My Puerto Rico Proposal
Months before Jessica and I ventured into the Caribbean for some much needed time off, I was feverishly devising a plan to integrate this trip into an epic wedding proposal to my girlfriend of 5 years. The proposal was going to be a complete surprise and I would have to carefully go about purchasing the engagement ring and carry it with me undetected. Even little details like ensuring Jessica cleared the security checks before me — in case they held me up and went through my bag — had to be thought through.
The good news is that there were no hiccups during this entire process and by the time we had arrived at our Airbnb, I was confident that I would be able to pull this proposal off exactly the way I had envisioned.
We always made an effort to view the beach at least once a day, but unbeknownst to Jessica, I was scouting for that perfect spot. I had to see all of the contenders in person first before finalizing the backdrop for where I’d pop the question.
Once I had my sights set on a particular location, I checked the weather for the following day and was pleased to see nothing but sunshine. And with that, I knew tomorrow would be the right day.
The Proposal
I convinced Jessica to wake up super early the next morning to see the sunrise with me and she unquestionably agreed. I put on a dress shirt that was spiffier than I’d typically wear crossing my fingers hoping that this wouldn’t be the thing to spoil the surprise (luckily it didn’t sound any alarms). We made our way down the shoreline and over to the spot I had picked out.
I had brought my DSLR camera (as I typically do) so nothing was of suspicion yet. Since Jessica was already familiar with my love of photography, it was completely normal of me to take shots of her and the sunrise that morning.
After a few minutes of shooting, I reminded Jessica of my camera’s “action mode” which takes blur-free burst shots of moving subjects. I instructed her to keep her back to me, walk forward and do a twirl toward the camera.
I, of course, had no intention of actually taking this picture and the moment she turned her back to prepare for the shot, I put down the camera, pulled out the ring and dropped to one knee.
Jessica completed her twirl, looked back at my goofy face and realized there was no lens capturing her. Puzzled, she looks further down only to see the shimmering diamond ring I had picked out for her. It took her a couple seconds to register exactly what was happening and once it all sunk in, she shrieks “baby!!!”
Midway through my confession of love, Jessica just runs over and gives me a big kiss and says “YES!”. I forgo the rest of the speech and just slip the ring on her finger.
We talk about how she was completely blindsided by the whole thing and as we do, she begins to get a bit teary eyed. I see this as a perfect opportunity to capture her expression and take a picture of her — for real this time.
In turn, Jess takes the camera and now points it at me, creating the image we affectionately refer to as “The Sandy Knee Proposal”.
We then made our way to the bike rental shop and pressed on to what was very well one of my favourite days ever.
Exploring San Juan
One wonderful aspect of this city is that they’ve made great strides in promoting green living, particularly by way of dedicated bike paths. There are several kilometers of dedicated bike lanes adjacent to busy car traffic that’s completely buffered by trees, shrubs and plants. This makes for one heck of a comfortable and safe bike ride.
We made our way to the first of San Juan’s famous fortresses — Castillo San Cristóbal. This is the smaller of the two forts on the main island as a means to protect the larger fortress El Morro and the city from land attack.
During a guided tour through the fortress, the most standout moment for myself was when we were informed that the field adjacent to the fortress was booby trapped. We learned that underneath the battlefield were tunnels that soldiers wired with explosives as a last ditch effort to stop the enemy from advancing. Due to the Spanish’s strong defenses, it never came to use.
We actually had the opportunity to walk the tunnels below the field — something inaccessible to the public without a tour guide. These tunnels are quite short in height (around 5 feet tall on average), forcing us to crouch most of the time.
The larger fortress El Morro is just a 30 minute walk from Castillo San Cristóbal (less if you catch a free city trolley) and viewable from the top deck of the fortress.
The lawn to El Morro is deliberately long to exhaust enemy soldiers and make for easy pickings from the guard towers.
El Morro was built to protect San Juan Bay’s deep harbour from sea attacks. Since it was the first good harbour for sailing ships to the New World after a grueling one to two month cross-Atlantic voyage from Europe, it was a prized port to control.
With time, El Morro evolved from an elevated cannon firing station to the massive six level structure that still stands nearly entirely intact today. For nearly 300 years the fortress was used to ward off enemies, never falling to attackers once, proving to be a worth while investment for Spain.
From El Morro, you can connect yourself to a shoreline walkway known as Paseo Del Morro located on the outside of the original defensive wall. It’s an absolutely delightful walking path that continually beautifies as you make your way South. Along this path you’ll discover the San Juan Gate (formerly the city’s official entrance), mature trees with gorgeous hanging branches (an area known as Paseo de la Princesa) and conclude with a stunning fountain at the head of a tree-lined pedestrian pathway toward the old city.
Jessica and I took that pedestrian walkway back into city but not without coming across this fabulous looking restaurant called Princesa Gastrobar and I must say this stop was a real treat. The restaurant has done an excellent job at not only preserving, but integrating the trees and plants into their establishment (with several of the trees piercing the rooftop)! The waiters were very caring and attentive, the live music was on point and with the historic wall as our backdrop, it made for a perfect dining experience. I would absolutely recommend stopping here for dinner.
Just steps away from Princesa Gastrobar is an outdoor botanical park that’s also worth a visit. While the park is quick to explore, it’s a wonderful pit stop to gawk over the exotic plants and trees. There’s also an outdoor gym circuit if you’re feeling particularly ambitious.
We stopped back at our Airbnb for a power nap and then headed back out again for some late night drinks at this great local patio called Mango’s just a few minutes away from where we were staying.
The next few days consisted of a lot of exploration by foot and local cuisine tasting although the most bizarre thing we tried was not exactly Puerto Rican. We tried these coloured burgers from a place called Blue Burger that essentially sells the ‘Pretty Patties’ from Spongebob Squarepants.
The buns were chewier as a result of the food dye process but the burgers, sides and drinks were all quite delicious and made for a very memorable experience! (We ended up feeling fine if you were wondering.)
Our next big adventure was visiting El Yunque National Forest. Located on the Eastern side of the island, this incredible forest was less than an hour by bus from San Juan.
Deeper in the forest is a lookout tower that elevates your vantage point to several kilometers into the distance. It’s an easy climb for the view you get in return.
While the cloud coverage did limit the range of how far we could see, it still had us appreciate the seemingly endless hills of woodland.
While we did also visit several museums, parks and local shops, I want to end this blog post with a few shots from a boat ride we took circling the San Juan Bay — an inlet adjacent to the old city.
As you can tell from the photos, the weather began to turn on us at the end as storm clouds approached. Though our timing worked out well as the rain only started to fall minutes before we docked, giving us enough time to run for shelter before getting poured on!
The day after we boarded our plane and headed back to Canada for the first time as an engaged couple. Now it was time to plan our wedding!
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This blog entry is part of the publication Robert Cekan Travels
Robert Cekan is a young entrepreneur and proud Hamiltonian. He is the founder of the Hamilton discovery website True Resident, as well as Cekan Group, a property management group. He is also a Hamilton REALTOR® with Ambitious Realty Advisors Inc., Brokerage and an active blogger.
For all of Robert’s projects, please visit robertcekan.com
