Southern Belle in Training

Fashion, Travel & Lifestyle Blog || Est. 2012 || Virginia Beach, VA

April 25, 2023

TRAVEL GUIDE: San Juan, Puerto Rico

      Puerto Rico is 100% one of my favorite travel destinations that I've visited in the past several years. Whatever expectations I had about visiting San Juan beforehand were wildly exceeded! My Puerto Rico trip was in July 2022, but I was still taking my extended blogging break, hence why I'm finally recapping the trip for you now (nine months later!). 

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      In March 2021, my friend Liane visited me in Virgnia Beach. She works as a Spanish and French professor at a college near Charlotte, NC. Liane told me that she'd be attending a Spanish professors conference in Puerto Rico in July. Her hotel room was big enough to take a plus-one, but her husband would be unable to attend with her. Liane asked if I'd like to be her plus-one instead! I jumped at the idea, but also knew I first had to make sure that it would work financially for me. I took a ton of weekend trips in winter/spring 2022, and my mom and I also had our big Ireland trip coming up in May, and I knew I wanted to save lots of spending money for that trip.

     I decided that if I had enough miles from my airline credit card to cover my flight to Puerto Rico that I'd do it. Not only did I have enough miles for both flights, but I had enough to fly to Puerto Rico in first class!! Meant to be!! When life gives you the opportunity to travel somewhere new and the flight and hotel are covered, you have to say yes!

About San Juan

      San Juan is the largest city in Puerto Rico and home to over 300,000 people. It's most famously known for Old San Juan, which is a historic area turned tourist district filled with colorful architecture. Old San Juan only makes up a small portion of the city though- there are tons of modern neighborhoods throughout, and the whole city is incredibly spread out! We stayed in the city of San Juan during our entire trip, but if I'm ever lucky enough to visit Puerto Rico again in the future, I'd love to explore more regions of the island.

      There is a good deal of poverty and some not-as-safe areas to San Juan (I saw some driving to and from the airport), but there are also plenty of amazing and super safe areas as well. I guess that's like any major city honestly! But I felt super safe in Old San Juan, and also on a solo outing I did to the Miramar area of the city. 

      San Juan truly feels like a foreign city! In fact, it even felt more foreign to me than some places in Europe that I've been (I kid you not!). A lot of locals that I met speak only minimal English, and a lot of people don't speak any. All of the signs for streets and businesses and listed in Spanish. Everything from the architecture to the plants and trees are so different from anything near where I live in the US. Visting San Juan truly transports you to another world that's so much further away than what it is. 


      Puerto Rico is a US territory, so no passport is needed to visit! It is honestly too easy to visit here. 😉 No passport, no currency change, no international charges for cell phone service and no time change for those in East Coast states! The largest airport in Puerto Rico is the one in San Juan. There are direct flights there from most larger US airports. I took a very early flight out of Virginia, had a quick flight in DC, and then about a three-and-a-half-hour flight from DC to San Juan. I was lucky to have enough miles to fly first class in United on the way down, which made for a very enjoyable trip! Liane and I used Uber to the entire trip and had no issue getting one from the airport to our hotel. It was about a 15-20 minute Uber ride to get to the Condado area (where the Caribe Hilton is located). 

     If you want to rent a car and explore other parts of the island, that is fairly easy to do in Puerto Rico! If I ever go back, I definitely would like to see more besides for San Juan. 

      I loved staying at the Caribe Hilton in San Juan so much that I wrote a whole Hotel Guide blog post about it! Check it out HERE. If you don't stay at the Caribe Hilton specifically, I think any beachfront hotel in Condado would be a good choice location-wise.   



      Old San Juan is filled with delicious spots to eat! Liane and I would eat lunch at our hotel everyday (since she was busy with her work conference), but we did most of our dinners in Old San Juan. Puerto Rican food is delicious! Lots of Caribbean influences, and some unique dishes that you'll only find in Puerto Rico as well. Mofongo is the most popular Puerto Rican dish, which is consists of mashed seasoned plantains. You'll find that on the menu of just about every place!

      Below are the places we ate at in Old San Juan. Everywhere that we ate at was fairly casual, but there are plenty of more upscale restaurants within Old San Juan if that is more your vibe! 

      *Senor Paleta (153 Calle de Tetuan, San Juan) - This is a gelato ice pop shop that makes the most delicious frozen treats! You can completely customize your pop with all sorts of fun toppings. Ours are pictured in the photos below- mine is the one on the right with a chocolate drizzle and almonds! The perfect spot for a sweet treat while exploring Old San Juan. 

      *La Verguenza (280 C. Norzagaray, San Juan) - This was probably my favorite meal of the trip. It is a very casual spot, this restaurant embodied the fun and laid back feel of San Juan. I can tell you without a doubt that I had the best cocktail of my life here! Their coconut mojito was the tastiest cocktail I've ever had. I had some other good mojitos throughout the rest of the trip, but none quite as good as this one. Liane ordered an acerola mojito (acerolas are a type of tropical cherry), and she loved hers as well. You can see both pictured below! For dinner, I had a fried pork dish with rice, salsa and onions and it was delicious. This spot is definitely casual but truly feels like Puerto Rico.

      *Vaca Brava (Calle Racinto Sur 29, San Juan) - This is like the Puerto Rican version of Longhorn Steakhouse! It's another more casual spot that specializes in all sorts of meat dishes. You can see the giant piece of pork on the stick pictured below that I had for dinner here! If you want a casual steakhouse experience, I'd eat here... but I'd also say there are probably better dinner spots in San Juan. The night we ate here we actually tried a couple of other restaurants that were recommended that all had too long of a wait, so this was a back-up option. I thought the cocktails here were also just okay. 

      *San Se Marisqueria (152 C. de San Sebastian, San Juan) - I know I've mentioned the other spots we had dinners at were casual... but this was the most casual of all! (Casual to the point that the restaurant AC was broken when we ate there but they were still making do and trying to stay open.) The prices here were extremely affordable, and the food was delicious! I had some great empanadas here and more delicious mojitos. 


     *Wander the colorful streets of Old San Juan - Old San Juan is a rainbow paradise of historic architecture and colorful buildings! You can easily spend a few hours just wandering and taking everything in without an agenda. There are also some fun souvenir shops scattered throughout Old San Juan, and Liane and I also came upon a fun outdoor market in one spot, too! Here are some of my favorite photos of all of the colorful buildings:

     *Calle de la Fortaleza- You've probably seen pictures of this iconic Old San Juan street before on Instagram- I know I had! La Fortaleza is the governor's palace in San Juan, and there are always beautiful and colorful decorations that hang across the street leading to it. Oftentimes the decorations are umbrellas, but when we were there it was bells. A security guard in the area told us the bells represented cancer patients in Puerto Rico. You used to be able to take pictures right in the street, but when we visited last summer there was a barricade up and the security guard told us that due to Covid they still weren't allowing people down the street. Maybe that's changed now? But I was glad we could still get pictures from behind the barricade! 


      *San Juan National Historic Site - This spot has over 500 years' worth of history! (You can read about the specific history of the forts here!) It is free to visit and operated by the National Park Service. Liane and I went at Sunset, and it was a beautiful time of day to see and experience it! 

      *Spot as many cats as you can in Old San Juan - Liane and I are both cat moms, and we got such a kick out of all of the street cats you can see in Old San Juan! These kitties are all very friendly and very bold- most will come right up to you for pets and cuddles. 

      *Beaches of San Juan - San Juan is a coastal city, so you absolutely need to spend some time by the ocean while you're there! Our hotel, the Caribe Hilton, had its own small private beach for guests. But if you're not staying a a beachfront hotel, check out this list of public beaches that are in and around San Juan!

      *MADMi Museum - I did a solo excursion here one afternoon! This small art museum focuses on modern art from Puerto Rican artists, and there are some cool exhibits. I also thought the museum building was just gorgeous!

     *Plaza Las Americas Mall - There was one exceptionally rainy evening on our trip (so much so that there were flash flood alerts on our phones), so that killed any sort of outdoor plans we wanted to do for a couple hours. Liane and I took an Uber over to Plazas Las Americas mall and had fun shopping. A lot of indoor malls seem to be dying out these days, but this one is really nice and well-maintained. There's a lot of American stores, as well as some European and local ones. They had a lot of my favorite stores that don't have locations near me in Viginia, like Zara and Mango. 

      Other things to do in San Juan that I didn't get a chance to do on this first visit:

      *Tour the CASA Bacardi Rum Factory 

      *Kayak at night in San Juan's bioluminescent bays (I am most sad I wasn't able to do this on our trip! The night we were considering booking a trip is the night it ended up raining heavily.)

      *Visit the high-end shopping district on Ashford Avenue

      *Book a hiking day trip excursion and explore beyond San Juan

      I truly can't recommend visiting San Juan, PR enough for a Caribbean vacation. This beautiful and historic city really exceeded my expectations. I hope to return to Puerto Rico again in future years! If you've been to San Juan before, I'd love to hear if you have any recommendations!!

      Here's a Google Map with all of the places I mentioned:

      God Bless,

      xoxo Annaliese


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