The rain seemed torrential, and the windows of the cab were all fogged up as it pulled into San Juan. We tried our best to get a glimpse of the cobblestone streets on which we were gliding through. Before long, we were at our hotel—the El Convento. We found it as a blind booking on Hotwire, but we did extensive homework, and were pretty darn sure it was what we would get. (Our newfound confidence wouldn’t serve us so well for some future trip-planning.)
El Convento
A monastery dating back to the 1600s, its present reincarnation into a hotel began in the 1960s during Puerto Rico’s period of industrial development. In the middle of the building is an open-air restaurant, Patio del Níspero, named after the ancient Níspero tree still standing there. The rooftop pool and terrace offer spectacular views of the old city. The open-air corridors are lined with Spanish tiles and supported by traditional mahogany beams. Tastefully European and full of old-world charm, the hotel is easily one of our favorite hotels anywhere.
One of our goals for the year was to get our Open Water diver certifications. While we did our confined water dives at a pool and dive school in Pacifica, local options for the open water dives would likely put us in the murky, frigid waters of Monterey Bay; diving in the Caribbean seem like an unequivocally more desirable option.
Old San Juan
The rain continued the day after we arrived. We had a full day to explore Old San Juan before our diving adventures. The city felt so colorful and refreshingly European that we were too excited to let the occasional downpours stop us from spending the day traipsing around town. Every street we saw in old San Juan is brilliantly multichromatic, almost as if some law mandated that no two buildings share the same color.
After discovering the brand new delight of guava butter at breakfast, we walked east toward Plaza Colón, where we got a first view of Castillo de San Cristóbal. We would pay a visit there in a few days; for now we continued south towards Plaza Arturo Somohano, ending up at Plaza Dársenas on the south shore of the peninsula.
A large cruise ship was docked at the pier. Street vendors and food trucks also set up at the small park here, but the morning was quiet today and we had the views of the harbor all to ourselves.
Paseo de la Princesa
La Puntilla is an area of Old San Juan at the southern tip of the peninsula, much of which is occupied by the U.S. Coast Guard. Along the northern border of La Puntilla is Paseo de la Princesa, a charming tree-lined promenade. At the west end of it is the magnificent Raíces Fountain. Though the promenade dates back to the 19th century, the fountain itself is a modern installation, completed in 1992 with bronze statues to celebrate the island’s heritage.
We lingered here for a while to enjoy the beautiful views of San Juan Bay. Looking north, we could also see sections of the old city wall, with various bastions and historic gates.
The south end of Paseo del Morro starts near here but the entrance was closed, so we retraced our steps along the promenade and climbed up to the Bastión de las Palmas de San José just to our north.
Parque De Las Palomas
One of the most pleasantly unexpected discoveries along our walk today was Parque De Las Palomas, a somewhat secluded park at the end of Calle de Tetuan. The panoramic views of the bay here are stunning to be sure, but what’s so unexpected about it are the hundreds of pigeons living here. In hindsight, the park’s name should make this no surprise, but a real brick wall of pigeonholes is an interesting curiosity nonetheless—I don’t think I had ever seen a real pigeonhole until then.
El Morro
Walking back towards the hotel, we stopped for a light lunch at El Patio de Sam and sat at its inner open-air courtyard. The rains continued on and off, but as soon as it relented, we headed back out to explore the streets. Caleta de San Juan is almost completely canopied by tall tropical trees on both sides. At its east end is Plaza de la Catedral, a small quiet square bordered by the El Convento and the 16th-century San Juan Bautista Cathedral. Heading a couple hundred feet west would lead us to La Puerta de San Juan; this used to be a main entrance into the city, and of the six such gates through the city walls, this is the only one remaining.
The grounds of El Morro cover a large portion of the northwestern tip of the peninsula. We entered near Casa Rosa, an old barrack painted in bright pink befitting its name. It would be just another short hike before we saw the vast headlands of the old fortress.
El Morro is just one of the two giant fortifications in Old San Juan. Its western counterpart is Castillo de San Cristóbal, which we would visit in a few days. The fort was closed by the time we got here, so we spent the next half hour exploring the high grounds.
From the northeastern side of the fort, one can get a broad view of the northern shoreline of the city, as well as Capilla del Cementerio Santa María, a 19th-century cemetery that is the resting place of many prominent Puerto Ricans. We wish we could spend more time here, but the rains were getting heavier, and clouds more restless and ominous by the minute.
Dinner tonight would be at Carli’s Fine Bistro and Piano, a cozy restaurant just a few blocks from our hotel. We came here for the live music, but the food was equally impressive.
Scuba Diving
The drive to Fajardo would take about an hour. This region on the eastern shore of the island is a recreational boating hub, and so it’s fitting that our dive school would be based here at the Puerto Del Rey Marina. We sat at the back of an SUV, peeking out into the rural areas that we were traveling through. The weather cleared up just in time for our diving trips and exams over the next two days. Despite that, my first scuba diving boat ride would turn out to be absolutely treacherous and nauseating, as it was for all the others who weren’t dosed up on Dramamine.
As soon as we got to the first dive site, Sandslide, our dive instructors got the most nauseous of us into the water, promising that we would feel much better once we were in. My first open-water dive would be well worth the otherwise insufferable boat rides today. Even though I knew beforehand that I’d have trouble equalizing under water, the dive went smoothly, and was an absolutely surreal experience.
After a brief break, we headed to Cayo Diablo for the second dive. The waters were crystal clear. Our tests took up only a small portion of the dives, so we got plenty of time to see sting rays, eels, and even sea turtles.
The first place we visited after we got back to San Juan was a pharmacy to get Dramamine for the next day. And after a long (and well-deserved) siesta, we enjoyed authentic Puerto Rican food at Deaverdura, a cozy local restaurant just a few blocks away. The popular sample platter was filling and delightful.
Our group would be slightly smaller the next day; a few who got really sick from the boat rides didn’t show up for the dives around Culebra, an island 17 miles east of the main island. The skies and water were crystal-clear blue. In between dives, we did some snorkeling closer to shore.
We passed our exams and became newly minted certified open water divers. In truth, the hardest part of diving was enduring the choppy boat rides. But on the second day, things felt much calmer—we weren’t sure if the waters were less wild, or if Dramamine is in fact some wonder drug. Dinner would be at St. Germain, a comfy local bistro and restaurant. The decor was simple and bright, and the food was fresh and hearty.
Castillo de San Cristóbal
The weather on our last full day in San Juan would be markedly different than on our first. The sun was out and the skies were clear, and the already colorful streets looked even more vivid.
Our destination today would be Castillo de San Cristóbal, the eastern counterpart to El Morro. But first, we took a detour south to get breakfast at Café Cuatro, a charming little café with rustic, natural decor and an open courtyard.
The walk to the fortress took us through more European, cobblestone streets which were a delight to photograph on a clear day like this. We walked through Plaza Colón with a statue of Columbus, who discovered the island in the 15th century. Just north of the plaza is one entrance to the fort; and unlike our visit to El Morro, we would get to explore this inside and out.
This fortress is supposedly Spain’s largest in the new world. Like El Morro, the grounds were vast, and offered impressive panoramic vistas of the coast.
Perhaps because the fort is so colossal, it felt very quiet; we saw only a few fellow visitors, and at times felt like we were the only ones here. We did the self-guided tour and explored the somewhat circuitous structure, with multiple levels and tunnels, corridors, and staircases opening into other rooms, courtyards, sentries, and dungeons.
We went back to the hotel in time for lunch at El Picoteo, an exquisite little tapas bar on a terrace overlooking the hotel’s open-air courtyard and restaurant. The menu was extensive, and the seafood-heavy plates we got would get us through the rest of the afternoon.
Casa Blanca
We got up early the next day because it would be the last day of our trip, and we wanted to explore a bit more before heading out. After taking a brief peek inside the nearby San Juan Bautista Cathedral, we headed up the hill along Calle Sol, walking past rows of houses painted in colors that we can neither name nor identify.
Just around the corner is Casa Blanca, a 16-century residence of Juan Ponce de Leon, a Spanish explorer and the first governor of Puerto Rico. Completely tucked away and hidden behind the old city walls, this inconspicuous little house is now a museum with a quiet and elegant garden. It’s a hidden gem of a stop that we were glad we made.
Along the way back to the hotel, we passed by Plaza del Quinto Centenario. Its modern fountain and overall look is an interesting contrast to the old buildings surrounding it. At the center of the square is El Tótem Telúrico, also a modern work created to commemorate the discovery of the New World.
Our flight back home would be in a few hours, so we hurried back to the hotel to pack and head out. We thoroughly enjoyed Old San Juan and all of its charm and history, and we knew we would miss both the city and our stay at the El Convento. As a souvenir to ourselves, we had gotten a plaster plaque of the hotel’s façade from a local shop, so we could feel like we brought a piece of Old San Juan back home.
We came here to get some perfunctory diving certificates, but left with so much more.