Walking holiday in Tuscany and Siena, Italy
The 8 day walking route traverses ancient paths and dirt tracks, past Tuscan farms and forests, culminating in the magnificent city of Siena. Experience a landscape characterised by remote villages, scattered cypress trees, and undulating vineyards.
From £815 Twin and £1390 Single
Greentraveller’s Top Tips: The greener way to experience this walking holiday is to travel to Tuscany by rail, rather than air. Certaldo and Siena, the starting and finishing points of this hoiday are quick train journeys from Florence, which is easily accessible by rail from the UK. It's really just a hop onto the train at London St Pancras for a spectacular overland journey to the Tuscan capital via Paris. If you've time between train connections in Florence, the ciy is small and compact, so exploring the historical and cultural landmarks is best done on foot. Walking also gives visitors an opportunity to discover the charms and magic of everyday life in Florence. We recommend wandering through the Boboli gardens behind Pitti Palace; an excellent choice for a stroll and picturesque views of the city.
>> For full details on transport, see: Train from London to Florence
Details of Walking Holiday in Tuscany and Siena
Its gently rolling hills are strikingly familiar from the classical backdrops of Renaissance art, and its charm is immutable - the perfect merging of medieval and modern worlds. Uncover the history of Certaldo, walk through timeless Tuscany, see Siena's outstanding architecture, experience the rustic charm of rural life, savour regional cuisine, and sip luscious locally produced wines.
Summary Itinerary
Day 1 Certaldo: Known for its ties to poet Giovanni Boccaccio, Certaldo features a medieval upper city surrounded by fortifications.
Days 2-3 San Gimignano: Wander the narrow stone streets to appreciate the architecture, walk the walls for far-reaching views or just soak up the atmosphere at a pavement cafe.
Day 4 San Gimignano to Colle di Val d'Elsa: Hike through woods and fields to the quaint town of Colle di Val d'Elsa, it's modern lower town and historic upper town.
Day 5 Colle di Val d'Elsa to Monteriggioni: There are plenty of photo opportunities on the walk to Monteriggioni. This historic village is encircled by huge walls and 14 impressive towers.
Days 6-8 Monteriggioni to Siena: Wander through vineyards and olive groves to the beautiful city of Siena. Enjoy a day of well-deserved rest or take an optional city walk to discover its history and culture.
What price includes
- Intrepid trip representative
- Luggage transported en route
- Walking guide & maps (with comprehensive route directions)
- 7 Breakfasts
- Guesthouses (7 nights)
- Carbon offset: 87 kgs per person
Location
Plan your journey by train
Meeting point:
Intrepid is currently contracting a great new hotel in a central and convenient location in Certaldo. Please check the detailed itinerary for details.
Certaldo train station
Transfer to meeting point:
Guests make their own way to meeting point
Take the train from Florence (SMN station) to Certaldo (52 mins journey).
How to get there:
Train from London to Certaldo (via Florence)
Plan your journey by train
Finish point:
Intrepid is currently contracting a great new hotel in a central and convenient location in Siena. Please check the detailed itinerary for details.
Siena train station
Transfer to finish point:
Guests make their own way to station
Take the train from Siena to Florence SMN station (1h30 mins). I
How to get back:
Train from Florence to London







