Sicily: Agrigento, Taormina & Aeolian Islands

7 DaysStarting at $5,295


In more ways than one, Sicily is the ultimate Italy. Geographically, it’s the southernmost province— warm, golden, and sprinkled with blindingly white Greek temples that are among the world’s best preserved. And culturally it’s more like Italy as we’d have imagined it a hundred years ago. Farmers still get to market by donkey. Mt. Etna is active even today and is the backdrop to almost every view. Even the bread is rougher and crustier—better to match vibrant food unlike any other you’ll find in Italy. We’ve scouted a remarkably scenic walking tour circuit that captures the spirit of Sicily. There’s Palermo, of course…and the rock-clinging seaside beauty of Taormina. From beautifully sited lodgings, we set out on walks among the temples of Agrigento and immerse ourselves in the archeology of Siracusa. Offshore, we wander the jewel-like Aeolian Islands. And we’re inclined to agree with the poet who wrote: "To have seen Italy without seeing Sicily is not to have seen Italy at all."

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Travel + Leisure


In sunny Palermo (1 night), we spend a leisurely afternoon exploring colorful piazzas and the spectacular Duomo of Monreale.

Traveling into the heart of Sicily, we stop near Regaleali. A friend invites us into his kitchen for a special treat—a taste of the renowned local wines and a cooking instruction. Later in the day, we drive to the Valley of the Temples near Agrigento (2 nights). We'll walk among Greek temples that date from 400 BC and are scattered amid lovely hills with wildflowers, herds of sheep and the sea in the distance.

En route to Taormina (3 nights), we pay a fascinating visit to Siracusa—a city once more powerful than Athens and now home to remarkable archeological remains of the Greek and Roman empires. We’ll ferry out to Lipari, largest of the Aeolian Islands. We’ll have time for walks through olive plantations and vineyards, plus some cafe-hopping and shopping. The return ride to Taormina offers a great view of how the town clings to the cliffs over the Ionian Sea with Mt. Etna’s snow-capped cone as a backdrop. In the morning, we head to the slopes of Mt. Etna for a walk in a breathtaking landscape of lava dunes before a memorable picnic of local specialties. After returning to our villa hotel, we wander the medieval streets of Taormina and pay a visit to the Greek theater with its panoramic view of the sea. After a final leisurely morning in Taormina, we part company in Catania.
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  • Starting Point:

    Palermo – 2:30 pm – Lobby of first night hotel
  • Ending Point:

    Catania – 1:30 pm – Airport

Dates & Prices

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Family Departure

Select our “Family Departure” to travel with other families.


Villa Athena

Located in the Valley of the Temples, this 5-star hotel is an 18th-century villa, the only lodging inside the archaeological zone. The villa offers the opportunity to dine al fresco while the temples are illuminated against the night sky.

Grand Hotel San Pietro

A 5-star luxury property, this beautiful and elegant hotel nestles into its own quiet park near the heart of Taormina. The sea views from the balcony of your room and the glamorous swimming pool are nothing short of spectacular.

Grand Hotel Piazza Borsa

Grand Hotel Piazza Borsa, in the city center, is located in an ideal position to explore Palermo. In the heart of the historical center, easily reachable both the main monuments as well as the airport of Palermo. The perfect hotel for a holiday in Sicily

What’s Included

  • Award-winning boutique hotels that provide you unlimited access to the people and places, culture and history you came to experience
  • All breakfasts, 2 lunches (1 cooking instruction), 5 dinners
  • Full-time experienced guide(s) who are with you throughout the trip and handle behind-the-scenes logistics
  • Admissions to tastings, historic sites and other scheduled events as noted in the detailed daily itinerary
  • Gratuities for hotels, meals, and baggage
  • All land transportation during the trip

Above & Beyond Benefits

Invisible Check-In

  • When your group arrives, we whisk you and your bags to your room immediately. No waiting – no tipping.

Perfect Pairings Dinners

  • A special dinner prepared by one of our favorite chefs with a procession of wines tailored to each course.

Wine on Us

  • In many regions, we uncork wonderful local wines at every dinner, compliments of Classic Journeys.

Privileged Access Events

  • One-of-a-kind access to remarkable people, places and activities arranged just for you.