Fly internationally to Catania, Sicily’s second largest city.
Once you land, Christopher and his team will meet you at the airport and drive you north to Taormina, where you’ll stay at the breathtaking Grand Hotel Timeo, a Belmond property, for your entire trip.

Relax by the pool, rest from your flight, and enjoy the views.

Soak in the ancient, yet modern surroundings in beautiful Taormina.

After breakfast at the hotel, we will spend the morning showing you some of our favorite spots in Taormina, like the Teatro Antico di Taormina, an ancient Greek theater with breathtaking views of the sea and Mt. Etna.

After exploring the town’s winding cobblestone streets and charming shops, we’ll take you to a private area on the beach for afternoon swimming and sunning. In the evening, we’ll plan an amazing aperitivo and dinner experience for you at one of our favorite restaurants, like the Osteria Santa Domenica.

See Sicily’s stunning coastline from the water.
In the morning, we’ll board a private sailboat to take us down the eastern coast of Sicily. Sit back, relax, and enjoy the scenery. We may stop and spend a few hours exploring Siracusa or Ortigia, both charming destinations in southern Sicily.

When we return to Taormina, we’ll plan a laid-back private tasting event for you and your group to try Sicily’s greatest comfort food dish — pasta alla norma! Every Sicilian chef makes it differently, and every version is amazing!

Participate in the local citrus harvest.
One of our favorite things to do in Sicily during spring is participating in local citrus harvests! We’ll plan a private outing for you and your travel companions to visit a family-owned citrus vineyard where we’ll pick red oranges and lemons.

Afterwards, enjoy a crisp glass of Sicilian white wine and a fresh lunch.

Hike the base of Mt. Etna, go rock climbing, or enjoy a private fishing charter.
For the adventurous at heart, we absolutely suggest planning a day to see another side of Sicily! One of our favorite activities is hiking in Etna National Park, located at the base of Mt. Etna, Europe’s largest active volcano.

We can also plan private rock climbing excursions, fishing charters, and private kitesurfing lessons for our guests — among many other activities!

After a day on the beach, enjoy a private sunset dinner cruise with a renowned local chef.
Spend your day swimming, walking down the beach, and sipping on cocktails. In the evening, we’ll plan a private sunset dinner cruise for you, hosted by one of our dear friends and the best chefs in Sicily, Jacqueline Ragusa.

Aboard a 72’ sailboat, enjoy a Michelin-level meal featuring some of the freshest Sicilian cuisine — the perfect ending to a perfect day.

We’ll ride the local ferry to Calabria, a region known for its ancient villages.
After breakfast, we’ll take a 30-minute ferry from Taormina to Calabria, a region in Southern Italy. While in Calabria, we can plan a private boat tour of the coast, take you to gorgeous beaches, or visit nearby historical sites.

In the late afternoon, we’ll return to Taormina. After resting, you’ll get to experience a private sunset dinner at one of our dear friends’ homes.

Explore an ancient port city with a view of Mt. Etna.
In the morning, we’ll board a private boat to take us to Catania, a bustling port city just south of Taormina. After wandering the streets, shopping, and eating lunch at a local osteria, enjoy a leisurely ride back to Taormina.

We may dock the boat in an area where you can swim and relax for the afternoon. In the evening, enjoy an outdoor dinner at Osteria Rosso Divino.

We’ll spend your last day however you wish.
A private wine tasting, beach day in a new town, another private sail, a hike near Mt. Etna, one more meal with Chef Jacqueline — we’ll adapt to your mood and plan your perfect last day in Sicily, whether you want one more adventure or a slow day by the sea.

We can also return to any of the locations we’ve taken you during your stay.

We’ll transport you to the airport and ensure you have all of your belongings.
The last day is always the hardest part of the trip — no one ever wants to leave Sicily! We’ll be in touch with you after you arrive home to share your leather-bound book with pictures from your journey.