I'm planning on Spain in May 2012. We have worked out a good itinerary starting in Barcelona, going to Andalusia, and ending in Madrid. Many good suggestions for where to go have included mention of festivals in places such as Madrid, Cordoba, and Jerez, which are all on our itinerary. How soon should I just stop planning and make decisions and reservations for preferred hotels or B&Bs, given these festivals, etc., in May. Should I just decide now, and make resv (esp if they could be changed or cancelled without major penalty) or would I be safe waiting till, say, early February to fish or cut bait?
Planning and booking go hand in hand. We tweaked our original itinerary quite a bit, depending on the lodging we found. For example, our travel from Barcelona to Madrid landed us there on a major holiday, May 1. We decided we would rather be in a small town and headed the short distance to Toledo. It turned out to be a great option as our apartment there was much less expensive than a hotel room in Madrid (at our standard) would have been. We enjoyed the evenings in Toledo much more than the one evening in Madrid, so it was a good decision. Our dates in Granada were driven by availability at the place we wanted to stay, Hotel America inside the Alhambra (note this is not the expensive parador, it is sweet little family-run place with cramped rooms and a nice patio for breakfast and lunch.) The I discovered we would be in Cordoba during Patio Festival and we were able to get a room there by booking early. Short answer is start looking at prices and availability now, since you will be traveling durin gfestival season. Adjust your itinerary as you find things you particularly like or dislike, and then I'd say start booking in January. And remember you can save a lot on your train travel by booking in advance (62 days ahead) on Renfe. That would be early March for early May travel. You'll want to have hotels or at least cities finalized by then as the Web fare tickets (60% off) are non-refundable.
Really depends on how much time you have to waste/spend second guessing your decisions. I usually come to a point where I just want to know what I am doing if I am making reservations (I do travel a lot without them, but many times I do want resv. Big cities during peak season.... the night before departure) So, in order to make things easy for me I usually do all my hotels through Bookings.com (yes, I know some say they get it cheaper by going through the hotel directly) but I can then go and easily cancel a hotel if I find something better right through the same website. For me, this keeps that part of my trip organized and I am not going to forget a resv. I made and need to cancel. I make a car reservation asap and then continue to check rates till right before I go and change that if a cheaper rate comes up.... usually does. I do not prepay my car and typically go with Budget, Avis, Hertz or Sixt and have not had problems. With the hotels most of them have no cancellation penalty if within a few days, and some you can still cancel before 4 on the day or f arrival.
Start now. At least get a hotel reserved for Barcelona. If you can reserve places that have a generous cancellation policy, all the better. I often use venere.com. Sometimes I've cancelled reservations and have had no problem, no penalty. Just follow their rules by reading the small print. Spain is great in May. Lots of other travelers have figured this out, too. So, your first or second choices may be gone already.
I agree with Swan. It's time to begin locking in your reservations. You don't mention ariline tickets so I hope that you have those locked in as well. The important thing is to determine where you will be staying each night, do your homework and then make a choice and lock it in. We always are fully booked on our accomodations about 5-6 months out. We then fuss around a bit on our daily travels and things to do but the major things are locked in.
I would book as soon as possible. Some of the smaller hotels in Barcelona were booked already (for a late May visit) when I was looking at reservations in December the year before. If you know your exact travel dates, use http://www.whatsonwhen.com and find out the dates of the festivals in the towns you will be visiting. If you're thinking Feria in Jerez, chances are you'll pay a lot more for a hotel room just because of the festival, it is very popular. Many hotels don't charge you cancellation fees if you book directly with them. Venere has a decent policy too depending on the hotel.