Traveling to Spain in May

I cannot help with the "when to buy" question for airline tickets, but I will say that for our trip to Spain last May (2011), we saved hundreds of euros on our travel around Spain by purchasing train tickets 62 days in advance on the Spanish train website, Renfe.es. We also saved quite a bit on hotels by booking in advance (several months, anyway). I cannot comment on the flight question because we went on miles tickets, obtained well in advance.

Now! They look to be a good price right now...

We used to find the best prices for our annual late May trip two to three months prior; but I would be watching for great deals right after the 1st of the year. (and I would have auto notices set up now on a few web sites; Kayak, Airfarewatchdog, etc.) Our best price last year was an "open jaw" flight; into one city and out of another. The lowest cost "out of " flight was from an obscure location: Malaga.

Highly amusing - 'an obscure location: Malaga'