Long Weekend in San Juan, Puerto Rico Trip Report – Introduction

* I am going to try something new here on the blog and do a full trip report for our trip to Puerto Rico last month. It will be a 4 part series in which I’ll go over the miles/points/travel hacking aspect to the trip, followed by reviews of our flights and hotel stay and ending with some activities and dining we did to spur ideas for a possible trip for you to Puerto Rico. I’ll update each link below once the relevant post is up.

1) Introduction (this post)

2) Flights – American Airlines Business Class JFK – SJU & American Airlines Economy Class SJU – JFK 

3) Hotel – Courtyard Marriott Isla Verde

4) Activities & Dining

The first ever trip I took with my then girlfriend (now wife) was to Puerto Rico back in 2008. This was before I was into points and miles so I remember thinking back then I got a deal when I booked a vacation package on Orbitz.com for $500+ a person for a 4 night stay. Obviously now I wouldn’t consider that a deal especially considering my trip to Bora Bora cost less but I digress. For this trip, we were looking for a relaxing getaway for the weekend that was within a few hours of NY, had good weather and most importantly, had award availability for flights to make this trip as cheap as possible. The one location that met this criteria almost immediately was a return trip to Puerto Rico.

Puerto Rico - 2008

Puerto Rico – 2008

For our flights, I’ve written about this before but being based in NY, British Airways Avios are quite valuable for trips to the Caribbean. The only limitations was that flights had to be on American Airlines and had to be direct to maximize the Avios award chart. I’ll go over the flight selections in the next post on the flight reviews but I was only able to find award availability to San Juan. There was none on the way home which wasn’t especially surprising since everyone is looking for a late Sunday flight home after a weekend getaway. Thankfully, I had some AA gift cards to burn for the return flight.

For the hotel, it was a trip down memory lane as stayed in the same hotel we did back in 2008 – The Courtyard Marriott Isla Verde. I wasn’t trying to be nostalgic but it made the most sense from a financial standpoint, which I’ll get into when I review the hotel. It is located about 5 minutes from the airport and I’d argue the beach at the Courtyard Marriott is nicer then the Ritz Carlton’s which is down maybe a half mile. It’s also #AVGeek heaven as the runway is located across the street from the hotel so you have some amazing views of planes taking off.

I hope you will stay tuned for my first trip report on the blog and if this proves successful, I plan to go back and review some of the bigger trips I’ve taken. My goal for doing this is by showing you how easy it can be to accumulate the miles/points, I hope to inspire you to start taking your own trips. I think seeing pictures and descriptions of the activities we did will only entice you more to make these trips a reality. I know this worked on me when I first started collecting points and miles as I would see bloggers post amazing pictures of their trip in Europe or Asia, followed by pictures of their first class seat or luxury 5 star hotel room that they got for free due to points and miles. Hopefully, this will have the same effect on you.

Puerto Rico - 2014

Puerto Rico – 2014


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