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Tuscany – North of Siena

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Homepage > Italy > Tuscany – North of Siena
  • Duration: 6 Nights
  • Difficulty: Level 2
  • Tour Type: Self Guided
  • Availability: Daily April to October
  • Location: Siena
Tour Details

We are proud to present this fantastic walking tour of Siena and the surrounding countryside to the North of the city. This trekking holiday in Italy is over 6 nights on a self-guided basis with a grading of level 2.

During your week-long walking tour of Siena, you will experience hilltop fortified towns, Etruscan ruins, medieval boroughs, vines and olive gardens.

You will explore the wonderful countryside of this part of Tuscany starting from the superb Siena, the medieval Pompeii. From the medieval walled citadel of Monteriggioni to the towered town of San Gimignano and its gentle vineyards of Vernaccia to the Etruscan and medieval town of Volterra.

Why not get a taste for the real Italian way of life and join us on this tour?

Starting Location


Price Includes

  • 6 nights bed and breakfast
  • Navigation by Smart Phone App
  • Information Pack
  • Luggage transfers
  • Welcome Meeting

Price Excludes

  • Transport before and after tour
  • Single Rooms
  • Flights
  • Entrance to Attractions
  • City Tax
  • Travel Insurance
Trip Info


A level 2 walk. Trips with easy day walk which are interspersed with more strenuous sections. Four to five hours walking per day (excluding breaks) in hilly to mountainous areas using well kept but sometimes stony paths.


A mixture of very nice 3 stars hotels and guest houses,  all comfortably located within the historical centre, most of them are family-run.

Travel Insurance

It is a requirement of booking this tour with Hooked on Walking that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.


Day 1Arrival to Siena, explore the old town (3km)

Our representative will meet you in Siena and will introduce you to your walking tour. If you arrive in enough time have an exploratory walk in the main roads and narrow alleys. Siena is one the best-preserved medieval cities in Europe, a true masterpiece of art and architecture with its gothic Duomo, the museums and famous buildings and the shell shape  square “Il Campo” the scene of the holy (because dedicated to the Virgin), and mad horse race “The Palio”

Day 2Siena transfer to S. Colomba walk to Strove 7.5 miles 12 km

A walk today on paths and gravel roads across rolling hills. Some small sections are steep. You will walk through some beautiful woods of the Montagnola Senese – a home of wild boars.

Day 3Strove- Monteriggioni – Strove 8.75 miles 14 km

Today you will see some wonderful views of Tuscan towns and countryside, the evergreen oak wood of the Montagnola Senese and the stunning medieval citadel of Monteriggioni. Strove is a small medieval Tuscan village. Monteriggioni is a medieval hilltop village with its very well preserved crown of city walls and watchtowers.

Day 4Strove – Colle di Val d’Elsa 6.25 miles 10km

Today you continue your walk across this wonderful Tuscan countryside. Of course, stop for lunch or take a picnic but enjoy this shorter relaxing day. Your destination Colle Val d’Elsa is a medieval market town. Today Colle is famous for its crystals (a medieval tradition). There is also an interesting Etruscan Museum.

Day 5Colle di Val d’Elsa – S.Gimignano 8.75 miles 14km

Views of Tuscan towns and countryside today as your path will enter the medieval  Pilgrim way to Rome “Via Francigena”. This is still today a popular pilgrimage route as the “Camino di Santiago”. San Gimignano one of our favourite towns lies on the site of an Etruscan settlement dated 3rd century B.C. It developed during the middle ages thanks to the pilgrimage route, the Via Francigena,  which runs through the town. Of the original 72 medieval towers, only 14 remain to witness the great power and richness of the past.

Day 6  S.Gimignano – Sensano with transfer to Volterra, 8.75 miles 14km

Today you can continue to admire beautiful views of the countryside and the Vernaccia vineyards. Then you will pass near the ruins of a medieval castle and will cross a beautiful evergreen oak wood. Volterra is surrounded by two defensive walls one Etruscan the other medieval, it is one of the most important centres of Tuscany for its monuments that testify to 3000 years of civilisation and its traditional alabaster craftsmanship.

Day 7Departure

End of tour after breakfast. From Volterra, bus connections are available to Cecina on the coast. From Cecina train station you can reach Pisa,  Florence and Rome. If you wish to stay longer we can book you a wonderful 4-star hotel, formally a farm estate but now a stunning hotel with a nice pool, gym, wellness and stunning surroundings.


How to get there

The best airport is Pisa where you can transfer by train in around 2 hours.

Book Now

2024 Prices – For complete tour price breakdown please click the book now button and select your holiday tour date. Prices will then be listed.

 Tour Code Prices From (per person) Book Now
NSiena (6 Nights) from £1116 Book Now
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