I woke up around 8:30 in the morning, which meant I missed hotel breakfast, but I took myself to the chocolate/coffee shop connected to the hotel. This was my first experience with Puerto Rican coffee, which was fantastic. Chocobar Cortés is a recommendation from me, and I even ended up bringing back some of their chocolate spices and bars (though the bars were cheaper to buy at a grocery store). I still need to figure out what cookie creation is going to come from those.
I called a ride share to get to Old San Juan, and for not the first time, I am shocked at how affordable getting around San Juan is. It’s rare to see a less than $10 ride anywhere in Chicago, but I saw it routinely in PR. I had the driver let me off near Castillo San Cristóbal, which is a sprawling fortress built by the Spanish dating back to the 1500s. It was the largest fortification built in the New World. It is now a UNESCO World Heritage Site and under the auspices of the United States National Parks Service.
I bought my ticket, and I wandered around the fort for a while. It was pretty hot that day, but the breeze off of the ocean was keeping it somewhat manageable. Castillo San Cristóbal is just gorgeous structurally and the views it has of the coastline, Old San Juan, and San Juan itself, are superb. While obviously Spanish, it very much reminded me of Topkapi Palace in Istanbul, but that might have been because I was writing the Istanbul throwback blog post at the time.
After wandering those grounds for a bit, I moved further into Old San Juan, which was pretty quiet on a Sunday morning. While there were some shops, bars, and restaurants open, I chose a cute little avocado toast place called the Stuffed Avocado Shop, and then I wandered even further into town.
My friend, Sheila, had mentioned that she knew an artist who had several sculptures throughout Old San Juan, and I made my way to see one of them, La Rogtativa by Lindsay Daen from 1971. It’s a gorgeous, modern bronze sculpture of the bishop and women who may or may not have scared off the British fleet.
I then walked up a steep and beautifully treelined street, which brought me to the steps of the San Juan Bautista Cathedral. By this time, I was pretty sweaty in my shorts and tank top, and I hesitated for a moment trying to go in, especially since I got reprimanded by a nun in Prague for trying to go into St. Nicholas Cathedral in the same state, but I since there were several tourists wandering around, I went in.
The Catholic cathedral is one of the oldest buildings in both Puerto Rico and all of the Americas, and it contains the remans of Juan Ponce de León, which I didn’t realize until now….guess I need to go back in November! While it may not be as grand as some of the churches I saw in May, it still scratched that church and ceiling itch that defines my travel tastes. Plus, since it is pretty much an open air church, there were CATS! I love street cats.
That pretty much wraps up the trip into Old San Juan, and I needed to get back to the hotel to meet up with my trainer, JoAnn, and her daughter, Julianna, and friend for dinner.
Since Monday was a work day, I’d decided to not venture out after dinner, and I met JoAnn early to head to the training site, which was about an hour’s drive out of San Juan. There is not much to report from this stop because it was pretty standard suburbia. Once the training was up and running and after lunch, I grabbed a ride share back to the hotel to do some work.
Once I was done with work, I walked a few laps on the beach, which is something I tried to do each day. As I mentioned earlier, I am not much of a beach person. I get bored laying out, and I hate sand getting everywhere. However, I did enjoy walking up and down the beach a few laps. The water was fairly rough, which made walking along the shoreline pretty difficult and there was a lot of seaweed and other ocean “stuff.”
After leaving the beach and getting cleaned up, I decided to walk to a SuperMax grocery store to see if I could find some affordable coffee outside of the tourist area and peruse the baking aisle for unique ingredients to bring back. It was mission accomplished all the way around because the coffee was very affordable. I bought some for myself and my family, since I was flying from San Juan to Indianapolis on Wednesday. As mentioned, the Cortés chocolate bars were much cheaper than the coffee shop, too.
I didn’t do dinner with JoAnn’s crew that night, but Julianna wanted to go out to some bars, even though it was a Monday night, and while I had planned on going to the training again on Tuesday, I acquiesced. Julianna is in her early 20s, and I have long ago outgrew the fun of going to straight bars. However, I wanted to expense more of San Juan.
We went to La Placita, which is pretty much a nightlife wonder. Founded over a century ago, La Placita de Santurce during the daytime is a traditional farmer’s market, which I will most definitly try to go to next time, but in the evening, it becomes a nightlife destination with a number of bars and restaurants for you to do a centralized bar crawl. JoAnn mentioned that as lots became available around the market, the owners bought them up to create their own entertainment district. Obviously, for a Monday night, it was not exactly hopping, and we were there kind of early, too. However, I could see this being a reasonably fun time for straight bars. Of course, even for a Monday, there was a bachelorette party.
Since I was basically being the adult on this excursion, and honestly, drinks were a little pricey, I was not going all out, but since this was a low density night, a lot of the bars were offering free shots to come in the bar. My compatriots just kept doing them, and they got pretty wasted, which was entertaining until it wasn’t. Once I got them shoved into a car to head back to the hotel, I walked over to El Purgatorio to gay decompress and check out their Monday night. We’ll just say it was a black out party and leave it at that.
I decided that I didn’t really need to go to the second day of training, but I still met JoAnn in the lobby and walked to Starbucks with her. Since today was the last day of the training followed by another round in Ponce, she was leaving that night to drive to that location. So, this was farewell. She also told me that Julianna projectile vomited when she got back to the hotel. Amateurs.
I spent most of the day catching up on work and getting packed from the flight to Indianapolis on Wednesday. I made one more visit to the beach, but I had decided to spend the evening back in Old San Juan.
After a quick stop at Chocobar Cortés for my last iced americano of the trip, I took another cheap ride back to Old San Juan. I had settled on a small restaurant, La Madre, which had good reviews. I arrived a bit before they opened, and I was by far their first customer. They weren’t quite ready, but once they opened, I sat at the bar and had a very spicy tequila cocktail, and I throughly enjoyed the meal.
Once I was done with dinner, I decided to make my way to parts of Old San Juan I had not seen in the previous trip, which meant walking up some steep inclines (more Istanbul flashbacks) to the north side of the city. I walked towards San Felipe Castle. I didn’t get all the way out there (next time!), but I got some gorgeous pictures of the sunset.
My main goal of the walk was to get to the one LGBT bar in Old San Juan, La Sombrilla Rose, which is also next to the social media famous El Cafetin bar, which is known for it’s very hot, very shirtless bartenders. My energy level was ebbing, and I was too chicken to go into El Cafetin by myself as a 50+ year old gay man. I did sit at the bar at La Sombrilla Rose. It was still VERY hot, and I’m not big on hot and drinking. After chatting with the bartender and taking a few pictures, I made my way back down to get a car back to the hotel.
I really fell in love with San Juan and Puerto Rico, and as I type this on a flight back from Denver, my next flight is back to San Juan for a conference in November. I cannot wait to explore more!
