Signature Tours
SIGNATURE EASTERN SICILY JOURNEY October 2026
Journey type
Signature (small group)
Dates
October 15, 2026
-
October 24, 2026
Starting price
$6,750
10 Days / 9 Nights
Maximum Group Size
14
Pace
Relaxed and immersive
Start / End Location
Catania
Price per Person
Single occupancy
€7,450
Double occupancy
€6,750
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 60 days before departure.
This journey doesn’t just show Sicily, it reveals some of the island's most beautiful secrets — Ortigia, a small island part of Syracuse, where every corner holds an ancient beauty; Ragusa, a golden hilltop town that unfolds beautifully and always has more to share; and Taormina, where the views alone would justify the trip, but this journey will welcome you with much more than that. Each of these places are extraordinary on their own and together they show you exactly why Sicily brings people back again and again.
Nothing on this journey has been left to chance. Each destination has been chosen carefully and thoughtfully with you in mind. Together these places share a portrait of Sicily that is honest, warm and layered. We are eager to share the island with you.
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
Accommodations
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.
Accommodations
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.
The 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.
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...
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 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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