Agrigento, Taormina & Aeolian Islands

Sicily Cultural Walking Tour

7 DaysStarting at $6,995


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 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 ancient archeology. 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."

Start on the Amalfi Coast! Join our Amalfi tour the week prior to your Sicily departure for an amazing Italian vacation. Call 800.200.3887 for details.

Classic Journeys provides unbeatable access to experiences around the globe.”
Travel + Leisure


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Begin with a walk to scenic Mount Pellegrino before exploring Palermo, on foot at eye level

Walk through charming countryside in the heart of Sicily near Regaleali, where a friend invites us into his kitchen for a special treat — a taste of the renowned local wines and a cooking instruction.

Luxuriate in your perfectly-sited accommodations 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.

Sip and stroll your way through an organic winery followed by a gourmet picnic while on the island of Lipari.

Get the 'only with Classic Journeys' access to a local family's olive grove to learn about the olive oil making process and sample the fine results.

Explore magnificent views of Taormina as it clings to the cliffs over the Ionian Sea with Mt. Etna's snow-capped cone as a backdrop.

Head to the slopes of Mt. Etna for a walk in a breathtaking landscape of lava dunes before a memorable picnic of local specialties.

• Boat to the Aeolian Islands for walks through vineyards at an organic winery

Walk the medieval streets of Taormina and pay a visit to the Greek theater with its panoramic view of the sea.

Download Full Daily Itinerary


  • Starting Point:

    Palermo – 1:30 pm – Lobby of Grand Hotel et Des Palmes
  • Ending Point:

    Catania – 1:30 pm – Catania airport
Itinerary Map

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Dates & Prices

The earlier you book, the more choice you’ll have and the lower your price. And you can always change your mind — you won’t be charged to transfer to a different trip before your final payment is due. Talk with one of our travel experts at 800-200-3887.

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Family Departure

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

Why Choose Classic Journeys

Travel + Leisure has awarded Classic Journeys the #1 World’s Best Tour Operator multiple times and says, “Classic Journeys provides unbeatable access to experiences around the globe.” Here’s what that access means for you.
  • Experience Sicily on foot and at eye level. Each day, join your guides on the most cinematic footpaths in the region, including with a volcanologist on Mt. Etna, through vineyards on the Aeolian islands, and through olive groves and working estates.
  • Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, sharing their lifelong connections as well as engaging anecdotes about the history and culture of this fascinating island.
  • Small groups that provide you unrivaled access. An average of 10 guests per departure means we can offer you special ‘only with Classic Journeys’ access to sites like the Valley of the Temples in Agrigento so you experience it with a forensic archeologist who brings the temples to life, a cooking instruction with a family on their farm that other companies cannot arrange because of larger group sizes, and vineyard walks with a winemaker on the Aeolian Islands.
  • Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in Sicily, including the only accommodations in the archeological zone in Agrigento, White Lotus-worthy retreats in Taormina, and award-winning properties that show up on World’s Best and Gold lists.
  • Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of the Sicilian people. From gourmet picnics in the vineyards overlooking the sea in the Aeolian Islands to coveted local restaurants, our meals offer you opportunities to explore native food traditions and fine dining.
  • Handcrafted itineraries with all activities included. With our long-term friendships, we know Sicily more personally than anyone else. So you get thoughtfully curated itineraries that combine explorations of the villages, organic farms, archeological sites and the people who know them best.
  • Regenerative Travel that supports the history, culture, people and places you’re visiting with us in Sicily. We put our local currency into the pockets of the people who live where we travel. It’s your guarantee that you’ll have authentic, up-close experiences on your trip. Best of all, our person-to-person approach helps sustain their ways of life.


We spend years cultivating personal relationships with our hoteliers to provide you thoughtfully selected accommodations that reveal the true character of the region. Here is a sampling of our favorite hotels on this tour. 

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.

Doric Boutique Hotel

Perfectly located in Agrigento with magnificent views of the Valley of the Temples, Doric Boutique Hotel offers upscale accommodation, modern amenities, and warm Italian hospitality.

Grand Hotel Piazza Borsa

Located in the heart of the historical center, the hotel is in an ideal position for exploring Palermo and is within easy reach of the city’s most important monuments.

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.

NH Collection Taormina

This luxurious 5-star hotel is located heart of Taormina’s historical center with picture-perfect views of the coast. Enjoy the contemporary design, enchanting rooftop terrace, and exceptional service during your memorable stay.

Grand Hotel Et Des Palmes

An iconic property in Palermo, the Grand Hotel et Des Palmes is perfectly located in the heart of the historic city center. This luxurious property has a rich history and immerses you in Art Nouveau for a glamorous retreat in Sicily.

La Plage Resort Taormina

La Plage Resort is a luxurious retreat perfectly located within the Isola Bella Nature Reserve in Taormina. Enjoy staying in this relaxing oasis with its tranquil rooms, modern amenities, upscale cuisine, and stunning sea views.

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.

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