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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…

Italy Self-Guided Holidays

Gastronomic Barolo Self-Guided Walk

Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this gastronomic walking holiday.

Walking & Trekking
Suitable for:
Age 12+
Activity level:
Leisurely / Moderate
9 Days from $3,879
Self-Guided (Excl. Flights)
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Loved this trip - it was my first self-guided trip and my first trip with Headwater. They have a...

Adventure Coordinators, 2019 Self-Guided 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 Self-Guided Walk

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

David Bruce, 2017 Self-Guided Walking in the Italian Dolomites