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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…

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Italy Self-Guided Holidays

A Walk from Spello to Spoleto

This 6-night linear trip is a great mix of wonderfully scenic walking and historic hilltop towns.

Walking & Trekking
Activity level:
Leisurely / Moderate
Ages: 8+
7 Days from $1,699 USD
Self-Guided (Incl. Taxes)
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Contrasts of Puglia Cycling

Explore Puglia's unspoilt villages, gently rolling hills with a backdrop of the clear, emerald Adriatic.

Activity level:
Leisurely / Moderate
Ages: 12+
8 Days from $2,279 USD
Self-Guided (Incl. Taxes)
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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 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