Castles atop craggy cliffs. Cobblestone streets paved with blue bricks. Chirping Coqui frogs. Mountains, Caribbean Sea, tropical rainforest, and bioluminescent bays. Welcome to Puerto Rico, a lush, enchanted place that defies simple explanation. It is both an island and an archipelago with its own small islands; it has a strong Latino identity despite belonging to the U.S. as a territory; its language, food, culture, and history are informed by a mix of Indigenous Taíno people, Spanish colonizers, West African people brought against their will, immigrants from Europe, China, other Caribbean, and Latino countries, and mainland USA. Its complexity is also its beauty, and its story is still unfolding. And it is a magical place to visit.
Spending 4 days in Puerto Rico is just enough to get a taste of what the island has to offer. On our 4-day Puerto Rico itinerary, you’ll explore the historic city of San Juan, wander the colorful, blue-cobblestone streets of Old Town; snorkel in the clear blue waters of Culebra, one of the islands off the coast; hike through the tropical rainforest of El Yunque in search of waterfalls and lagoons; and kayak through a bioluminescent bay.
Disclaimer: Our trip was sponsored by Southwest Rapid Rewards™ Credit Cards from Chase. All opinions, recommendations, bad jokes, and mistakes made during this trip (we made so many mistakes, y’all, it’s almost impressive) were 100% my own.
Psst: Take a look at these other posts to help plan your Puerto Rico itinerary:
Visiting Puerto Rico from the U.S. is surprisingly quick and easy—you don’t even need a passport, or to exchange currency! But we do have a few tips to minimize stress during your trip.
San Juan is a colonial city, and Puerto Rico—colonized by Spaniards—feels like a Latin country. But it is a U.S.-owned territory, a colony somewhere between the boundaries of statehood and the independence of self-governance.
This is a complex liminal space that I’ve been somewhat familiar with for my entire life without fully grasping because a not-small portion of my family is Puerto Rican. On my mother’s side, seven first cousins were born and raised in Puerto Rico; they all had a bunch of kids, and now I have a TON of cousins in Puerto Rico. My mom grew up close to her first cousins, making frequent trips back and forth—she to their hometown of Arecibo, Puerto Rico, and they to her hometown of Louisville, Kentucky.
But for various reasons, she hasn’t visited Puerto Rico since the late 1970s. The Puerto Rico my mother remembered was crumbling around the edges: boarded-up buildings, rampant poverty, and a dangerous place for a young woman to be out alone at night. But since then, the city has completely transformed itself, thanks to the hard work of the community and a groundbreaking commitment to historical preservation.
So, when Southwest Rapid Rewards Credit Cards from Chase offered to fly us to any of Southwest Airlines’ many destinations, I picked San Juan. I wanted my mom and I to reunite with our cousins, and for them to meet Jeremy and Baby A for the first time ever!
Plus, it was a once-in-a-lifetime opportunity to take a three-generation trip: a 9-month-old baby, my 70-something-year-old mother, and me. (…And Jeremy, of course!)
And thank goodness we had my mother along—not only did she help us out by watching Baby A while we were off snorkeling, scuba diving, and kayaking, but she talked us off of many, many ledges during the course of this trip.
You see, we’ve always been disaster-prone travelers. (It’s kind of our claim to fame. Notoriety? Anyway, it’s definitely our thing). But throwing a baby in the mix? Y’all.
Like, our brains have ceased to function as they once did. We are half-humans. It is truly impressive how many absolute rookie mistakes we made on this trip. For instance:
Yeah. Rough. We are so out of practice. But we made it through. And honestly? Our trip was still absolutely incredible!
And lucky us, we had my mom, who spent much of her trip sitting in the backseat with Baby A exuding calmness and Grandma Energy as Baby A screamed and we panicked. She had snacks. She had toys. She managed to get Baby A to sleep! My baby-friendly travel tip? Bring your mother along with you!
… And not just for the assistance, either. There’s something so wonderfully fulfilling about traveling with your extended family, and I’m truly grateful for the opportunity to travel for my true love and make new memories with my mom. We traveled together with my grandmother Katy, my travel icon and muse, well into her 90s. I can only hope that Baby A still wants me to join her on adventures when I’m older!
Anyway, back to the itinerary. See, every time we fumble the ball and make dumb mistakes (which is … well, every trip, honestly) we learn what NOT to do. And then pass that along to you, dearest traveler, so that you can avoid making all of our many, many mistakes.
So, this itinerary has been planned around what we WISHED we did, as well as the things we did do that we really, really enjoyed. We also sprinkled in a few baby-friendly travel tips for those of you who will also be toting along tiny travelers.
Without further ado, let’s jump into your first day in Puerto Rico!
You’ll start your 4-day Puerto Rico itinerary by exploring the colorful streets of Viejo San Juan—the second oldest city in the Western Hemisphere. The blue-bricked streets of this beautiful 500-year-old city are lined with bright pastel facades painted salmon, sky blue, bubblegum pink, apple green, lilac, or canary yellow—a specifically selected and approved color palette determined by historical preservation that dates back to the 1950s. You’ll learn all about that on your tour today!
You’ll begin your day with the best possible way to experience a new place—stuffing your face full of its food—on a walking food tour with locally-owned tour company The Spoon Experience. This fascinating and informative tour combines stops at local cafes and restaurants with deeply researched insights into San Juan’s past, connecting threads of history and cuisine with Puerto Rico’s Caribbean relatives, Indigenous peoples, and the enslaved African peoples who brought their own cooking techniques and ingredients with them to contribute to the culture and culinary melting pot of Puerto Rico.
You’ll taste sweet pan de Mallorca over locally brewed coffee; learn about the Indigenous Taíno people while sampling a dish that has barely changed since the Spanish colonizers realized it had healing powers; sip cocktails and sample fresh fish ceviche while learning about Caribbean cuisine; and top it off with a sweet paleta. And a whole bunch more.
After your tour, you’ll walk away with a full belly, some Rapid Rewards points, and a deeply informed context for the history of San Juan and Puerto Rico, ready to see the city in a new light.
… You’ll also be stuffed, so we’re skipping lunch (and possibly dinner) today!
For the rest of the afternoon, you’ll be taking it easy and exploring any parts of the city that you didn’t get a chance to see on your tour. Consider doing a self-guided walking tour if you’re up for it, or—if you’re anything like us and have to go take a siesta to sleep off your food coma—save it for the last day of your trip when you’ll be revisiting all the stuff you were too tired to do today after your food tour.
There are several museums in Old San Juan, several beautiful plazas, and TWO centuries-old castles—three if you count the mansion that looks like a castle.
Here’s what we recommend seeing in Old San Juan:
If you’ve got room for dinner, pick up a bite to eat from a food truck at Plaza Dársenas. It’s easy to find: just look for the absolutely enormous cruise ships docking in the harbor and follow the crowd of sunburnt tourists!
Puerto Rico is a Caribbean island surrounded by warm, brilliant blue water full of marine life—so you’ll spend your day exploring underwater on a snorkeling tour to beautiful Culebra, an island off the coast of Puerto Rico.
Oh, did we mention Puerto Rico is an archipelago??? With its own islands?!! Yup!
Located 20 miles off the eastern coast of Puerto Rico, Culebra’s white, sandy shores are surrounded by cays hosting vibrant underwater landscapes. It’s what you’re probably picturing when you think of snorkeling on a Caribbean Island.
Well, except for the giant, rusting, graffiti-covered tanks. They don’t usually make the screensaver-worthy mental images, but they’re an iconic feature of Culebra’s beaches and hearken back to the time when Culebra was a naval base, shortly followed by the time everyone packed up and went home and was like eh, moving these tanks is a whole thing, let’s just leave ‘em here. Still, they do make a neat selfie backdrop!
In the clear, calm blue waters off Culebra you’ll find turtles munching on seagrass, as well as remoras, bluetail fishes, angelfish, and even stingrays, all enjoying the thriving ecosystem in the protected Culebra National Wildlife Refuge.
To make your visit stress-free, we recommend booking a snorkeling tour that includes pickup, drop off, and lunch, so all you have to do is show up in your swimsuit. This tour begins with a boat trip to Carlos Rosario Nature Reserve to snorkel with yellowtail snapper and eagle rays, then lunch on the sandy beaches of beautiful Cayo Luis Peña—book it on Viator.
For dinner after your snorkel tour, head to Deaverdura in Viejo San Juan. Heads up, there is usually a line out the door—if that tells you anything! The no-frills restaurant has a limited menu that changes regularly but always includes delicious Puerto Rican staples, like roast pork with a delicious cilantro sauce, the best red beans and rice we enjoyed during our entire trip, and phenomenal coconut flan. Enjoy it with a rum and tamarind cocktail.
Now that we’ve told you what we recommend, let me tell you about what we actually did. We couldn’t exactly take a baby on an all-day snorkeling trip (she’s more of a scuba diver), so instead, we each booked a short tour at a beach near San Juan, Escambron Marine Park. The lagoon there is a nice calm spot to swim, with a tiny beach and shallow water (great for little ones). If you bring some snorkeling gear (like this set), you can try to spot turtles!
Jeremy took a scuba diving tour with Scuba Dogs. They helped to rebuild and conserve marine life in this bay after a devastating oil spill, and they’re a fantastic and ethical company. It’s a calm and quiet place to dive, and you’ll see some interesting structures built from salvaged building materials that are now being converted into coral reefs. If you’re brand new to snorkeling and don’t feel comfortable doing it on your own, you can take a snorkeling tour with them, too.
If you have a car and just want to do a self-guided beach day (for baby-related reasons or not, we don’t judge), here’s what we recommend:
El Yunque National Forest is one of the United States’ only tropical rainforests, and it’s enchanting. Located just 45 minutes away from San Juan, it’s an easy day trip. The winding drive through the rainforest on its main path is stunning: you’ll climb up the mountains as the lush forest stretches below you until you can see all the way to the bright blue Caribbean Ocean.
There are many stops along the road in El Yunque, where you can find gushing waterfalls, azure pools ready for swimming, cliffs to jump off into said azure pools, and hikes winding through the lush rainforest, most of which lead to azure pools. Say azure pools one more time, Lia.
It’s sort of a road-to-Hana situation, where you drive along and enjoy the view and pull off to make stops here and there, except minus banana bread and plus mountains.
The trick is to know which stops to make ahead of time, since you won’t have any cell service once you enter the park (surprise!). You’ll want to plan out where you want to go in advance, or stop by the visitor’s center once you arrive.
But planning stuff out ahead of time takes effort, so the easiest way to do a trip to El Yunque is with a tour that will pick you up from your hotel in San Juan, take you to some fantastic spots to swim and hike (azure pools!!), feed you, and then drop you off back at your hotel again. You don’t have to worry about making a reservation to enter, driving, or finding food in the middle of a rainforest while an overtired baby screams at you from the backseat.
This El Yunque day trip is perfect for adventurous travelers: you’ll hike, swim in the … you know whats, cliff-jump, do some Tarzan rope swinging, and zoom down a natural waterslide.
For a more laid-back day, try this tour: you’ll swim, slide down a natural waterslide, and do a 15-minute hike, and then you’ll head to the nearby town of Luquillo to chill on the beach and eat dinner at the famous Kioskos de Luquillo (which is, incidentally, also where we recommend eating lunch or dinner if you do this day trip on your own).
As for us, we made a few fantastic stops on our self-guided trip. We climbed up the Yokahú Tower to take in the view stretching all the way to the coast of Luquillo. We also found a lovely, short little path along Juan Diego Creek, which led to some gorgeous swimming holes and waterfalls, plus a log that Baby A was like, enthralled by. I think maybe we’d never shown her a log before? Anyway, she loved it.
We were hoping to do a few other easy hikes that are supposed to be fantastic with kids, including Angelito Trail (which is actually outside the park entrance, and a shorter drive) but after her big log adventure, Baby A was too close to needing a nap to be flexible enough to let us stop and explore. Still, what we did get to do was wonderful.
After your rainforest excursion and dinner, it’s time for another bucket-list adventure: kayaking after dark in a bioluminescent bay.
A bioluminescent bay is incredibly rare—there are just five in the world, and not to brag or anything, but Puerto Rico is home to three of them. These ecosystems occur when microscopic, single-celled organisms called dinoflagellates grow in quantities big enough to produce a “glow-in-the-dark” effect when stimulated by movement. When you paddle or splash the water, the tiny organisms light up like tiny fireflies or dancing sparks in the water.
You can only see them when it’s pitch black (our tour had us huddle under a tarp to block out ambient light) and you’ll need to make movements underwater to see them—so don’t expect to see like, a whole glow-in-the-dark bay. We’ve heard (from my cousins) that on extremely rare occasions, you can even jump in the water and swim. If you do get the opportunity, please tell us about it so we can marinate in our jealousy!
You won’t be able to capture the bioluminescence with your phone or a camera, (any ambient light at all will make them disappear, like little water faeries) but the sunset over the palm tree-studded hills of Fajardo was so stunning that I wish I’d brought my phone or camera in a waterproof bag like this one (but of course I forgot to pack it because my brain only functions half as well as it used to since having a baby).
Puerto Rico is home to bioluminescent bays in Fajardo, on the island of Vieques, and in Ponce. All three will require a trip from San Juan to see them; and although Vieques is considered the “prettiest,” Fajardo is the closest one to the city as well as El Yunque, which is why you’ll be squeezing in both adventures on the same day (we are all about #lowstress here).
The best way to fit in both El Yunque and the bioluminescent bay kayaking trip is to book a tour that combines both, like this one which picks up and drops off from San Juan and includes lunch and dinner, plus hiking and swimming in El Yunque and the sunset kayaking tour. (You can also book a tour individually, like this one, if you have a car and can get yourself to the tour in a timely manner, which as we mentioned earlier, took us two attempts).
We recommend booking your tour right at sunset: that way you get a beautiful sunset kayak and view over the bay and then a cool night kayak! Honestly, the actual bioluminescence part of the tour, while cool, is pretty brief—but a sunset and evening kayaking tour is still really freakin’ cool.
On your final day in Puerto Rico, you’ll likely be exhausted from two straight days of adventuring and want to spend your last day taking it easy. (Ask me how I know).
So, for today, you’ll be exploring Old San Juan again and stopping at the many museums, plazas, historic homes, and castles you didn’t get a chance to visit on your first day because you were passed out in a food coma.
But first, start your day off right by putting yourself back into a food coma with brunch at Chocobar Cortes, a chocolate shop slash brunch spot slash coffee shop. The menu creatively incorporates bitter, nutty Caribbean-grown chocolate in totally unexpected ways, like chocolate vinaigrette, chocolate ketchup, and chocolate-ham-and-cheese croquettes (they’re delicious)!
Try their twist on traditional Puerto Rican foods like pan de Mallorca and upgraded versions like chalupitas de mofongo, stuffed mofongo shells with chocolate guacamole (kinda weird? Yes. Kinda good? Also, yes). Delicious. The cost of your meal will benefit Fundación Cortés, which supports Caribbean art and local artists.
After brunch, get out and explore those blue-bricked streets! Pop into local stores to pick up souvenirs (you can browse locally-crafted souvenirs at the handicraft market in Plaza Dársenas), hit up more museums and plazas, see whichever castle you skipped on day one, and grab a sweet paleta from Señor Paleta to cool off in the heat.
For your last evening in San Juan, take a beautiful sunset cruise in the bay at the foot of the historic forts and walls of the old city. You’ll enjoy cocktails and appetizers on board a schooner as the sun sets over the Caribbean horizon.
Once you’ve said your final goodbye to the sun, head to one of the best restaurants in Puerto Rico for dinner: Santaella. The flagship of world-renowned Chef Santaella features upscale versions of authentic Puerto Rican dishes and cocina criolla crafted lovingly with local ingredients (sourced from a farmer’s market a few feet away, as local as it gets) made tapas-style, which is my favorite because it means you get to try lots of things without really committing.
After dinner, make your way back to your hotel one last time. Say goodbye to the friendly stray cats along the way, the chirping Coquí frog, and that warm trade wind breeze. Maybe stop by a bar for one last piña colada, because like, they were invented here so you probably can’t get them at home, right??
And then, finally, say your goodbyes. Adios, Puerto Rico—you were magical.
For our itinerary, we recommend staying in San Juan and taking day trips to explore nearby attractions on the East Coast of the island. This means you won’t have to rent a car or worry about transportation other than taking an Uber to and from the airport—easy peasy.
What we actually did during our trip, though, was a little different since we were traveling with a baby (being stuck on a day tour with a baby—can you imagine?!). We rented a car and moved midway through our trip from San Juan to a beach town close to El Yunque National Park and the bioluminescent bay in Fajardo, so that we were close to our day trips and minimized the time spent with a cranky baby in a car seat. But if you aren’t traveling with a baby, that’s completely unnecessary and honestly not what we would recommend based on our experience.
That is, unless you can snag a reservation at the El Yunque Rainforest Inn, a gorgeous eco-lodge that we really wanted to book but didn’t work out with our dates!
When it comes to accommodations in San Juan, you’ll see a lot of beachfront resorts near the old city in an area called Condado, about a 10-minute drive from Viejo San Juan. Personally, we really aren’t resort people and we prefer to be within walking distance to “stuff,” so we chose to stay within Viejo San Juan itself, which was awesome. The city is small and walkable, so we were always just a few minutes away from our hotel. We were happy to trade off a private beach for ocean views from the high walls around the city, walkability, and colonial charm!
As ethical and sustainable travelers, it’s deeply important to us that we have a positive impact on the places we visit. Puerto Rico has a strained relationship with tourism. On the one hand, the income from tourists directly supports locally-owned businesses—so long as visitors like you continue to seek out and patronize them! On the other hand, as a U.S. territory, Puerto Ricans tend to feel like the beauty of their island is often sold to the highest bidder, leaving locals and communities without a say in the development and preservation of their homes.
Puerto Rico, like many Caribbean islands, is also subject to frequent hurricanes. In recent years, the islands have been devastated by multiple hurricanes—and while it has bounced back in tremendous ways, there is still much work to be done. A local travel blogger friend of ours, Jen Ruiz, wrote a fantastic article on the importance of visiting Puerto Rico even in the wake of hurricanes—read it here.
We’d encourage you to take your patronage of locally owned businesses a step further and consider donating to these non-profit organizations which are working to maintain, improve, and support Puerto Rico’s local community. This list was provided to me by one of my Puerto Rican cousins and consists of organizations either she or her network have been involved with personally.
A community-based feminist non-profit organization focused on providing resources and education on female development in areas like health & healthcare, economic empowerment, reducing domestic violence, and activism. They also provide emergency relief and funds to women in impacted communities (for example, when Hurricane Fiona hit, they were actively working in Loíiza—a municipality that was unable to get quick assistance from FEMA and the Red Cross—to provide a soup kitchen and supply drive).
Domestic violence and gender-based violence are huge issues in PR. Governor Pierluisi issued a state of emergency on the issue in 2021 (that lasted until June 2022) to research it. Even Bad Bunny has released two songs raising awareness of it, “Solo de Míi” and “Andrea.”
This is an organization that aims to have 33% of Puerto Rico’s land under protected status by 2033 to protect Puerto Rico’s ecological systems. Not only do they manage various lands around the island (which are donated to them or they purchase), but they also offer educational tours that range from the history of sugar plantations to one of Puerto Rico’s three bioluminescent bays, volunteer activities like tree planting or bird counting, and scientific research opportunities.
As a Caribbean Island, Puerto Rico is highly at risk to the impact of global warming (which you can see in the frequency of deadly hurricanes like Maria or Fiona). Coastal sealines are disappearing and flooding is becoming more and more frequent. By protecting Puerto Rico’s ecological systems, Para la Naturaleza hopes to keep these systems intact to help keep the island ecologically sustainable and provide residents and tourists alike a new appreciation for connecting with their environment and the impact they have.
You’ll see stray animals all over the island. Save a Gato works exclusively with the feral cat colony in Old San Juan (you’ll probably see them while walking around!). They practice trap and release (TNR) where they capture the feral cats, neuter or spay them, and release them back into the colony as these cats are too skeptical and aggressive to humans to be rehomed. However, if a female cat is pregnant, they let her go fully to term and have the kittens adopted once they are of age.
Not only are there tons of stray cats, but stray dogs as well (here in PR they’re called “satos”). Additionally, many of these stray animals escaped abusive or hoarding situations.
Amigos de los Animales is a shelter and educational non-profit that not only fosters and adopts stray or abused animals to loving homes, but also provides a six-week animal cruelty and investigation course to local police, animal welfare, and animal control centers (or anyone in general) to raise awareness on the signs of animal cruelty and abuse.
This is a no-overhead fund that invests 100% of donations to affiliated organizations working in critically affected areas in Puerto Rico. It goes to both short- and long-term humanitarian efforts from emergency supplies after a hurricane to re-building schools or community facilities.
Both a non-profit and fund, United Way works with 123 organizations throughout the island providing them with funds and resources to continue their work. Their main focuses are education, financial independence, and health, but also provide an emergency relief fund during times of crises like Hurricane Fiona.
Casa Julia de Burgos was the first domestic violence shelter in Puerto Rico and continues to provide resources, awareness, and assistance to those facing domestic violence. Not only do they offer shelter and a rapid re-housing program, but they also offer trauma-informed childcare to the children of domestic violence.
Are you ready to pack your snorkel fins and head to Puerto Rico? What questions about visiting can we answer?
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Disclaimer: Our trip was sponsored by Southwest Rapid Rewards Credit Cards from Chase. Learn more here. All opinions, recommendations, bad jokes, and mistakes made during this trip (we made so many mistakes, y’all, it’s almost impressive) were 100% my own.
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