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 the island of Sicily. 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.
Here are several of our top Italy walking holiday destinations.
Lusting after a coastal setting for your walking holiday in Italy? This is for you. You can embark on different routes that showcase the breathtaking, picture-postcard Amalfi Coast, covering beautiful towns like Positano, Ravello, and Sorrento in all their pastel-coloured glory.
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.
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.
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.
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.
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Sitting prettily in the Bay of Naples lie the beautiful yet diverse islands of Amalfi: Procida, Ischia and Capri. This 7 night self-guided walking holiday takes you on a discovery of these stunning isles, from Procida's multi coloured harbours, to the thermal spas and terraced vineyards of Ischia, to the glamour of Capri's elegant piazze.
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This 7-night linear trip is a fantastic mix of scenic walking, medieval towns and panoramic hilltop villages, following a mix of quiet country lanes, paths and trails. Along the way, admire the stunning valley vistas from the slopes of Monte Subasio, discover the secluded hermitage of St Francis nestled amongst ancient oak forest, and explore some of the lesser known but stunningly beautiful medieval towns that dot the sun drenched Umbrian landscape.
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This triple centre holiday explores the unspoilt north western tip of Sicily and the nearby Egadi islands. It's a relatively undiscovered region where highlights include pristine sandy beaches, coral-lined grottoes, ancient hill villages and marvellously preserved nature reserves.
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There are few places in Italy as stunning as the Amalfi Coast with its emerald seas, plunging gorges and pastel villages linked by ancient walking paths. This linear walk follows the coast from elegant Ravello to chic Sorrento, taking in en route vertical Positano and (optional) the beautiful island of Capri.
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Undoubtedly one of the most spectacular, varied and unique walks in our portfolio, taking in the beautiful Aeolian Islands as well as the immense and impressive Mount Etna - the largest active volcano in Europe!
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The Amalfi Coast is one of the most dramatic coastlines in Europe. Mountains jut steeply out of the Mediterranean and picturesque towns nestled in the coves below. Walking the ancient hillsides studded with lemon groves and framed by deep gorges, we descend from the Agerola Plain to the quaint towns of Positano, Ravello and of course Amalfi itself. No visit to the Bay of Naples would be complete without a trip to see the remains of Pompeii under the imposing volcanic cone of Mount Vesuvius. The best is saved till last with arguably the world's best coastal walk: the 'Walk of the Gods'. Away from the trails, sample incredible food and wine just like the Italians do.
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Independent walking trip allowing you to discover the beauty of Puglia and Matera. Starting in the heel of Italy in beautiful Baroque Lecce, you head north through gently rolling countryside filled with olive groves and vineyards, stopping at the white city of Ostuni and Alberobello with its iconic 'trulli' houses. Your final destination is the UNESCO World Heritage site of Matera with its unique cave houses.
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The wonderfully unspoilt Venetian countryside is only an hour or so from the great city of Venice, but couldn't be more different! Here is a landscape of rolling hills, shady forests, vineyards and fields ablaze with colourful flowers.
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The Italian Dolomites are a Mecca for high-level walkers and this holiday combines superbly varied walking by day with luxury 4 star comfort at night - a highly sought-after mix! Excellent birdspotting, stunning flowers and unrivalled Alpine views.
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Based in the town of Chianciano Terme, on this single-centre walking holiday you’ll experience archetypal Tuscany: stunning timeless landscapes, delicious rustic cuisine, friendly local people and, of course, interesting walking routes.
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This single centre, self-guided walking week gives easy access to some of the most stunning alpine scenery. Picture postcard villages surrounded by alpine meadows and the jagged limestone mountains of the UNESCO Dolomites.
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Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night walking holiday! The route takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of La Morra and Barolo.
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The Amalfi Coast stretches 50km from Sorrento to Salerno and is one of the most breath-taking coastlines in Europe. Steep terraces full of scented lemon groves fall sheer into a deep blue Mediterranean sea; whitewashed houses cling precariously to unforgiving slopes while sea and sky merge in one vast blue horizon. Colourful towns are pasted onto the steep slopes and have a history dating back 100’s of years.
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Explore Puglia’s pristine coastline, accompanied by glittering sea vistas, fragrant wild flowers and the gentle murmur of ocean waves as you head from Lecce towards Puglia’s most southerly point.
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Discover Cilento, a region whose beauty rivals that of the nearby Amalfi Coast,with superb coastal walks, numerous glorious beaches and the ancient site at Paestum.
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Discover the beautiful Liguria region and its remarkably well-preserved landscape steeped in tradition on our 6 night holiday based in Sestri Levante. Choose each day from the selection of walks available, exploring the coastline from the Cinque Terre to Portovenere as well as Portofino and the UNESCO island of Palamaria. You'll be dazzled by the colours, from the green and blue shades of the sea to the pastel-coloured houses perched above it, to the rich Mediterranean vegetation and lush hillside terraces of vineyards.
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An impossibly scenic discovery of western Sardinia’s natural beauty and centuries old history, from the black Montiferru mountains to the prolific birdlife of the Sinis wetlands, and from rugged limestone cliffs dotted with panoramic watch towers to the ancient site of Tharros, with plenty of opportunity to visit the picture perfect sand and white quartz beaches en route.
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Walk through the beautiful wine-growing area of Classic Chianti, visiting the World Heritage cities of Florence and Siena.
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This 8-night walking holiday combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. You'll stay in a mix of friendly, family-run hotels, enjoy superb meals and relax by panoramic pools - views extend as far as Corsica on a clear day!
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Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night walking holiday! The route takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of La Morra and Barolo.
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A 10-night walking holiday that explores the fabulously unspoilt Chianti countryside, with the chance to visit the world-famous cities of Florence and Siena too! Stay in friendly, family-run hotels, including a beautifully restored 12th century abbey, and enjoy superb meals.
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The Amalfi Coast is one of the most dramatic coastlines in Europe. Walking the ancient hillsides studded with lemon groves and framed by deep gorges, we descend to the quaint towns of Positano, Ravello and of course Amalfi itself. We visit the remains of Pompeii under the imposing volcanic cone of Mount Vesuvius and also tackle the world's best coastal walk: the 'Walk of the Gods'.
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This guided walking holiday explores the fascinating region of Puglia taking in the UNESCO towns of Matera and Alberobello and the 'white city' of Ostuni. Walk over rolling hills, through ancient olive groves and past vineyards overlooking the coast.
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A 7-night guided tour exploring Sardinia's stark beauty: crystal clear waters, golden beaches, rocky mountains and undulating limestone ridges. Delicious local cuisine and wines too!
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Based in the heart of the 'Prosecco Road', we spend a week walking through picturesque rolling hills and sampling the area's delicious cuisine and authentic bubbles.
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Guided trekking through the Italian Dolomites. We enjoy an excellent choice of routes with the opportunity to relax in comfort at the end of a day's walking. During the week, we venture into the Fanes-Sennes and Dolomiti di Sesto National Parks for great views of the Tre Cime di Lavaredo.
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The Francigena Way is an historical journey; a road which once led from Canterbury to Rome and which has been walked by thousands of pilgrims. Your journey will take you from the medieval town of Orvieto, known for its impressive cathedral, through picturesque villages to the grand finale - the 'eternal city' of Rome!
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If being out and about in nature or soaking up local culture sounds like the perfect getaway , then a walking holiday tour is the ideal escape for you. You'll be active for most of the day, so if this suits you, you'll have a brilliant time. The option to choose between a guided or self-guided walking holiday in Italy, as well as a walking grade that matches your ability and preferences, means you can tailor your trip into one that works for you.
We choose accommodation that oozes charm and offers something a little different, from farm hotels in Tuscany to spa hotels in the Dolomites. We look for friendly hosts who take a keen interest in their guests, ensuring they get the most out of their stay.
It's important that you pack the right clothing when embarking on a walking holiday in Italy. Having an awareness of what your chosen routes entail will help you get a clear idea of what to pack, and checking the weather is key. We'd recommend that you bring sturdy walking boots that support your ankles and thick socks are a must.Depending on the season, you might need clothing suitable for hot weather, like shorts and breathable layers. Many opt for a cap that covers their neck, as well as sunglasses. You might need a waterproof jacket with a hood, plus waterproof or lightweight trousers that will dry easily.
SPF and sun protection is a given for your walking holiday to Italy, along with protective gear like hats and sunglasses, especially if the weather is due to be hot. Even overcast days can expose you to UV rays so it's important to protect your skin as you'll naturally be spending most of your time outside. Snacks and a water bottle or water pack will mean that you can fuel your body throughout the trip and feel on top form throughout.If you are doing a self-guided walking holiday across some of Italy's trickier terrain especially, you may want to pack a first aid kit.
We give each walking holiday a level so that you can make an informed decision about which option best suits your experience.
Not sure which level to choose? You can get in touch with our expert team and they will be able to advise you further.
As well as considering the level and your desired destination, think about whether you would prefer to do guided or self-guided walks during your holiday in Italy.
Guided walking holidays are ideal if you're looking to socialise during your walks. You'll be placed in a small group and led by a local guide.
Self-guided walking holidays offer different rewards. You'll be able to tackle the route at your own pace using clear instructions on how to get to each point across a designated route.
Providing walking holidays you won't forget in a hurry is what we do best – and Italy is one of our top destinations. Thanks to our secure booking process it means you can commit knowing we have your best interests at heart, as we've been refining our experiences over the past 35 years. So, what are you waiting for? Let us help you find your next adventure.We're highly regarded – We've been rated 'Excellent' by our customers on Feefo for our personable walking holidays.
Picture-perfect locations – We use a five-step approval process to curate our walking tours, ensuring we include breathtaking destinations and hand-picked hotels with hosts who will make your experience uniquely memorable.
Award-winning walking holidays – We're proud to run award-winning tours. With impeccable customer service and attention to detail, our company has been recognised by the British Travel Awards.
We can arrange your flights – After providing us with a few details, we can take the reins and arrange flights on your behalf.
Sustainable Travel – Our People, Places & Planet plan reinforces our mission of running our tours as sustainably as possible while working towards becoming Nature Net Positive and reducing our impact on the surrounding environment.
ABTA- and ATOL-protected – You can book with confidence knowing our walking holidays in Italy are ABTA- and ATOL-protected. Find out more about what your key rights are when booking with us.
We aim to empower communities – Working together with our sister company, Exodus Travels and their Foundation we aim to empower and protect the communities we visit and the environment we explore.
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