Adventure tours to Italy

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.

Looking to plan your next adventure holiday to Italy?

Italy is a country that offers so much for an unforgettable getaway but don't just take our word for it - see it for yourself. If you're about to plan your next holiday and have any questions about one of our adventure tours to Italy, one of our experienced team will be able to help.

Where can I go on an activity holiday in Italy?

We offer countless outstanding destinations for your activity holiday in Italy, as well as the possibility of multiple exciting spots just in one trip! Here are just a few of the places that you could visit:

THE AMALFI COAST

There are few places in Italy as stunning as the Amalfi Coast, with its emerald seas, pastel villages and scented lemon groves. You'll get to walk along the world's best coastal route, the 'Walk of the Gods', as you explore a region made up of the diverse islands of Procida, Ischia and Capri. As you travel through the gently rolling countryside filled with olive groves and vineyards, you'll take in the great shadow of Mount Vesuvius.

THE DOLOMITES

The Italian Dolomites are a Mecca for high-level walkers and cyclists so, if you're looking for an Italy adventure holiday that challenges you, then you're in the right place. Savour the snow-covered vistas of this UNESCO World Heritage site while you take advantage of country skiing and snowshoeing. Take routes leading into the Fanes-Sennes National Park and the jagged peaks of Tre Cime di Laverdo. Unrivalled alpine views are around every corner as you travel through the likes of Bolzano and Alta Val Pusteria.

VENETO

Our Veneto activity tours are the perfect choice for adventurers looking for a genuine grass-roots experience of Italy. Travel the winding paths and vineyards of the Venetian countryside before reaching famous Italian cities such as Venice and Verona. Explore the culture-rich streets of Padua and Vicenza, full of Renaissance history and charm, before stopping off to sample the delicious regional cuisine!

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Why choose Headwater?


Cycling from the Dolomites to Venice
Italy: The Dolomites

Cycling from the Dolomites to Venice

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07DL
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2045per person, tour only

  • 2 Reviews
  • All accommodation
  • All buffet breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
The Islands of Amalfi Walk
Italy: The Bay of Naples

The Islands of Amalfi Walk

Sitting prettily in the Bay of Naples lie the beautiful yet diverse islands of Amalfi: Procida, Ischia and Capri. Discover these stunning isles, from Procida's multi coloured harbours, to the thermal spas and terraced vineyards of Ischia and the glamour of Capri's elegant piazze.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07IN
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2045per person, tour only

  • 8 Reviews
  • All accommodation
  • All breakfasts and one evening meal
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Undiscovered Villages of Umbria Walk
Italy: Umbria

Undiscovered Villages of Umbria Walk

This trip combines 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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07UR
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2075per person, tour only
  • NEW FOR 2024  

  • 1 Reviews
  • All accommodation
  • All continental breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Journey through Puglia to Matera
Italy: The Bay of Naples

Journey through Puglia to Matera

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeT07PG
  • Holiday typeIndependent tour
  • Duration7 nights, hotel-to-hotel
  • Excellent for
  • From US$2195per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Heel of Italy - Alberobello to Lecce
Italy: Puglia

Cycling the Heel of Italy - Alberobello to Lecce

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07PI
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2255per person, tour only

  • 30 Reviews
  • All accommodation
  • All breakfasts and 1 evening meal
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
The Wine Trails of Umbria Cycling
Italy: Umbria

The Wine Trails of Umbria Cycling

This trip 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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07UR
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2375per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Brenner Pass to Venice Cycling
Italy: Trentino

Brenner Pass to Venice Cycling

Taking 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 to the canals and waterways of Venice.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC09VE
  • Holiday typeSelf-guided cycling
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2780per person, tour only

  • 3 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Heel of Italy - Matera to Lecce
Italy: The Bay of Naples

Cycling the Heel of Italy - Matera to Lecce

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC11PI
  • Holiday typeSelf-guided cycling
  • Duration11 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3185per person, tour only

  • 5 Reviews
  • All accommodation
  • All breakfasts and 2 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Secrets of Sicily Walking
Italy: Sicily

Secrets of Sicily Walking

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07MR
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2450per person, tour only

  • 91 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
The Amalfi Coast Walk
Italy: The Bay of Naples

The Amalfi Coast Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08AC
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3920per person, tour only

  • 81 Reviews
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Volcanoes of Sicily Walk
Italy: Sicily

Volcanoes of Sicily Walk

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!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07AI
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2555per person, tour only

  • 4 Reviews
  • All accommodation
  • All continental breakfasts
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
E-bike Cycling on the Costa Smeralda
Italy: Sardinia

E-bike Cycling on the Costa Smeralda

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07SM
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2720per person, tour only

  • 3 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Paths of the Amalfi Coast
Italy: The Bay of Naples

Paths of the Amalfi Coast

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. Walk the ancient hillsides studded with lemon groves and framed by deep gorges, from the Agerola Plain to the quaint towns of Positano, Ravello and Amalfi. The best is saved till last with arguably the world's best coastal walk: the 'Walk of the Gods'.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07BO
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1565per person, tour only

  • 21 Reviews
  • All accommodation
  • All continental breakfasts, 4 picnics and all evening meals
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Walking Amalfi's Path of the Gods
Italy: The Bay of Naples

Walking Amalfi's Path of the Gods

Discover some of the highlights of the world renowned Amalfi Coast, along panoramic footpaths lined with terraced vineyards and fragrant lemon groves, connecting Amalfi, Ravello and picture perfect Positano.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07AG
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1700per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All continental breakfasts
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Self Guided Walking in Puglia: From Lecce to Matera
Italy: Puglia

Self Guided Walking in Puglia: From Lecce to Matera

Independent walking trip to discover the beauty of Puglia and Matera. Starting in the heel of Italy’s Baroque Lecce, head north through gently rolling countryside filled with olive groves and vineyards. Visit the white city of Ostuni, Alberobello with its iconic 'trulli' houses and the UNESCO World Heritage site of Matera with its unique cave houses.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07PM
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1805per person, tour only

  • 27 Reviews
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Heart of Veneto Cycling
Italy: Veneto

Heart of Veneto Cycling

The 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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07VN
  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1970per person, tour only

  • 69 Reviews
  • All accommodation
  • All continental breakfasts and evening meals
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Walking in the Venetian Hills
Italy: Veneto

Walking in the Venetian Hills

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08VN
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2030per person, tour only

  • 84 Reviews
  • All accommodation
  • All continental breakfast and 6 evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Bolzano, Verona & Venice Ride
Italy: Veneto

Bolzano, Verona & Venice Ride

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. Ride through the beautiful cities of Verona, Padova and finally exploring the canals and waterways of Venice.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07VE
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2150per person, tour only

  • 14 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Secrets of Sicily Cycling
Italy: Sicily

Secrets of Sicily Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07MR
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2360per person, tour only

  • 20 Reviews
  • All accommodation
  • All breakfasts and 1 evening meal
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walks in The Italian Dolomites
Italy: The Dolomites

Walks in The Italian Dolomites

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07DL
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2495per person, tour only

  • 120 Reviews
  • All accommodation
  • All buffet breakfasts and evening meals
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Venetian Villas and Vineyards Cycling
Italy: Veneto

Venetian Villas and Vineyards Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC08VN
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2540per person, tour only

  • 54 Reviews
  • All accommodation
  • All continental breakfasts and 6 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
A Taste of Tuscany Walking
Italy: Tuscany

A Taste of Tuscany Walking

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07ST
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2675per person, tour only

  • 26 Reviews
  • All accommodation
  • All breakfasts and 4-course evening meals
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
A Taste of Tuscany Cycling
Italy: Tuscany

A Taste of Tuscany Cycling

Introducing you to quintessential Tuscany, this cycling holiday 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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07ST
  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2750per person, tour only

  • 24 Reviews
  • All accommodation
  • All breakfasts and 4-course evening meals
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Walking the Dolomites of Alta Badia
Italy: The Dolomites

Walking the Dolomites of Alta Badia

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

JFMAMJJASOND

  • Holiday codeW07DS
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2945per person, tour only

  • 20 Reviews
  • All accommodation
  • 4 nights on Half Board and 3 nights on B&B
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Secrets of San Gimignano Cycling
Italy: Chianti

Secrets of San Gimignano Cycling

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!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC08TY
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3185per person, tour only

  • 55 Reviews
  • All accommodation
  • All continental breakfasts and 5 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling through Baroque Sicily
Italy: Sicily

Cycling through Baroque Sicily

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC08BS
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3200per person, tour only

  • 18 Reviews
  • All accommodation
  • All continental breakfasts and 3 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Julian Alps to the Adriatic Cycling
Slovenia / Italy

Julian Alps to the Adriatic Cycling

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

JFMAMJJASOND

  • Holiday codeC10SV
  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$4070per person, tour only

  • 99 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals included
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Contrasts of Puglia Cycling
Italy: Puglia

Contrasts of Puglia Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07PU
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2795per person, tour only

  • 120 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Gastronomic Barolo Walk
Italy: Piedmont

Gastronomic Barolo Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08PD
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3590per person, tour only

  • 91 Reviews
  • All accommodation
  • All continental breakfasts and 4 gastronomic evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Gastronomic Barolo Cycling
Italy: Piedmont

Gastronomic Barolo Cycling

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

JFMAMJJASOND

  • Holiday codeC08PD
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3635per person, tour only

  • 80 Reviews
  • All accommodation
  • All buffet breakfasts and 4 gastronomic evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Undiscovered Puglia Walk - Discovering the South-East Coast
Italy: Puglia

Undiscovered Puglia Walk - Discovering the South-East Coast

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07PL
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1850per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Coastal Cilento Walk
Italy: Campania

Coastal Cilento Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08CT
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1850per person, tour only
  • NEW FOR 2024  

  • 1 Reviews
  • All accommodation
  • All breakfasts and 3 evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking in the Cinque Terre and Portofino
Italy: Liguria

Walking in the Cinque Terre and Portofino

Discover the beautiful Liguria region and its remarkably well-preserved landscape steeped in tradition based in Sestri Levante. Explore the coastline from the Cinque Terre to Portovenere as well as Portofino and the UNESCO island of Palamaria.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW06CT
  • Holiday typeSelf-guided walking
  • Duration6 nights, single centre
  • Activity level
  • Excellent for
  • From US$1895per person, tour only

  • 3 Reviews
  • All accommodation
  • All breakfasts and 6 dinners
  • Route notes provided
  • Flights from London (if booking incl. flights)
Gems of the Amalfi Coast Walking
Italy: The Bay of Naples

Gems of the Amalfi Coast Walking

Stretching 50km from Sorrento to Salerno, the Amalfi Coast 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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07AM
  • Holiday typeSelf-guided walking
  • Duration7 nights, twin centre
  • Activity level
  • Excellent for
  • From US$2000per person, tour only

  • 1 Reviews
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking on the Francigena Way
Italy: Umbria

Walking on the Francigena Way

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!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW09VF
  • Holiday typeSelf-guided walking
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2105per person, tour only

  • 8 Reviews
  • All accommodation
  • All buffet breakfasts, 1 evening meal and 1 picnic are included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Secrets of Sardinia Walking
Italy: Sardinia

Secrets of Sardinia Walking

A 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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07SA
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2120per person, tour only

  • 7 Reviews
  • All accommodation
  • All breakfasts
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling in Tuscany: Pisa to Florence
Italy: Tuscany

Cycling in Tuscany: Pisa to Florence

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07PF
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2135per person, tour only

  • 5 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Wine & Walk in Chianti
Italy: Tuscany

Wine & Walk in Chianti

Walk through the beautiful wine-growing area of Classic Chianti, visiting the World Heritage cities of Florence and Siena.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07TU
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2150per person, tour only
  • All accommodation
  • All breakfasts and 1 evening meal
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Emilia Romagna – Bologna to Parma Cycling
Italy: The Bay of Naples

Emilia Romagna – Bologna to Parma Cycling

Discover the flavours and art cities of Emilia Romagna on this tasty tour pedalling from Bologna to Parma.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07EM
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2600per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Undiscovered Sardinia Cycling
Italy: Sardinia

Undiscovered Sardinia Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07SA
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2600per person, tour only

  • 13 Reviews
  • All accommodation
  • All breakfasts and 1 evening meal
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Volterra to San Gimignano Walk
Italy: Chianti

Volterra to San Gimignano Walk

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

JFMAMJJASOND

  • Holiday codeW08TY
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2750per person, tour only

  • 62 Reviews
  • All accommodation
  • All continental breakfasts and 3 evening meals
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Italian Lakes
Italy: Lombardy

Cycling the Italian Lakes

Journey between seven beautiful Italian Lakes as you explore this colourful and cultural region.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07TL
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2780per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking the Wine Villages of Piedmont
Italy: Piedmont

Walking the Wine Villages of Piedmont

Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night walking trip! The route takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of La Morra and Barolo.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08PB
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2990per person, tour only

  • 3 Reviews
  • All accommodation
  • All continental breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Chianti Classic Walk
Italy: Chianti

Chianti Classic Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW10TY
  • Holiday typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3050per person, tour only

  • 33 Reviews
  • All accommodation
  • All continental breakfast and 3 evening meals
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Wine Villages of Piedmont
Italy: Piedmont

Cycling the Wine Villages of Piedmont

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

JFMAMJJASOND

  • Holiday codeC08PB
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3065per person, tour only

  • 5 Reviews
  • All accommodation
  • All buffet breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Classic Chianti Cycling
Italy: Chianti

Classic Chianti Cycling

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

JFMAMJJASOND

  • Holiday codeC10TY
  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3605per person, tour only

  • 26 Reviews
  • All accommodation
  • All buffet breakfasts and 5 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Sicily: Vino & Volcanoes
Italy: Sicily

Sicily: Vino & Volcanoes

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeT07SI
  • Holiday typeIndependent tour
  • Duration7 nights, hotel-to-hotel
  • Excellent for
  • From US$3800per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All breakfasts
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Highlights of Puglia Cycling
Italy: Puglia

Highlights of Puglia Cycling

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

JFMAMJJASOND

  • Holiday codeC10PU
  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3920per person, tour only

  • 7 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals included
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)

Frequently asked questions

What activities are available in Italy?

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.

What time of year is the cheapest to go to Italy?

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.

What to expect from your activity holiday in Italy?

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.

What to pack for an activity holiday in Italy?

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:

  • Water bottles
  • SPF and other sun protection products
  • Sunglasses and hats
  • Bike helmet (if required)
  • Comfortable shoes and clothing
  • Waterproof clothing (if required)

What to wear on an activity holiday in Italy?

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.

What time of year is best for an activity holiday in Italy?

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.

Where in Italy is best for an active holiday?

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.

Why choose Headwater for your adventure holiday to Italy?

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.

  • Highly rated holidays - We have a 4.6 rating from many satisfied customers on Feefo so you can trust that our activity tours come strongly recommended.

  • Stunning destinations - Thanks to our five-step approval process, you get to pick from only the most beautiful locations and outstanding hotels.

  • Hassle-free booking - Not only do we craft your activity tour to Italy but we'll arrange your flights, too!

  • Winning awards - We've been recognised by the British Travel Awards for our adventure holidays across the globe, so you're guaranteed to get a holiday to remember.

  • Sustainability at heart - The People, Places & Planet plan is in place to help our tours to run sustainably and move us forward to becoming Nature Net Zero.

  • Benefitting communities - The Exodus Travel Foundation means that we're making a difference in social, conservation and disaster relief causes.

  • ABTA- and ATOL-protected - Book your Italy adventure tour with confidence thanks to both ABTA and ATOL protection. Learn more about your key rights when booking a holiday with us.

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