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The Best Activities for 1 Weekend in San Juan

Updated September 11, 2023

With so many incredible things to do in Puerto Rico, it can be hard to narrow down what to do in just 1 weekend. Luckily for you, we’ve put together this list of San Juan activities to help you craft your ideal itinerary. From enjoying the beach to appreciating PR’s history, to taking some truly epic excursions, these are the best activities for 1 weekend in San Juan. Questions? Let's chat!

Want to explore Puerto Rico differently? Have a local plan your trip.

Day 1: Thursday


We fully embrace the concept of Friday Jr, and hey—it’s vacation! With so many things to do in San Juan at night, you might as well get a head start—especially exploring the city’s incredible food scene. Your Thursday night food activities:

  • Savor dinner at a farm-to-table restaurant: There are tons of amazing restaurants in San Juan that use locally sourced ingredients. Dine at Santaella or El Blok for the freshest food in town.
  • Check out a chinchorreo: Make dinner an adventure and check out a chinchorreo—basically a dive bar with cheap food and drinks. It’s one of those great Puerto Rican attractions that feels authentic and won’t break the bank.
  • Enjoy some local flavor: Better yet, ask a San Juan local about their favorite dinner joints. Yes, travel agencies that go to Puerto Rico will have some popular (if touristy) suggestions, but we’d only locals know the up-and-coming places, the classics, and *all* the neighborhood favorites.

Day 2: Friday

Morning and afternoon:

Once you’ve enjoyed a classic Puerto Rican breakfast (we recommend mallorca: a ham, egg, and cheese sandwich on sweet pastry bread) it’s time to seize the day. There are a ton of things to do in San Juan, so here are a couple of the best activities for Friday:

  • Explore an ancient fort: If you’re traveling in Puerto Rico with kids, you may want to start at the monumental Castillo San Felipe del Morro. The city’s amazing historic fort is basically a huge stone playground for kids and adults alike. You may even catch one of San Juan’s best free activities: a battle reenactment!
  • Get off the beaten path: There are a bunch of activities in San Juan that don’t make it into guidebooks. Enjoy an off-the-beaten-path San Juan adventure like taking in a baseball game, exploring the Old San Juan Cemetary, or visiting the seaside La Perla neighborhood (where the music video for Despacito was filmed).
  • Feast at a food truck: As we said, one of the most satisfying activities in Puerto Rico is sampling its delicious cuisine. Lunch on Friday is the perfect time to indulge in some Puerto Rico treats. For an immersive culinary experience, check out the Miramar Food Truck Park in San Juan’s Santurce neighborhood.

Pro tip: Traveling to San Juan is enhanced by a visit to Santurce, one of the hippest neighborhoods on the island. There’s tons of great art, food, and nightlife in this corner of town.


Whether you’re looking to relax with a drink or head out on a nighttime adventure, there are plenty of activities in San Juan once the sun goes down. Here’s what you should do:

  • Debate the origins of the piña colada (while drinking a piña colada): Launch yourself into the national debate over the origins of the Pina Colada. Indulge in a taste test at the Caribe Hilton Hotel and at Barrachina Restaurant—both of whom claim to have invented the iconic cocktail.
  • Take a sunset stroll around Old San Juan: Treat yourself to one of the best things you can do in Puerto Rico: wandering around Old San Juan as the sun sets. Stroll about, build up an appetite, and enjoy the warm evening air and colorful buildings as you consider dinner options.

Day 3: Saturday

Morning and afternoon:

Saturdays in San Juan are lit (and if you don’t know what that means, ask the kids). Between beach mornings and wild nights, it’s one of our favorite days of the week. Enjoy some of these beach-centric activities for a relaxing Saturday start.

  • Be a beach bum in the heart of San Juan:  The beaches in Puerto Rico are jaw-droppingly gorgeous. Spending a day lounging in the sand is definitely among the best things to do in Puerto Rico—especially since some of the greatest beaches on the island are in San Juan itself, or only a short drive away.

Pro tip: Be sure to talk to a local travel expert about their favorite beaches, since there are *so many* to choose from. No matter what kind of experience you want to have, locals can help point you in the right direction.

  • Picnic in Piñones: This gorgeous seaside town is a quick drive from San Juan. While in the area, enjoy the boardwalk and the incredible selection of street food. Perfectly safe during the day, this area can get dodgy once the sun goes down—get some insider safety tips from a Puerto Rican local if you plan on visiting.
  • Revel in rum: Continue the beach theme by indulging in one of Puerto Rico’s treasures—rum! The Bacardi Rum Factory is one of the top tourist attractions in Puerto Rico, and for good reason! Take the rum tasting tour for a fun way to sample different types of rum (and, obviously, to learn about the rum making process).


Sufficiently rested and educated, put your new knowledge to the test and spend the night out on the town.

  • Revel in La Placita de Santurce: This is one of the best places in Puerto Rico to visit, day or night. By day, La Placita is a farmer’s market (rad!). But by night, it transforms into the best nightlife in town—packed with bars, restaurants, tons of music, and spurts of dancing—making it a great night activity.

Pro tip: While Puerto Rico is safe, Santurce can get a little sketchy at night. So be smart about it and call an Uber when it’s time to go home. (Or better yet, pick Santurce as your place to stay while in Puerto Rico)

  • Take in a jazz show: There are tons of great options for live music in San Juan. Follow your ears, or have a Puerto Rico trip planner help you craft a night out that includes the most rocking places.
  • Saturday night salsa: Salsa dancing is ubiquitous in San Juan. Check out Club Brava or the awesome Piso Viejo 1917 bar to salsa things up. It’s a great night activity (but your feet may be a little sore in the morning).

Day 4: Sunday

Morning and afternoon:

Sunday is the perfect time to go day-tripping. And this is where you’ll definitely want a local’s advice. Travel agencies can be very in their planning, so we’d recommend traveling independently with a local’s help instead.

  • Hike through El Yunque: El Yunque, Puerto Rico’s rainforest, is an excellent day trip. Visitors can hike, enjoy nature, and try to spot colorful Puerto Rican parrots.
  • Visit the town of Ponce: San Juan is awesome, but there are so many things to do in Ponce as well. It’s well worth the two-hour drive. With tons of history, great food, and more than one island nearby, it’s a fun place to spend the day.
  • Go on a coffee quest: One of the best excursions in Puerto Rico involves exploring all the island’s coffee plantations. Yes, Puerto Rico is known for rum. But Puerto Rican coffee is killer. This is a great way to learn about the history of this magical bean. Add a plantation visit to your Puerto Rico itinerary for maximum caffeinated goodness.

Pro tip: Keep in mind that while Puerto Rico is safe to visit now and largely recovered from Hurricane Maria, there are spots of the island that are still struggling—so get the inside scoop before planning your visit.


Top off your weekend with a classy cocktail at one of Puerto Rico’s best vacation spots (and one of the world’s best bars): La Factoria. You deserve it.


There are so many amazing things to do in Puerto Rico, and these activities in San Juan will make for a wonderful weekend. Now, all that’s left is to get in touch with a local trip planner! It’s like having a best friend in Puerto Rico help you plan your trip. Still have questions? Send us a message! And don’t forget to check out:

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