Signature Tours
SIGNATURE EASTERN SICILY JOURNEY October 2026
10 Days / 9 Nights
Maximum group size
14
Starting price
$6,750
Snapshot
Journey type
Signature (small group)
Group size
14
Dates
October 15, 2026
to
October 24, 2026
Start / End Location
Catania
Pace
Relaxed and immersive
Price per person
Double occupancy
€6,750
€7,450
Single occupancy
Deposit To Reserve:
€3,000
Per person deposit confirms your place and is fully refundable in the first 14 days. The remaining balance is due at your convenience, up to 60 days before departure.
Why this journey?
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.
Preview Your Journey
Over ten days, the journey unfolds from the historic streets of Ortigia to the countryside of Ragusa and the dramatic landscapes surrounding Mount Etna, ending along Taormina’s Ionian coastline.
Each day is thoughtfully planned, balancing guided experiences with time to explore, rest, and enjoy Sicily at an easy rhythm.
Day 1: Arrival in Sicily
Arrive in Catania and transfer to Ortigia. Settle into your hotel before an evening stroll through glowing piazzas and a welcome dinner together.
Day 2: Markets, Myths & Marina
Views Explore Ortigia’s lively market, visit the ancient Greek Theatre, and enjoy a sunset aperitivo overlooking the marina.
Day 3: 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 family-run trattoria.
Day 4: From Coast to Countryside
Travel inland to Ragusa, check in at a peaceful countryside retreat, and enjoy a quiet evening surrounded by olive groves.
Day 5: History & Hilltop Towns
Visit a grand 19th-century castle and gardens, then spend the evening in a hilltop baroque town, ending with a traditional dinner.
Day 6: Chocolate & Leisure
Meet local chocolatiers, learn historic techniques, and enjoy a relaxed afternoon at leisure in the countryside.
Day 7: Toward Taormina
Lunch in a hilltop village with almond wine, then arrive in Taormina for an evening stroll through elegant streets and ancient sites.
Day 8: Mount Etna & Wine Country
Journey up Mount Etna and enjoy a private winery visit with vineyard lunch featuring Etna wines.
Day 9: Taormina at Leisure
Begin the day with granita at a renowned café, enjoy free time, then gather for a closing gala dinner.
Day 10: Departure
Breakfast together before private transfers to the airport.
What's Included?
Everything is thoughtfully arranged. You simply arrive.
Your Stay & Comfort
• 9 nights in boutique 4- and 5-star accommodations
• Daily breakfast
• 7 dinners and 6 lunches featuring regional cuisine
• All private ground transportation throughout Sicily
• Personal hosting by Santi and Dara
• Certified local guides
• All scheduled activity and site entry fees
• Curated welcome gifts
Experiences Included
• Mount Etna wine experience
• meet the wine makers experience, visit with tasting and hosted lunch
• Traditional caseificio visit and tasting
• Chocolate artisan experience with tastings
• Coastal village tour
• Grand 19th-century castle and gardens vist
• Ancient Greek Theater visit and tour
• Farm-to-table countryside lunch
• Hilltop village lunch paired with traditional almond wine
• Traditinal granita experience
• Scheduled spa access at resort
• Sunset aperitivo overlooking marina
• Casual pizza dinner
• Professional photography session to capture timeless moment
• Gala arrival and farewell dinners
Featured Stays
Throughout the journey, you’ll stay in a collection of hand-selected boutique properties, chosen for comfort, character, and connection to place.
Stays may include:
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.
Each property is selected for quality, atmosphere, and warm Sicilian hospitality. Listed accommodations are representative and may be substituted with comparable properties of equal standard.
Featured Stays
Throughout the journey, you’ll stay in a collection of hand-selected boutique properties, chosen for comfort, character, and connection to place.
Stays may include:
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.
Each property is selected for quality, atmosphere, and warm Sicilian hospitality. Listed accommodations are representative and may be substituted with comparable properties of equal standard.
Good To Know
ACTIVITY LEVEL MODERATE ACTIVE
This is a moderately active and immersive tour best suited for travelers in good health who are comfortable walking reasonable distances. Exploring Sicily often involves cobblestone streets, narrow passageways, and some uneven or gently sloped terrain. Walking portions are always optional, and you may choose to remain on the coach at any time.
The journey involves walking in historic towns and archaeological sites so comfortable and sturdy footwear is important
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.
Why 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 Join This Journey?
Please select single or double occupancy
Reserve your spot now by paying a deposit - the balance is due 60 days before your journey starts
Or pay the full amount now
A member of our team will be in touch with next steps once your reservation is confirmed.
Ready To Join This Family Journey?
To learn more about this tour and pricing for your family group, please send us a message and tell us about who will be travelling with you and their ages. We'll get back to you as soon as possible.
From The Journal
