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Hidden Gems
Cycling Hemingway's Sierra de Guadarrama

Cycling Hemingway’s Sierra de Guadarrama


Sierra de Guadarrama, the mountains between Madrid and Segovia, are an unexpected cyclist’s paradise, beautifully described by Ernest Hemingway in his famous novel For Whom the Bell Tolls. It is a real surprise to find such alpine scenery so close to a big city like Madrid. This is a great trip for those who are passionate about enjoying nature by cycling along unpaved tracks and paths passing at the feet of an amazing sierra.

This trip will take you to historical and cultural sites like the Monastery of Escorial. You will continue cycling along historic cattle routes and single tracks enjoying the delicious local gastronomy in the different villages you will pass through. The route ends in the impressive Lozoya Valley, surrounded by mountains well above 2000m. 

When developing the itinerary, we have made our best to avoid asphalt roads, so you will enjoy scenic dirt tracks and paths most of the time

Click to view map


Day 1: Arrival in El 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, the impressive Abantos. You can walk or cycle to the beautiful monastery and in the evening enjoy the terrace bars and the great restaurants of Escorial.

Day 2: Escorial Circular Ride | 25 km

Once you get out of El Escorial and into the countryside you will be able to enjoy the landscapes of the whole sierra. The circular route will take you on undulating paths, passing “La Silla de Felipe II”, the place from where the King was said to sit and keep track on the progress of the works on the El Escorial Monastery. End your day enjoying a well-deserved refreshment at a terrace bar.

Day 3: Escorial to Cercedilla | 38 km

During the first part of today’s route, you cycle on flat terrain followed by a steady ascent to get to Guadarrama National Park at 1350m. Riding down to the mountain village of Cercedilla, you will enjoy great views of the massive and dramatic Seven Picos Ridge. 

  • Cycling for the day: 38 km, ↑600 m
  • Overnight in Casa Peña Pintada or similar
  • Included meals: breakfast, dinner

Day 4: Cercedilla to Miraflores | 45 km

Enjoyable stage through the outskirts of the National Park, passing through the typical mountain village of Navacerrada at the feet of the massive Maliciosa peak. Cycle further to Manzanares, a town with a lovely castle close to a reservoir and at the feet of the Pedriza, one of the biggest granite formations in the world. Your day ends in Miraflores, a nice town of stone houses placed at the base of the high peaks.

  • Cycling for the day: 45 km, ↑700 m
  • Overnight in El Horreo or similar
  • Included meals: none

Day 5: Miraflores to La Cabrera | 30 to 50 km

The Sierra of La Cabrera is really dramatic, with sharp and vertical granitic ridges. Today you can choose between two routes:

Option 1: Miraflores de la Sierra – La Cabrera (30 km, accumulated elevation gain 600 m). Direct route with a short initial section of road to get back into the natural park.

Option 2: Miraflores de la Sierra – Hoya de San Blas – La Cabrera (50 km, accumulated gradient 900 m). You go back to reach the amazing hidden valley called “Hoya de San Blas”. You return to Miraflores again to start the direct route.

  • Cycling for the day: 30 km, ↑600 m or 50 km, ↑900 m
  • Overnight in Huerto de San Antonio, a lovely finca with a nice garden and terrace to relax and enjoy a quiet evening. If not available, this stage will finish in the nearby village of El Berrueco, and your overnight will be in La Casona de la Dehesa.
  • Included meals: breakfast, dinner

Day 6: La Cabrera to Garganta de los Montes | 48 km

You leave the town and cycle towards the largest reservoir in the province of Madrid, visiting the walled town of Buitrago de Lozoya until you reach the start of the wonderful Lozoya Valley at the village of Garganta de los Montes, full of typical stone houses.

  • Cycling for the day: 48 km, ↑550 m
  • Overnight at Hotel Rural Quercus or similar
  • Included meals: breakfast

Day 7: Garganta de los Montes to Rascafría | 30 km

Your last stage is at the magnificent valley of Lozoya surrounded by the highest peaks of the Sierra de Guadarrama. Today you can choose between two alternatives:

Option 1: Garganta de los Montes – El Paular – Rascafría (30 Km, Accumulated gain: 200 m). Direct route with little gradient through the impressive Valley of Lozoya surrounded by mountains higher than 2,000 m above the sea level. Pass through the Monastery of El Paular (14th century) and arrive at the mountain village of Rascafría as the end of the trip.

Option 2: Garganta de los Montes – El Paular – Angostura – Rascafría (48 km, Accumulated gain: 550 m.). Once you arrive at the Monastery of El Paular you will get on a circular route through a forest of oaks and pine trees, cycling up to a viewpoint of the valley and descending to the edge of the Lozoya River and the Monastery, to finally reach Rascafría. 

  • Cycling for the day: 30 km, ↑200 m or 48 km, ↑550 m
  • Overnight in El Caserón de Trastámara or similar
  • Included meals: breakfast

Day 8: Departure

Optional transfer back to the airport, or to Madrid in case you prefer to stay for some days to enjoy this wonderful city.

  • Included meals: breakfast

What to Expect


On this walking holiday, you will be staying in private en-suite rooms 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, El Horreo,  Huerto de San Antonio (or La Casona de la Dehesa in El Berrueco), Hotel Rural Quercus, El Caserón de Trastámara

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.


The package includes breakfast on 6 days and 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

The average cycling distance per day is between 25-50 km, with a cumulative altitude gain ranging between 200m and 700m, as some of the days provide an easier option as well. The routes are not hard, but the better your physical shape is, the more you will enjoy the trip. 80% of the cycling is on dirt roads and tracks so you will not be bothered by car traffic most of the time (read more about difficulty grades). 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. We strongly advise you to follow only marked trails and never try to shorten the path through the unknown and unmarked terrain.

When to go

This trip is available in April, May, early June, late 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. It is too hot for cycling in July and August.

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
  • To get to San Lorenzo del Escorial: take a train from the airport or metro and a bus from Madrid. Departures every 30 minutes.
  • A taxi lift on departure day to Madrid airport or downtown can be booked in advance. You can take the bus via Lozoyuela as well.



  • Welcome briefing by our local representative (in person or via Skype prior to the tour, depending on the availability)
  • 7 nights in comfortable hotels and country inns
  • 6 breakfasts (no breakfast in Miraflores)
  • 2 dinners (in Cercedilla and La Cabrera, drinks not included)
  • Luggage transport when changing hotels
  • Tourist and cultural information, route notes, maps and GPS tracks
  • 24/7 phone assistance by our local office/representative


  • Flights and airport transfers
  • 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

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)
  • Bike rental
  • Extra nights before, during or after the holiday