“We should tuck the mirrors in,” I said as we eyeballed the passage through the narrow arch ahead of us. We were on the Plaza de Espana in Medina-Sidonia, a forty-minute drive from Cadiz. But we couldn’t be further away, as it felt like a passage in time to centuries past as we drove into the village. Folks have lived on this hill since before the Phoenicians settled Cadiz in 1100 BC, making the village one of the oldest settlements in western Europe. But it is with the Phoenicians and later the Romans, Visgoths, Moors and finally the Spanish that the village grew. Sitting 1,000ft above the fertile rolling plains below, the highest point for miles around, the village offers incredible vistas of the surrounding countryside out to the Atlantic Ocean. The pueblo blanco we see today has its roots with the Moors in the 8th century.

The plaza was nearly deserted when we strolled across it, mid-week in the middle of March, looking for a café. While the plaza was empty, we found a café, Restaurante Paco Ortega, bustling with activity. We ordered Tostadas de Jamón and Alfajor, a sweet gingerbread-like confectionary from the Arab period, that the town is famous for. We enjoyed the tostadas and the lively chatter of the café, but we were pointed across the plaza to Pasteleria Aromas de Medina for the Alfajor. True to its name, delicious whiffs of fresh baked pastries greeted us as we crossed the threshold of temptation. The Alfajor de Medina Sidonia was heavenly. It’s made with local honey, nuts, breadcrumbs, and a variety of spices – what’s not to like? The only question was how much to buy.


The day was really the first one of our Andalucian road-trip. Previously we had stayed for multiple days in Jerez de la Frontera and Cadiz (click to read those blogs.) Medina-Sidonia was the first of two stops, before we stayed in Castellar de la Frontera.


I swear the 12th century Arco de Belén, one of the original gates into the old walled Arab village, was slimmer than the one at the plaza. Located on a narrow, uphill blind curve, it took me two tries to align the car correctly for safe passage through the wall.

It’s a nice walk from the plaza in front of the cathedral to the ruins of the ancient castillo that once crowned the crest of the village. It must have been magnificent when it was the seat of the Dukedom of Medina Sidonia in the 15th century. The hereditary dukedom was one of the oldest in the kingdom of Spain and its land holdings encompassed most of Andalucia. But the castle eventually lost its significance, and its massive walls were slowly dismantled. The castle’s stones used to expand the village are now hidden behind plaster and white paint. Interestingly, the 7th Duke of Medina Sidonia was commander of the Spanish Armada that sailed to attack the south of England in 1588. Currently the 22nd Duke of Medina Sidonia resides in Madrid.


Next to the cathedral there is another set of ruins, one massive corner of which is all that is left of the Torreón de Doña Blanca, named for Doña Blanca (who was Blanche of Borbón,) the 14-year-old child bride of King Peter of Castile. They married in 1353 for King Peter to secure an alliance with France. However, there were difficulties in receiving her promised dowry. Shortly after their marriage, Peter abandoned Blanche for his lover, the Castilian noblewoman Maria de Padilla, who many believed he had married in secret before Blanche. He ordered Blanche, now officially the Queen of Castille, imprisoned in the Castle of Arevalo. In 1361 she was moved to the tower in Medina Sidonia to prevent rescue by French forces that were now battling King Peter. He ordered one of his noblemen to execute Blanche, now 22, but the knight bravely refused the king’s command, saying it was treasonous and would cause further disorder in the country. However, she was handed over to the King’s willing crossbowman, Juan Pérez de Rebolledo of Jeréz, who executed her. I can only imagine how many bags of silver changed hands. Peter only lasted another eight years on his throne until his half-brother, Henry of Trastámara, defeated him.



Built in the 16th century on the foundations of the village’s old mosque, the Iglesia de Santa María la Mayor still gracefully commands the hilltop. With Gothic and Renaissance elements inside and out, we found it to be one of the more interesting churches we had visited in Andalucia, not including Seville.


It is filled with wonderful pieces of religious art and has a very fine baroque sculpted altar, depicting stories from the Bible, and an ornate choir stall. The church also has a very nice arched cloister. The 135-foot-tall belltower, its upper portion built upon the minaret of the former mosque, was definitely worth the climb for the fantastic aerial views of the town and surrounding farmlands.


Next to the church, we were delighted to find that the Monasterio De Jesús, María Y José has a dulce turno. This is a lazy-susan type cabinet that allows you to purchase cookies and pastries made by the sequestered nuns who follow the convent’s centuries old recipes. It’s an interesting experience, talking in our inadequate Spanish through the wall to the invisible nun on the other side. We now seek out this opportunity wherever possible. The convent’s church has a noteworthy octagonal floor plan with its ceiling decorated with mural paintings.



Alcalá de los Gazules, a half hour away, was our next destination. Along with Medina-Sidonia and several other pueblos blancos, it is on the Ruta del Toro. This route through the open ranges of Cadiz Province highlights the region’s equestrian traditions on large fincas that raise Spain’s famous fighting bulls for the ring, as well as for their beef. Along the roadside here the iconic Osbourne Bull billboards playfully promote their brandy.


Rounding a curve, the hillside before us glittered with impressionistic white dots, which were nearly blinding in the midday sun. As we approached, their definition improved and revealed the old Arab village. The ancient footprint of the town hasn’t changed in centuries. The village is composed of multiple levels of terraced dwellings built above each other, along staircases, winding narrow lanes and alleys that traced the natural topography of the hill to its apex.

One of the advantages of shoulder season travel is that it is much easier to find a parking space. The disadvantage, though, is that some sites of interest have off-season hours, which was what we encountered with the Iglesia Parroquial de San Jorge and the Castillo de Alcala de los Gazules.


Since the Romans first laid stones for a fortress, the town has had a castle at its summit. It was the Moors though who built a small but substantial fortification that used the sloping wall technique, copied from the Templars, to build the Homage Tower. This impressive tower is all that is left after Napoleon’s troops blew apart the rest of the castillo as they exited following a brutal occupation of the town in 1810.


After the Reconquista, the towns’ Moorish past was erased with the construction of the Iglesia Parroquial de San Jorge above the old mosque. Its ornate gothic façade, carved from soft stone, now shows centuries of erosion. Later with the building of the Santo Domingo monastery, in 1506, the town was decreed to be a religious learning center. Although the monastery served as a training center for priests, it was also used for centuries to hold prisoners of the Spanish Inquisition.


A few minutes outside of the village, before continuing onto Castellar de la Frontera, we stopped for a late lunch/early dinner at los Corzos. It’s a large facility with a restaurant, café, grill and charcuterie shop, all featuring typical Andalusian fare. Though it appears to be geared for tourist buses that ply the route between Malaga and Cadiz, they take their cuisine very seriously and we had a splendid lunch.


The de la Frontera attached to many village names in Andalucia refers to a region officially called “Terra Nullius,” a ‘no man’s land.’ A fluctuating border area was established in the 1200s, when the first Reconquista, led by Ferdinand III of Castile-León, ran out of resources to continue their conquests farther. For two-hundred years this was an unclaimed land, in which Christian crusaders and Islamic jihadists continued to clash.

Castellar de la Frontera, still remotely isolated in the cork forests of Los Alcornocales Natural Park, truly exemplifies a wilderness fortress; with only one serpentine road in and out, it’s many miles off the main road. Today it is one of Europe’s best-preserved examples of a medieval village existing within a castle. But in the 1960’s it was a different story, when after centuries of neglect, and a dwindling population due to emigration, the remaining residents were relocated to a newly constructed town, Nuevo Castellar, ten miles away.





In the 1970s, northern European “hippies” discovered the fine Andalucian weather and the now abandoned village, squatting in some homes, and building rough shelters outside the castle walls. The old town was eventually obtained as an investment by the Rumasa Group, Spain’s largest conglomerate and the country’s leading hotel chain in the 1980’s. Later the company’s financial troubles led the Spanish Government to expropriate Castellar. They declared it a ‘Historical and Artistic Monument,’ and invested funding to restore the old castle and its village. Today rooms in the castle and several casas in the old village are reservable through Tugasa Castillo de Castellar Tugasa is a hotel organization formed by the Cadiz regional government and operates nine hotels and nine separate restaurants throughout the province.

We didn’t realize our modestly priced (under €100) room would be ideally located in the Torre del Homenaje, the highest part of the castle with spectacular panoramic views. Getting to it was a bit of a challenge, even with the use of an elevator. The castle was built atop a huge multi-faceted rock protrusion, so that each ledge of the stone became one floor for rooms. While there are hallways from the elevator landings, they branch off and have short flights of stairs, up and down, to the rooms in various wings of castle. Signage was rather lacking, but after a few wrong turns we located No. 206.


We were further surprised when we discovered that a narrow alcove in our room, with a twist and a turn, led to a sitting area with a small bedroom. Geez, if we had known we would have invited our kids. Better still, a set of stairs led to the top of the tower – our private mirador! To the manor born, for the next two days! We enjoyed incredible views: to the west over the Guadarranque reservoir, below the village, and southeast to the Rock of Gibraltar and the coast of Morocco beyond.


“Hey Rosa,” a lanky toothless patron smiled as he yelled, “tienes clientes,” you have customers, after we stood at the bar long enough to learn the gentleman was one of the original squatters of the 70’s. Two beers were all we could get from Rosa, as the kitchen was only open on weekends until the tourist season started later that Spring. Fortunately, we had purchased some bread, cheese, and sausage at los Corzos earlier, and we still had a vermut with us from Jerez de la Frontera, so we were set for a picnic dinner.

We rose for sunrise the next morning and watched kestrals zip along the castle’s walls. Over the reservoir a kettle of griffon vultures circled for a while before flying off. The medieval village within the castle’s wall is very compact and it was easy to wander through its attractive lanes. Outside the walls we spent a good bit of time walking about looking for the best vantage points to photograph this pretty village, which is recognized by Los Pueblos más Bonitos de España as being one of the nicest in Spain.

Later for coffee we stopped at the Hotel La Almoraima, located off the only road between the old town and Nuevo Castellar. The stunning hotel is set in what once was a 1600s convent and takes excellent advantage of the orange tree-filled courtyard and surrounding old cloisters, now renovated into chic rooms.

The convent’s original chapel has also been lovingly restored and is used regularly for weddings. The history of the architecturally distinctive tower that stands next to the cloister is vague, with some thinking it was an Arab watch tower, when this was the “Terra Nullius,” and existed before the religious complex was built. The old convent and its extensive lands, a vast 34,000-acre cork forest, eventually became the property of the Dukes of Medinaceli, who turned it into a palatial hunting estate, one of the largest in Spain.

By the 1890’s it was the destination for Spanish nobles and English aristocrats from Gibraltar, who participated in Royal Equestrian Hunts, and the Duke had a private station built on Henderson’s railway for their use. In 1922 Queen Victoria Eugenie of Spain exited at the Duke’s station and then traveled by horse drawn carriage to the estate and the ancient castillo for a brief visit. The eroded cart track to the castillo was finally improved and paved in 1924. In 1973 the 18th Duchess of Medinaceli sold the estate, which included the old hilltop castle, to the Rumasa Group. It was later seized by the Spanish government in the financially troubled 2010s and the Mexican actress Salma Hayek expressed interest in acquiring it before the government decided to manage the estate itself. I find these obscure histories fascinating!


Bar el Molino, a small taberna on the edge of Nuevo Castellar’s central plaza, was a wonderful untouristy spot. With shaded outside tables, cold beer and delicious food, our lunch was perfect. In an effort to experience as many different places as possible, we’ve started to take our after lunch or dinner coffee and dessert at a different establishment.



With this in mind we found Pasteleria Gastrokook, off by itself on the edge of town. Wow! We were so fortunate to stumble across this incredible pastry shop. This gourmet pastelería is reason enough to visit Castellar de la Frontera or even Spain. It is definitely worth a detour especially if you are near Gibraltar. We quickly conferred and declared a calorie-free day! I mean, what is the point of exploring all these distant locales without enjoying their cuisine. Geez, at our home in Georgia, USA, we can’t even find artisanal bread! I did gently chide the two cyclists that pedaled over from Gibraltar for ordering only black coffee. Surely, they would have burnt off all those calories by the time they returned to the rock. Sometimes, willpower is simply deprivation by choice.
Till next time,
Craig & Donna
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