From Philly, Puerto Rico is all but a four-hour direct flight away, making it one of the easiest tropical escapes from the East Coast. Nicaragua was my 4th of July side quest in 2025, and I knew I wanted another adventure this year. Naturally, I booked a solo trip to Puerto Rico… one week before leaving.
I’m a Type B traveler at heart. Sure, there’s comfort in having a plan. But I’ve learned the best stories come from the moments no one could have orchestrated. Sometimes you just have to book the flight, figure it out along the way, and trust adventure will find you!
The last time I visited PR, I was 23 years old on a cruise. I only had six hours on the island, and my then idea of experiencing PR at the time was drinking slushies at Señor Frog’s. Not exactly the most authentic experience lmao. In hindsight, that cruise was a turning point. It marked my realization I was capable of taking chances, saying yes more often (if you had a dollar for each time I said “yolo” on this trip, you’d be rolling in it), and quitting waiting for life to happen to me. If I never had that experience, I would’ve never grown into who I am today. Through this PR trip I learned nobody returns to the same place because no one returns as the same individual.
Day 1: Arriving in SJU & Checking Into Mango Mansion
I landed in San Juan around 10pm. That warm air hitting my body as soon as I walked out the revolving doors purported a “I missed you,” hug. It was a 20 min Uber to Mango Mansion Hostel, a place mentioned repeatedly through word of mouth during prior travels. Traveler recommendations are something I trust more than anything else. There’s something innately reliable about hearing, “You HAVE to stay here,” compared to reading a random online Google review.
Upon drop-off, I wasn’t sure I was at the right place. I glanced to my left to see the absense of a welcome sign or an entrance. I just stood there like🧍♀️wondering if I was dropped off at someone’s house or the post-work delirium took over.
After ringing the bell, I was immediately welcomed inside by the staff (Jax, you rock). Within minutes, I got a tour of the hostel, including the hangout area, the smoking area, and where I’d be sleeping.
I’d compare Mango to a friend’s house you feel comfortable at as soon as you step foot through the door. When I entered my room, someone claimed what was supposed to be my bottom bunk. Boo. The remaining option was the top bunk, bed number 11. As corny as it sounds, I took it as a sign. I see 11:11 everywhere (if you’ve been around me and I’ve seen it you know how excited I get). Hence, to to find a positive, perhaps bed 11 was where I was supposed to be!
No sarcasm, I prefer staying in larger hostel rooms. I love the social aspect! I lucked out by having the most amazing roommates. Everyone in my room ended up hanging throughout our trip! It was like a huge sleepover. The beds don’t have curtains and instead of traditional lockers, there are more like cubbies for storing belongings. However, the beds were comfortable, and I slept like a baby. (AC was blasting yeahhh)
For about $70 nightly, it was pricier than most hostels I’ve stayed at. Though, it was still cheaper than any hotel I’ve stayed at in the States. I booked through HostelWorld, the best app to meet others solo traveling! Breakfast was included as well as shower towels (some hostels make you rent one), laundry is available, and you can’t beat the location. Beach towels could be rented for $6 too!
Some practical things about Mango: because it’s a smaller hostel, there’s only two showers / three bathrooms. Compared to my hostel in Peru, this was a walk in the park (war stories). In Huacachina my hostel had one ensuite shower for 16 people and we’d have to wait in line nightly lmao. Upstairs, they have a bookshelf (one day I’ll bring a copy of mine to place there!), TV area, and lockers for smaller valuables.
Shameless self promo: you can buy my travel memoir “Little Bird” here!
Day 2: Finding My PR Tribe / Hostel Workday
I woke up early and headed outside for breakfast, served from 8-10 am. Breakfast included papaya, waffles, cinnamon rolls, coffee, toast w/ jelly, and hard-boiled eggs. If you want the eggs, get there early because they go quick!
Mango Mansion isn’t a party hostel, but it is a social hostel. All you needed to do was walk into the common area and you’d end up sitting around talking with strangers who felt like family within five minutes. At check in, a QR code is pinned above the sink to join the MM WhatsApp group! The tours MM offers are coordinated with others staying at the hostel, creating a colloquial experience in contrast to booking through a tour company.
Mango is remote-work friendly, as WiFi was reliable! During my Teams call, Puerto Rico decided it wanted to remind me it was the rainforest. Once the rain finally stopped, others and I puttered around to the grocery store 10 minutes away. One being a fellow journaler. My people. There is great value in writing about these memories as you live them! We grabbed the essentials: Water, snacks, and reds. The hostel traveler holy trinity. We tried a new piña colada-inspired Sunkist flavor, the store was handing out samples! (soo refreshing)
In the evening, our group decided to grab food near La Placita, one of San Juan’s most notable nightlife areas. During the day, it functions as a traditional market. At night it transforms into a lively party filled with restaurants, bars, music, and dancing. It’s touristy, but worth checking out once!
For dinner we walked to Restaurante Airelibre, an outdoor restaurant nearby. The restaurant was a tight squeeze with our hostel crew. As karaoke goers sung their hearts our, chairs were shuffled around, everyone shared stories, and in no time I was having dinner with people I met that morning that now felt like family.
Everyone tried mofongo, one of Puerto Rico’s most iconic dishes made from fried green plantains that are mashed together with seasonings, traditionally including garlic and pork cracklings, and served with different meats, sauces, or toppings. I ordered a rum and coke, as others got coconut mojitos. It felt like that one Spongebob episode where the one fish tries jellyfish jelly on a krabby patty and he’s like, “AMAZING. I NEED to TELL SOMEONE ABOUT THIS.”
Restaurants & Food to Try 🍽️
Puerto Rico has incredible food, and there are a few things you need to try:
🍌 Mofongo
Mofongo is one of Puerto Rico’s most iconic dishes. It’s made from mashed fried green plantains mixed with garlic and often served with meat, seafood, or sauce. I tried it multiple times during my trip, and each version had its own personality.
🍢 Pinchos
Pinchos are Puerto Rican skewers, usually grilled meat served on a stick. They’re a simple street food, but after a long day exploring, they hit the spot. Eating pinchos while watching the sunset on the beach was a book moment fs
🍹 Piña Coladas & Coconut Mojitos
Puerto Rico is the birthplace of the piña colada, so you have to try one while you’re there! I’m sure you’ve had one before, but you’ve gotta say you’ve had one in it’s birthplace! They can get expensive (my beach one was definitely a “vacation price” ), but sometimes you’re paying for the experience.
That night our group ended up at Calle Cerra: a more local nightlife area, where we stopped at El Patio de Calle Cerra. All the streets had a fun atmosphere, a photo booth, good music, and the experience I love finding while traveling.
I spent the night salsa dancing with my new hostel friends in the street while the smell of pinchos filled the air. And that was only my first full day in Puerto Rico.
Day 3: Exploring El Yunque Rainforest With Hostel Friends 🌿
After staying up way too late the night before, I woke up around 9 to squeeze in breakfast before it ended at 10 and make it on time for my tour to El Yunque Rainforest. (mango knows whats up)
Breaky was devoured, and six of us piled into a Kia with one of the guys from the hostel who led the tour. I loved that this tour was organized through the hostel’s owner. Many hostels partner with third-party companies, which can still be great, but the sense of community is more favorable.
El Yunque National Forest
El Yunque is the only tropical rainforest in the United States National Forest System and one of Puerto Rico’s most famous natural landmarks. A must-do for sure! The rainforest is filled with waterfalls, hiking trails, mountain views, and incredible biodiversity. It’s also home to the famous coquí frog, a tiny frog that has become one of Puerto Rico’s most recognizable symbols (You may recognize it from Bad Bunny’s Spotify artwork!)
Our guide Ale spitballed facts about the rainforest, the area’s history, and pointed out how coquí frogs hide throughout the forest. He explained the word “hurricane” traces back to the Taíno word “hurakán,” connecting Puerto Rico’s Indigenous history to something that has shaped the Caribbean for centuries.
The second stop after the waterfall was Yokahú Observation Tower, where we climbed to the top for scenic views over the lush green mountains and coastline below. (it’s not too bad of a climb, don’t worry!)
Some can see faces within the mountain landscape, which I thought was such a cool reminder of how humans have always looked at nature and found stories hidden inside 🙂 Mother nature is one hell of a painter! Angelito swimhole is the next attraction. The group took a small hike to part of the river where you can swim and cool down from the heat.
Taking in the views, we continued deeper into the rainforest for the more adventurous parts of the day. Now, I should probably mention a fun detail. I was extremely hungover (i’ll only be 26 in PR once, let me live). The only shoes I brought were sandals. Would I recommend this decision? Absolutely not. BUT, with tactful walking, I only slipped once. While visiting El Yunque, please don’t be like me wear proper hiking shoes or water shoes. Trails are rocky, uneven, and slippery, especially around the waterfalls! After a short hike the six of us arrived at a natural swimming area to cool off. The water was filled with striped fish of all different sizes swimming all around us.
Then came natural waterslides. Not gunna lie, standing at the top of them: they look a lot more intimidating. The rocks are uneven, so water shoes are helpful, and yes, your ass will hurt afterward- but that’s part of the experience.
One by one, we slid down the natural waterslides, jumped into the pools below, and watched everyone debate who was brave enough to go first. Eventually, I said: “You know what, If I don’t go first, I’m going to think about it too much.” That is my biggest piece of advice for anyone in life: always go first. It was a blast watching everyone take turns jumping in, laughing, and cheering each other on.
Ale drove us to a beach and a nearby strip of restaurants where we tried one of PR’s other famous foods: pinchos. Everyone was starving after hiking!
We sat together to watch the game, crisp coke in hand, and watched the atardecer loom over the horizon. The sun danced across the ocean like it was waving goodbye to us after an incredible day. It was so peaceful:)
A Night Exploring Viejo San Juan
Returning to Mango Mansion, everyone took a very necessary shower and regrouped before heading out. We took an Uber to Viejo San Juan, where I visited years before during my cruise. This time I was experiencing it completely differently as the alchemized Holly lol
One of my roommates and I met up with a few others at La Factoría, a bar that ends up on just about every “must-visit” list in Puerto Rico. One hallway led to another, which opens into another bar, which opens into another dance floor with a disco ball with a dj spinning house music! Every corner has a different vibe, so it’s fun to wander around for a while.
La Factoría is known for its signature cocktails. Every drink coming out looked like the bartender had spent five minutes making it, meticulously topping each glass with fresh herbs, fruit, or some garnish that made each look like a work of art!
We made our way toward La Perla for afters, a neighborhood tucked below the walls of Old San Juan known for its colorful streets, ocean views, and complicated history. As the filming location for the Despacito music video, it brought international attention to the neighborhood. Long before it became a recognizable backdrop, La Perla was a community built outside the city walls in the 1700s where enslaved people, laborers, fishermen, and other marginalized communities lived because they weren’t allowed to reside inside the fortified city.
Today La Perla has a strong cultural identity, but its reputation often overshadows its history. I’d personally recommend visiting during the day instead of at night, especially if traveling solo. You’ll likely be offered drugs within a few minutes of walking in at night lmao, I’m aware this sounds tone deaf asf but I never felt unsafe. Locals are protective of their neighborhood and don’t want visitors walking around with their phones out filming or taking pictures. La Perla is a real community where people live, not a tourist attraction. If you visit, be respectful, keep your phone away unless you have permission, and remember you’re stepping into someone’s home.
The night ended how the best hostel nights always seem to end. Sitting in a circle. Talking about life. Sharing stories. Around 4 am, surrounded by people who had been strangers only a few days before. Those are the moments that remind me why I keep traveling. Not because every day is planned by the hour. Not because every destination is about checking off a list. It’s because that’s what makes us the most human. Nor doomscrolling or endless attempts to get the perfect photo. Sitting with people from around the world, talking about dreams, life, and everything in between, makes you feel free.
Day 4: Spending Fourth of July at Condado Beach & Exploring San Juan Nightlife 🇵🇷
After two days of constantly being on the move, Fourth of July became our day to slow down. My group packed up towels, speakers, sunscreen (which, spoiler alert, I clearly did not use enough of), and headed to Condado beach. A bunch of us spent hours stretched out on the sand, taking turns body surfing in the waves, blasting music, and passing time the way summer days are supposed to be spent!
No beach day is complete without a piña colada. And in PR, you’ll find plenty. Would I normally pay $20 for one? Absolutely not. It was worth every overpriced sip to have one in it’s birthplace. (Also I just really wanted the little flag for my junk journal, priorities)
The only thing I regret that day was severely underestimating the Caribbean sun. I thought I was getting a nice tan. Instead, I earned what would become the worst sunburn of my entire life. By the time we packed up around dinner, I had officially crossed the line from “slightly pink” to “this is going to hurt tomorrow.”
Before heading out, we taught each other card games and I got one of the biggest laughs of the entire trip. Someone texted: “Are we going to La Placenta?” Instead of La Placita. I woke everyone up in the hostel from laughing so freaking hard that was the best typo I’ve ever seen.
We went to Reina, a restaurant located in the La Placita area. This was my favorite mofongo of the trip. Reina’s stood out because it had the perfect amount of heat and flavor.
On the courtyard at Mango we continued playing blackjack and got ready for another night out! Our group made our way to Calle Cerra. I told the beach group that I would be going to Ibiza for two weeks in a month. Given everywhere in Philly closes at 2 and nothing closes in Ibiza, I told the group, “Shit. I’m going to need to train for Ibiza now.”
Our crew and I shook on staying up until sunrise and going swimming in the ocean. There we were, still kicking at 4am. Back at the hostel we swung in the hammocks, talking, laughing, and enjoying those quiet moments before sunrise.
By the time the sky started getting lighter, we walked to the beach for sunrise. The birds just starting to sing their morning song. The cold sand slipped between our toes en route to our corner. It didn’t take long to realize the sunset wasn’t going to be picturesque, but it didn’t matter. Deciding to end the night with one last spontaneous adventure made it worthwhile: going skinny dipping! Jumping wave by wave, my fellow travelers told me, “TRAINING COMPLETE, you did it Holly!”
Probably not the most responsible travel recommendation I could give, but it was one of those unforgettable moments that could only happen when you’re surrounded by people who started as strangers and became people you’ll share special memories with forever. Yolo
Final Thoughts & Takeaways
As a female solo traveler, I felt incredibly safe exploring Puerto Rico. Staying at Mango Mansion made the experience even better because the social atmosphere makes it so easy to meet people. Between the common areas, WhatsApp group, and everyone hanging out throughout the day, you won’t have any trouble finding people to grab food with, make plans, or explore with.
If you’re nervous about taking your first solo trip, Puerto Rico is a great place to start. It has the adventure of exploring somewhere new while still having some familiarity as a U.S. territory, which can make that first step into solo travel feel a little less intimidating.
My biggest regret from this trip was not spending more time in Viejo San Juan. I had only briefly visited on my cruise years ago, and even this time I still feel like I only scratched the surface. I could have spent hours wandering the colorful streets, stopping into little shops, grabbing coffee, and taking in the history of the city. I’d recommend exploring the castillos, especially Castillo San Felipe del Morro and Castillo San Cristóbal, two of the most iconic historical sites in Puerto Rico. Maybe even now I still have unfinished business in PR!
Puerto Rico reminded me you don’t always need to travel halfway around the world to find a new adventure. Sometimes revisiting a place you’ve already been can show you an entirely different side of it 🙂
Where The Wind Takes Me. 
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