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.
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.
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:
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 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.
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!
Self-guided walking
7 nights,
twin centre
Level: 2
Moderate
Bed and
breakfast
Self-guided cycling
11 nights,
hotel-to-hotel
Level: 2
Moderate
Breakfasts plus
2 meals
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Breakfasts plus
11 meals
Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Bed and
breakfast
Self-guided cycling
7 nights,
single centre
Level: 1
Leisurely
Half board
Self-guided walking
7 nights,
hotel-to-hotel
Level: 1
Leisurely
Bed and
breakfast
Self-guided walking
8 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Breakfasts plus
6 meals
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Breakfasts plus
4 meals
Self-guided cycling
7 nights,
single centre
Level: 2+
Moderate plus
Breakfasts plus
4 meals
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Breakfasts plus
1 meal
Self-guided walking
7 nights,
single centre
Level: 2+
Moderate plus
Half board
Self-guided walking
7 nights,
single centre
Level: 2+
Moderate plus
Breakfasts plus
4 meals
Self-guided cycling
8 nights,
hotel-to-hotel
Level: 2
Moderate
Breakfasts plus
3 meals
Self-guided cycling
10 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Bed and
breakfast
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Breakfasts plus
2 meals
Self-guided cycling
8 nights,
hotel-to-hotel
Level: 2
Moderate
Breakfasts plus
4 meals
Self-guided walking
7 nights,
twin centre
Level: 2+
Moderate plus
Bed and
breakfast
Self-guided walking
5 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Self-guided walking
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Bed and
breakfast
Self-guided walking
6 nights,
single centre
Level: 2
Moderate
Half board
Self-guided cycling
6 nights,
single centre
Level: 2+
Moderate plus
Bed and
breakfast
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Breakfasts plus
1 meal
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Bed and
breakfast
Self-guided walking
6 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Cultural tour
7 nights,
hotel-to-hotel
Bed and
breakfast
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Bed and
breakfast
Self-guided walking
7 nights,
twin centre
Level: 2
Moderate
Bed and
breakfast
Self-guided walking
7 nights,
twin centre
Level: 2
Moderate
Bed and
breakfast
Self-guided walking
8 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Breakfasts plus
3 meals
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Self-guided walking
9 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Breakfasts plus
2 meals
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Breakfasts plus
1 meal
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Bed and
breakfast
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Breakfasts plus
1 meal
Self-guided cycling
7 nights,
single centre
Level: 2+
Moderate plus
Breakfasts plus
7 meals
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Breakfasts plus
5 meals
Self-guided walking
8 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Cultural tour
7 nights,
hotel-to-hotel
Breakfasts plus
1 meal
Headwater
Navigation App
Self-guided walking
8 nights,
hotel-to-hotel
Level: 2
Moderate
Breakfasts plus
4 meals
Self-guided cycling
10 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Breakfasts plus
2 meals
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Self-guided walking
8 nights,
hotel-to-hotel
Level: 2
Moderate
Bed and
breakfast
Guided group walking
7 nights,
single centre
Level: 2
Moderate
Printed route
directions
Guided group walking
7 nights,
single centre
Level: 2
Moderate
Printed route
directions
Winter snow holiday
7 nights,
single centre
Printed route
directions
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Where appropriate, we grade our holidays based on distance, terrain, elevation gain, remoteness, etc and categorise them into 4 relative groups. This is ultimately subjective and may vary slightly day to day; for more advice, please see the specific trip page or call one of our friendly team.
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.