Request your free brochure for adventure inspiration. Order now >>

Walking along Latemar route (Alberto Campanile)

Self-Guided Holidays in Italy

Self-Guided Holidays in Italy

Italy is an incredible mix of scenery, culture and history, and the slow pace of life here is perfectly explored on a self-guided holiday. Walkers & cyclists have a wide choice of destinations, from the jagged Dolomites to the rolling hills of Tuscany and the magnificent Amalfi coast.

The regional variety is astounding here, but wherever you go it’s underpinned by some classic Italian traits: friendly locals, beautiful buildings, good wine and sumptuous food.

We’ll take care of your luggage, supply detailed route notes, information about points of interest, help with translations, and details of cafés and restaurants. You’re free to travel at your own pace, so there’s always time for a paddle in the sea or detour to that vineyard…

Call us on
1 844 227 9087

Italy Self-Guided Holidays

Walking in Assisi and Spoleto

Highlights of this beautiful region that discover UNESCO sites, historic pilgrimage trails and stunning landscapes

Walking & Trekking
Activity level:
Moderate
Ages: 8+
7 Days from $1,599 USD
Self-Guided (Incl. Taxes)
View More Details

Hidden Umbria Walk

This 7-night linear trip is a fantastic mix of wonderfully scenic walking, historic towns and panoramic hilltop villages

Walking & Trekking
Activity level:
Moderate
Ages: 8+
8 Days from $1,949 USD
Self-Guided (Incl. Taxes)
View More Details

Undiscovered Umbria Walk

This 9-night linear trip is a fantastic mix of wonderfully scenic walking, historic towns and panoramic hilltop villages

Walking & Trekking
Activity level:
Moderate
Ages: 12+
10 Days from $2,279 USD
Self-Guided (Incl. Taxes)
View More Details

Loved this trip - it was my first self-guided trip and my first trip with Headwater. They have a...

Adventure Coordinators, 2019 Walking in the Italian Dolomites

This was a wonderful break. You stay at a number of very beautiful places: Scapello, Marettimo...

adam wardman, 2018 Secrets of Sicily Walk

Dobbiaco was a tremendous centre and the Park Hotel Bellevue was everything that we would have...

David Bruce, 2017 Walking in the Italian Dolomites