Discovering San Juan, Puerto Rico

First off, Happy New Year to everybody! It’s another year to start over fresh, take what you have learned from the past and use it for better in the future. I wanted to start off my first post of the year talking about my time in San Juan. Recently I just came back from 9 days in the Caribbean and my first stop was on the Green Island known as Puerto Rico.


I’ve been to Puerto Rico a couple of times, and each time I gravitate to the well-known Old San Juan. But this time I decided to stay in the neighborhood of Condado, which is apparently the new, nice, and gay part of San Juan. Didn’t know that when I booked but it was nice to see tan, fit, good-looking gay men walking around outside my hotel every morning.

I stayed at the Coral Princess, a hotel that provided free breakfast with coffee, a somewhat walk-able distance from Old San Juan and the best beach nearby out of all of San Juan, Condado Beach. Apparently this is also the gay beach of San Juan because it is in Condado, fyi. The gay bars are also located near Condado but they are in a littler more dodgy part, so keep that in mind.

Discovering San Juan Puerto Rico - Picture of Puerto Rican Flag

I learned that from Condado, on Ashford Avenue, it is possible to take a bus to Old San Juan on the 21 or 53 heading west. It’s only .75 cents and it’s very easy to do. The only problem is that they only come like every 30 or 40 minutes. But taxi rides are very expensive in San Juan and can cost something like 17 bucks just for one way. Honestly it’s kind of ridiculous but those are your only options if you decide to stay in Condado.

Why Old San Juan?

Most tourists will head here anyways but why should you go? Many travelers are against going to touristy places but Old San Juan should be visited. Established in 1509, it is the oldest city in Puerto Rico and probably the oldest in the US (Puerto Rico is a territory). It still retains a certain charm from its past days as a fort city and its past Spanish influence. Also it still has small, narrow, with cobble stoned roads; something very hard to find in North America.

Discovering San Juan Puerto Rico - Street in Old San Juan

Discovering San Juan Puerto Rico - Girls dancing in Old San Juan

Discovering San Juan Puerto Rico - Colorful buildings of Old San Juan

What is there?

Surprisingly much of the charm hasn’t left. There are many chances to take quality pictures and tour the forts that are still apart of Old San Juan. San Felipe del Morro and San Cristobal are worth the mere 5 bucks you have to pay to get in to both. You can even walk along the a sidewalk above the fort walls and the La Perla neighborhood that connect the two but it takes a good 20 minute walk to get to one from the other. Just don’t walk in La Perla because it’s one of the most dangerous neighborhoods in all of San Juan. There is a trolley that comes sporadically but you’re out in the sunshine with beautiful scenery so my advice is to walk it.

Discovering San Juan Puerto Rico - San Cristobal

Discovering San Juan Puerto Rico - From San Felipe del Morro Fort

Discovering San Juan Puerto Rico - View from San Felipe del Morro Fort

You should walk around Old City and take pictures of the architecture, people, and the food. There is plenty of old styled Spanish influence buildings that are painted bright, bold and beautiful colors. Perfect for unique photos. There are narrow streets to walk down and much of Old San Juan is very hilly, so you’ll get some exercise. Honestly there are some art museums and other cultural things to do but I just enjoyed walking and taking it in rather than worrying sbout something to do.


In downtown San Juan there is something like 600 restaurants, so a lot to choose from. We ate at some of the top choices while still remaining a budget. Honestly we didn’t have a bad meal in Old San Juan and you should always look out for mojito specials! That is the go to drink for most Puerto Ricans.

  • Fatty’s – Jamaican food in a cramped one room restaurant. It was delicious though!
  • Café Manolin – Great breakfast food although bring a jacket because it was kind of cold.
  • Casa Cortes Choco Bar – Chocolate bar that was worth the calories.
  • Hotel Milano Restaurant – Great views of San Juan and great food and mojitos.
  • La Mallorquina – Little more expensive but great food and central location.

Discovering San Juan Puerto Rico - Choco Bar

What to buy?

There is some shopping to do with a variety from authentic crafts right down to the kitsch souvenirs. I AVOID kitsch souvenirs at all costs. One store that we had a lot of success at was Eclectika located near the Plaza Colón. This store had hand crafted wood souvenirs, jewelry and a variety of unique home pieces. Surely you can find a souvenir to bring home.

Discovering San Juan Puerto Rico - Eclectika

Other than that I honestly didn’t have much success with shopping this time around. But honestly much of the souvenirs are crap and the rest is very Americanized, or items that you can find back in states. You may be able to find deals on these items but from what I saw they are mostly the same price. There is shopping in Old San Juan but perhaps not the type you’d like.

Going on a Cruise from San Juan

I stayed in Condado and commuted to Old San Juan. The city of San Juan has two ports that cruises use and one of them is closer to Condado while the other one sits right in Old San Juan. From my understanding Carnival uses Old San Juan while Royal Caribbean and Celebrity use the other port. So if you’re booking a hotel you should verify the exact port your cruise will docked because that will determined where you should get a hotel. If you prefer to stay in Old San Juan no matter what you may have to pay one taxi ride.

From San Juan I left on a cruise to the Eastern Caribbean, and I’ll talk about the islands I visited and some of my experiences in upcoming posts.




images by: shawnvoyage

By | 2015-07-20T07:37:35+00:00 January 1st, 2015|


  1. Joe January 1, 2015 at 11:00 am - Reply

    Good article, however, I wouldn’t recommend walking from one fort to the other since you will be walking thru one of the most dangerous neighborhoods in Old San Juan, La Perla. Also, Condado has always been the gay area. The most common gay beach is the portion known as Atlantic beach in front of the hotel bearing the same name and Bar Oceano.

    • Shawn January 1, 2015 at 11:10 am - Reply

      Thank you for your comment! I didnt know that Condado has been established as the gay area for a while. It felt so modern today. I have heard of that Atlantic beach, I didnt realize its right in front of that hotel. I walked the path I believe above La Perla. Maybe I should clarify! Thanks!