Travel Guide: San Juan, Puerto Rico πŸ‡΅πŸ‡· 🌴 ✈️

UPDATED: April 2024 

 For my birthday this year, I decided to venture off to San Juan, Puerto Rico to celebrate this big milestone year. Although it’s still considered U.S. territory, I haven’t been out of the country since right when the pandemic started! I was itching to get back on somebody’s island since then and my prayer and dream came true. 

It being a life changing experience is an understatement. The island of Puerto Rico is full of wonder, adventure, and relaxation. Let’s get into the details of the journey. 

Flying: How To Get There 

Here are two cool travel hack ideas: 

1. Booking flights one way instead of round trip is a huge money saver. I flew Southwest to Miami as a “layover” stop. From there I ventured to San Juan via American Airlines instead of paying a whopping $300+ round trip from Chicago to San Juan. I ended up paying about $150 if I’m not mistaken. 1B. I love flying with Southwest because they’re fairly inexpensive especially when flying across the country. Plus you get two bags free, you can’t beat that! Southwest is always going to be my go-to company. 

2. With all that being said, when you’re traveling to the Caribbean, Mexico, Central or South America, utilize the first step and always make Miami your one way, inexpensive layover stop. Unless you already reside there or in Florida. It’s always the gateway to get to those countries. 2B. Use the app ibotta to purchase a gift card from Southwest and use it to purchase your ticket. You get cash back or you can use your balance too!

From Chicago to Miami, I had a layover in Nashville in between, then from Miami to San Juan, it took about 3 hours to get to my final dest8nation. Yeah, I was literally traveling from 4am CST until 10pm EST. 

Lodging: Where To Stay

I decided to try Airbnb for the first time because I’ve always seen so many people talking about it. There’s even an ongoing debate about the quality, accommodations, perks and more with Airbnb vs hotels. We’ll discuss that at a later time. The stay was in the Ocean Park neighborhood. It was a little rough around the edges chile, but I enjoyed it. I’m from Chicago I’m good in any hood anywhere. 

It was definitely a lot more inexpensive than staying at a hotel as the point was to not break the bank on the first out of the country it not really trip in 2 years. What I really liked about this place was the location being close to where the locals were. It’s right by a neighborhood called Loiza which is well known for their street vendors but also in a close proximity to tourist areas like Condado. Next time I come back I’ll be bounce and stay in a hotel. 

Unfortunately I didn’t take any photos of the interior or exterior because I got in late and was in and out.

Here are some great hotel choices in San Juan:

  • Courtyard by Marriott San Juan 
  • Hyatt Place San Juan
  • Hotel El Colonial 
  • CasaBlanca Hotel 
  • Caribe Hilton
  • Embassy Suites by Hilton San Juan Hotel & Casino
  • San Juan Water and Beach Club Hotel 
  • Sheraton Puerto Rico Resort & Casino
  • Fairmont El San Juan Hotel 
  • Residence Inn by Marriott San Juan Isla Verde
  • Aloft San Juan 
When To Visit 

Puerto Rico is located in the Caribbean and as we know, is a hub for hurricane season which is from June to November, the worst time. That means anytime between December to May is an ideal time to visit. This also can be applied to average month weather, rainfall, and other factors. 

Food: Where To Eat 

As you all know I’m vegan. A proud but non obnoxious vegan.  It makes me so happy that so many cities home and abroad are popping up with vegan restaurants and more vegan options on their menus at regular spots. San Juan is certainly a vegan friendly city. The first spot I went to wasn’t vegan but I did have some tasty mushroom tacos and a banging margarita. This was La Pachanga “Margaritas & Fiesta”. Great Mexican spot for a quick lunch.

For my birthday brunch I went to the Dreamcatcher Hotel, which is a hotel but it also has a restaurant there. While the portions are small, the food was everything. I had a fruit bowl, sprouted avocado toast, caramel cake and soursop juice. 

My birthday dinner was at Cafe Berlin in Old San Juan. The drinks were great but I honestly wasn’t too thrilled at the food. I had vegan mofongo and carrot cake. It’s a lovely place but the food was a bit overwhelming. You can definitely tell it’s watered down for the sake of tourists. 

I did have some late night food at a place I totally forgot the name of and some food I ordered from a delivery app. Overall the food was just okay. I wasn’t too impressed by anything except the brunch. When I return I would like to try other vegan spots I had in mind and experience some yummy street food. 

The real star of the show was definitely the drinks. Unlike here in the States, not nann drink in San Juan was watered down. One of the spots visited is Barrachina where the first pina colada was created in 1963. 

Sightseeing: What To Do In San Juan

San Juan is the oldest city in America (I mean it’s not America, but…yeah. Another topic for another time). As a huge history nerd and lover, I was so impressed and loving all of the colonial buildings everywhere. The history of the city is plentiful in Old San Juan, hence the name. OSJ is the main area the first Europeans colonized upon arriving to the shores of present day Puerto Rico in the 1500’s. While there’s a bloody history behind it, the island also celebrates the original history of the indigenous native Tainos who thoroughly inhabited the island before Spanish and English arrival. 

OSJ is definitely a place you want to visit for the historical experience. There are also plenty of cats everywhere and street art. Some dope spots I saw were Castillo San Felipe del Morro, Castillo San Cristobal, Santa MarΓ­a Magdalenade Pazzis Cemetery, and La Fortaleza. 

What’s also super dope is that I took a photo shoot for my birthday and a walking history tour of OSJ was included with taking pictures at each site. 

Neighborhoods like Condado are more modernized are hubs for tourists and beaches. Calle Loiza is a local have that embraces the arts and partying. 


I only visited one beach and that was for a photo shoot. This was Playa Ocean Park which was a few blocks away from my Airbnb (another reason I wanted to choose that location in specific). It wasn’t too sunny when I went either but from what I saw getting my pose on, it was super cute. A lot of locals and people who travel there frequently say that the best beaches are on the west side of the island. 


When in San Juan, get your dancing shoes ready! After my birthday dinner them photo shoot I had an absolute BALL. Coincidentally, while doing my shoot another birthday girl was also added to the tour which ended with the photographer taking us to a spot called El CafetΓ­n for mojitos. She invited my to tag along to a bar crawl and I’m like “sure, why not”. We met two other lovely ladies and it ended up being a night to remember! 

Old San Juan has plenty of bars and spots to salsa dance at, but for me the real winner was La Placita. This is where many of the locals party and cracking isn’t even the word. There are also a lot of clubs in Condado too. 

Another spot the locals frequent is La Perla. Now La Perla is kinda sketchy. It’s not recommended to visit, right off the edge off OSJ and many know it for being the location of where the song “Despacito” was filmed. Baby, it’s the trenches. You can’t pull out any cell phones and the police refuse to go to the area. My crew and I visited and we were okay, but definitely take precaution if you decide to go. 

I ended up leaving San Juan a day earlier than expected because I had work business to tend to in Las Vegas (travel guide to the hotel coming soon) , but I had a beautiful time there. The next time I’m in the Caribbean it will be for carnival for sure! 

Have you ever traveled to San Juan or would you travel there?



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