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How to Spend 3 Days in San Juan, Puerto Rico

When you’re on vacation you want to see, taste, and do it all. A sense of exploration aan take over you, leaving you with a desire to discover everything that you can possibly find. It’s especially easy to feel like this in a place like San Juan, Puerto Rico, where history, culture, food, and the beach all co-exist in one thriving city. It may feel overwhelming or impossible to see it all in such a short amount of time, but with our three-day-guide, you’ll have all of our tips and tricks to make the most out of your visit to Puerto Rico’s capital city.

San Juan Travel Tips:

These are a few helpful things to keep in mind while you plan your vacation to Puerto Rico.

  • Puerto Rico has two official languages: Spanish and English. If you are staying in San Juan, you will most likely be able to speak English in most places.
  • The official currency of Puerto Rico is the US Dollar.
  • US citizens do not need to have a US passport to visit Puerto Rico.
  • Depending on where you are staying you can reach most of the places on this guide by walking or taking a bus, taxi, or Uber. A rental car is not needed to follow this guide, but it is a good idea to see if your hotel offers any shuttle service around San Juan.
  • It is truly impossible to explore all of San Juan in just three days. This guide we will mainly focus on the neighborhoods of Old San Juan, Condado, and Ocean Park.
  • Most cell phones providers work in Puerto Rico just like they do in the US. Please check with your cell phone provider to make sure before leaving on vacation.

Day 1

If you are going to Puerto Rico you’ll most likely be flying into Luis Munoz Marin International Airport in San Juan. Assuming you had an early flight and were able to get to your hotel not too long after, you can easily be in Old San Juan by the afternoon. If you don’t plan on staying in Old San Juan then head over there after getting yourself settled into your hotel.

Get Acquainted

One of the best things to do when you are in a new city is to get yourself familiar with your brand new, exciting surroundings. A great way to do this is through a walking tour throughout the city. On a Flavors of San Juan Food & Culture Tour you get to explore the streets, culture, history, and of course, food, of Old San Juan. Visit major landmarks like the Governor’s Mansion, Capilla de Cristo, and the second oldest church in the Americas, all while enjoying authentic and local Puerto Rican food. Not only is this a reliable way to learn about the city that you’ll be spending your next three days in, it’s is also incredibly fun and delicious!

After you feel more introduced to the city go in and out of all the shops featuring handmade and artisan goods. Old San Juan is the best place to find unique souvenirs and locally made items.

Take in all the beautiful colors and architecture that surround you. From the blue cobblestone streets to the vibrant apartments and buildings, Old San Juan is the most charming city in Puerto Rico is a can’t miss when on vacation!

Extra Tip: It might sound daunting to try and fit seeing the city all in just a few hours but it is totally doable in Old San Juan. With an endless list of amazing places to shop, eat, and learn, Old San Juan truly has something to please everyone all in just a few short blocks. The most important thing to remember is that this is your vacation, and just enjoy it however you want to.

Learn Some History

Once you’re done with your food tour, you’re going to want to walk off all of the delicious food that you just had. The best way to do this is by wandering up the blue cobblestone streets to Castillo San Felipe Del Morro. El Morro, as its more commonly known, is a 400-year-old fort that guarded Old San Juan against neighbors and attackers alike back in the day. It closes at 6pm and costs about $5 to enter. Once inside you can take yourself back through time with a guided tour or explore the fort on your own.

Extra Tip: If you’re still feeling full from the food tour (which is very likely) then stick around to fly a kite and watch as the sun sets over El Morro’s massive lawn. This is easily one of the best photo-op opportunities you’ll have in San Juan. Grab a piragua (a shaved ice treat) to cool off while you take in the ocean views and historic scenery.

Night Life

Old San Juan has a nightlife that is just about as colorful and vibrant as the buildings that line the blue cobblestone streets. There is an endless list of places you can go to enjoy a night on the town. If you’re looking for a more reserved and calm night then head over to El Convento Hotel and grab a seat at El Picoteo where you can enjoy out-of-this-world wine and tapas. Those who are looking to bust out their dancing shoes should go to Nuyorican Cafe. You’ll practically feel like a local at this salsa bar and before you even know it you’ll find yourself dancing along to the live salsa music and blending right in. Other notable and fun places to visit are La Factoria and El Batey.

Day 2


After your night out on the town, you need to make sure that you’re properly fueled for your second day of exploring. There is no better place in San Juan to grab a delicious breakfast than at Caficultura. Not only do they offer breakfast all day (so no worries if “breakfast” accidentally ends up being at 2pm), their central location, easy going vibe, and practically life-giving coffee serve as the perfect place to recharge and plan out your day.

Extra Tip: If you’re looking to save a little bit of extra money then head over to the iconic La Bombonera. They’re known for having some of the absolute best breakfast food all at an affordable price. But be prepared because you may have to wait in a line.

Explore Condado

Depending on where you’re staying, Condado is just a quick taxi or Uber ride away. Condado is a neighborhood right next to Old San Juan and features many hotels, restaurants, and shopping. Just like Old San Juan, Condado has something for everyone but in a more modern and luxurious feel.

If you’re really jonesing to feel the sand underneath your feet and the ocean breeze in your hair then La Playita in Condado is perfect for you. While we have other beaches we’d recommend for a full beach day (keep reading to find our favorite beaches in San Juan), this beach is the perfect spot for someone who wants to get a little fix and a quick dip .

Another great way to enjoy some water activities is by paddle boarding or kayaking in the Condado Lagoon. This is a great option for families since the water in the lagoon is both very clean and calm, making it easier to swim in for the little ones. You may even be able to see a few manatees if you go early enough!

You can also take a stroll or ride a bike through the new Paseo Puerta de Tierra. Connecting Old San Juan and Condado, this boardwalk is a beautiful way to take in the peaceful ocean views and get some relaxing exercise.

After all that physical activity you might start to build up an appetite. Wandering through Ashford Avenue, the famous street that houses most of the hotels in Condado, will quickly solve your hunger pains. Some gems include the Ben and Jerry’s, Bajuice, Pannes, and Budatai. You can also do some major shopping (or window shopping) on Ashford Avenue, with stores ranging from Gucci and Cartier to fun souvenir shops.

Extra Tip: If Condado doesn’t sound like something that would interest you, fear not. The great thing about San Juan is all the different options you have to explore this city. A unique experience is visiting the Bacardi Factory, which is just a short drive away from San Juan. The factory offers three different types of tours and is perfect for those who enjoy learning about the history behind rum production and rum in general.

Another option, if you have a rental car, is to drive about 45 minutes from San Juan to Rio Grande and explore El Yunque. El Yunque is the only tropical rain forest in the United States National Forest System and is a great option for those who want to do some real exploring on their trip. You can find different guided tours or grab a map and explore the various enchanting trails yourself.

Test Your Luck

After spending your day in the hot Puerto Rican sun head inside to one of Condado’s many casinos and play your night away. Perfect your poker face at the San Juan Marriott Resort & Stellaris Casino or Conrad Plaza Hotel and Casino, just to name a few. Condado is famous for having many casinos, which means you have plenty of places to choose from. Whether you’re looking to try your luck at the slot machines or win big at a table game, you can easily combine the thrill of Vegas with the laid back nature of the Caribbean at any of the casinos in Condado.

Extra Tip: You don’t have to roll the dice to enjoy your night out in Condado. Oceano is a unique bar that can give you three different experiences all in one spot thanks to its three different levels and direct beach access.

Day 3

Day 3 will be spent in Ocean Park. Ocean park is just a quick and easy taxi or Uber ride from Condado and Old San Juan. Ocean Park is a laid-back neighborhood within San Juan that features one of the city’s best beaches and a wide variety of cuisine.


Eat like a true local at Kasalta Bakery, a Puerto Rican classic, and beloved breakfast spot. Kasalta is so good that even President Obama had to make a pit stop during his visit to the island. Located in San Juan’s Ocean Park neighborhood, this spot is the perfect place to enjoy an authentic and delicious breakfast or dessert (who says you can’t have dessert for breakfast, you’re on vacation!)

Release Your Inner Beach Bum

Did you really go to Puerto Rico if you didn’t spend at least one day at the beach? Make all of your co-workers jealous of you newly sun-kissed skin by spending your day at Ocean Park Beach. Loved by both locals and travelers alike, Ocean Park Beach is one of the best beaches in San Juan thanks to its clean and relaxing atmosphere. Sparkling turquoise water and lush white sand leave you feeling like you feeling relaxed and spoiled after two jam-packed days of exploration and activities.

Either pack a lunch and have a fun beach picnic or go explore the different cafes and beachside restaurants lining Ocean Park. Find delicious and healthy meals at Cocobana, unique seafood based dishes at Mere Pescao, or eat with your toes in the sand and breeze blowing through your hair at Pamela’s.

Extra Tip: Add some adventure to your beach day by taking a windsurfing lesson at Ocean Park. Whether it is your first time or you’re a seasoned pro, windsurfing and kitesurfing are a great way to turn the notch up on your typical beach day.

Keep It Casual

For your last night in paradise, we recommend keeping it mellow in Ocean Park’s laid-back bar and pub scene. Flip flops and shorts are welcomed with open arms at places like El Bar Bero and Funky Buddha. Enjoy your last night in paradise with good drinks in an easygoing atmosphere.

This three-day guide to San Juan is a simple model that helps jam-pack all the things to do that San Juan has to offer in just a few short days. We hope our tips and tricks can help you have the vacation of a lifetime and truly enjoy all that the Island of Enchantment has to offer.

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