Walking Holidays in Italy

There's something very special about Italy. Whether you're a first-time visitor or a seasoned traveller, you'll soon fall under its spell. When you choose walking holidays in Italy with Headwater, you'll get under the skin of this beautiful country. You can stroll the great art cities of Tuscany and Umbria, admire the rolling hills and ancient forests of Venetia, with their stunning array of beautiful wildflowers, or enjoy the dramatic coastlines of Sicily or Sardinia. We have an array of walking journeys for all abilities to enjoy, including guided and self-guided options, helping you tailor your adventure to your preferences.

Browse our walking holidays in Italy below to find gentle coastal trails and scenic walks past the world-famous Barolo, Barbaresco, and Moscato vineyards in Piedmont. Alternatively, you can take on more challenging walking tours in northern Italy with the dramatic backdrop of the towering Dolomites.

Where to go walking in Italy

Here are several of our top Italy walking holiday destinations.

The Amalfi Coast

Renowned for its dramatic coastline, sparkling waters and picture-perfect towns, the Amalfi Coast is a must-visit for those wanting to experience the best of Italy. Head to the charming towns of Positano, Amalfi and Ravello to wander the narrow streets. Immerse yourself in the historic remains of Pompeii and see the iconic Mount Vesuvius. You'll also have the opportunity to walk one of the most famous trails in the world: the Path of the Gods, which offers unrivalled views over the Bay of Naples.

Sardinia

Situated off the west coast of Italy, Sardinia is a large island known for its beautiful beaches, magnificent coastline and spectacular mountains. There are plenty of fantastic hikes to enjoy here, taking you through picturesque gorges with incredible sea views. As you explore Sardinia on foot, you can discover archaeological sites, relax on the beach or go wine tasting at a local vineyard.

Lake Como

Lake Como is a serene destination with endless gems to discover as you skirt your way around the water and beyond. You'll uncover quaint villages and 12th-century abbeys, topped off with unrivalled viewpoints.

Sicily

From volcanic landscapes to dramatic coastlines, Sicily is a haven for anyone wanting to soak up the geographical landforms that make this part of the world so unique. Expect varied routes that take in the imposing Mount Etna and the Aeolian islands.

Italian Dolomites

If you want a walking holiday to Italy that promises a challenge, look no further than the Italian Dolomites. This route allows you to get up close to nature as you tackle striking Alpine terrain. Best suited to experienced walkers, it promises a truly unique experience.

Tuscany

Rolling landscapes, rustic cuisine, and welcoming locals bring the very best of Italy into a walking holiday you won't forget in a hurry. This trip is as much about the food and wine as it is about the walking, all of which you can enjoy against a backdrop of vineyards, olive groves, and freshwater ponds.