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."
- Begin in sunny Palermo, where we spend a leisurely afternoon exploring colorful piazzas and the spectacular Duomo of Monreale.
- Walk through scenic 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 a 5 star villa hotel that is perfectly-sited for us to walk from it 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.
- Make 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.
- Ferry out to Lipari, largest of the Aeolian Islands, for walks through olive plantations and vineyards, plus some cafe-hopping and shopping.
- 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.
- Wander the medieval streets of Taormina and pay a visit to the Greek theater with its panoramic view of the sea.
Starting Point:Palermo – 2:30 pm – Lobby of first night hotel
Ending Point:Catania – 1:30 pm – Airport
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 the world on foot and at eye level. Each day, join your guide on the most cinematic footpaths in the region.
- Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, share their lifelong connections as well as engaging anecdotes about the history and culture of the region.
- Small groups that provide you unrivaled access. An average of fewer than 10 guests per departure means we can offer you special access to sites like Stonehenge so you experience the stone circle when it's closed to the general public, a guided visit to Zion Narrows that other companies cannot arrange because of larger group sizes, and vineyard walks with a count and countess in Tuscany.
- Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in the region you're exploring, including rainforest lodges, 16th century villas, 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 places you visit with us. From gourmet picnics 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 our walking tour regions 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.
- Sustainable travel that supports the places you're visiting. 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.
Dates & Prices
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Select our “Family Departure” to travel with other families.
- 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
- Award-winning boutique hotels that provide you unlimited access to the people and places, culture and history you came to experience
Above & Beyond Benefits
- 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.
- 6 days
- Starting at $5,895
- 7 days
- Starting at $5,495
- 7 days
- Starting at $5,495
- 7 days
- Starting at $5,395