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 luxury San Domenico Palace, a Four Seasons property, for your entire trip.

Relax by the pool, rest from your flight, and enjoy stunning sea 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 local destinations for shopping, meals, and sightseeing throughout Taormina. We’ll also see some pretty impressive views of Mt. Etna and the sea.

After exploring the town, 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 grape harvest.
One of our favorite things to do in Sicily during the fall is join our friends in their family grape harvest. We’ll plan a private outing for you and your travel companions to visit a local vineyard. Take part in the timeless ritual of grape harvesting — even join the traditional stomping, if you wish — before tasting last year’s vintage.

Afterwards, enjoy a glass of Sicilian 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. If you visit in October, we may see changing foliage, which is absolutely stunning!

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.

Sicily is known for its rich, full-bodied olive oils.
After breakfast, we’ll plan a private olive oil harvest and tasting for you and your group. Sicily is known for its robust olive oils. The area’s soil is very fertile because of Mt. Etna’s volcanic ash and the warm Mediterranean climate.

Wander groves of ancient olive trees, hand-picking ripe olives alongside local farmers. For lunch, we’ll enjoy an authentic Sicilian meal and taste a variety of olive oils.

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, hike near Mt. Etna, stroll through a vineyard, or slow beach day — we’ll adapt to your mood and plan your perfect last day in Sicily, whether you want one more adventure or a day of relaxation.

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.