Signature Tours
SIGNATURE EASTERN SICILY JOURNEY May 2026
10 Days / 9 Nights
Maximum group size
14
Starting price
$6,750
Snapshot
Journey type
Signature (small group)
Group size
14
Dates
May 4, 2026
to
May 13, 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 with 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 Sicily itself.
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
Upon arrival to Catania, your driver will greet you at the airport and bring you comfortably to your hotel in Ragusa. Settle in as you enjoy the Sicilian countryside filled with olive groves and vineyards. That evening, come together for a memorable welcome dinner which is the perfect moment to meet your fellow travelers and begin the journey ahead.
Day 2: History & Hilltop Towns
History, beauty & the heart of Ragusa begins with a guided visit to a grand 19th-century castle and its gardens, offering a glimpse into Sicily’s aristocratic past. In the evening, stroll through the charming streets of a Baroque hilltop town, with cobblestones and golden architecture. End the day with an authentic dinner in the heart of town, surrounded by locals and warm Sicilian hospitality.
Day 3: Chocolate & Leisure
Visit to local chocolatiers, where you’ll learn centuries-old techniques and sample the rich, distinctive flavors that make this chocolate so famous, all set among winding streets and grand churches. After a light lunch, enjoy a relaxed afternoon at your leisure with the evening free for you to dine and unwind at your own pace.
Day 4: From Countryside to coast
From Countryside to coast begins with a relaxed seaside lunch in the marina before heading toward the coast. Enjoy a warm welcome to Ortigia and check in at an elegant boutique hotel in the heart of the island, surrounded by sea views and Baroque charm. Settle into the rhythm of coastal Sicily and end the evening with a tranquil dinner at the hotel, savoring farm-fresh ingredients and quiet sunset views from the terrace.
Day 5: Markets, Myths & Marina Views
This day invites you to explore Ortigia’s lively market, immersing yourself in the vibrant sights, sounds, and scents before savoring a legendary panino lunch at a beloved local caseificio. Continue with a guided visit to the ancient Greek Theatre, a magnificent testament to Sicily’s storied past and dramatic spirit, then unwind in the evening with a sunset aperitivo overlooking the marina.
Day 6: Seaside Villages & Baroque Beauty
You are brought to a colorful seaside village where you’ll soak in the charm of sunlit piazzas, artisan shops, and a relaxed coastal atmosphere, followed by a leisurely seaside lunch with fresh seafood and authentic Sicilian flavors. Later, wander the golden Baroque streets of a historic town before ending the evening with dinner at a beloved family-run trattoria.
Day 7: Toward Taormina
Travel north for a memorable hilltop lunch paired with a tasting of the region’s sweet almond wine while taking in sweeping views of the Ionian Sea. Upon arrival, check in to your seaside hotel. At sunset visit one of Sicily’s most iconic ancient theatres before enjoying an elegant evening stroll through Taormina’s charming streets, lined with boutiques, cafés, and timeless Mediterranean allure.
Day 8: Mount Etna & Wine Country
This day takes you on a memorable journey up the slopes of Europe’s most active volcano, followed by a private winery visit where you’ll enjoy a guided tasting and vineyard lunch perfectly paired with Etna wines and local cuisine. Return to Taormina in the evening for relaxed free time and dinner at your leisure.
Day 9: Taormina at Leisure
Start the day with a traditional Sicilian granita at a renowned local café. Enjoy a free afternoon for shopping, strolling, or one last swim in the Ionian Sea, then come together in the evening for a memorable gala dinner featuring an intimate chef’s table experience filled with exceptional food, wine, and heartfelt celebration.
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.
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.
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
