You can land in Jerez at lunchtime and be on a terrace in Vejer by four. We have done it twice. Here is what we would do with the two days that follow.
The first morning, do nothing. This is not a poetic instruction; it is a tactical one. The Sierra works on the body. The light is high and the air is dry and most people arrive having been awake since five for the flight. Sit. Have the breakfast at the hotel. Walk twenty minutes in any direction and come back. The afternoon is more useful if you don't burn the morning on a list of villages.
In the afternoon, drive to Grazalema. It is forty-five minutes north and the road is empty for most of it. Park outside the village and walk in. There is a square with a bar called El Mirador. Order a beer and a portion of chicharrones. Do not order a cocktail. The bartender is patient with foreigners but only up to a point.
Drive back via Ubrique if you have time. The leather workshops there are real, not for tourists, and a wallet you buy in the Calle Solis costs a third of what you would pay later in Seville. The shopkeepers are honest about which workshop made what.
Dinner the first night should be at the hotel. Two hours, one wine, then bed.
The second morning, the beach. Bolonia is the answer. It is a fishing beach with a Roman ruin at one end and a sand dune at the other and a row of chiringuitos in between. Las Rejas does the grilled fish properly. Ask what came in that morning, accept the recommendation, do not specify how you'd like it cooked. The cook will glare.
Drive back inland in the late afternoon. The road from Bolonia to the Sierra crosses a windy stretch where the kite-surfers are; stop and watch them for ten minutes if you have a kite-surfer at home who would appreciate the photograph.
The second evening, take the car five minutes from the hotel to a venta called Las Palomas. It is signposted only by a hand-painted board on a fence. Ask the owners at the hotel; they will draw you a map. Eat what is on. Drive home. The road has stars over it and the cicadas are loud.
That is the trip. Nothing on this list takes more than an hour to organise. Nothing requires a booking. If you stay a third night, repeat the first morning's instructions. The Sierra rewards repetition.