Sicily is not just an island — it’s a world of its own. Greek temples rise beside Baroque palaces, fishermen mend nets in tiny harbors while volcanoes smolder on the horizon. On this walking journey, we explore the quieter eastern side of the island, away from the crowds: Siracusa’s Ortigia, the golden streets of Noto, and the enchanting Aeolian Islands. A quick stop in Taormina. After all, how could we skip the majestic vibe of its Greek Theater?
We walk through nature reserves where flamingos glide over saltwater lagoons, climb the crater of Vulcano, and wander Lipari’s cobbled alleys. Every day is also a feast: farm lunches under olive trees, pane cunzato seasoned with anchovies and capers, sweet cannoli filled with ricotta, and local wines poured generously.
This is Sicily off the beaten path — where the land, the people, and the food tell stories you’ll never forget.
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6 nights in handpicked hotels (one 5-star, one 4-star).
All breakfasts, 5 lunches, 4 dinners, with local wine always included.
Luggage transfer hotel-to-hotel.
Boat rides between islands.
Entrance tickets for archaeological sites and cultural visits.
1 guide for groups under 10; 2 guides for 10+ guests.
All taxes
We meet in Siracusa and explore Ortigia, the island-heart of the city, with its dazzling Cathedral Square and the spring of Arethusa. The streets breathe history: once a Greek temple, now a baroque church. Dinner tonight is Sicilian seafood, paired with local wine.
A coastal walk through Vendicari reveals flamingos, ancient tuna fisheries, and Mediterranean scrubland. Lunch is at a farm where olive oil, vegetables, and wine come straight from the land. In the afternoon, we admire the honey-colored Baroque of Noto, with time for gelato or granita before returning to Siracusa. Dinner in town.
We reach Taormina, perched above the sea, where our walk offers stunning views of Mt. Etna and the Ionian coast. We stroll Corso Umberto and the ancient theater before heading to Milazzo and boarding the hydrofoil to Lipari. Dinner at our hotel by the sea.
A panoramic hike reveals vistas over the island of Vulcano, through Mediterranean shrubs and villas. In the afternoon, we explore Lipari town and its hilltop castle. Dinner is relaxed and festive: a pizza feast on the main street of Lipari.
We sail to Vulcano and hike to its smoking crater (optional easier stroll for those who prefer). From the rim, we gaze over the Aeolian archipelago. Lunch is rustic: pani cunzato, bread seasoned with anchovies, capers, tomatoes, and mozzarella. Afternoon at leisure in Lipari; dinner is on your own.
We sail to Salina, lush and green. A bus takes us to Leni, where we begin a ridge walk with sweeping views of the Aeolian chain — Alicudi, Filicudi, Stromboli on the horizon. Lunch is al-fresco with panini and local wine. Back in Lipari, we celebrate our last night with a farmhouse dinner of Aeolian specialties.
Hydrofoil back to Milazzo, then transfer to Catania. We reach the airport and train station in the early afternoon. Flights should depart after 4 pm.
A noble palace turned boutique hotel, in the historic Umbertino district, walking distance from Ortigia.
A stylish coastal resort with pool and gardens, perfect base for the Aeolian Islands.
golden fried rice balls, stuffed with ragù, mozzarella, or spinach. Crunchy outside, melting inside.
prawns, swordfish, calamari — grilled, stewed, or fried, always kissed by lemon.
rustic bread topped with tomatoes, anchovies, capers, pecorino, and olive oil. A peasant dish turned gourmet.
almond or lemon granita, paired with a warm, soft brioche col tuppo — the Sicilian summer breakfast.
crisp pastry shells filled with sweet ricotta and pistachio.
Nero d’Avola and Frappato for reds; Grillo and Catarratto for whites; Malvasia delle Lipari for a sweet farewell.
Price per person changes depending on the occupancy number of your private group.
More guests? Please ask us a quote. We can also tailor the tour to your needs.
| Number of guests | price in double room (euros) | single supplement (euros) |
| 1 | contact us | |
| 2 or 3 | 6190 | 380 |
| 4 or 5 | 4490 | 380 |
| 6 or 7 | 4250 | 380 |
| 8 or 9 | 3950 | 380 |
| 10 or 11 | 3790 | 380 |
| 12 or more | 3590 | 380 |
Hotel in Siracusa
4.00 PM
Catania train station & airport
2 PM
Walking/jogging 3x a week for 60 minutes before the tour is recommended.
Walking shoes with traction, hat, swimwear, sunscreen, refillable bottle. No dress code for dinners. Walking sticks provided.
1 dinner on your own (~€20–25 pp) + daily coffees/gelato (€5 avg).
Not obligatory; appreciated if you wish to thank guides/drivers.
Mild year-round. Summers are hot but breezy, spring and autumn mild with some rain.
1–18 guests
no limit
farmhouse lunches & historic town dinners
away from tourist crowds
My husband and I spent 7 days in September walking the Tuscan Hills with Gianni and Rudy. As I read my journal from our trip almost 3 months ago it brings a smile to my face as I relive those treasured moments of hiking beautiful vineyard hillsides, making pasta at a local restaurant, listening to arias from well known Italian operas, drinking glorious wines with local wine makers, eating fabulous foods, learning about making cheese, doing yoga in a beautiful vineyard and listening to Gianni play his flute.Gianni’s organizational skills and ability to relate to all his guests was a large part in making this trip so memorable and enjoyable.
The Best Way to See Italy Forget Rick Steves and sign on with Gianni for a wonderful exploration of some of the best Italy has to offer–countryside, history, food, and people. Gianni’s deep knowledge of all these adds so much richness to the experience of walking through picturesque medieval towns and gorgeous rolling hillsides of vineyards, fields and orchards. The accommodations were comfortable and centralized, often with wonderful views.Although this was a tour through the areas surrounding Siena, Montalcino and Pienza, Gianni offers tours in other areas and I would expect the same high level of engagement and effort to provide unique experiences. Truly exceeded my expectations!
Walk about Tuscany Loved this tour and would highly encourage others to go. Our guides Gianni and Sara were great, everything ran smoothly from day one. Excellent choices of hotels, restaurants and walking trails. The perfect size group, lots of laughs and good memories. Looking forward to the next one. Grazie, Monica
Under the Tuscan Sun…and a big black cloud but only once I have just returned from 8 fabulous days with Walk About Tuscany hosted by Gianni and Rudy and helped by their hard working transportation crew who ensured we were picked up on time, we traveled safely and no luggage was lost. We had many moments of fun and laughter and even a couple of flute recitals just for a change of pace!! In the end, I have Gianni to thank for this experience. His thoughtful organization and attention to detail were key in delivering a superb product, a memorable adventure and a trip of a lifetime. Walk About Tuscany is highly recommended! Grazie, Gianni
The unforgetable Tuscany I am so amazed with Gianni who operated our tour with his in-depth knowledge of every single steps and buildings around Tuscany. Not to mention his creativeness in every moments of our walks. You will have great lunches and dinners with lots of special-2-thumbs-up wines. We also visit Olive Oil producer and given sampler at which is the best (and fresh) olive oil that I had ever tasted ! The scenery view is very awesome, just like the post card. Highly recommended and wouldn’t mind to do this tour again.
Group Tour of Tuscany Hill Towns with Walk About Tuscany Tours I had a marvelous time on this trip. Our guide, Gianni, provided gorgeous walks and unique experiences with local organic producers of wine, produce, cheese, and olive oil. Definitely experiences I couldn’t have had without his guidance and that helped me to appreciate what makes this region unique. Gianni is knowledgeable and expended every effort to ensure that our trip was memorable and unique. We walked, ate very well, drank wonderful wines and learned a great deal about this region of Tuscany and why it is among the most delightful of all Italy.
