Puerto Rico was my second trip major trip with my now fiancé. I had always wanted to go to Puerto Rico, and we had been dating for close to 2 years, and we weren’t getting any younger. I had always dreamed of getting engaged in a magical place. Who knows when our next trip would be, so I thought Puerto Rico would be the perfect place to pop the question. Once it was in my head that I was going to ask Gerlie to marry me, there was no stopping me. I got the ring and began to plan how and where I was going to do it.
In all my research, San Juan looked beautiful, so there would be plenty of locations that would suffice. We were going to Flamenco beach, El Yunque Rainforest and many other locations. But risking losing the ring in the Jungle or in the water? Hell no. Plus, those activities were later in the trip, I wanted to calm my nerves and get this done ASAP.
Gerlie loves sunsets, and I’ve seen my share of reggaeton videos, many filmed in San Juan and in the area surrounding Castillo San Felipe del Morro, the old fort and castle overlooking the sea. Views of the sea, a large, lush green field and views of Old San Juan sounded like the perfect place to propose. It was done, I’d do it our first full day and relax the rest of the vacation. The plan was after exploring the city and then relaxing for a bit in our accommodation, the Old San Juan Guesthouse, to go for a nice dinner with time to catch the sunset. Oh, and I had to sneak out for my tattoo consultation before dinner too.
After we were done exploring, the waiting game was on, so to calm the nerves I began to down the Medallas (Puerto Rico’s beer). Well partially to calm the nerves, and hey, we were in Puerto Rico and on vacation. Beers, tattoo consultation, check. Now it was time to get back to the guesthouse and wake up Gerlie so we could go for dinner. When I got back, she was sleeping and it took a long time to get her up, then it took time for her to get ready. Time was going by too fast, the sun was setting soon, and we weren’t going to have time for dinner, I guess my appetite would have to wait until later.
Aside from the lack of time, there were a few problems. The sky wasn’t very clear, it was hazy. Well, it’ll have to do, because it was in my head and this was getting done regardless of the clarity of the sky. The sunset colours will still look nice above the ocean. Also, I need to find a good spot with panoramic sunset and Caribbean views. Now, how the hell was I going to sneak the ring out? The box was too big, and I didn’t want to just put it in my pocket. So, I stuck it in a plastic Home Depot bag and put that in my backpack. But what if she looks in my bag? Well, I’ll put a shirt on top and a few beers on top of that. Sure enough she asked, “why do you need to bring a bag?”
“Well I might need to change my shirt.” She looked at me like I was crazy. “And I want to bring a few beers.” Then she looked at me like I was an idiot.
After the sideways glances, we headed off. We walked through the beautiful streets of Old San Juan. Cobblestone streets, colourful buildings and colonial Spanish architecture; Old San Juan was beautiful. We got to the Fort and had to walk through the large surrounding grass field. My nerves were kicking in so I cracked a beer. She wasn’t happy. Now I had to find a good location where I’d do it. And I had to figure out how I was going to get someone to take my picture without spoiling the surprise.
As we walked around the grounds of the fort we took in the amazing views. There was a yoga class going on in the field. Panoramic views of the city, the water, and the cemetery. Now I know you’re thinking that’s grim, but the cemetery looks cool and provides opportunities for some cool pictures overlooking the water. The sun was setting fast and we couldn’t enter the castle, it’s only open during the day…. And that was where we’d get the best views of the water and sunset, if you could call it that, the sky was hazy, but the colours were still nice, but they would be better if you could enter the castle.
I saw a group of young people speaking Spanish, I’d ask them to take some photos and tell them what was about to go down in Spanish, so Gerlie wouldn’t understand. As I approached them, they took off in the other direction. Then there were old people who I knew would take shitty photos. So, I settled on a group of young ladies, I didn’t tell them what was happening but asked if they could take our photo. That was when I froze, I got down on one knee, forgot everything I had planned to say and was fumbling around for the ring. Finally, I pulled out the ring, as it was still in the plastic home depot bag. I held the ring out in the box, and the only thing I could think of saying was “will you marry me?” Meanwhile, I forgot to put the ring on her finger, so the crowd of onlookers were screaming “PUT IT ON HER FINGER!”. So I did… on the wrong hand.
The whole thing was a blur, I didn’t notice the sunset, I didn’t pay attention to the views and didn’t realize how many people were watching. But when the dust settled and she said yes, I got to appreciate the beauty of the views from the Castillo San Felipe del Morro and San Juan. We walked around in shock, taking in the sights, and finally made our way back down through the colorful streets of Old San Juan for a nice well deserved and overpriced meal.
Even though I wasn’t the smoothest operator, the experience was amazing, and the location was the perfect place for an engagement. I won’t get sentimental because this is supposed to be a story infused with a review of the castle.
I didn’t go inside, but I could tell the view from the inside of Castillo San Felipe would be tremendous. The cost to enter is $10 and with that you can get into Castillo San Cristobal which is close by. Next time in San Juan, I’ll check it out. But regardless of our spot and imperfect angle facing the sunset, the views from the surrounding area, and the lush green field are marvelous, plus the sky still looked good. You will get a ton of good photos, views of San Juan, views of the cemetery, views of the Caribbean and maybe you will even join an outdoor yoga class. Then after you’ve explored the castle grounds, take a stroll through Old San Juan and marvel at the architecture, the colourful buildings all while walking on the cobblestone streets.
Note: the girls we asked for photos didn't get any good action photos of the proposal
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