Overview
A seven day self-guided adventure, walking in Tuscany on a luscious linear route between the divine city of Siena and historic town of Cortona. We categorise this as an easy to moderate walking holiday, walking between 7-23km all experiencing Tuscany at its most tranquil. Bask in the idyllic landscapes of Crete Senesi and Val di Chiana, veer onto the historic Via Lauretana pilgrim trail, and look on in awe at the ridiculously beautiful hamlets, hilltop towns and even swim in hot thermal pools. And that’s before we even mention the charming hotels and wine.
- Siena
- Crete Senesi
- Biancane Di Leonina and Sito Transitorio
- Thermal baths in Rapolano Terme
- Val di Chiana
Itinerary
Day 1: Arrive in Siena
Arrive in Siena, a much celebrated medieval city. If time allows, head for a stroll to Piazza del Campo, the city’s shell-shaped square in the historic centre. Visit the impressive town hall, Palazzo Pubblico, and perhaps climb the steps of Torre del Mangia for panoramic views over the city. Duomo di Siena, the city’s Romanesque-Gothic cathedral, is also worth a visit, to see the intricate marble design of both the façade and the interior.
- Accommodation: Hotel Chiusarelli or similar in Siena
Day 2: Siena – Asciano | 16-23km
Take a short transfer to the starting point of today’s walk. The walk can be shortened by starting further along the route. Head through the heart of the Crete Senesi area, surrounded by views of rolling hills, dotted with ancient farmhouses and cypress-lined country lanes. Follow the trail through Biancane Di Leonina, an area of unique dome-shaped formations on a mostly barren and clay-like terrain, before reaching the stone sculpture and landmark known as Sito Transitorio. Take a break in the village of Vescona, before ending your day of walking in Asciano.
- Walking for the day: 23km, 6h, ↑690m, ↓690m (shorter option: 16km, 4h, ↑340m ↓310m
- Accommodation: Hotel La Pace or similar in Asciano
Day 3: Asciano – Serre di Rapolano | 7-15km
Today’s route is not very demanding, however, there is also the option of a shortened version. Some sections of the route can become muddy and slippery after rainfall, due to the clay soil. Walk through the area of Crete Senesi, heading towards Rapolano Terme. Spend the afternoon here, relaxing at the thermal bath complex, which is supplied with water from the nearby hot springs and dates back to the 13th century. Continue walking for the final few kilometres of today’s walk, before reaching Serre di Rapolano.
- Walking for the day: 15km, 4h, ↑269m ↓161m (shorter option: 7km)
- Accommodation: B&B Palazzo Bizzarri or similar in Serre di Rapolano
Day 4: Serre di Rapolano – Sinalunga | 20km
Leave Serre di Rapolano and walk through a variety of landscapes including woodland, vineyards, olive groves and pastures, with the trail offering extensive views over Val di Chiana along the way. The route leads away from Crete Senesi, entering a wooded area of oak trees, before taking you through the medieval village of Scrofiano. The final destination of today’s walk is the town of Sinalunga.
- Walking for the day: 24km, 7h, ↑700m ↓700m
- Accommodation: B&B Maison Tuscany or similar in Sinalunga
Day 5: Sinalunga – Farneta | 18km
Today’s route heads down country roads, passing through fields and along the banks of the canals, which were dug to drain the valley. Midway through today’s walk, there is the option of a short detour to visit the village of Bettolle. When you get to Farneta, be sure to visit the pre-Romanesque Abbazia di Farneta, just opposite your accommodation.
- Walking for the day: 18km, 6h, ↑240m ↓313m
- Accommodation: Hotel Farneta or similar in Farneta
Day 6: Farneta – Cortona | 16km
The final day of the tour consists of a long but gentle walk over the hills and plains of Val di Chiana. From here, some sections of the walk follow the famous Via Romea Germanica, an ancient pilgrim route. Continue walking along a flat winding path, passing through several small hamlets. Reach Pieve di San Michele Arcangelo, one of the oldest churches in the region, from where the climb up to Cortona begins. It is also possible to avoid the ascent by taking an alternative route to Camucia-Cortona railway station, where there is a bus service to Cortona (payable locally).
- Walking for the day: 10km, 6h, ↑360m ↓186m
- Accommodation: Hotel San Michele or similar in Cortona
Day 7: Departure
Departure after breakfast, or extend your stay with an extra night in Cortona.
What to expect
Accommodation
Accommodation on this tour includes a mix of small, locally-owned hotels, B&Bs and traditional guesthouses. They have been carefully selected based on a variety of criteria including their location, warm hospitality, fine local food or commitment to responsible tourism. All rooms have en-suite or private bathrooms.
Click to view default hotels
- Hotel Chiusarelli (Siena)
- Hotel La Pace (Asciano)
- B&B Palazzo Bizzarri (Serre di Rapolano)
- B&B Maison Tuscany (Sinalunga)
- Hotel Farneta (Farneta)
- Hotel San Michele (Cortona)
Accommodation is subject to availability. In the event of a particular hotel or guesthouse being fully booked for your chosen dates, we will replace it with a hotel of equal value and quality level. We will provide exact accommodation details to you upon booking confirmation.
Meals
Breakfast is included on all days. When no restaurant location is available en route, lunches and snacks can either be bought from local shops or packed lunches can be pre-ordered from your hotel the night before. Dinner is included on day five in Farneta. On other days, dinner is available either at the accommodation or from restaurants in the local area.
Difficulty and terrain
This tour is rated easy to moderate, with daily walking distances ranging between 7-23km and daily maximum elevation gains of between 240-700m. Most of the walks are relatively easy, due to the low elevation gains, making this tour accessible to those with less walking experience. However, a good level of fitness is required to get the most out of this tour. The routes mainly follow paths and gravel roads, with some sections on asphalted roads. Some walks are quite long and more demanding, but there are options to shorten the routes using local public transport or by arranging private transfers (read more about difficulty grades).
We strongly advise you to only follow marked trails and never try to shorten the path through unknown and unmarked terrain. We will provide you with detailed route notes and maps and you can call our 24/7 local assistance phone number anytime. More detailed information on route navigation will be included in your holiday information pack.
When to go
This trip is available from the beginning of April until the end of October. The flexibility of self-guided holidays means that there are no fixed dates, meaning you can start your trip on any date during the season.
The summer months in Tuscany are hot, with little or no rain and average daily temperatures between 27-30C. The spring and autumn months are usually cooler with more rain, but still with plenty of dry days and pleasant conditions for walking. For more information, see our blog on the Best time to go to Italy.
Getting there
Click to view travel options
By plane
Our recommended airports for this tour are Pisa Airport (PSA), Florence Airport (FLR), Rome Fiumicino (FCO). Other Italian airports are also well connected to the area.
By train or bus
If you are able to travel to Italy without flying, this holiday is reachable by rail, with railway stations in Siena and Cortona. For more details, see the national rail operator Trenitalia, or use the Omio planner above.
Arrival in Siena:
- From Rome Fiumicino, take the bus (50mins) or train (30mins) to Rome Termini station, from there take the train to Siena (3h 30mins), changing in Florence
- From Florence Airport, take the bus or tram to Florence Santa Maria Novella railway station, from there take a direct train (1h 30mins) or bus (1h 15mins, line 131R) to Siena. For more information about buses, see Autolinee Toscane
- From Pisa Airport, take the shuttle (5mins, see Pisa Mover) to Pisa Centrale railway station and then take a train to Siena (1h 45mins), changing in Empoli
- For further information about train timetables and tickets, please see Trenitalia or use the Omio planner above
Departure from Cortona:
- From Cortona there are train services to Rome (2h 30mins), Florence (1h 30mins) or Pisa (2h 30mins, two changes). See above for further details of how to get from the railway station to the airport
Inclusions
Included
- 6 nights accommodation
- 6 breakfasts and 1 dinner (day five)
- Transfer to the start of the walk on day two
- Luggage transfers on all walking days (one piece per person, up to 15kg)
- Detailed digital holiday information pack and navigation app, including GPS-checked and regularly updated route descriptions, road notes and maps. Please note that the information pack is emailed to you prior to departure, and no printed documents are mailed or provided locally
- 24/7 phone support by our local office/representative
Excluded
- Airfare and connecting land transfers
- Lunches and dinners, drinks and snacks
- Travel insurance (required – get a quote online)
- Local tourist tax and entry fees (payable locally)
- Personal expenses
- Any items not specifically listed as included
- eSIM data for international travel (get an eSIM)
Options, extras and supplements
- If you’re travelling in a group, a supplement applies to group members who would like to have a room of their own
- This holiday is available for solo travellers. However, a supplement will be charged as the cost of rooms and also luggage or private transfers (when applicable) is not shared. Please note that solo travellers are always accommodated in their own room. For logistical reasons, we don’t offer an option for solo travellers to share rooms with other solo travellers.
- Extra nights
- Printed documents at the first accommodation
- Additional luggage
