Dreaming of seeing Italy on foot? Fall may be the best time to do it.
The fierce heat of summer has eased, the light takes on a softer quality and the countryside begins its seasonal transformation. Paths through vineyards, olive groves and rolling hills become especially inviting, while historic towns and villages feel more relaxed without the summer crowds. And after a few hours walking, an outdoor table, a plate of something delicious and a glass of local wine somehow taste even better.
There’s still time to join us this fall, in two very different corners of Italy. In Tuscany, walk through an elegant landscape of villas, gardens, vineyards and Renaissance towns. In Western Sicily, discover ancient ruins, wild Mediterranean coastlines, salt pans and hilltop villages.
Both offer the chance to experience Italy at a slower pace with plenty of time to walk, explore, eat well and simply enjoy being there. But don’t delay! Contact us now to secure your place.
There’s something especially appealing about Tuscany when summer begins to loosen its grip. The light softens, the countryside settles into its seasonal rhythm, and the hills, vineyards and cypress-lined roads seem to invite you to slow down and look a little closer. Our September Walk is a chance to do just that. We explore the elegant heart of Tuscany on foot, with time for beautiful gardens, Renaissance towns, long lunches and a glass of something local.
This is Tuscany beyond the postcards. Walk through the Val d’Orcia, explore Siena and Pienza, follow quiet paths through vineyards and olive groves, and step behind the gates of remarkable private estates including Villa La Foce, Castello di Celsa and Villa di Geggiano. With our Florence-based horticulturist Walk Leader Alessandro bringing his local knowledge to the journey, it’s a particularly lovely way to discover a quieter side of Italy.
If you love the idea of Italy with a little more wildness, Western Sicily in fall is hard to resist. The heat of summer has eased, making the coastal trails of Lo Zingaro and Monte Cofano a pleasure to explore, with dramatic cliffs, Mediterranean views and quiet coves along the way. Wander through the medieval hill town of Erice, watch the ancient windmills turn above the salt pans of Trapani, and take a boat to tiny Mozia, where Phoenician ruins recall a history stretching back thousands of years.
And then there’s the delicious business of Sicily. Walk through olive groves and vineyards, pause for an organic farmhouse lunch and visit the historic Florio winery in Marsala for a taste of the island’s famous wine. Ancient Greek temples at Segesta and Selinunte provide a spectacular finale, but it’s the combination of landscape, history, food and that unmistakable Mediterranean light that stays with you. Our October departure offers a wonderfully uncrowded way to experience this less-traveled corner of Italy.
Find our fall 2026 departures here