Day 1 — Friday, September 24

Welcome to Taormina

The Sicilian adventure begins in Taormina, one of the Mediterranean’s most captivating towns.

Perched above the Ionian Sea, Taormina is a spectacular combination of ancient history, elegant streets, flowering gardens and unforgettable views. Our home for two nights is Hotel Villa Schuler, a historic villa surrounded by botanical gardens in the heart of town.

Guest accommodations feature beautiful sea views, placing the coastline and Mount Etna directly outside the window.

This evening, gather for a welcome aperitivo followed by a celebratory Sicilian dinner. It is the perfect beginning: wonderful food, local wine, new friendships and the lights of Taormina glowing all around.

Day 2 — Saturday, September 25

The Beauty of Taormina

Begin with a privately guided visit to Taormina’s extraordinary ancient theatre.

Built by the Greeks and expanded by the Romans, the theatre occupies one of the most dramatic settings in the world. Beyond its ancient stone arches, Mount Etna rises above the coastline and brilliant blue Ionian Sea.

A private guide brings Taormina’s story to life while continuing through its elegant piazzas, historic lanes and colorful main street.

The remainder of the day is yours to enjoy. A lunch allowance allows each couple to choose the café or restaurant that catches their eye. Browse Taormina’s boutiques, relax on the hotel terrace, visit the gardens or settle into a sunny piazza with a glass of Sicilian wine.

Tonight, reunite for another wonderful group dinner in the heart of Taormina.

Day 3 — Sunday, September 26

Checking Out by Land, Arriving by Sea

Today, we trade an ordinary hotel-transfer day for a private adventure on the Ionian Sea.

After breakfast, our luggage is collected and transported ahead to our next hotel. We travel light to Giardini Naxos, where a private boat is waiting to carry us from the Taormina coast to an entirely different destination near Mount Etna.

This is not a round-trip sightseeing cruise. We board in one place and step ashore somewhere new.

Our route takes us beneath Taormina’s dramatic cliffs and past Capo Taormina, Isola Bella, coastal grottoes and secluded swimming coves. Along the way, there will be time to swim in the clear Mediterranean water, relax in the shade and enjoy a generous Sicilian lunch with wine and beverages aboard.

With Mount Etna rising ahead of us, we continue south and arrive by boat at Porto dell’Etna in Riposto. Our transportation—and our luggage—will be waiting at the marina.

From there, we travel into the peaceful landscapes of northern Etna and check into Villa Neri Resort & Spa.

It is a wonderfully fun way to change hotels: check out in Taormina, spend the day swimming and dining on a private boat, and arrive at the next chapter of our Sicilian adventure by sea.

This evening, we gather for a relaxed dinner surrounded by the atmosphere of Mount Etna.

Day 4 — Monday, September 27

Private Mount Etna Adventure

Mount Etna is more than a mountain. It is a living landscape that has shaped the villages, vineyards and culture of eastern Sicily.

Explore Etna’s northern flank in private Land Rover-style vehicles. Travel through forests, historic lava flows and extraordinary volcanic terrain as local guides reveal the fascinating story of Europe’s highest active volcano.

Short, approachable walks offer opportunities to step onto the volcanic landscape, photograph its sweeping views and experience the remarkable contrast between black lava, green forest and distant sea.

Return to Villa Neri for lunch and a completely free afternoon. Relax beside the pool, enjoy the gardens or settle into the quiet rhythm of the Sicilian countryside.

Gather again for dinner and an evening devoted to the flavors of Etna.

Day 5 — Tuesday, September 28

E-Biking Through Etna Wine Country

Discover northern Etna from a fresh perspective during a privately guided e-bike ride through the countryside surrounding Linguaglossa and Castiglione di Sicilia.

The scenic route winds through vineyard landscapes, Sicilian villages and sections of a historic railway corridor. Electric assistance makes the rolling terrain enjoyable while allowing time to absorb the scenery and volcanic surroundings.

Finish with a relaxed local lunch celebrating the food and traditions of the region.

In the afternoon, travel to Zash Country Boutique Hotel, a striking retreat hidden within a fragrant citrus estate. Historic architecture and contemporary design come together among gardens, orchards and views of Mount Etna.

Settle in, relax and enjoy dinner on the property.

Day 6 — Wednesday, September 29

The Wines of Mount Etna

Today is devoted to one of Sicily’s most celebrated wine estates.

At Benanti, discover how altitude, volcanic soil and Mount Etna’s many exposures create wines of remarkable character. A privately hosted experience introduces Etna’s native grape varieties, including Carricante and Nerello Mascalese, while revealing the dramatic differences between the volcano’s individual slopes and growing districts.

The polished and engaging wine experience is followed by a beautiful seated lunch with Benanti wines.

Return to Zash for a leisurely afternoon among the citrus groves. Enjoy the pool, gardens and peaceful estate before gathering for an elevated Sicilian dinner.

Day 7 — Thursday, September 30

Noto and Nero d’Avola

Leave Etna behind and travel into southeastern Sicily, where the landscape changes from dark volcanic soil to pale limestone hills, almond orchards and sun-washed Baroque towns.

Explore Noto, one of Sicily’s greatest architectural treasures. Its magnificent cathedral, sweeping staircase and honey-colored palazzi create an unforgettable scene as the limestone glows beneath the Sicilian sun.

Continue into the countryside to Planeta’s Buonivini estate. Here, vineyards unfold among almond, olive and carob trees near the meeting point of the Ionian and Mediterranean seas.

Discover the estate’s Nero d’Avola and innovative underground winery before sitting down to a private lunch with regional wines and Sicilian flavors.

Later, continue to Ortigia and check into Palazzo Artemide, an elegant historic hotel steps from Piazza Duomo.

This evening, walk through Ortigia’s glowing streets for a memorable group dinner.

Day 8 — Friday, October 1

Ancient Syracuse and Timeless Ortigia

Begin with a privately guided visit to the most compelling highlights of Syracuse’s Neapolis Archaeological Park.

Stand inside the ancient Greek Theatre, one of the largest surviving theatres of the Greek world, and experience the remarkable acoustics of the Ear of Dionysius, carved into the limestone quarry.

Continue to Ortigia, the ancient heart of Syracuse. Explore Piazza Duomo, the Fountain of Arethusa, waterfront promenades and atmospheric streets shaped by Greek, Roman, Arab, Norman and Baroque history.

The Cathedral of Syracuse tells this layered story beautifully: its graceful Baroque exterior surrounds the original columns of a fifth-century BC Greek temple.

After lunch, enjoy a free afternoon to explore Ortigia’s boutiques, cafés and waterfront at your own pace.

The journey concludes with a wonderful farewell dinner—an evening of Sicilian food, wine, friendship and stories gathered over an extraordinary week.

Day 9 — Saturday, October 2

Arrivederci, Sicily

Enjoy breakfast in Ortigia before transportation to Catania Airport or the next stop in your travels.

Leave Sicily with memories of volcanic landscapes, warm seas, beautiful wines, ancient civilizations and evenings spent together beneath the Mediterranean sky.