The Tracks & Trails of Tuscany

Prices from £1,145


13 May 2020 - 23 Sep 2020
Duration: 6 days
Ref: RETUTW0620


Prices from £1,145
Single Supplement: £195
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Rolling hills, cypress groves and undulating shades of green are the rich canvas against which we’ll discover a host of Tuscan gems. Immerse yourself during walks through this beautiful landscape where medieval hilltop towns reveal a centuries’ old-culture. Take a vintage train ride and uncover the hidden charms of the Val d’Orica characterised by the sinuous flow of its river. Two amazing cities are included in our trove of Tuscan treasures. Siena, shining in medieval magnificence, and Florence, ‘Cradle of the Renaissance’ and the jewel in Tuscany’s crown.


  • Return flights from London to Pisa
  • Five nights’ bed and breakfast in Siena
  • Coach transfers for our excursions
  • Packed lunch on two walking days
  • Lunch in a local restaurant on day five
  • Dinner in a local restaurant on four evenings
  • Services of an experienced local walking guide and Tour Manager

Your rail journeys:

  • Treno Natura vintage steam train journey through the Val d’Orcia
  • Local train to Florence

Your guided walks:

  • Walk in the Val d’Elsa along the River Elsa
  • Explore the Tuscan countryside around Volterra
  • Full day excursion to Florence with guided walking tour
  • Discover the enchanting landscape on a walk through the Val d’Orcia

Day 1: London – Siena

Today we fly from London to Pisa and transfer to our hotel in the Siena area. Dinner will be served in a local restaurant.

Day 2: Val d’Elsa

Perched upon a hilltop, the historic market town of Colle di Val d’Elsa is the start of this morning’s walk. With our local guide we follow a path along the charming turquoise River Elsa looking out for the herons, little egrets, mallards and Eurasian wrens that call this place home. Dotted along the way there are plenty of comfortable areas with wooden seating and picnic tables where we can enjoy our packed lunch surrounded by lush, green countryside typical of Tuscany. After the walk we return to Siena where you’ve time at leisure to explore the beautiful, historical centre. The Piazza II Campo, Duomo and Palazzo Pubblico are just a few of the not-to-be-missed sights. After you’ve finished exploring, it’s just a short downhill walk, or quick public bus ride, back to our hotel. Tonight, we’ll enjoy dinner in a local restaurant.

Moderate walk – Duration: approx. 4 hours, distance: approx. 6 miles. Terrain: Uneven paths/ground.

Day 3: Volterra

Medieval Volterra is the oldest, continuously-inhabited town in Tuscany. Surrounded by beautiful rolling Tuscan hills, this walled town has over 3,500 years of history to discover. Today’s guided walk from Volterra shows us one of Tuscany’s more dramatic landscapes. The Balze is an awe-inspiring spectacle of abrupt crevasses created over the centuries by the continual erosion of layers of sand and clay. Today an 11th century abbey sits on a precipice awaiting a fate already shared by churches, monasteries, streets and even a necropolis that was washed away. In the afternoon you’ve time at leisure to enjoy the timeless atmosphere of Volterra’s historical centre and perhaps visit the handicraft workshops where artisans work with alabaster, a traditional art dating back to Etruscan times. Tonight’s dinner is served in a local restaurant.

Moderate walk – Duration: approx. 4 hours, distance: approx 6 miles. Terrain: Uneven ground on ancient railroad tracks.

Day 4: Florence

Today we’ll take the train from Siena to Florence, a city famed for its wealth of art and architectural treasures. Florence’s historical centre is small and we’ll explore on foot. The Piazza della Signoria is one of the most beautiful squares in the world with the graceful Loggia dei Lanzi - its very own open-air sculpture gallery. In the famous Piazza San Giovanni, we can admire Giotto’s Bell Tower, the Baptistery and Florence’s Cathedral with its magnificent Renaissance dome. We’ll also see Ponte Vecchio, the city’s oldest bridge and an everlasting symbol of Florence. At the end of our guided tour you can explore the city further before our train journey back to Siena. This evening is at leisure and you may choose to dine in one of Siena’s many fine restaurants.

Day 5: Val d’Orcia & Treno Natura

Treno Natura, or the ‘Nature Train’, traces the old Asciano – Monte Antico line taking in some of the most beautiful scenery in Tuscany. From the moment we step aboard this vintage steam train we’ll enter an enchanting landscape crossing through the Crete Senesi and the Val d’Orcia passing small villages seemingly frozen in time. During the journey we’ll alight in one of the many quaint medieval villages and enjoy a walk through the countryside stopping for a traditional local lunch. We take the Treno Natura back to Siena where we’ll enjoy a farewell dinner.

Easy walk: Duration: approx. 2 hours, distance: approx. 3 miles. Terrain: dirt track walking, some hard soil tracks.

Day 6: Siena – London

After breakfast we return by coach to Pisa Airport for our flight to London.

What walking equipment will I need?

All of our walks are of an easy-moderate nature and therefore we recommend that you have a reasonable level of fitness for our Off the Beaten Tracks range of holidays. It is also important to ensure you bring the right equipment with you and for our walking tours we would recommend:

  • A pair of good quality walking boots
  • Weather appropriate clothing – including layers
  • A comfortable rucksack
  • A water bottle
  • Walking poles (not essential but can aid climbs and descents)


    Outward Journey


    Return Journey


Hotel Colonna or similar

Our charming 3-star hotel sits in the Tuscan countryside, just a 30-minute walk downhill from Siena’s historical centre. Traditional in style, this 28-room property has a stunning outdoor terrace complete with sun loungers and a small, shallow pool. The simple yet spacious rooms have TV, complimentary WiFi, a minibar and air-conditioning. The en-suite bathrooms have a shower or bath, hairdryer and amenities. Breakfast is buffet-style and dinner will be taken in a local restaurant.