Southern Belle in Training

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

June 13, 2024

TRAVEL GUIDE: San Juan, Puerto Rico (Updated!)

     Puerto Rico is 100% one of my favorite warm weather travel destinations. I was lucky enough to visit two years apart in 2022 and 2024! I fell in love with Puerto Rico and the charm of San Juan during my first trip, and my second trip just deepened those feelings. San Juan is the capital and largest city in Puerto Rico. PR is a US territory so there is no passport required to visit, and no time change if you're coming from the East Coast! Win win!! I'm excited to update my first San Juan Travel Guide from my 2022 trip, and to now be able to share the best recommendations from my 2022 and 2024 trips! 

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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! I've spent time exploring the neighborhoods of Old San Juan, Condado, and Mirarmar (and also visiting the CASA Bacardi distillery in another party of the city). All of those felt very safe! 

      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. As of the time that I'm updating this post, there are now direct flights to San Juan right from the Norfolk Airport in Virginia near where I live!! (Those flights hadn't started yet for either of my trips, so I've always personally had a brief layover on the way there.) 

     I've always gotten around in San Juan by using Uber. It is fairly affordable in Puerto Rico. I did want to note that while my friend Liane and I had no issues with Uber wait times back in 2022 during my first trip, Ryan's family and I did have a lot of issues with having longer wait times with Uber during certain days of our more recent trip. Not sure what's changed (less drivers now, higher demand, or both?), but I did want to note that!

       If you prefer to rent a car instead and wish explore other parts of the island, that is fairly easy to do in Puerto Rico! 

      I've gotten to stay at two resorts in San Juan: The Caribe Hilton on my first trip, and La Concha Renaissance on my most recent trip. Both of them are excellent resorts and I would recommend both! (Just a heads up: neither are all-inclusive as Puerto Rico is a US island, and the US doesn't have the same types of all-inclusives that you find in Mexico or other Caribbean islands). If I had to pick one favorite bewteen the two... I think I would go with The Caribe Hilton! This resort made my first trip to Puerto Rico so magical, and I truly fell in love with the pool at this resort. But La Concha definitely is still a great resort as well in its own right! Here are some pros and cons to both hotels:
  • The Caribe Hilton
    • Pros: Incredible pool and pool bar, free daily resort activities for guests, spacious rooms, lots of on-property food options, secluded location that's still near the city, excellent spa (extra cost), the Pina Colada was literally created at a bar at The Caribe Hilton (so it is extra cool to drink a Pina Colada here!)
    • Cons: Small beach, further to walk or drive to off-property restaurants
  • La Concha Renaissance
    • Pros: On a large stretch of public beach, walkable to lots of bars and restaurants in the Condado neighborhood, great beach views in rooms, amazing nachos on the menu at the hotel lobby bar 
    • Cons: Public casino brings a lot of non-guests into the hotel, pool set-up is more spread out, less complimentary resort guest activities

The amazing pool at the Caribe Hilton

Room at The Caribe Hilton

A high up view of two of the pools at La Concha Renaissance

La Concha Renaissance, as seen from Condado Beach


      San Juan is filled with delicious eateries. 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. I've eaten at my fair share of restaurants in Old San Juan and Condado, but I'm keeping fine tuning my recommendations to be just my absolute favorites from both of my trips!

      *Senor Paleta (153 Calle de Tetuan, San Juan) - This spot was so good that I went on both of my Puerto Rico trips! I loved it so much on my first trip that I had to take Ryan's whole family when we were in Puerto Rico. Senor Paleta 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. My visit from my first trip to Puerto Rico is pictured in the photos below- mine was the gelato pop on the right with a chocolate drizzle and almonds! The perfect spot for a sweet treat while exploring Old San Juan. 

      *La Verguenza (Locations in both Old San Juan and Condado) - The other eatery that I loved so much that I ate there on both trips! La Verguenza is a very casual spot that has a variety of great drinks and Puerto Rican food. It kind of feels like a Caribbean version of a casual sports bar? This was actually the first restaurant in Puerto Rico that I ate at on both of my trips (different locations though). Sometimes a casual spot with good food and drinks is just what you want after a long travel day! Their coconut mojito is one of my favorite drinks that I've ever had. I also got a delicious fried pork dish both times for my main entree, and enjoyed it both times. The Old San Juan location is a bit more scenic than the Condado location, but both have the same menu! 

      *El Viejo Almacen (251C Calle de Cristo, San Juan) - This is a phenomenal and more upscale Argentinian restaurant in the heart of Old San Juan. I loved the ambiance! We ate here on my most recent trip with Ryan's whole family for our more special meal of the trip (it was actually Ryan's birthday dinner!). I had a phenomenal cheese and ham pasta dish for my main course, but the appetizers that we had first were excellent as well. I would definitely eat here again on a future trip for a romantic date night or a nicer occasion.

     *Christianson (1131 Ashford Ave, San Juan) - This bar and restaurant in the Condado area is decorated in such a cool way. The entire bar area was covered in flowers on the ceiling and walls! We didn't eat a full meal here, but Ryan, his mom and I sat at the bar and got cocktails here before one of our dinners on my most recent Puerto Rico trip. The cocktails were phenomenal! I wish we could've eaten a full meal here, but I'd definitely check this out again on a future trip.

     *Tayzan (1157 Ashford Ave, San Juan) - A great sit-down Chinese and Japanese restaurant. The portions are very generous, and the food was so good. This spot actually inspired Ryan and I to want to find a good sit-down Chinese restaurant in Virginia Beach after our trip!! (We typically just got Chinese from a takeout-only spot near our apartment.) This restaurant would be a great choice if you want a break from Caribbean food for an evening.

     *Tavola (1131 Ashford Ave Suite 3, San Juan) - Tavola is an Italian restaurant located in Condado. I ate here with Ryan's family on the first night of our most recent trip. What makes this restaurant very unique is that one of the dining areas is a legit speakeasy!! We ate our meal back there and it was truly something. They have a variety of Italian favorites, and the portions were good as well. 

Drinks at La Verguenza

Delicious Puerto Rican meal at La Verguenza

A Pina Colada at the home of the Pina Colada- The Caribe Hilton

Dining in the speakeasy at Tavola

Gelato pops from Senor Paleta


     *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 over the street leading to it. You used to be able to take pictures right in the street, but unfortunately both times that I've visited the street itself has been barricaded off. But it was still fun to take pictures of from further away!


      *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 the grounds, but you do have to pay a small admission fee if you'd like to go inside. It is operated by the US National Park Service. 

      *Spot as many cats as you can in Old San Juan - I noticed way more street cats on my first trip versus my second, but anytime that I see a sweet and friendly cat while traveling it makes my day! Here are some photos of all the cute kitties I saw on my first trip to San Juan. 

      *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! The ocean water here does tend to be a little bit darker than other parts of the Caribbean, but it is still beautiful. Riptides are a frequent problem in the San Juan area, so it isn't recommended to swim out very deep. But you can still have a fun time at the beach enjoying the sand and sun, and avoiding the deep water. Condado is where is the longer strip of public beach is! 

      *Book a guided excursion to the rainforest - Did you know that there is a beautiful rainforest within an hour of San Juan? El Yunque National Forest is managed by the US Forest Service, and there are tons of companies that offer guided day trip excursions to see and experience it. It is important to keep in mind the level of adventure that you're signing up for on whichever tour you book. Some rainforest tours feature a lot more physically demanding or thrill seeking activities. When Ryan's family and I did our tour, we booked it through our hotel concierge, and specifically picked one with less thrill components. We still got to do a fun but brief hike in the rainforest, and our guide took us to a swimming hole area that did have a cliff that people could optionally jump off (I opted not to, but Ryan did!). Our guide then drove us up a mountain to show us a waterfall and a beautiful lookout point. I definitely recommend a day out of the city and getting to visit the natural beauty of El Yunque!

      *Tour the CASA Bacardi Rum Distillery - Bacardi Rum's largest distillery is located in San Juan, and did you know that this location is also the largest rum distillery in the world? It's open to the public for tours, which is a very cool experience! Your tour ticket also gets you your choice of a complimentary Bacardi cocktail while you wait for your tour to begin. It was fascinating to learn more about one of the world's most iconic rum brands. Ryan and I did this tour with his parents on our most recent Puerto Rico trip!

      *MADMi Museum - I did a solo excursion here on my first trip to Puerto Rico. 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!

      And a couple other suggestions for things to do:

     *Plaza Las Americas Mall - There was one exceptionally rainy evening on my first trip to San Juan (so much so that there were flash flood alerts on our phones), so that killed any sort of outdoor plans for that evening. My friend 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. 

      *Kayak at night in San Juan's bioluminescent bays - This is the only other must-do activity in Puerto Rico that I haven't gotten to do on either of my trips! Puerto Rico is home to a few bioluminescent bays, and you can book guided night kayaking trips to experience the beauty. There's only a handful of these special bays in the entire world, so it's crazy that a few of them are in Puerto Rico! 

      I truly can't recommend visiting San Juan, PR enough for a Caribbean vacation. This beautiful and historic city has exceeded my expectations on both trips. 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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