The departure point for our epic journey is the Basque city of San Sebastian, or Donostia to the locals, which sits on the Bay of Biscay a little over 20km from the French border.

In the evening you will have a chance to meet your guides and fellow Skedaddlers and sample some typical pinchos as you wander the narrow streets of the charming old quarter. There is no tapas here! That’s Spanish rather than Basque! Instead delicious toppings are placed on fresh bread held together by cocktail sticks.

• Meals: Breakfast, lunch
• Ascent: 2,100 Metres Approx.

The first day in the saddle is a big day with plenty of climbing, however the gradients are generally gentle and by the time we arrive in the lovely town of Arbizu we will have made a significant start to our journey south. A chain of mountains forms a frontier right across northern Spain and starts to rise up just a few km inland from the coast, so for the early part of the day the only way is up. We sneak out of central San Sebastian on an asphalt cycleway by the river before taking on a busier section through the suburbs of Astigarraga and Hernani.

After leaving the coast we leave any heavy traffic behind and head out on quiet lanes with little other company than local cyclists and the occasional car as the route winds upwards alongside the Rio Umrumea on one of Europe’s most southerly salmon rivers. The route passes over a series of small cols during the day, the highest being the Puerto de Zuarrarrate (7.8kms – 804m) passing through Lekunberri. The lanes around this area are surprisingly tranquil and the views fantastic. Already the coastline feels a world away.

We will spend the evening in small resting place of Arbizu. It may only be the start of our journey but you will have earned your rest this evening on an undulating first day.

• Meals: Breakfast, lunch
• Ascent: 1,970 Metres Approx.

The terrain is more forgiving on today’s ride as the route heads into La Rioja, Spain’s most famous wine-producing region. From Arbizu, we will make our way towards Agurain-Salvatierra, following a small road that will lead us to the Opakua pass at 1020m, offering spectacular panoramic views of the Urbasa mountain range in the nearby Navarrese lands.

After descending, we will cross the Entzia mountain range and the Izki Natural Park. The route climbs a bit on secondary roads, providing an excellent view of the vineyards as we enter the Ebro Valley. Here, we will pass through the picturesque hilltop town of Laguardia, perched on a rocky promontory, overseeing the surrounding vineyards. The road gently ascends towards the end of the journey to reach the village of San Millán de la Cogolla, where we will enjoy a stylish dinner tonight!

• Meals: Breakfast, lunch
• Ascent: 2,100 Metres Approx.

Today begins with a long but steady climb to Puerto el Collado at 1,400m in the Sierra de la Nela. There’s a big wolf population in this area and it is frequently the coldest area in Spain in winter so we won’t hang around! The route passes a couple of smaller cols before reaching the town of El Burgo de Osma where we will spend the night.

• Meals: Breakfast, lunch
• Ascent: 1,700 Metres Approx.

The morning ride starts by descending into the Parque Natural Cannon del Rio Lobos. A series of dramatic switchbacks plunges us into the bottom of the limestone canyon created by the River Ucero. The first major settlement of the morning is the small cathedral city of El Burgo with perfectly preserved ancient medieval streets and half timbered houses.

Leaving El Burgo on the Senda del Duero a cycle path around the region which, for the section we ride is quality asphalt, we shortly reach a minor road where we cruise past arable farmland in the direction of Gormaz. The route rises affording great views of the Moorish fortress of Gormaz sitting prominent and proud, guarding the Rio Duero valley and its valuable farming plains. Our evening is spent in the restored village of Valverde de los Arroyas.

• Meals: Breakfast, lunch
• Ascent: 1,900 Metres Approx.

This morning’s ride takes us on a roller-coaster through the Reserva Nacional de Caza De Sonsaz as the road plunges then climbs in and out of many river valleys.

The route clings to the hillside above the Atazar reservoir before descending and following the contours of the foothills of Sierra de Guadarrama, before ending the day in the small town of Miraflores del a Sierra.

Unless you catch a glimpse below it’s hard to know you are so close to the capital of Madrid just 30km away!

• Meals: Breakfast, lunch
• Ascent: 1,500 Metres Approx.

The area squeezed between the high peaks of the Sierra de Guadarrama and Madrid is incredibly popular with local road clubs and leisure cyclists heading for the hills, so we might have company for some of today’s ride! The route is slightly busier than we have seen so far but it is more than compensated for by the great pedalling as the road is squeezed between the Santillana reservoir and the granite outcrops of the Guadarrama. We stop for a morning coffee stop near the monastery of El Escorial. Commissioned by King Fillipe II in the 15th century, this spectacular building dominates the town on San Lorenzo de El Escorial. Filipe had steps carved out of rocks on a nearby hilltop so he could watch his commission being built. We approach El Escorial on a back road that offers a great perspective of the monastic site and attached royal residence.

Shortly after El Escorial we turn away from the Madridista and head up into the stone pine forests and rolling roads tucked into the hillsides. We dart between the trees and along the valley that straddles the gap between the mountain chains of the Sierra de Guadarrama and the Sierra de Gredos. We spend the night on the plain on the northern side of the range as we reflect on the journey so far and look forward to the halfway point of the trip tomorrow night.

• Meals: Breakfast, lunch
• Ascent: 1,870 Metres Approx.

Today we tackle the Collado de Serranillos, the highest point of the trip at 1,580m. Though the climb is long is is fairly gentle and easily manageable with a steady approach. The rewards are well worth it though, with breathtaking views and an amazing descent sweeping downwards, clinging onto the hillside and losing nearly 1,000m in height. This col is a significant moment on the journey as we break through the physical barrier of the Sierra de Gredos which divides north and south Spain, with the air usually becoming instantly warmer as you descend. For the night, we’ll find ourselves in the charming village of Oropesa, renowned for its historic castles.

• Meals: Breakfast, lunch
• Ascent: 1,600 Metres Approx.

Today’s stage begins with undulating terrain, passing through the town of El Puente del Arzobispo where we will cross the Tajo River, gradually leaving behind the landscapes of Castilla la Mancha and its agriculture until we reach Carrascalejos. Here, we will start the ascent towards the Arrebattacas pass (911m), covering a distance of 13.5 km with a total ascent of 433m. This is where we enter Extremadura.

As we progress, the landscape becomes wilder and less influenced by agriculture as we approach the village of Guadalupe. This popular tourist destination is nestled in the Sierras of the same name, which attract pilgrims who come to visit its churches, monastery, and the famous image of the black virgin.

• Meals: Breakfast, lunch
• Ascent: 1,900 Metres Approx.

Quiet backroads lead us to the Garcia de Sola reservoir and across its dam. Many rivers in this dry area are dammed so that water supplies last through the summer. After the reservoir the road undulates through the Siera de Siruela on a stunning minor road which sees little traffic. We rest up in the town of Almaden with a rich mining and bullfighting history including a well preserved Plaza del Torros which is still in use.

• Meals: Breakfast, lunch
• Ascent: 1,750 Metres Approx.

Another long stage but not too much climbing as the route rolls through holm oak and wild olive clad hillsides. After the village of San Benito we pass into Andalucia and our final province of the trip. This far north, Andalucia is carpeted in rolling dehesa, Mediterranean scrub and abundant agarvi cactus, and it feels a world away from the Basque country. We are now closer to Africa than our start point! This rural route is occasionally interrupted by immaculate whitewashed villages such as Conquista, a maze of narrow streets with a church at the centre. The route descends to El Carpio and a twisting, flowing road which dances and winds round corners will take us to the Guadalquivir River. Depending on availability, we may overnight here in El Carpio (making today’s ride 80 Miles / 128 Kms) or we may ride on to nearby Montoro.

• Meals: Breakfast, lunch
• Ascent: 1,450 Metres Approx.

Today is a more gentle day after two longer stages with olive groves lining the road virtually all day. After 40km the route passes through Baena where the pungent aroma of olive pressing fills the air. The town is at the centre of the high grade olive oil industry and we see some hand pickers at work amongst the modern pneumatic shakers. The route then takes us to Zuheros for lunch. This pueblo blanco, with its 9th century castle built by the Arabs, is perched on a limestone crag to peer down on the rolling hills and olive groves. We spend the late afternoon and evening relaxing in an old olive farm which is now a hotel in the Parque Natural de la Sierra Subbetica.

• Meals: Breakfast, lunch
• Ascent: 1,800 Metres Approx.

The Sierra Subetica, where we start the day is classic Andaluz; a heady cocktail of parched dry land, olive groves and white washed villages. The riding is quiet and rural before climbing away from the Iznajar reservoir where the road becomes a little busier towards Antquera. After passing through this old town with the obligatory cobbled street the route skirts the northern edge of the Sierra de Chimena before arriving to El Chorro.

• Meals: Breakfast, lunch
• Ascent: 1,350 Metres Approx.

Today is by far the shortest day of this epic ride giving us chance to take stock and rest our legs to enjoy the ultimate finale and the charms of Ronda, our destination for the day. However, this is still a fantastic ride and well worth your time in the saddle.

As we set off on our penultimate day we climb steadily out of El Chorro past the reservoir at the end of the gorge. The gorge is up to 400m deep and as little as 10m wide in places, where the Rio Guadalhorce has carved its way through towering limestone. Huge, awesome, cliffs surround the area that is a popular destination for climbers. It all makes for a dramatic scene as we pass Bobastro, where there are remains of a remarkable Mozarabic church, which is dramatically carved out of the surrounding rock.

After reaching Puerto del Viento (1,190m) we can contemplate the awesome beauty of the Sierra de las Nievas (Range of the Snows) we are about to ride over. The range is rugged and complex with twisting barrancos, deep ravines, caves and hidden valleys. In the distance we are now able to see the historical mountain town of Ronda and the Sierra de Grazalema rising beyond. The descent takes a wide, smooth, curving road that will rush us at speed to the centre of stunning Ronda.

We’ll have time to take a wander through the ancient Moorish quarter and marvel at the views of the Tajo gorge, which dramatically splits the town in two, giving a relaxing afternoon before a local feast to fuel us for the final challenge.

• Meals: Breakfast, lunch
• Ascent: 1,700 Metres Approx.

Riding out with excitement on our last day of this fantastic route we cross the majestic Puente Nuevo and roll along the mountain ridge road before it drops dramatically down through the Serrania passing impressive limestone crags and picture postcard perfect white villages hillsides.

The road is magnificent as it drops, climbs and weaves in front of us. Some exhilarating kilometres later we’ll arrive at the stunning white mountain village of Gaucin. Set on a natural vantage point looking out across the sierras and down to the Mediterranean and the imposing rock of Gibraltar, Gaucin is a beautiful place. On a clear day it’s possible to see deep into the Rif mountains of north Africa!

On reaching Puerto del Negro our vista is dramatically changed as it’s the first view we have of the Los Alcornocales NP, a huge wilderness of forested rolling sierras comprising the largest cork oak forest in the world.

The descent to come is a just reward for the work we’ve put in over the last two weeks as it curves and glides down the mountainside before the road drops and then undulates on a twisting curve all the way to the white hilltown of Jimena de la Frontera.

A few km of well received flat terrain take us around the town of Algeciras, before we head into the Straits of Gibraltar Natural Park. This is a beautiful stretch of wild, mountainous coastline that has fantastic views across to the majestic Rif Mountains in Morocco. We’ll soon be able to spot our final destination, Tarifa and also the Moroccan port of Tangiers.

The descent is speedy until it meets the eastern old town wall of the ancient port of Tarifa. From here we head to Isla de Las Palomas – the most southerly point of mainland Europe as well as the natural divide between the Mediterranean and the Atlantic, a fitting point to end our magnificent journey. We’ve made it. Congratulations!

A revitalizing dip and a couple of celebratory drinks whilst we watch the sun set over the Atlantic is a memorable way to finish this tour. Back for a shower at the hotel in the heart of the old town and then out to celebrate with some tasty tapas and drinks in downtown Tarifa!

• Meals: Breakfast

Hopefully there’ll be time to take a stroll along the beach and take a dip in the sea before transferring to Gibraltar for onward travels.