor, and connection.
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
Days 1-4
RAGUSA: CASTLE, COBBLE & CHOCOLATE
Donnafugata’s grand castle, cobbled streets of Ragusa Ibla, lunches by the marina, dinners deep in old town and to complete, Modica’s ancient chocolate. Ragusa reveals itself slowly and entirely.
Days 5-6
ORTIGA: ISLAND, MARKET & TIDE
A market experience alive with colour and flavour, a caseficio lunch, a greek theatre, sunset aperitivo, a stroll through Marzememi and a tour of Noto. Ortiga offers you her vivid beauty and generosity during every moment.
days 7-10
TAORMINA: VOLCANO, VINE & VIEW
The almond wine of Castelmola, a greek theatre at golden hour, Mount Etna by day, a winery visit on volcanic slopes, a granita workshop and a gala dinner to complete your Sicilian journey. Taormina closes this journey in an unforgettable way.
What's Included
Luxurious 4- and 5-star accommodations throughout your stay
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
Welcome dinner and sunset aperitivos by the sea
Visits to vibrant local markets and immersive culinary moments
Private boat tour along the coast with beach club access
Guided explorations of baroque towns and historic villages
Castle visit with garden walk and countryside lunch
Artisan chocolate experience and tasting
Mount Etna day with winery visit and tasting
Hands-on granita workshop
Cultural highlights including a historic theatre visit
All site entries and activity fees
Private local guides who bring depth and meaning to every place you visit
A curated welcome gift to begin your experience
An hosted gala dinner to celebrate your time in Sicily
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
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
Arrive in Catania and transfer to Ragusa. Settle into your hotel and enjoy some free time before a welcome dinner all together.
Day 2
History & Hilltop Towns
Visit a grand 19th-century castle and its gardens, then spend the time exploring the beautiful Ragusa Ibla, ending with a traditional dinner in the heart of old town.
Day 3
Chocolate & Leisure
Visit to local chocolatiers, to learn centuries-old techniques and sample the rich, famous chocolate. After a delicious lunch, enjoy the rest of the day at your own pace.
Day 4
From Countryside to Coast
Enjoy a final meal in Ragusa at the marina before journeying to Ortiga. Settle into your new stay and have a quiet dinner with the flavours of this coastal town.
Day 5
Markets & Beauty
Enjoy Ortigia’s lively and colourful market and take in the history at the ancient Greek Theatre. The day will come to a close with a sunset aperitivo overlooking the marina.
Day 6
Seaside Villages & Baroque Beauty
Discover a colorful seaside village, enjoy a leisurely lunch by the water, and wander a baroque town before dinner at a loved family-run trattoria.
Day 7
Toward Taormina
Lunch upon a hilltop village with a taste of almond wine before arriving in Taormina and settling into your new hotel. In the evening stroll through elegant streets and enjoy a sunset visit to the Greek theatre.
Day 8
Mount Etna & Wine Country
Journey up the breathtaking Mount Etna and enjoy a private winery visit with a lunch amidst the vines, featuring Etna wines. Return to Taormina to have a relaxing evening at your own pace.
Day 9
Taormina at Leisure
Begin the day with granita at a renowned café and enjoy some free time with the beauty around you. To finish, gather for a gala dinner featuring an intimate chef’s table filled with exceptional food, wine, and heartfelt celebration.
Day 10
Departure
Farewell breakfast together before private transfers to the airport.
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.
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