San Juan, Puerto Rico Anniversary Trip


Latita Colmada in San Juan

Hi everyone! I wanted to do a blog about our anniversary trip to San Juan this month. I’ll preface this by saying this is my first time doing travel content, so please bear with me. I did not record or take pictures of everything because I was just in the moment. I’ll do better on the trip we have planned for late June. Anyway, this blog may be lengthy, so if you don’t want to read it in it’s entirety, skip to the part that you want to see (where we stayed, the weather, where we ate, activities, etc.). Thank you in advance for reading! About San Juan: Puerto Rico is a beautiful Caribbean island that is also a U.S. territory. We were able to learn a little bit of history behind the island regarding who the original Puerto Ricans were and how they were completely eradicated by the Spaniards. So much history and way too much for me to tell you. You'll have to explore for yourself!

Where We Stayed: Our first stay was at the O:Live Boutique Hotel which advertises itself as a luxury hotel and has lots of great reviews. We looked at the photos and said, " Oh yes, let’s book it! When we arrived, it was small and quaint and I was like, “oh, this is cute”, but I should’ve known it was about to be some mess when they told us the elevator was broken AND there was no one to help with our bags. You cannot market yourselves as luxury when the most basic of amenities are lacking. So here we were dragging our bags up the steps to the third floor.

Before I jump into the rest of our stay at this hotel, I have to say that if your elevator is broken, as a "luxury" hotel, I expect that you will have someone out there to fix the elevator immediately (especially if you are also charging luxury prices). But no… day 1 came and left… the elevator was still broken. Day 2 came and left…. Elevator was still broken. Day 3 came and left… and you get the gist, it was still broken. So if you happened to be handicapped, you would have had to cancel your reservation. Anyway, we get to our suite. We were staying in the O:Live Style Suite. The room was very small and the bathroom inside the bedroom was encased in glass. You open the door in the bedroom to the outside terrace and there was a beautiful outside shower/tub that was absolutely divine.

The veranda gave all the Spanish vibes. There was a small seating area out there if you’d like to eat and drink your coffee as well.

The terrace is the selling point for their hotel rooms because that’s honestly why I booked it. However, by the end of day 1…. I was telling my husband to get me outta there. The entire bedroom smelled like a pool, whenever we took a shower, the water from the shower would leak into the bedroom and the whole bedroom floor would be wet ALL DAY! I was so tired of having to walk around the bedroom in shoes because the floor was wet. It was obviously a structural design flaw with the shower because I’ve had flat showers in a hotel before and never did they leak into the bedroom. At one point the toilet stopped flushing, so someone had to come to fix that. I just think the price point is not equivalent to the quality you get at this hotel. After a few days, it was time to go and we headed over to the AC Hotels Marriott San Juan. We should’ve just stayed here the entire time and I can’t tell you how happy I was to finally be there. The AC Hotel was large, modern, spotless, and had endless amenities & offerings for you during your stay. It wasn’t luxury per se, but the hotel was still extremely nice. Complimentary snacks, wine, cheese, and crackers are brought to your room. Free drink tickets for drinks on the rooftop during your stay. These are the simple things I would expect from a luxury hotel. Literally, anything we asked for, they gave it to us, and did I say the hotel was cheaper?


Activities: While there are many activities, I will be the first to admit that I am not a major outdoor person…. So my outdoor activities were limited. However, I will tell you a few things we did and give you some recommendations for other activities you can do if you visit! Whenever we take a trip anywhere, I always do a tour because I want to learn about the history of the destination we’re visiting. We did a tour on the second day that I booked through Airbnb with a guy named Harry. Harry was absolutely amazing! He really knows everything about his hometown and took us around San Juan (I’ve linked his tour if you’re ever in San Juan and interested in booking him).

Our next activity was hopping on a floating deck! We rented a floating deck from Aqua Fitness to just relax on the water. The base price for renting is 200.00 for two hours (and it’s more if you want to rent it for longer). You can add items onto your floating deck such as wine or champagne, a charcuterie board, fruit, rose petals, etc.

Floating deck that we rented from Aqua Fitness in San Juan to float on the lagoon

We also did a salsa lesson that came with a traditional Puerto Rican lunch afterward. Charlotte was our salsa teacher and she also was amazing. She was very personable, obviously a professional dancer, and took her time making sure we were getting the steps right. (I’ve linked her class if you’re ever interested in booking).


Salsa Lesson w/Charlotte

La Playa Condado

We couldn't come to Puerto Rico without spending time at the beach. We went to Condado beach which was beautiful during the day and at night. There weren't many people there any time of the day, so it's a great place to go, relax, and take photos.


We also visited some of Puerto Rico's famed castles/fortresses which are also part of the U.S. National Park Service.


Castillo Felipe del Morro and San Cristobal Castle. These fortresses were built ages ago and were battlegrounds. They overlook the coast and you can tour the grounds yourself or take a tour.


Where We Ate: We don’t typically eat breakfast. We’ve been conditioned to just get up and start working most days, so breakfast was never really an option while we were here. However, we did eat well for lunch and dinner!

Raya - Caribbean fused Asian cuisine (reservations required) #55 Barranquitas Street, San Juan, Puerto Rico 00907 Let me start by saying I was so hungry when we got here that I definitely did not take pictures of the food. I only managed to get a picture of the cauliflower soup that I had. But I ordered the oxtail guisado dumplings and the honey garlic chicharron lo mein and it was soooooo good. I literally inhaled it. This place stays booked, so if you ever visit San Juan, I 100% recommend going here for dinner. This was so good, I was ready to double back another night!

1950 Condado PR - Puerto Rican Cuisine

110 Ashford Drive, San Juan, Puerto Rico 00907

The food at this place was absolutely delicious. Everything was super flavorful and also affordable. It's another place that locals go to, but tourists also eat here because it’s just that good. I got the Kan Kan Fried Pork Chops w/mompansteo rice and a side of shared plantains. The husband got an order of ribs with chocolate bbq sauce with rice and peas. The portion size was more than enough.

Kan Kan Porchops and Mamposteao Rice

Pork Ribs w/Chocolate BBQ Sauce and Rice & Peas