SIGNATURE EASTERN SICILY JOURNEY September 2026

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 Ortigia.  After settling in, enjoy an introduction to the coastal town with a walk through the historic center. 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: 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 3: 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 4: From Coast to Countryside

Travel inland to Ragusa after a relaxed seaside lunch in the marina, then arrive and check in at a new hotel, your peaceful countryside retreat surrounded by olive groves and rolling hills. Settle into the slower rhythm of rural Sicily and end the day with a tranquil dinner at the hotel, savoring farm-fresh ingredients and serene evening views from the estate’s terrace.

Day 5: 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 6: 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 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.