Long Weekend in San Juan, Puerto Rico Trip Report – Activities & Dining – Old San Juan

1) Introduction
2) Flights: American Airlines Business Class JFK – SJU & American Airlines Economy Class SJU – JFK
3) Hotel: Courtyard Marriott Isla Verde
4) Activities & Dining – Old San Juan

As I mentioned in the hotel review, the Courtyard Marriott Isla Verde is close to the airport but not too far from Old San Juan, which was about a 15 minute cab ride. On Saturday evening, we decided to head down to Old San Juan for drinks and dinner. The hotel was able to call a cab for us and the 15-20 minute ride cost $21 dollars for the two us.

We didn’t go in with any set plans other than dinner at 7:30 – we planned to just walk around, maybe a find a bar at first and kill time people watching. Little did we know, there was a weekend festival that was going on and the cab driver mentioned to us he couldn’t take us to the heart of Old San Juan and would have to drop us off a few blocks away.  No matter as it was actually a nice night to walk around and we quickly saw several streets closed with people everywhere. It turns out the festival was the SOFO Culinary Fest which was from August 14 – 17 and involved many street vendors selling all types of food, drinks and other goodies.

We quickly found someone making mixed drinks in freshly cut pineapples so I had to get Andrea one. I think it was a pina colada but I don’t quite remember. The best part about the festival was that open container laws were waived so we take our drink to walk around and check out the rest of the festival. There was live music on several street corners and with the weather being perfect, there was a great atmosphere in the streets.

Andrea with her drink

Andrea with her drink

After walking around for a while, it was time for our dinner reservation at Marmalade which is ranked as the #1 restaurant in San Juan on Trip Advisor. It didn’t disappoint. The interior has a very unique vibe that I can’t quite put my finger on – maybe a modern setup influenced with Middle Eastern themes. The photo doesn’t do the place justice but it was on the most unique dining atmosphere for me in a while.


They have a very eclectic drink menu and of course, we had to try something off it. I had the Global Warming, complete with chilies in my drink, while Andrea tried the Jimi Hendrick’s. The waiter recommended drinking my drink quickly as it “heats up” the longer you let it sit.

menu - Copy drink2 - Copy Drink

The food was excellent and they had several creative takes on food. For example, we ordered Popcorn Shrimp as an app but their take on it included laying grilled shrimp on a bed of spice-crusted popcorn (yes actual popcorn). Unfortunately I forgot to take a picture but it was delicious. That was followed by their signature white bean soup, which had truffle oil and pancetta dust in it. For our main courses, I had the pork belly with a black bean puree while Andrea had the spaghetti squash which looked nothing you’d like expect (again we were so hungry we forgot to take photos). Both dishes were quite unique and very different from what we normally have.

After dinner, we walked around and enjoyed the live music playing in the streets. When we eventually got tired of it, we took a cab back to the Courtyard Marriott which came to $20. For the rest of the trip, we didn’t do too much other than relax by the pool and beach. We wanted to relax and that was the perfect remedy for us. One night, we did walk from the hotel to the convenience store to pickup a few things and passed by a cockfighting arena. We obviously didn’t partake but found it interesting.

cockfight - Copy

In all, this was a successful, short 3 night getaway to Puerto Rico that allowed us to explore Old San Juan for the first time. We had some amazing food and drinks and I wouldn’t hesitate to go back for another long weekend.


Long Weekend in San Juan, Puerto Trip Report – Courtyard Marriott Isla Verde

1) Introduction
2) Flights: American Airlines Business Class JFK – SJU & American Airlines Economy Class SJU – JFK
3) Hotel: Courtyard Marriott Isla Verde
4) Activities & Dining

As mentioned in the introduction, this was actually my second stay at the Courtyard Marriott Isla Verde. The first time we stayed there was way back in 2008 on my first ever trip out of the continental United States (I’ve come a long ways now) and we had quite an enjoyable stay. Looking for hotels on this trip to San Juan, we wanted a hotel right on the beach and was close to the airport to minimize our driving time.

Many hotels of the hotels we were considering were ranging from $135/night to $225/night, including the San Juan Marriott Resort & Stellaris CasinoInterContinental Hotel San Juan and the Courtyard Marriott Isla Verde.  Points for these hotels ranged from 35,000 to 50,000 a night but with cash rates so low for the hotels, it didn’t make sense to redeem points for our stay. Instead, I had a $500 Marriott Gift Card I purchased for 19% off (for a total of $405) during the American Express Daily Getaways, so my preference was for a Marriott hotel. In the end, we went with the cheaper option at $135/night for the Courtyard Marriott Isla Verde.

View From Our Balcony

View From Our Balcony

In doing some research on the hotel, I noticed it was undergoing a renovation in which rooms on the top few floors were completely renovated while the middle to bottom floors remained untouched. About a week prior to our stay, I emailed the hotel requesting a newly renovated room and they responded they would do their best but could not guarantee it. Our flight landed around 9:30pm, and since the hotel is only a 5-7 minute drive from the airport, we were at the hotel around 9:50pm after making our way out of the airport and finding a taxi.

Upon walking in to the lobby, the check-in area was deserted (not surprising considering it was almost 10pm) but an agent quickly checked us in without any issues. We were assigned a partial ocean view room on the 8th floor, but as you can see in the picture above, the partial ocean view was actually quite nice and not just some small sliver of the ocean. Our room also happened to be a newly renovated room and you could tell what a difference that made as everything was brand new with no marks, scuffs or scratches anywhere on the furniture.

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The room was modestly sized but had some character to it with the painted wall behind the bed and new wood cabinetry and furniture throughout the room. It was well designed, as the TV could swivel out depending whether you were on the couch or the bed and the mini-fridge could actually hold several large bottles of water and snacks. I forgot to take a picture of it but the room opened up to a nice balcony outside which had a small table and two chairs. Each morning, we would run downstairs to the little coffee shop in the lobby and come back to our room to have breakfast on our balcony.

Our favorite part of the hotel was the wide stretch of white, sandy beach right behind the hotel. As I stated in the introduction to this trip report, I think the beach here is nicer than the beach in front of the Ritz-Carlton. My reasoning behind it is even though it is the same stretch of beach (you can just make out the blue cluster of Ritz Carlton chairs in the top photo), the beach gets much narrower by the Ritz and the cluster of chairs makes the beach feel much smaller. Additionally, there are large apartment complexes or hotels on each side of the Ritz, crowding the beach even further, while the Courtyard Marriott Isla Verde is the last hotel on the strip and has a lot more privacy. Each morning, you could walk down to the beach and helpful hotel employees would set up an umbrella and chairs wherever you liked on the beach.

In addition to the umbrella and chair setup, their was food and drink service on the beach which is something that was non-existent the last time we went 6 years ago. Service was generally good though it sometimes took a while to get a drink since they came from the pool bar which was usually crowded. Speaking of the pool, it felt like a standard hotel swimming pool with a nice swim-up bar but the pool was always too crowded for our liking. The food and drinks from the pool bar were good with frozen cocktails averaging $8-$10 a drink and sandwiches/burgers/salads ranging from $10-$12 at lunch. I’m not sure what the prices are at the Ritz down the beach but I guarantee they are much higher than those prices.

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There were also several other features of the hotel we didn’t get to experience including the fitness center which was large and overlooked the pool area. We didn’t have an opportunity to eat dinner at the hotel but we noticed on Sundays, they had a Puerto Rican dinner buffet complete with a whole roasted pig. There was also a small casino inside the hotel (right off the lobby) that had several blackjack, roulette, and craps tables in addition to tons of slots machines.

For a long weekend of 3 nights, I think at this price point (<$150 night), this hotel can’t be beat. It’s close to the airport yet only 15 minutes from Old San Juan (stay tuned for the next post in this series) and has a great beach which is definitely the highlight of this hotel. The renovated rooms are nice though I’m sure I would have been disappointed with a non-renovated room as they are probably still the same room we had 6 years ago. The staff is generally friendly and the drinks/food at the pool bar were good especially when they could be delivered to your beach chairs for no additional fee.

Feel free to ask me any questions about this hotel, I’d be happy to answer them. I’ve included a few additional photos of our room and the grounds.


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

1) Introduction
2) Flights: American Airlines Business Class JFK – SJU & American Airlines Economy Class SJU – JFK
3) Hotel: Courtyard Marriott Isla Verde
4) Activities & Dining

I’ll start by covering our outbound flights to San Juan, for which we redeemed 20,000 British Airways Avios per person for Business class seats. I actually already wrote an Award Trip Breakdown post on the flights here but to summarize, I had the option to use Avios at a rate of 10,000 Avios per person for economy or 20,000 Avios for business. I wanted to start off our long weekend in style so I opted to burn the extra Avios for business class. And that is where I think I made a mistake.

I chose business class primarily due to the fact I literally have millions of points/miles and with them constantly devaluing, it made sense to me to start burning through some of them. I could “afford” the extra cost in miles and I would be able to have a little more comfort in a bigger seat, be able to enjoy a meal during dinnertime (since the flight was 5:30pm to 9:30pm) and some free drinks.

I knew American flew older 757’s on these routes and our seats definitely showed the age of the aircraft. As you can see in the photos below, our business class seats were straight out of the 1970s (which might have been when this plane was put into service). It was literally just a slightly bigger seat with limited recline and no in-seat entertainment. Seriously when was the last time you saw a business class seat on a mainstream jet without a personal TV? Better yet the overhead TV in business class wasn’t functioning properly with lines running throughout the picture and the color just non-existent (Andrea actually though the movie was in black & white).



The hard feature of the flight (seat, entertainment) were a letdown but the soft product (food, service) was pretty good. With American Airlines, you can pre-order your dinner up to 30 days in advance of your flight if you are confirmed in business or first class. I chose the chicken dish which came with a cocktail shrimp appetizer, salad, and bread. Andrea had the pasta dish (sorry I forgot to take a photo of it) but both dishes were perfectly edible and filing for us as our dinner. For dessert, we had ice cream sundaes and another round of drinks. The purser in business class was excellent, constantly offering to bring new drinks and generally was very proactive in his service.



For the return flight back to NY, I’ve already mentioned the lack of award availability for the flights we desired since we wanted to spend all day Sunday at the beach. Since we were “paying” for this flight with American Airlines gift cards, we were limited to economy seats that cost $208.50 each, quite steep for a one-way since I have seen roundtrip flights from NY to Puerto Rico under $240. However, we are American Express Platinum card holders and each calendar year we are entitled to a $200 airline credit, so our flights only cost us $8.50 each out of pocket.

I’ll keep this part short since the return flight in economy was uneventful and everyone knows what an economy flight is like. Thankfully we had priority boarding (due to the Citi Executive card) as the overhead bins filled up quite rapidly. We were in row 29 and AA’s 757 have about 31 inches of seat pitch, making it kind of tight for a 6’3” guy like myself. Again, no seatback entertainment but I caught up on some work for the blog and the 3.5 hour flight passed smoothly enough. One mild surprise? The flight attendant gave us the whole can of soda (yes I know I’m stretching for something exciting on this flight).

So to summarize the flights, was business class a better experience than economy? No doubt. But was it worth the extra 10,000 Avios per person which conservatively is valued at $150-$200 dollars per person? That’s where its a bit tougher and I’m leaning towards no. Yes, the meal and drinks were a nice touch but I had ample time to eat before my flight and I wouldn’t have paid for any drinks in the airport. The seat was marginally better but definitely not worth it as it was the worst business class seat I’ve ever seen.

For this short flight I was probably better off saving 10,000 miles to sit in economy. This is especially true for those out there who are just beginning in this game of ours or have smaller mileage balances. Those 10,000 miles could get you a roundtrip NY to Boston flight as I described here. Or it could have covered my return flight home if there was award availability. For shorter flights (under 4 hours), I won’t be redeeming miles for business class unless I have an overly compelling reason to, such as to try a premium product or a shorter red eye where a better seat does go a long way.


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

Award Trip Breakdown: Flights for a Long Weekend in Puerto Rico for $26!

Greetings from San Juan, Puerto Rico!


Andrea and I decided to get away for the weekend and decided upon San Juan to “relive” our first trip we took back together in 2008. That was before I was involved in the points and miles game so I think I spent over $1,000 for a 4 night stay + flights last time. Thankfully I’ve gotten a little smarter since 2008 and with the help of this amazing hobby of ours, Andrea and I booked our flights for a whopping total of $26 and ended up with a great rate on our hotel (and I used giftcards I acquired at 19% off to pay for the room). Here is how I did it.


Departing: American Airlines – Business Class – JFK-SJU  for a cost of 20,000 miles plus $2.50 in taxes per person.
Return: American Airlines – Economy Class – SJU-JFK for a cost of $208.50 a person, paid with $200 of American Airlines Gift Cards acquired as part of American Express Platinum card each.

I will get into this some more in my trip report but I used British Airways Avios instead of American Airline miles because of the uniqueness of British Airways award chart. Since it’s distance based, it cost 20,000 Avios for business class or I could have used 17,500 American miles for economy – easy choice there. British Airways miles can be obtained via transferring either Amex Membership Rewards points (which is what I did), Chase Ultimate Rewards, Starwood SPG points or by having the British Airways credit card. In short, there are a lot of easy ways to rack up Avios.

For the return, I was focused on flights that left after 6pm on a Sunday so I could maximize my time in San Juan. By doing this, I limited my flight options and there was no award availability for either economy or business class on the way home. I ended up choosing a 7pm American Airlines flight that cost $208.50 each but I only ended up paying $8.50 of it per person.

That is because I am an American Express Platinum card holder and each calendar year you are entitled to a $200 airline credit. With this credit, you can buy airline gift cards (though the rules technically prohibit this but it still works) twice in a one membership year. In other words, I signed up for the card in 2013 (and paid the $450 annual fee) BUT I got $400 of that back when I bought $200 of AA gift cards (technically 4 gift cards at $50 each) in March 2013 and again in January 2014. I simply applied this gift card to these flight and paid the remaining $8.50 per person.


Courtyard (Marriott) Isla Verde Beach Resort- 3 Nights. 

The Beach at the Marriott in Isla Verde

The Beach at the Marriott in Isla Verde

I know this isn’t the fanciest hotel on the nice strip of beach in Isla Verde as its right next store to the Ritz-Carlton San Juan and the InterContinental San Juan but it was far by the cheapest for our stay and I was able to use Marriott gift cards I acquired at 19% off to pay for the room!

AAA rates were only $122 for the first night and $139 for the remaining two nights so it didn’t make sense to redeem Marriott points for this stay since a free night would have cost 35,000 points a night resulting in a very poor value per point (.003 per point, not even half a penny!). Additionally, I had a $500 Marriott Gift card burning a hole in my safe that could be used for this stay. I only paid $405 for this $500 gift card via American Express Daily Getaways which typically happens once a year in which Amex partners with variouis companies to sell discounted travel.

Stay tuned for the trip report in which I’ll provide a little more detail on the flights and hotels and decide whether it was worth it.