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Hidden Gems
Explore Hemingway's Sierra de Guadarrama

Explore 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 2,000m.

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, 2,428 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


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

Walk to the place where King Philip II was said to sit to check the progress in the works of the Monastery and climb up to the beautiful Machotas peaks (1,410 and 1,466 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

Climb up the beautiful Abantos peak (1,753 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 an always open 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: 19 km, 7h ↑1050m ↓600m (end at El León pass), or 16 km, 6h ↑↓850 m (end at Guadarrama reservoir), or 9 km, 3h ↑↓350m (Collado Mediano circular walk), or 12km, 4-5h ↑↓ 750m (walk to Abantos)
  • Overnight at Casa Peña Pintada

Day 4: Fuenfría Valley

Enjoy the many hiking possibilities of this valley, including the walk along the remains of a Roman road that climbs up to a 1,792 m high pass! You can even hit 2,100 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

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 (2,096 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.

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

Day 6: Valsain valley, La Granja and Segovia

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, 4h ↑↓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.


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.

Sample 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.


Our recommended airport for this holiday is Madrid.

Please note that flight information can change rapidly, and not all flights run daily. Please do check directly with the airlines’ websites or Skyscanner before finalising any booking with us. Please do not book your flights before we have confirmed your booking.

Transfers to/from Airports

  • To get to San Lorenzo del Escorial: take a train from the airport or metro and a bus from Madrid. Departures every 30 minutes.
  • To return to Madrid from Segovia: take a bus or train, departures every hour.

Check public transfer options from Madrid

Private Transfers

Airport transfers by public transport are recommended for this trip.

Baggage Transfers

All hotel to hotel luggage transfers on walking days are included (maximum one piece of 20 kg per person).

A comprehensive and reputable travel insurance policy is essential to your enjoyment and peace of mind while on an active holiday. It is highly recommended when booking with us that all group members have a valid travel insurance which includes cover for all activities included in your trip. We have teamed up with World Nomads Logo to offer you adequate cover at a great value from a reputable insurer, and it takes only a few minutes to buy online.

Buy travel insurance online

Country Info

Up-to-date travel advice on Spain is available here. Detailed travel information and hints will be provided in your holiday information pack.

Trip Info

Difficulty Grade: Moderate (standard) / Moderate to Strenuous (optional)

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.

Route Navigation

Most the routes are on waymarked paths and trails and in general, the itinerary is easy to follow.  We strongly advise you to follow only marked trails and never try to shorten the path through the unknown and unmarked terrain. We will provide you with detailed road notes and maps, and you can call our 24/7 local assistance phone number anytime. More detailed info on route navigation will be included in your holiday information pack.

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.


The continental Mediterranean climate, typical of the peninsular interior, overlaps in the Sierra de Guadarrama with the mountain climate, with very cold winters and dry chilly summers.

The Guadarramas have climatic features, characterized by considerable temperature changes between summer and winter and a very dry summer. But, as in any mountainous zone, the climate on the mountains proper changes markedly with increases in height, and can be differentiated into discrete climatic zones.

Between 800m and 1,400m, the average annual temperature is 10-11 °C, with a summer high of 28 °C and winter low of -6 °C. Average annual precipitation is between 700 and 800 mm, predominantly in non-summer months. At this elevation, much of the precipitation falls as snow, between December and February, although there are always exceptions, and the snow rarely remains unmelted for more than three days. It is in this region that all cities and the majority of people live; this also means that of all distinguished elevations, it is the most susceptible to damage from human traffic and intrusion.

Between 1,400 and 2,000 m, the average annual temperature is 8-9 °C, with a summer high of 25 °C and winter low of -8 °C. Average annual precipitation increases with the height to 900-1,000 mm, again primarily during the non-summer season in the form of snow, but between December and April. Much of the snow remains on the ground for the duration of the winter, especially on the range’s north slope.

What to Bring

We recommend that you travel as light as possible – airlines might charge you an extra fee, and during ground transfers, the place might be limited. Ideally, you should bring one piece of luggage weighing not more than 20 kg (to be checked in) and a daily pack (15 – 20 l rucksack) for your everyday essentials (snacks, drinking water, camera, etc.). Below is a non-exclusive list of what you should bring to this trip. More detailed info will be included in your holiday information pack. If you need further advice, please contact a reputable outdoor retailer or us.

  • Good hiking boots
  • Hiking socks
  • Several t-shirts (cotton or preferably breathable/fast drying)
  • Packable waterproof and windproof jacket with hood
  • Synthetic mid layer or warm fleece
  • Trainers and/or sandals – to relax and wear inside accommodation
  • Sunglasses, sunscreen and lip salve
  • Hat/Baseball cap
  • Personal First Aid kit (wet wipes, flu remedies, stomach remedies)


  • 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


  • Where individual members of a group require a single room, a single room supplement is applicable.
  • This holiday is available for solo travellers. As costs are not shared, a supplement is payable on the standard trip cost

Other Trip-Related Costs

  • Entrance fees for attractions and museums


  • 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
  • Personal expenses such as snacks, drinks, phone calls, extra transfers, tips, etc.
  • Any items not specifically mentioned as ‘included’ in the programme

Extensions and Optional Extras

  • Extra night in Segovia after the holiday



Average rating:    from 3 reviews

Gavin P

I mostly enjoyed peaking on walking days 2, 3 and 4. Customer service was good after a slight miss-communication at the start. The contact I had with Aznar was of great benefit, not only with route and travel, but with all aspects. No complaint what so ever. Will almost certainly take you up and another holiday in future.

Gavin P

The contact I had with local rep Aznar was of great benefit, not only with route and travel, but with all aspects. Will almost certainly take you up and another holiday in future.

Russell F

The walk from Cotos to La Granja (short version) was the highlight. Ensure your plane to Madrid at the start of the holiday lands early enough to allow for contingencies / delays. Ideally try to make time to visit the monastery at El Escorial and not just do the walks. The smartphone app was useful as backup but mainly used the maps and written directions (which were excellent). It was good to have options of differing difficulty offered. Accommodation – excellent. Food at Cercedilla was great. Transfers - excellent. Local rep - excellent. Overall – excellent.

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