Destinations like Turks and Caicos, Aruba, and Exuma Bay (Bahamas) garner much of the tourism attention in the Caribbean. I’ve always wondered, why isn’t Puerto Rico as popular? Is it because of the financial instability? The presence of nicer beaches on different islands? What is it?

I’m not sure what the answer is, but I can tell you Puerto Rico is absolutely stunning and you should place it at the top of your Caribbean travel list — especially if you are a United States citizen (due to there being no customs clearance).

This past May my girlfriend and I decided to take a week long trip to Puerto Rico, specifically the Condado Beach area of San Juan, which in the effort of full transparency, is perhaps the nicest and safest part of the island. We’ve never been to Puerto Rico and quite honestly didn’t know what to expect. I had my guard up and thought it wasn’t going to be that great — boy was I wrong.

View from the Balcony Suite at the La Concha Resort (Marriott property).

We booked a Oceanview Balcony Suite at the La Concha Resort. The total was around 300,000 Marriott points over a holiday weekend for around 6-7 nights. The Oceanview room is 100% worth it so if you are on the fence, don’t be. Book it. They have standard Oceanview rooms (not just Suites). The hotel was absolutely gorgeous and perfect for a nice getaway.

I digress. I don’t want to make this a hotel review post, but more so want to highlight San Juan as a whole.

What You Should Do

There are numerous activities and sights to see and do in Puerto Rico. We read rave reviews about neighboring islands of Culebra and Vieques as well as the El Yunque Rainforest, but quite honestly we weren’t interested in venturing that far away as it takes a decent amount of planning and money to do so. For example, if you want to get to Vieques or Culebra, you have two options — ferry or airplane. The ferry leaves from Fajardo which is roughly a one hour drive from Condado. The catch is you’ll have to arrive at dawn to get your place in line. No thanks. Your other option is to fly, but tickets can be pretty expensive so unless you are staying at the W Vieques, a day trip may be a bit too much.

Flights to neighboring islands from San Juan can be pricey. ~$400 for two travelers in this example.


We spent a majority of our time on the beach at the La Concha (below) and in Old San Juan.

Old San Juan

Old San Juan is a 15 minute drive from Condado. You can catch a cab for around $15 each way (pricey) or take an Uber for $15 round trip. Understandably so, Uber and taxi drivers bump heads quite often so when you order an Uber, it’ll have you walk down the block a bit to pick up the ride, which wasn’t an issue for us at all. Puerto Ricans are incredibly nice and hospitable, which just added to our experience.

Most of our vacation was made up of lounging on the beach, drinking, eating, and walking around OSJ. Our stay was maybe one night too long. You could definitely do this trip over a long weekend. No doubt about it.

View from atop the Castillo de San Cristobal…

Old San Juan is chock full of cool colors and Spanish-style homes…


Much like Venice, Old San Juan is a very “walk and get lost” type of town…



Go visit Puerto Rico. The island is in desperate need of your money and it’s a beautiful place with friendly people, amazing food, and amazing beaches. They didn’t pay me to say this. Before going I had a negative view of PR. I thought it was run down and dingy. Don’t get me wrong, the island has its share of badlands, but I didn’t have a single bad experience. We thoroughly enjoyed our time there and I am happy to share any tips/tricks in the comments below!


Our Top Places for Food/Drink/Sightseeing

Cafe Puerto Rico — get the churrasco mofongo with sweet and dry plantains.

Caficultura — get a cortadito.

Raices — get the churrasco steak with rice and beans.

La Taberna Lupulo — the best beer bar in OSJ/Condado. Period.

Castillo San Felipe del Morro

Pannes — awesome breakfast/lunch/dinner spot. Quick eats and great coffee!

El Vagón — the most amazing tacos you’ll have….

Parcela Gastropub — incredible little restaurant with a great beer selection, awesome bartenders, and artisan food!


All images are © The Short Final.