AITO: The Association of Independent Tour Operators
The Hill-Top Towns of Tuscany

The Hill-Top Towns of Tuscany

The Hill-Top Towns of Tuscany Overview

The joy of this holiday is to feel the timelessness of the Tuscan countryside, and to discover scenery immortalised in the works of great artists.

  • self-guided hotel-to-hotel walking, luggage transported
  • discover Tuscany’s rich culture and timeless countryside
  • the famous wines and beauty of the Chianti hills
  • stay in atmospheric San Gimignano

Nestling between the great art cities of Florence, Siena and Pisa, the Chianti hills are as famed for their beauty as for their dark red wines. Hill-top villages crown the rolling landscapes, and idyllic churches are dotted along the quiet paths. An extraordinary sense of history pervades the region, from Siena’s wide Campo to the Etruscan town of Volterra.


This walk takes you from Volterra through the Chianti vineyards and San Gimignano to the Sienese hills and magnificent Siena itself. The joy of the holiday is to feel the timelessness of the Tuscan countryside, and to discover the landscapes immortalised in the works of some of the world’s greatest artists.

Inntravel website: walking holiday, Tuscany, Italy

Reviews of this holiday

The Hill-Top Towns of Tuscany by Sascha, 7 Sep 2018
Traveller rating:

Walking hotel to hotel in Tuscany visiting hill top towns. Lovely walks, views, food, hotels etc. read more

The Hill-Top Towns of Tuscany by Merryl, 2 Jul 2017
Traveller rating:

The Tuscany section was a self guided walk, and the Bavarian section a self guided cycle ride. Walking and cycling notes ... read more

The Hill-Top Towns of Tuscany by Theo Wells, 24 Oct 2016
Traveller rating:

We walked the Hilltop Towns of Tuscany. The routes were diverse and beautiful - and well paced. The walking notes were spot on... read more

The Hill-Top Towns of Tuscany by Scotty, 23 Sep 2016
Traveller rating:

This holiday allows gentle walking in the Tuscan countryside while visiting a range of hill top towns from the very busy ... read more

The Hill-Top Towns of Tuscany by Frank, 13 Jul 2016
Traveller rating:

We spent 2 nights in Pisa and 2 nights in Florence enjoying the history, culture art and shopping before undertaking a walking ... read more

The Hill-Top Towns of Tuscany by Stephen, 4 Jul 2016
Traveller rating:

A walking holiday with luggage transfered from Volterra in the west to Siena in thr east via San Gimignano and Colle Val d'Elsa... read more

The Hill-Top Towns of Tuscany by Raring to go, 1 Oct 2015
Traveller rating:

This was a special 'big' birthday holiday for me, providing many new challenges. As non experienced travellers we felt it ... read more

The Hill-Top Towns of Tuscany by Dr John, 26 May 2015
Traveller rating:

a walking holiday in Tuscany read more

Overall Holiday Rating
100%
Excellent 8
Good 0
Average 0
Poor 0
Terrible 0
Reviews Submitted: 8
Reviews Accepted: 8
Reviews Rejected: 0
The Hill-Top Towns of Tuscany by Sascha, 7 Sep 2018
Traveller rating:

Walking hotel to hotel in Tuscany visiting hill top towns. Lovely walks, views, food, hotels etc. read more

The Hill-Top Towns of Tuscany by Merryl, 2 Jul 2017
Traveller rating:

The Tuscany section was a self guided walk, and the Bavarian section a self guided cycle ride. Walking and cycling notes ... read more