Day 1 – Puerto Rico: Old San Juan & Condado

Hello friends – This week’s adventure takes us to the tropical island of Puerto Rico! I’ll be traveling there with my mom and aunt Gloria, meeting up with my mom’s best friend Iris who lives there, and hanging with the fam for 3 days. Then on Thursday the girls will arrive & my bachelorette weekend officially kicks off! It’s going to be one hell of a week and I am SO EXCITED. Vamos!

My alarm went off at 5:30am and I got ready to head to the airport. Overall It was a smooth morning and only took me 7 minutes from the drop off point until I was through security, a new record. However I realized I forgot my travel pillow – Oh well. I didn’t feel like spending $45 on one in the airport & thankfully the flight was only 3.5 hours. I decided to use one of my United Club passes to enjoy the breakfast buffet which was delicious. I guess the regular TSA line was long because I only saw my mom and Gloria just as I was boarding the plane. The flight was smooth but I was extremely cold the entire time and there was no option to turn the air blowers off which was annoying. Regardless I slept for the first hour and then watched the movie Anyone But You until we arrived.

Stepping out of the airport the skies were overcast, but the temperature was perfect – high 70s with a light breeze. Iris picked us up in her cute white Kia and we were off to our hotel – the Condado Ocean Club. We arrived by 12:30pm and to our surprise the rooms were ready so we were able to check in early.

We freshened up, changed, and ubered to Old San Juan for lunch. Our destination was Deaverdura but upon arrival the line was around the corner. Luckily I noticed we passed El Jibarito on the way there which was another place that I read about, so the uber dropped us at the corner and we walked two blocks back. By this time it was 2pm and we had dinner reservations at 7:30, but all of us were starving. Instead of each ordering entrees we decided to do a tapas style lunch and share a bunch of local Puerto Rican appetizers that were on the menu. Our lunch for 4 included the following: Acapullia (beef stuffed inside a fried plantain), bacalaito (cod bites), empanadas de pollo (chicken empanada), tostones (fried green plantains), Maduros (sweet plantains), arroz con gandules, (yellow rice with pigeon peas), & mofungo with garlic sauce (mashed plantain). Although it was a lot, they were all little bites leaving us satisfied but not overly full. My favorite was the acapullia.

After lunch we walked around Old San Juan. I wanted to see the famous umbrella street (Los Paraguas de la Fortaleza) but to my disappointment the umbrellas were gone and replaced with odd looking American cancer signs. I was so upset & can’t believe I’ve still seen influencers posting about this umbrella street when it hasn’t been there for a few years apparently?? Next we stopped at Parque de las Palomas (pigeon park) where you can enter and feed the pigeons. That was not for me but Iris went inside and enjoyed feeding the birds.

We continued to wander the streets of Old San Juan and stopped along the water overlook, popped into a cute shoe store that sold hand made espadrilles, walked past the main city center fountain, and then into Chocobar Cortes for some dessert. Iris & I shared the rum and chocolate flight along with the PB&J drink that was delicious (but I forgot to take a picture). Mom was getting tired so she ordered a coffee which smelled so strong I felt more awake just from taking in the coffee bean aroma.

After dessert we decided to head back to the hotel and lay out by the pool for a bit. It was overcast and cloudy but after all the walking I needed to relax and lay out. Iris ended up going in the pool and was like a fish doing laps back and forth – she was cracking me up. Eventually we went upstairs and got ready for dinner. Tonight we were going to Santaella which was rated as one of the best restaurants in San Juan, I was very excited. The restaurant was located right in La Placita de Santruce and was very unassuming from the outside, but as soon as you walked in the vibe was upscale modern, and it smelled delicious.

We got a cozy corner table in the back of the restaurant which was perfectly tucked away from the main dining room crowd. To start I ordered a strawberry mojito and the mint was so fresh you could literally eat the leaf. All of the drinks ingredients were so fresh. For appetizers we got ahi tuna lollipops & Spanish octopus with chorizo and potatoes. The tuna chunks were BIG, super fresh, and out of this world delicious. For dinner mom and Gloria had the seabass , Iris got the filet mignon, and I ordered the veal cheeks. I’ve only ever had veal cheeks once before and loved them (at DAOU winery in Paso Robles,CA), and it’s not a common dish back home so I was pleasantly surprised to see them on the menu. The veal cheeks did not disappoint and melted in my mouth with every bite. We all had wine with dinner and dessert for Gloria’s birthday. After dinner we walked down the street and the La Placita bars were pumping music. We went into one of the bars and danced a little before our uber arrived. Off to the casino! I’m not much of a gambler but I blew $20 and lost it all. Gloria and mom hit the slot machines but after an hour we decided to call it a night. Mom and I had a rainforest hike planned the next morning with a 6:30am pickup so I was ready for sleep. Overall an excellent start to the trip & looking forward to what tomorrow brings.