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Activity holidays in Italy

Italy is a country that offers so much, with charming scenery, cities rich in history and a seductive way of life that will leave you wanting more.

Few countries are as diverse as Italy - a country of mountains, sparkling coastlines, ancient history and sumptuous cuisine. Whether you're strolling through the great art cities of Tuscany and Umbria, or admiring the rolling hills and ancient forests of the Veneto with their amazing array of beautiful wild flowers, or enjoying the dramatic coastlines of the Island of Sicily you can really get 'under the skin' of Italy on a Headwater holiday.


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 typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £999per person, tour only

  • 53 Reviews
  • All continental breakfast and evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 **** comfort at night - a highly sought-after mix! Excellent bird-spotting, stunning flowers and unrivalled Alpine views.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1109per person, tour only

  • 84 Reviews
  • All buffet breakfasts and evening meals
  • Route notes and maps provided
From the Dolomites to Lake Garda Cycling
Italy: The Bay of Naples

From the Dolomites to Lake Garda Cycling

Offering a stunning yet dominant backdrop to the region is the UNESCO Dolomites, their jagged rock walls overlook the deep green meadows, acres of fragrant apple orchards and, further south, the lush vineyards of Trentino below.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1149per person, tour only

  • 16 Reviews
  • All buffet breakfasts
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Cycling the Wine Trails of Umbria
Italy: Umbria

Cycling the Wine Trails of Umbria

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 mediaeval Bevagna, Etruscan Perugia, picture-postcard Spello and ancient Assisi.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1249per person, tour only

  • 47 Reviews
  • All breakfasts and 6 evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
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 typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1269per person, tour only

  • 58 Reviews
  • All continental breakfasts and 2 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1389per person, tour only

  • 84 Reviews
  • All continental breakfasts and 3 evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Amalfi to Sorrento Walk
Italy: The Bay of Naples

Amalfi to Sorrento 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 Amalfi to chic Sorrento, taking in en route vertical Positano and (optional) the beautiful island of Capri.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1529per person, tour only

  • 57 Reviews
  • All breakfasts
  • Route notes and maps provided
  • Luggage transfers between hotels
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 Barbaresco and Barolo.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1699per person, tour only

  • 62 Reviews
  • All continental breakfast and gastronomic evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1819per person, tour only

  • 49 Reviews
  • All buffet breakfasts and gastronomic evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
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 typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1915per person, tour only

  • 52 Reviews
  • All continental breakfasts and 4 evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Heart of Veneto Cycling
Italy: Veneto

Heart of Veneto Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £959per person, tour only

  • 52 Reviews
  • All continental breakfasts and evening meals
  • High quality bikes provided
  • GPS route navigation provided
A Walk from Spello to Spoleto
Italy: Umbria

A Walk from Spello to Spoleto

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1029per person, tour only

  • 4 Reviews
  • All continental breakfasts and 5 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Walks in the Umbrian Hills
Italy: Umbria

Walks in the Umbrian Hills

This 7-night linear trip is a great mix of wonderfully scenic walking and historic hilltop towns. Starting in Spello, spend time wandering the narrow cobbled streets of one of Italy's best preserved medieval 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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1099per person, tour only
  • All continental breakfasts and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1159per person, tour only

  • 37 Reviews
  • All continental breakfasts and evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Footsteps of St Francis Walk
Italy: Umbria

Footsteps of St Francis Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1159per person, tour only

  • 35 Reviews
  • All continental breakfasts and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1195per person, tour only

  • 10 Reviews
  • All buffet breakfasts and 4-course evening meals
  • Route notes and maps provided
A Taste of Tuscany Cycling
Italy: The Bay of Naples

A Taste of Tuscany Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1219per person, tour only
  • All buffet breakfasts and 4-course evening meals
  • High quality bikes provided
  • GPS route navigation provided
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 holiday! The route takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of Barbaresco and Barolo.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1249per person, tour only
  • All continental breakfasts
  • Route notes and maps provided
  • Luggage transfers between hotels
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 typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1259per person, tour only
  • All buffet breakfasts
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Walking the Olive Trails of Umbria
Italy: Umbria

Walking the Olive Trails of Umbria

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

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1279per person, tour only
  • All continental breakfasts and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Volterra to San Gimignano Walk
Italy: Tuscany

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 typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1299per person, tour only

  • 45 Reviews
  • All continental breakfasts and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Mediaeval Umbrian Cycling
Italy: Umbria

Mediaeval Umbrian Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1409per person, tour only

  • 13 Reviews
  • Continental breakfast and 6 evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Secrets of San Gimignano Cycling
Italy: Tuscany

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 typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1449per person, tour only

  • 41 Reviews
  • All continental breakfasts and evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Chianti Classic Walk
Italy: Tuscany

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 C12 abbey, and enjoy superb meals.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1459per person, tour only

  • 27 Reviews
  • All continental breakfast and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1565per person, tour only
  • 5 nights on Half Board and 2 nights on B&B
  • Route notes and maps provided
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 typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1639per person, tour only

  • 4 Reviews
  • All continental breakfasts and 4 evening meals
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Classic Chianti Cycling
Italy: Tuscany

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 typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1699per person, tour only

  • 25 Reviews
  • All buffet breakfasts and 6 evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Heel of Italy Cycling
Italy: Puglia

Heel of Italy 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 typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1915per person, tour only
  • All continental breakfasts and 3 evening meals included
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Self-Guided Walking in the Cinque Terre and Portofino
Italy: Liguria

Self-Guided Walking in the Cinque Terre and Portofino

Discover the beautiful Liguria region and its remarkably well-preserved landscape steeped in tradition.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration6 nights, single centre
  • Activity level
  • Excellent for
  • From £629per person, tour only
  • All breakfasts and 3 dinners
  • Route notes and maps provided
Cycling the Adriatic: Venice to Porec
Italy: Veneto

Cycling the Adriatic: Venice to Porec

Cycle through three different countries from Italy to Croatia

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £799per person, tour only
  • All breakfasts
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Self-Guided cycling in Tuscany: Pisa to Florence
Italy: Tuscany

Self-Guided cycling in Tuscany: Pisa to Florence

Explore the city of romantic Florence

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £879per person, tour only
  • All breakfasts
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Self-Guided Walking in Puglia and Matera
Italy: Puglia

Self-Guided Walking in Puglia and Matera

Independent walking trip allowing you to discover the beauty of Puglia and Matera

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £999per person, tour only
  • All breakfasts, 1 dinner & 1 typical product tasting
  • Route notes and maps provided
  • Luggage transfers between hotels
Walking in Sardinia
Italy: Sardinia

Walking in Sardinia

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!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £999per person, tour only
  • All breakfasts, 5 picnic lunches, 5 evening meals and 1 wine-tasting
  • Led by experienced local guide
Sicilian Volcanoes
Italy: Sicily

Sicilian Volcanoes

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1029per person, tour only
  • All continental breakfasts, 1 lunch and 1 evening meal
  • Led by experienced local guide
Walks in Puglia and Matera
Italy: Puglia

Walks in Puglia and Matera

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1049per person, tour only

  • 21 Reviews
  • All buffet breakfasts and 1 evening meal
  • Led by experienced local guide
Walking the Prosecco Hills
Italy: Veneto

Walking the Prosecco Hills

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1049per person, tour only
  • All continental breakfasts, 4 lunches, 2 dinners and 2 wine-tastings
  • Led by experienced local guide
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