Originally Posted by
boylstonboy
@Oreto : As I stated above, my initial budget, assuming I was using miles for air tickets, was somewhere around $1000 for hotel stay and activities. I am assuming I will have to double the budget to $2000 If I buy air tickets (because spending so many miles may not make sense). I planned to stay in Old San Juan so that I would be centrally located to everything and can walk to the attractions/restaurants/etc. Since I was planning the trip for only 3 nts/ 4 days, I did not want to rusgh and see everything. Seea few things, have good food, relax and go back refreshed. That was the thought.
If the potential devaluation of airmiles concerns you, you should definitely use them now and make other plans to accumulate miles for your Hawaii trip. The cost/mile calculation is something that you need to determine and not base it on anyone else's.
For your situation, I'd say that securing transportation should be your first concern as the longer that you wait, the more that it may cost you in miles as the award seats diminish. Also, if taking separate airlines is out, you can always buy 1 ticket and use miles for the other if you are short the full miles or the award seats zero out.
It sounds like you have some choices for hotels. You may want to price them out and see where you stand. Better bidding may be of use if you can use Priceline at all. Of course, that would mean that there would be no hotel guarantees but El San Juan is a decent property and money saved could be applied to a rental car. Additionally, your Old San Juan hotel may be on the Priceline list.
If it were me, I'd budget my room at $150 all-in or less/night and take the remaining $400+ and make an itinerary based on that. A cheaper room would be better as $400 can be spent quickly. Most of my suggestions tend to be on the pricier side but I suppose that tripadvisor would have other activities that are gentler on the wallet.
$1000 for this trip is possible. A day at the beach or renting a car to go to El Yunque can be frugal activities as well as stress-reducing ones.