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.
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Navigation App
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided cultural tour
7 nights,
hotel-to-hotel
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
9 nights,
hotel-to-hotel
Level: 2
Moderate
Navigation App
Self-guided walking
8 nights,
hotel-to-hotel
Level: 1+ & 2
Headwater
Navigation App
Self-guided cycling
11 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided walking
7 nights,
twin centre
Level: 2
Moderate
Headwater
Navigation App
Self-guided walking
8 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Headwater
Navigation App
Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
7 nights,
single centre
Level: 1
Leisurely
Headwater
Navigation App
Self-guided walking
8 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Navigation App
Self-guided walking
7 nights,
hotel-to-hotel
Level: 1
Leisurely
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
7 nights,
single centre
Level: 2+
Moderate plus
Headwater
Navigation App
Self-guided cycling
8 nights,
hotel-to-hotel
Level: 1
Leisurely
Headwater
Navigation App
Self-guided walking
7 nights,
single centre
Level: 2+
Moderate plus
Headwater
Navigation App
Self-guided walking
7 nights,
single centre
Level: 2+
Moderate plus
Headwater
Navigation App
Self-guided cycling
8 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
10 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided walking
8 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
8 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Headwater
Navigation App
Self-guided walking
7 nights,
twin centre
Level: 2+
Moderate plus
Headwater
Navigation App
Self-guided walking
6 nights,
single centre
Level: 2
Moderate
Navigation App
Self-guided walking
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided walking
6 nights,
hotel-to-hotel
Level: 2
Moderate
Navigation App
Self-guided cycling
6 nights,
single centre
Level: 2+
Moderate plus
Headwater
Navigation App
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Navigation App
Self-guided walking
8 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Headwater
Navigation App
Self-guided walking
7 nights,
twin centre
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Navigation App
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
Self-guided pilgrimage
9 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Navigation App
Self-guided cycling
7 nights,
single centre
Level: 2+ & 3
Headwater
Navigation App
Self-guided walking
8 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided cultural tour
7 nights,
hotel-to-hotel
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Navigation App
Self-guided cycling
8 nights,
hotel-to-hotel
Level: 2+
Moderate plus
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
10 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Guided group walking
7 nights,
single centre
Level: 2
Moderate
Printed route
directions
Guided group walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Printed route
directions
Guided group walking
7 nights,
single centre
Level: 2
Moderate
Printed route
directions
Guided group walking
7 nights,
single centre
Level: 3
Stretching
Printed route
directions
Guided group walking
7 nights,
single centre
Level: 3
Stretching
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.
Whether you're an avid cyclist or hiker, we have a variety of activity holidays in Italy that will tick your boxes. If you're hoping to do a bit of both, then we've got you! Mix it up with a combination of walking the paths of the Amalfi Coast and then cycling the winding lanes of the Italian countryside.
You'll also find opportunities for swimming, skiing and city exploration in all of our Italy adventure tours, along with world-renowned historical sites such as Pompeii and Doge's Palace. Local delights such as wine tasting and sampling exquisite cuisine are also available.
Our active tours to Italy are available from February through to November and we curate our holidays to ensure that you get the best value for money from each one. Typically, travel to Italy is cheaper from March through May and September to November, though temperatures are more pleasant during the springtime.
Your experience comes first on our adventure tours to Italy. Whether you choose a cycling or walking tour, rest assured that your holiday will be carefully crafted with your enjoyment and convenience in mind.
You'll spend your time exploring the culture-rich regions and stunning natural beauty of the Italian peninsula. There is no need to carry heavy luggage with you on your journey; while you're en route to your next hotel, our team will transport your belongings ahead of you.
We've provided a handy rating system for most of our activity holidays to Italy so that you can make the most out of your trip. You can also choose between self-guided and guided options.
If you choose a cycling adventure, then you'll receive a briefing from our staff. This practical demonstration will cover all the information and equipment that you need to enjoy your journey. On our self-guided tours, you can use our Headwater Navigation App to access tailored directions for your route, as well as GPS mapping.
The activity that you've selected will affect what you need to pack for your holiday to Italy. You should always check the weather forecast in the days leading up to your departure to get an idea of what clothes you'll need. Your comfort comes first so there are some staples to bring along with you, including:
Choosing what to wear for your activity tour in Italy will depend on your preferences and the weather conditions at the time of your visit. You're going to be active outdoors for most of the day so comfortable shoes and thick socks are essential. Breathable layers and shorts are recommended for the warmer seasons. In the autumn and winter months, temperatures are cooler in Italy so you may need to bring along waterproof clothes or a windbreaker.
All of our adventure holidays in Italy are designed so that you can get the most out of your trip no matter the month in which you're travelling. June to September offers the best weather for your activity tour as temperatures are at their warmest and there is less chance of snow or rain.
Every destination for our Italy adventure tours offers a unique and picturesque experience of the country but some packages truly take the cake. If you're looking to explore the gentle terrain and stunning sights of Northern Italy on two wheels, then our cycling holidays to Tuscany are just the ticket. For panoramic views of the Mediterranean Sea, walking in Sardinia will deliver the activity holiday of your dreams.
We have a variety of activity holidays to Italy for every kind of adventurer, backed up by nearly 40 years of experience in creating getaways that stay with you forever. Whether you're cycling, walking or looking to do a bit of both, our team will do everything that we can to make the booking process as easy as possible.
