Few countries are as diverse as Italy. This sought-after destination offers everything that anyone could ever want from their holiday - spectacular cities, diverse scenery, beautiful beaches, incredible architecture and some of the most delicious cuisine you'll ever taste. With Headwater, 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.
From Tuscany and the Bay of Naples to Puglia and Sicily, no matter where you stay in this glorious destination, you'll have plenty of opportunities to make unforgettable memories.
Looking for walking routes through untouched greenery and an amazing array of wild flowers? Venice, Vicenza, Padua and Este offer wonderfully unspoilt ground to explore on. Or perhaps remarkably well-preserved landscape steeped in tradition is something you'd prefer to see? If so, head to Liguria.
Would you prefer to cycle? Allow one of our activity holidays in Italy to take you from Pisa to Florence, where you can cycle through famous spa towns, visit world-class art museums and take pictures at the leaning tower of Pisa. Or perhaps cycling the wine trails of Umbria sounds more appealing, where you can explore sun-drenched landscapes and panoramic views as you ride through fascinating towns and historic villages.
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 on 01606 369408.
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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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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 Amalfi to chic Sorrento, taking in en route vertical Positano and (optional) the beautiful island of Capri.
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Stay in a luxury hotel for the week and savour the stunning snow covered vistas of the jagged limestone mountains of the UNESCO Dolomites. Excellent for downhill skiing with the option of trying cross country skiing, snow shoeing and more.
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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 Barbaresco and Barolo.
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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.
DEPARTURE MONTHS
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
Independent walking trip allowing you to discover the beauty of Puglia and Matera. Starting in the UNESCO World Heritage site of Matera, you'll make your way south east, through gently rolling countryside filled with olive groves and vineyards, stopping at Alberobello with its 'trulli' houses and the White City of Ostuni before finishing at the heel of Italy in Otranto with a walk along the coastline.
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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 8-night holiday combines gentle pedalling through olive groves, sunflower fields and vineyards with time in gorgeous historic towns and sun-drenched villages. Highlights include medieval Bevagna, Etruscan Perugia, picture-postcard Spello and ancient Assisi.
DEPARTURE MONTHS
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 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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Start at Matera, one of the oldest inhabited cities in the world and cycle through the Alta Murgia National Park, the largest natural park in Italy. Reach the Adriatic coastline at Trani, known as the 'Pearl of Puglia' and continue your ride, south, along the coast to Bari and your final destination, Monopoli.
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Discover a unique fusion of German and Italian landscapes and architecture as you cycle through relaxed waterfront towns, cosmopolitan cities and traditional pastel-painted Alpines villages to Riva, 'Pearl of Lake Garda'.
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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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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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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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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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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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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 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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This 6-night linear trip is a great mix of wonderfully scenic walking and historic hilltop towns. The walks follow a mix of paths and trails, partly on the St Francis Way, partly on the 'Sentiero degli Ulivi', the Olive Grove Trail. Along the way you pass the great Abbey at Sassovivo and wander the ruins of Campello Alto.
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This 8-night linear trip is a great mix of wonderfully scenic walking and historic hilltop towns. The walks follow a mix of paths and trails, partly on the St Francis Way, partly on the 'Sentiero degli Ulivi', the Olive Grove Trail. Along the way, you explore the upper slopes of the 'bald mountain' Monte Subasio with stunning mountains vistas. You can discover the secluded hermitages of St Francis, pass the great Abbey at Sassovivo and wander the ruins of Campello Alto.
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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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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 Barbaresco and Barolo.
DEPARTURE MONTHS
Explore the undiscovered western coast of Sicily by bike to find pristine nature reserves, ancient monuments and Baroque towns. Highlights include Segetsa amphitheatre and Selinunte Archeaological Park.
DEPARTURE MONTHS
This 10-night linear trip is a great mix of wonderfully scenic walking and historic hilltop towns. The walks follow a mix of paths and trails, partly on the St Francis Way, partly on the 'Sentiero degli Ulivi', the Olive Grove Trail. Along the way, you explore the upper slopes of the 'bald mountain' Monte Subasio with stunning mountains vistas. You can discover the secluded hermitages of St Francis, pass the great Abbey at Sassovivo and wander the ruins of Campello Alto.
DEPARTURE MONTHS
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 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!
DEPARTURE MONTHS
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 10-night holiday combines gentle pedalling through olive groves, sunflower fields and vineyards with time in gorgeous historic towns and sun-drenched villages with 4 nights spent in Spoleto with its fantastic architecture and opportunities to visit Rome and Norcia, famed for its cured meats.
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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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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.
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!
DEPARTURE MONTHS
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.
DEPARTURE MONTHS
Start at Matera, one of the oldest inhabited cities in the world and cycle through the Alta Murgia National Park, the largest natural park in Italy.
DEPARTURE MONTHS
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'.
DEPARTURE MONTHS
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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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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Striking active volcanoes, black beaches, thermal springs and a stunning cobalt sea make the Aeolian Islands a unique must-see destination. Exploring the varied landscape by boat and on foot is without doubt the best way to take in the natural beauty and contrasts of this part of Sicily.
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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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Enjoy the spectacular scenery of the Dolomites by bike while avoiding the need to ride up any long climbs. We explore the beautiful valleys of the Alta Pusteria, visiting Brunico, Lake Toblach, Cortina d’Ampezzo and crossing into the Austrian Tyrol to explore mediaeval Lienz. We stay in a family-run three-star hotel in Dobbiaco with a spa and swimming pool.
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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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Cycle around four iconic lakes in two countries - Italy and Switzerland
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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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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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