Tre Cime di Lavaredo, Dolomites, Italy

Self-Guided Holidays in Italy

Flash Sale - Save up to 15% on any Guided Group adventure (and 10% on any Self-Guided adventure). Learn more

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 walking holiday. Walkers 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

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Headwater - Gastronomic Barolo Walk

Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night walking holiday!

Self-Guided Adventures

Walking & Trekking
9 days Excl. Flights
From $2,285 USD
Activity Rating - Leisurely/Moderate
  • ON OFFER
  • New

Headwater - Secrets of San Gimignano Cycling

This 8-night cycling holiday combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. 

Self-Guided Adventures

Cycling
9 days Excl. Flights
From $2,015 USD
Activity Rating - Moderate
  • ON OFFER
  • New

Headwater - Heart of Veneto Cycling

This single centre cycling holiday is a perfect choice for people wanting a genuine grass-roots Italian experience.

Self-Guided Adventures

Cycling
8 days Excl. Flights
From $1,305 USD
Activity Level: Leisurely
  • ON OFFER
  • New

Venetian Villas and Vineyard Cycling

Wonderfully easy hotel-to-hotel cycling route exploring the pretty villages, villas and castles of the Venetian countryside.

Self-Guided Adventures

Cycling
9 days Excl. Flights
From $1,545 USD
Activity Level: Leisurely
  • ON OFFER
  • New

Walking in the Venetian Hills

The wonderfully unspoilt Venetian countryside is only an hour or so from the great city of Venice, but couldn't be more different!

Self-Guided Adventures

Walking & Trekking
9 days Excl. Flights
From $1,335 USD
Activity Rating - Leisurely/Moderate
  • ON OFFER
  • New

Headwater - Classic Chianti Cycling

This 10-night cycling tour combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena.

Self-Guided Adventures

Cycling
11 days Excl. Flights
From $2,405 USD
Activity Rating - Leisurely/Moderate
Call us on 1 844 227 9087