Sit atop the Cerro del Castillo hill in Medina Sidonia, at an altitude of 1,000 feet (300 meters), and admire its medieval charm. Founded by the Phoenicians, the city became an important Roman colony and served as capital of the Muslim district of Sidonia. In the mid-15th century, it joined the domain of the Dukes of Medina Sidonia.

The town has been declared a historical site and was awarded the Prize for the Beautification of Andalusian Towns. See the areas many works of art attesting to its rich past, including the Santos Mrtires Hermitage, the oldest example of Visigoth art in Andalusia. Medieval remnants include the ruins of the castle, erected on the old Muslim fortress, and Torrestrella Castle (both dating from the 12th - 14th centuries). Other noteworthy medieval arches from the Muslim occupation period include the Arco de la Pastora (10th Century), Arco del Sol (10th -13th century), and Arco de Beln (12th - 15th Century). See the towns countless examples of religious architecture, including the Gothic and Plateresque Santa Mara la Mayor Coronada Parish Church.

Visit the towns numerous convents, including the San Cristbal, Jess, and Mara y Jos Convents, and the Carmelita del Cuervo monastery in Los Alcornocales Natural Park. Admire the architecture of the 17th-Century Mannerist-style Town Hall building, the Duke's Stables, the 18th-century House of the Enrile, and the 19th-Century Market Building. Sample the towns renowned pastries, including the Alfajor de Medina, awarded a Denomination of Origin quality label. The traditional Moorish cake is prepared using almonds, hazelnuts, flour, grated bread and spices (coriander, cloves, anise, sesame and cinnamon), and the finest pure bee honey. The tube-shaped pastry comes toasted with a slightly spicy aroma and the flavor of dry fruits and honey.