It depends on where you're flying into, and how long you're staying. But if you're flying into Madrid, stay there for a few days in Plaza Santa Anna. There are three or four really nice and reasonably priced hotels. Then, I'd rent a car at the Atocha Train station, and head to Granada. Stay there for two nights, walk through the Albicin, and definitely go see the Alhambra. From there, head south to Ronda, and check out the Plaza del Toros. After Ronda, hit up Segovia for a night, check out the Puente Romano, and eat dinner at El Duque. Order the suckling pig, or go fuck yourself. Then head to Sevilla, and check out the Catedral.
If you're staying for more than a week, then from Sevilla, you could head up north to Valencia for a few nights, and then Barcelona.
In Madrid, go to the Vinoteca in Plza Santa Anna, and ask for Richard or Alexi, they'll take care of you.
In Granada, go to Bar Antigua 1 for tapas, and ask for Alfredo. The Chupeteria, ask for Ismael. And El Estribo, ask for Jorge.
In Ronda, grab drinks on the patio of the Puente Hotel, over looking the cliff and river, ask for Priscilla.
In Sevilla, the bar names escape me, but anything near the Catedral will get you sorted out.
Barcelona, head over to the Cathedral, take a picture, and then head to Ramblas. The bars over there are plentiful, and are on every corner.