Few countries are as diverse as Italy. This sought-after destination offers everything that anyone could ever want from their adventure holiday - spectacular cities, diverse scenery, beautiful beaches, incredible architecture and the most delicious cuisine that you'll ever taste. You can experience all of this and more on one of our activity holidays in Italy. Whether you'd prefer to tackle the Paths of the Amalfi Coast, cycle the Venetian countryside, or walk the olive trails of Umbria, you can choose from a wide range of guided and self-guided options when you book your adventure tour to Italy with Headwater..
No matter where you stay in this glorious country, you'll have plenty of opportunities to make unforgettable memories.
Looking for walking routes through untouched greenery and an amazing array of wildflowers? Venice, Vicenza, Padua and Este offer wonderfully unspoilt ground on which to explore.
Perhaps you'd prefer to cycle? Allow one of our activity holidays in Italy to take you from Pisa to Florence, where you can pedal through famous spa towns, visit world-class art museums and take pictures at the leaning tower of Pisa. Alternatively, maybe cycling the wine trails of Umbria, where you can explore sun-drenched landscapes and panoramic views, sounds more to your taste.
If you want to upgrade your activity holiday in Italy to include flights, you can expect an average flight time of a couple of hours. To find out more information on flight prices and times, please get in contact with one of our team.
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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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From the northeastern Dolomites, cycle through the Alta Val Pusteria below the famous Drei Zinnen, through the valley of the ice cream makers and across the plains to reach Venice.
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Journey from the sweeping coastline of Puglia to UNESCO Alberobello and onto the ancient city of Matera. This independent tour highlights the very best of Puglia and neighbouring Basilicata.
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Firmly tucked away in the South, Puglia is a sun-soaked region of deserted white sand beaches, unspoilt villages and gently rolling hills backing the clear emerald seas of the Adriatic. Highlights include UNESCO Alberobello and whitewashed Ostuni.
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This 7-night holiday combines scenic pedalling through olive groves, sunflower fields and vineyards with time in gorgeous historic towns and sun-drenched villages. Highlights include panoramic Montefalco, picture-postcard Spello and ancient Assisi.
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This 9 night cycling holiday takes you from the stunning Dolomites to Venice. The cycle route starts at the Brenner Pass, on the border with Austria and you'll follow gentle riverside tracks through fragrant orchards and vineyards. Enjoy a ferry ride across Lake Garda and continue through the beautiful cities of Verona, Padova and finally exploring the canals and waterways of Venice.
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This 11 night cycling holiday starts in UNESCO Matera, in the Basilicata region and moves on to Puglia. Discover unspoilt villages and gently rolling hills, sandy beaches and interesting towns. Highlights include whitewashed Ostuni and Baroque Lecce.
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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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Let the e-bike do the hard work for you on this wonderful cycling trip discovering the highlights and lesser known inner heartlands of Sardinia's renowned Costa Smeralda. Have lunch in glamorous Porto Cervo, pedal around the stunning island of La Maddalena and admire the pristine white beaches lapped by those famous emerald waters.
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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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This single-centre cycling holiday is a perfect choice for people wanting a genuine grass-roots Italian experience. You'll stay on a family-run farm, in the heart of the Venetian countryside, with private pool and vineyards. Venice, Verona and Padua are all possible day trips.
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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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Spectacular riding from the stunning Dolomites to Venice. Starting from Bolzano, the capital of the South Tyrol, you'll follow gentle riverside tracks through fragrant orchards and vineyards to reach Lake Garda. Continue the ride through the beautiful cities of Verona, Padova and finally exploring the canals and waterways of Venice.
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Explore the undiscovered western coast of Sicily by bike to find pristine nature reserves, ancient monuments and Baroque towns. Highlights include Segesta's amphitheatre and Selinunte Archeaological Park.
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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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Wonderfully easy hotel-to-hotel cycling route exploring the pretty villages, villas and castles of the Venetian countryside. Lots of historic interest and great regional cooking! A day trip to Venice is a 'must' with Padua and Vicenza also within reach.
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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 cycling holiday introduces you to quintessential Tuscany; it has all the ingredients to create a wonderful lasting impression of this rightly famous region: the landscapes, the food, the people and, of course, perfect cycling routes.This is not just a cycling holiday it is an immersion into local Tuscan life.
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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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This 8-night cycling holiday combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. You'll stay in high quality hotels, enjoy superb meals and relax by panoramic pools - views extend as far as Corsica on a clear day!
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This eight-night, self-guided cycling holiday provides a wonderful introduction to Sicily's south east, a part of the island renowned for its beautiful, unspoilt coastline, spectacular Baroque architecture and sumptuous regional cuisine.
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Our 10 night holiday takes you from the turquoise waters of Lake Bled, nestled below Slovenia's jagged Julian Alps, along the Alpe Adria Trail, passing into Italy. Wind down through the mountains to the island of Grado on the Adriatic coast. On route pass through the historic towns of Venzone, Udine and Palmanova.
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Firmly tucked away in the South, Puglia is a sun-soaked region of deserted white sand beaches, unspoilt villages and gently rolling hills backing the clear emerald seas of the Adriatic. Highlights include UNESCO Alberobello and whitewashed Ostuni.
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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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Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night cycling holiday! The cycling takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of Barbaresco and Barolo.
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Spend 6 nights on Lake Garda, the playground of cycling! Your unique hotel has been transformed from an old rail station, close to the waters edge.
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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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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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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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Cycle from the iconic leaning tower of Pisa to the Ponte Vecchio in Florence, passing through beautiful Tuscan landscape that inspired artists and composers such as Leonardo da Vinci and Puccini. The gentle cycling is mainly along riverside paths and quiet roads, and there are the opportunities to lengthen the rides, or take the train at some stages to spend extra time at your destinations.
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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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Superb cycling discovering the south west of Sardinia, with its glittering turquoise seas and pure white sand beaches. The trip includes island hopping to St Antioco and St Pietro, visiting the archaeological site of Nora and pedalling along Sardinia's spectacular Costa del Sud.
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Discover the flavours and art cities of Emilia Romagna on this tasty tour pedalling from Bologna to Parma.
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Journey between seven beautiful Italian Lakes as you explore this colourful and cultural region.
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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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Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night cycling holiday! The cycling takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of Barbaresco and Barolo.
DEPARTURE MONTHS
This 10-night cycling tour combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. You'll stay in high quality hotels, enjoy superb meals and relax by panoramic pools with views that extend as far as Corsica on a clear day!
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Uncover the hidden gems and must-see sights of Eastern Sicily. From local wine tastings to volcanic walks up Mount Etna, this independent tour highlights the very best of the islands natural beauty.
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Firmly tucked away in the South, Puglia is a sun-soaked region of deserted white sand beaches, unspoilt villages and gently rolling hills backing the clear emerald seas of the Adriatic. Highlights include UNESCO Alberobello, whitewashed Ostuni and beautiful Baroque Lecce.
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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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Explore Italy's most impressive mountain range on snowshoes - this area of the Dolomites is perfect, with routes leading into the Fanes-Sennes Natural Park, along the shoreline of Lago di Braies and beneath the jagged peaks of Tre Cime di Lavaredo. Trek along forest trails and old military tracks to magnificent viewpoints and learn about the impact of WW1 in this area.
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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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Whether you're an avid cyclist or hiker, we have a variety of activity holidays in Italy that will tick your boxes. If you're hoping to do a bit of both, then we've got you! Mix it up with a combination of walking the paths of the Amalfi Coast and then cycling the winding lanes of the Italian countryside.
You'll also find opportunities for swimming, skiing and city exploration in all of our Italy adventure tours, along with world-renowned historical sites such as Pompeii and Doge's Palace. Local delights such as wine tasting and sampling exquisite cuisine are also available.
Our active tours to Italy are available from February through to November and we curate our holidays to ensure that you get the best value for money from each one. Typically, travel to Italy is cheaper from March through May and September to November, though temperatures are more pleasant during the springtime.
Your experience comes first on our adventure tours to Italy. Whether you choose a cycling or walking tour, rest assured that your holiday will be carefully crafted with your enjoyment and convenience in mind.
You'll spend your time exploring the culture-rich regions and stunning natural beauty of the Italian peninsula. There is no need to carry heavy luggage with you on your journey; while you're en route to your next hotel, our team will transport your belongings ahead of you.
We've provided a handy rating system for most of our activity holidays to Italy so that you can make the most out of your trip. You can also choose between self-guided and guided options.
If you choose a cycling adventure, then you'll receive a briefing from our staff. This practical demonstration will cover all the information and equipment that you need to enjoy your journey. On our self-guided tours, you can use our Headwater Navigation App to access tailored directions for your route, as well as GPS mapping.
The activity that you've selected will affect what you need to pack for your holiday to Italy. You should always check the weather forecast in the days leading up to your departure to get an idea of what clothes you'll need. Your comfort comes first so there are some staples to bring along with you, including:
Choosing what to wear for your activity tour in Italy will depend on your preferences and the weather conditions at the time of your visit. You're going to be active outdoors for most of the day so comfortable shoes and thick socks are essential. Breathable layers and shorts are recommended for the warmer seasons. In the autumn and winter months, temperatures are cooler in Italy so you may need to bring along waterproof clothes or a windbreaker.
All of our adventure holidays in Italy are designed so that you can get the most out of your trip no matter the month in which you're travelling. June to September offers the best weather for your activity tour as temperatures are at their warmest and there is less chance of snow or rain.
Every destination for our Italy adventure tours offers a unique and picturesque experience of the country but some packages truly take the cake. If you're looking to explore the gentle terrain and stunning sights of Northern Italy on two wheels, then our cycling holidays to Tuscany are just the ticket. For panoramic views of the Mediterranean Sea, walking in Sardinia will deliver the activity holiday of your dreams.
We have a variety of activity holidays to Italy for every kind of adventurer, backed up by nearly 40 years of experience in creating getaways that stay with you forever. Whether you're cycling, walking or looking to do a bit of both, our team will do everything that we can to make the booking process as easy as possible.
