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Hidden Gems
Explore Hemingway's Sierra de Guadarrama

Walking Hemingway’s Sierra de Guadarrama


Sierra de Guadarrama, the mountains between Madrid and Segovia, are an unexpected hiker’s paradise, beautifully described by Ernest Hemingway in his famous novel For Whom the Bell Tolls. It is a real surprise to most walkers to find such an alpine scenery so close to a big city like Madrid. The Machotas hills close to El Escorial are fun to walk and from their top, you will realise that a great walking experience is about to begin, including the Guadarrama ridge, the Seven Picos of Cercedilla and the massive granite peaks near Navacerrada and Cotos pass, rising well above 2000 m.

The Guadarrama Mountains is a mountain range forming the main eastern section of the system of mountain ranges along the centre of the Iberian Peninsula. The range runs southwest-northeast, extending from the province of Ávila in the southwest, through the Community of Madrid, to the province of Segovia in the northeast. The range measures approximately 80 kilometres in length. Its highest peak is Peñalara, 2428 metres in elevation.

This walking holiday in Spain will take you to high peaks offering amazing views, to historical and cultural sites like the Monastery of Escorial and the Royal Palace and Gardens of La Granja. End your journey visiting the beautiful Segovia, and do not miss its fine restaurants and lively bars.


  • The places where Hemingway’s For Whom the Bell Tolls is set
  • The Monastery of El Escorial
  • The views from the Machotas peaks
  • Peñalara Natural Park paths and its glacial landscape
  • The Royal Palace and Gardens at La Granja
  • Beautiful Segovia with the aqueduct, its amazing Romanesque churches, and its great restaurants

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Day 1: Escorial

El Escorial is very well connected with Madrid, both by bus and train. Enjoy your first evening in this elegant town: the views of the Machotas that you will walk tomorrow, the impressive Abantos. You can walk to the beautiful monastery and in the evening enjoy the terrace bars and the great restaurants of Escorial.

Day 2: Machotas Peaks | 15 km

Walk to the place where King Philip II was said to sit to check the progress of the works of the Monastery and climb up to the beautiful Machotas peaks (1410 and 1466 m) to enjoy the views. You can easily see the big four skyscrapers of Madrid! If you want an easier day, just skip the Machota Baja hilltop. Complete this fun circular walk and enjoy a well-deserved refreshment at a terrace bar.

Day 3: Escorial to Cercedilla | 19 km

Climb up the beautiful Abantos peak (1753 m) and keep walking along the ridge, with views for miles; you can also see the amazing 150 m high cross of Valle de los Caidos. You can keep walking to El León pass (there is a bar and restaurant) or descend to Guadarrama reservoir, where a taxi will pick you up to take you to Cercedilla. A nice and challenging circular walk up to Abantos is also available. But If you prefer an easier day, take a short but fun walk in Collado Mediano, with incredible views of the whole range and nice bars and restaurants at the end.

  • Walking for the day (option 1): 19 km, 7 h ↑1050 m ↓600 m (end at El León pass)
  • Walking for the day (option 2): 16 km, 6h ↑↓850 m (end at Guadarrama reservoir)
  • Walking for the day (option 3): 9 km, 3h ↑↓350m (Collado Mediano circular walk)
  • Walking for the day (option 4): 12 km, 4-5h ↑↓ 750m (walk to Abantos)
  • Overnight at Casa Peña Pintada

Day 4: Fuenfría Valley | 10 km

Enjoy the many hiking possibilities of this valley, including the walk along the remains of a Roman road that climbs up to a 1792 m high pass! You can even hit 2100 m high peaks, with views for miles. There is an easier option, and a challenging one with amazing views for experienced walkers and then an incredible ridge walk that you will not forget.

  • Walking for the day: 3 possible circular routes, from easy (10km ↑↓450m to moderate (12km ↑↓650m) and strenuous ridge walk (16km ↑↓850m). In the end, you can add a very pleasant 4 km walk back to your hotel, or take a bus.
  • Overnight at Casa Peña Pintada

Day 5: Cercedilla to Cotos Pass and to La Granja | 20 km

Take the mountain train from Cercedilla to Cotos pass. Peñalara offers amazing scenery with views over  Rascafria valley and several lakes and glacier formations. From Nevero pass (2096 m) you can easily descend to the elegant La Granja, popular as the Spanish Versailles. For a longer walk, you can also keep walking along the ridge for 5 km more. In case of bad weather, you can take a direct descent to Valsain valley and enjoy a gentle walk along a lovely stream.

NB! We will arrange a private transfer as the train line is under reconstruction at the moment.

  • Walking for the day: 19.5 km, 6-7 h, ↑550 m ↓1200 m
  • Walking for the day: 14.7 km 5-6 h, ↑400 m ↓1050 m
  • Overnight at Hotel Roma

Day 6: Valsain valley, La Granja and Segovia | 13 km

Today you can walk through the Valsain valley and, of course, you can also visit the Royal sites at La Granja: the gardens, the palace or the glass factory. Today’s route starts parallel to a lovely stream and then heads up to El Puerco hill, where you can visit the Spanish Civil War fortress and trenches and admire the views of the Valsain Valley. After that, take a taxi or bus to nearby Segovia, a unique city full of historic monuments and typical Castilian restaurants.

  • Walking for the day: 13 km, 4 h, ↑↓350m. You can skip this walk if you prefer to visit La Granja and arrive earlier in Segovia
  • Overnight at Hab Urban

Day 7: Segovia Extension, Departure, or Onward Travel

We highly recommend staying at least one more day in Segovia to explore this beautiful city.

What to Expect


On this walking holiday, you will be staying in family-run guesthouses, pensions and small hotels. We have carefully hand-picked all places and regularly monitor their quality. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour.

Click to view default hotels

Hotel Posada Don Jaime, Casa Peña Pintada, Hotel Roma, Hab Urban

Hotels are subject to availability. In case a particular hotel is fully booked for your desired 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.


Breakfast is included on 5 days, as well as 2 picnic lunches ans 2 dinners. When no restaurant location is available on route lunches and snacks should either be bought from local shops, or packed lunch can be pre-ordered from your hotel the night before. Please note that breakfast in the Escorial hotel is served after 9 am, so if you want to start early, you should go to a nearby cafeteria instead.

Difficulty & terrain

This holiday is appropriate for seasoned walkers and requires a good level of fitness; average walking time is 5-6 hours per day (14-15 km). Most stages can be optionally extended to a ‘strenuous’ grade (read more about difficulty grades). If you choose the strenuous walks, you will walk on average 17.5 km / 6-7 hours per day. Some of the optional walks are demanding and are appropriate for very experienced walkers, used to walk on stony/rocky terrain.

When to go

This trip is available in late April, May, June, September, October and early November.

The flexibility of self guided holidays means that there are no fixed dates and you can start your trip on any date during the season. Please note that in April there still might be snow on the high trails.

Getting there

FCO up-to-date travel advice

Click to view travel options

By plane

Our recommended airport for this holiday is Madrid.

By train or bus



  • Detailed pre-departure holiday information pack including GPS-checked and regularly updated route descriptions, road notes and maps
  • GPS tracks
  • Arrival meeting with our representative
  • 6 nights in small hotels and guesthouses
  • 5 breakfasts (note that breakfast in Escorial starts at 9 am)
  • 2 dinners (drinks not included) in Cercedilla
  • 2 picnic lunches Cercedilla
  • Luggage transfers from hotel to hotel on all walking days
  • Taxi lift at the stage Escorial to Cercedilla
  • Taxi lift from La Granja to Segovia
  • 24/7 phone assistance by our local office/representative


  • Flights and airport transfers
  • Train tickets from Cercedilla to Cotos (8-10€ per person)
  • Tickets for visits to Escorial Monastery or La Granja Royal Palace
  • Travel insurance (required – get a quote online)
  • Personal expenses such as snacks, drinks, phone calls, extra transfers, tips, etc.
  • Any items not specifically mentioned as ‘included’ in the programme
  • Entrance fees for attractions and museums

Options, extras & supplements

  • A supplement applies to members of a group who require a single room
  • This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)
  • Extra nights in Einsiedeln and Interlaken are available upon request
  • Extra night in Segovia after the holiday