Before I reply to each of you, let me say that you guys have been great in giving your valuable suggestions, options and more things to do than I could have ever thought of. I am so glad that I posted my questions on flyertalk. Thank you so much !!!

@arollins : You are right about the mileage requirements on each of these airlines for the BOS-SJU connection. We dont travel as much and all the miles that we have collected has been through the credit card offers and other mileage earning opportunities posted here on flyertalk. Signing up for more cards at this point doesnt look viable as I have already signed up for 2 cards this year. I was planning to use these mile because i have read here that these airlines keep on devlauing their miles and the longer you wait, the more the devaluation.

@MoreMilesPlease : Thank you for your PM last night. I was checking expedia after reading your suggestion and it looks like most of the hotels in the list are away from the Old San Juan area which is where I want to stay (if we go). but there were still a couple of decent hotels in the Old San Juan area that may work out. Since I was planning to use miles when I started to think about going to PR, I had kept my budget to $1000 for hotel stay and activities included. I will have to replan and assess If we can spend more than that on this trip

@Seat13F_AC_CRJ: You know what? That was exactly my thinking....why should I go down south when there is summer in New England. The only reason why I wanted to get out of here is because we have already done most of the big cities and towns in Northeast US. So, I did not not want my wife to feel (not that she would) that we were doing something similar. However, Montreal/Quebec City seems appealing to me and I am actually thinking of it as a good option considering the PR trip not working out for us with our small budget :|. The only thing is that we are not US citizens (yet) and we will have to obtain Canadian visas first. But I am hoping that shouldn't be much of a hassle. I will PM you if I decide on making a trip to the other side.

@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.