Weekend in Old San Juan, Puerto Rico

  San Juan, the capital of Puerto Rico

Photo: Unsplash/@rvrmakes

Photo: Unsplash/@rvrmakes

San Juan, the capital of Puerto Rico. A large urban capital on the coast of a lush tropical island. It includes the romantic “Old San Juan,” which was built during Spanish colonial times as well as dense urban areas. My recommendation is to hit the beach during the early morning, eat lunch, enjoy a siesta, and then head out for the night.

What To Wear

The best outfit to wear is one that allows you to feel cool in the heat and transitions from easily from day to night. Bring sunglasses, a bag big enough to carry any souvenirs you may purchase, and something light for your shoulders. And wear good shoes!


Like most cities, there is a variety of transportation options in San Juan, you can see the basics here. Lyft is gaining a foothold in Puerto Rico, and the apps may work, but it’s unclear to me what is really going on. From what I do understand, Lyft are not widely accepted and used yet.

About San Juan

San Juan has 18 individual districts, sort of like barrios. One district include Old San Juan which is the part of the city that was built during Spanish colonial times. Other nearby barrios are the Condado and Isla Verde which is where many hotels and resorts are located. Beyond that the rest of the barrios run along the beach and provides a quieter place for residents and long term guests to stay. Further inland, you have more city-like barrios that are set away from the beach and have their own shopping districts..

Day to Night in San Juan, Puerto Rico

Morning, 8am-11am: Hit up the Condado Beach, a small beach next to Condado Hilton. You can park in the parking lot next door. Arrive early, to avoid the crowds and hot sun. Get a piña colada in a fresh coconut from the vendor on the street. There’s a legend that goes along with this beach: La Piedra del Perro (or The Stone Dog). Off to the left side of the beach are a set of volcanic looking rocks. One of the rock formations looks like a dog, several legends explain where that dog-like formation came from. Look for the dog formation in the rocks as you gaze out on the ocean.

Mid-Morning to Mid-Day: This is when the sun is at its hottest, during this time it’s best to stay cool and relaxed. Grab a late breakfast or early lunch at one of the cafes in La Ventana, take a siesta in the shade and get rest for your adventure in Old San Juan.

Around 3pm: Arrive in Old San Juan by taxi or bus and walk its romantic streets. Dip in and out of stores while checking out local artisans and performers along the way. The Plaza Colon sometimes has street performers, across from the plaza is a cute cafe and gift shop called The Poet’s Passage. Make sure you also hit up some of the old favorites: El Morro, Capillo Del Cristo, La Princesa promenade (especially on a Friday or Saturday evening, where there are local vendors and performances).

6pm + Beyond: You can spend the afternoon and evening in Old San Juan, there’s no shortage of places to eat and things to see. But if you’d like to see other parts of the city, it’s easy to explore a little more. What follows are two of my favorite San Juan outings.

Santurce: One of San Juan’s barrios (neighborhood) is Santurce. Known for it’s public art and creative community, you can grab a bus or taxi to Santurce from Old San Juan. If you arrive before sundown, walk around to see the murals. For dinner eat at Lote 23, a pop-up food truck round up in a converted empty lot featuring local celebrity chefs serving up eclectic, delicious food paired with live music. Another great afternoon activity in Santurce is the Santurce Market, “La Placita.” Bring your cloth grocery bag to buy some fresh tropical fruit and enjoy a mojito at one of the outdoor cafes around the plaza. On the weekends and around holidays there’s usually live music and everyone is in a festive mood.

Boat trip to Cataño, “La Lancha”. If you want to go big, this is how you get to the Bacardi Factory, but it is also a nice and cheap boat ride across the San Juan bay, especially at sunset. You pick up the boat in across from the Walgreens near the piers in Old San Juan where the cruise ships dock. The boats run every 15-20 minutes so if you aren’t going to the Bacardi Factory you won’t have to wait long to come back to Old San Juan. On the Cataño side of the bay there is a restaurant called Don Tello’s where you can have a bite to eat before you get back on the ferry.

There is no shortage of things to do in San Juan. You will be able to experience so many facets of life on the island in one day—beach, city, and history. No matter what you choose to do during your time in this majestic city, you will always find yourself charmed by La Isla del Encanto.

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