San Juan is an excellent destination for a long weekend or for a longer holiday depending on your preference. I do believe that at least three to four days is necessary to enjoy what San Juan has to offer. Puerto Rico is more than just San Juan, but it is good to just start out with getting to know the capital city of this United States territory. I have various recommendations to focus on during your stay and there are still some places that I would check out for which I was not able to visit personally. Not only is San Juan a fun city but the weather in the Winter and Spring months will make you want to come back in the future.
- Visit The Beaches – On your 1st day in San Juan, I recommend checking out a beach or two to relax, enjoy the sunshine, go swimming, or even go windsurfing with the help of a guide especially if you had a long flight coming in. There are beaches that cater more to tourists such as Condado Beach, which are close to different resorts and hotels that are right on the beach within walking distance.
Condado Beach can be a bit crowded depending on the time of the year that you visit it, but it is clean, compact, and has enough chairs and umbrellas to go around if you decide to rent one. Personally, I prefer Ocean Park Beach, which is further from Old San Juan and the Condado Neighborhood, but for which is more local, laidback, and is likely to have less tourists. If you decide to split your beach days up, I recommend going to Ocean Park Beach the 1st day if it is closer to where you’re staying and then going over to Condado to explore the neighborhood and to visit that beach on your 3rd day in San Juan.
Other beach options in San Juan include Balneario del Escambron, El Alambique Beach, and Playa (Beach) del Capitolio, one of the great things about San Juan is that the neighborhoods that have a beach are quite walkable and are accessible to the public. While the hotels take up a lot of real estate and have their own areas of the beach for their guests only, each beach is still accessible to the public even if they are not staying nearby, which makes visiting multiple beaches during your four days in San Juan a good way to spend your vacation time there.
- Enjoy Nearby Nature – El Yunque National Rainforest is the only tropical rainforest in the United States National Forest System. There are hundreds of unique animal, bird, and plant species that call El Yunque home as well, making it must-see. While not in San Juan, it is only a 45 minute to an hour drive away. While I would not recommend an Uber to get there and back, it would be wise to hire a taxi to get to and from the rainforest to avoid paying for parking there. You can also join a tour group, large or small, to get there without splurging. Rental cars are also available that your hotel can arrange for you or that can be given at the San Juan airport. If you visit the rainforest, be sure to leave earlier in the morning so that your hike through El Yunque won’t be delayed by packs of tourists wanting to stop for selfies on the way up to the waterfalls.
However, you choose to get there, you will enjoy the beautiful, quiet, and peaceful nature of the rainforest. It is the largest protected forest in the country and where you can really enjoy hiking, swimming, and even doing rock climbing if you choose to. Parts of El Yunque also have natural pools where you can jump in from meters above or use a rope swing in certain areas. One area that I went to have a naturally formed waterslide with a smooth area of rock formation allowing you to slide down without hurting yourself.
Having a guide there will teach you a lot about the flora and fauna that inhabit El Yunque as well as the kinds of frogs, fish, birds, monkeys, etc. that call the rainforest home there. A trip to El Yunque would not be complete without stopping off for some fresh coffee or some fresh fruits or fried empanadas at a road stand where they wake up at the crack of dawn to start getting the produce ready. In between beach days, I highly recommend spending a full day at El Yunque to enjoy a bit of nature outside San Juan.
- Eat, Drink, and Dance – I love Salsa dancing and if you enjoy salsa music as I do, going to San Juan will allow you to indulge in some live dancing even on a weeknight! Old San Juan has many salsa bars and clubs along with for bachata and reggaeton if you prefer those music genres instead. My go to place would be La Factoria, which has been ranked among the Top 100 bars in the world. It’s not only known for its old school décor, six unique bars within a main bar, as well as its live Salsa bands playing most nights, but its cocktail drinks are fantastic and reasonably priced.
La Factoria has a very relaxed vibe, and the bartenders are friendly enough to give you their favorite drink recommendation. While the Salsa live music does not start until 10 PM, it doesn’t take long for the dance floor to be filled with people from Puerto Rico and all over the world who enjoy this fun genre of music. Puerto Rico is the home of many famous Salsa musicians including my favorite, Hector Lavoe. If you come to San Juan, I highly recommend this bar to visit and make sure to bring your friends or family with you!
For dancing and drinking good cocktails, San Juan has a lot of options and that is also the case with its food scene. As the capital, there are several good restaurants to check out with not just Puerto Rican cuisine but also seafood, pizza, and burgers available. My recommendations to check out would first be Kasalta, a famous bakery that even former President Barack Obama visited in his trip to San Juan. Kasalta is known for its sandwiches, local cuisine, but especially its desserts including its Tres Leches cake.
Other recommendations for dinner are La Cueva Del Mar, where they are known for their delicious fish tacos, and I would recommend the shrimp arepa as a starter dish. Lastly, while I am a native New Yorker, the best Pizza place in San Juan may be Pirilo Pizza Rustica, where the island’s influence extends to the pizza where you can order a delicious pizza pie with sweet plantains and shredded beef. It’s a good option for having a nice beer to go with your pizza and has outdoor seating as well to enjoy your meal with a cool breeze from the ocean. Lastly, for the coffee drinkers out there, you must go to La Coffeetera, with excellent coffee to stay or to go before hitting the beach with excellent paninis including one with egg, sausage, and cheese. It’s a great way to start one of your days in San Juan without question.
- Explore Old San Juan – No four days in San Juan is complete without spending some time in old San Juan, which is well preserved with its colorful houses, trendy shops, and beautiful murals that capture your attention. While it is nice to shop around in old San Juan, the main draw for me going there was to check out the famous and historic San Felipe del Morro Castle or Castillo. It’s right on the edge of the old part of the city leading into San Juan Bay, which juts out into the Atlantic Ocean. It is a very strategic point and one that exchange hands for centuries going under the control the Spanish Empire, the Puerto Ricans, and now the United States since the 1500s. It is a massive castle and one that is well worth a few hours with all the information to read and parts of the fort to explore.
San Felipe del Morro Castle is not only great for its history but has some great vantage points to see the coastline of San Juan, to see the bay in its full view, and to see the rest of the old city as well. You can really appreciate how much the island has changed in five hundred years but also see that not much has changed as well. If I had more time during my four days, I would have gone to see Castillo San Cristobal, which while younger than San Felipe del Morro, having been constructed during the late 1700’s, is still the largest of any fort ever built in the Americas including the one in Cartagena, Colombia.
To cap off the four days and to really enjoy old San Juan, I would recommend visiting Scryer Rum Barrelhouse and Rooftop for drinks to end your trip to the city. It has an excellent, spacious rooftop, with a pleasant overview of one of the old San Juan’s most bustling streets. You can get the Scryer rum brand that is only made in San Juan and is not exported currently and it’s good to mix with a cocktail or have a beer after at the impressive three-story bar. You’ll be glad to have a refreshing rum drink after a day of seeing the historic Spanish forts and walking the cobbled streets of the old city.
In terms of four days in San Juan, I hope you will follow the recommendations I have laid out but don’t be afraid to add or subtract other activities to bring to your own itinerary. I believe there are a lot of ways to spend time in San Juan and what I laid out is just a sampling of what the Puerto Rican capital can offer you. It is one of my favorite destinations for a short trip and since it was only four days total, you know I’ll be back for another visit soon! For a short getaway, you can’t go wrong with going to San Juan!