So you’re planning a vacation to Puerto Rico? Good call! In this article, I’ll review our vacation highlights, what we learned, liked, and disliked about Puerto Rico. All the details you’ll need to plan a Puerto Rico vacation are right here. Find out where to go and where not to go. I’ll include packing recommendations, transportation, and other practical travel tips that will make your Puerto Rico vacation enjoyable and stress-free. At the bottom of this article you will find the detailed travel plan we used. It can assist you when planning a vacation to Puerto Rico. As we do with most of our vacations, we used the TripIt app travel planner to organize the itinerary.
Check out the gear recommendations noted in this article. Some of my top recommendations are above (#commissionsearned). Puerto Rico is hot hot hot in the summertime. The Caribbean sun will sneak up on a gringo if you don’t pay attention, so be sure to use (sun) protection.
Pros | Cons |
Beautiful nature, beaches | Rough around the edges |
Vibrant culture & nightlife | Infrastructure challenges |
Unique, tasty food | Areas to avoid due to crime |
Old San Juan | Old San Juan |
What Makes a Puerto Rico Vacation Different?
If you go to Puerto Rico expecting a polished Maui or Cancun style beach vacation, I think you will be disappointed. Though there are some high-end beach resorts in Puerto Rico, that’s not the real Puerto Rico. If those types of places are diamonds, then Puerto Rico is a diamond in-the-rough (and I say that as a compliment). There is a lot of untouched authenticity in Puerto Rico. It lacks the white-bread spit-shine that you encounter in many modern tropical resort destinations.
Puerto Rico is raw tropical beauty the way nature made it, as is, before every major resort brand pounces. Don’t get me wrong, I’ve enjoyed lounging beside an obscenely-large swimming pool in Cancun, admiring the well groomed beach and surrounding (all-inclusive) resort landscape. That’s what makes Cancun. Overall, Puerto Rico is a bit grittier, sexier, and has an authenticity that you won’t find anywhere else.
Our (Delayed) Puerto Rico Vacation
Be sure to take hurricane season into consideration when planning a vacation to Puerto Rico. Our original Puerto Rico vacation was planned for October of 2017, but a deadly and destructive Hurricane Maria that September delayed our plan. It was disappointing to have to cancel the vacation, but it was the only realistic option at the time. The destructive category 5 hurricane destroyed many homes and key components of Puerto Rico’s infrastructure. There was no electricity, there were ongoing issues with running water, and food & medical supplies were limited. These issues would continue for months.
San Juan After Hurricane Maria
Seven months after the hurricane we descended into San Juan. To our left we saw the beauty of the deep blue ocean that surrounds the island. To our right, an ocean of blue tarps covered nearly every damaged rooftop. We knew that the island’s infrastructure was still in rough shape, so we had a baseline expectation that the Puerto Rico wouldn’t be in tip-top condition. Still, it was sad to see that so many people were clearly suffering, trying to rebuild their homes and livelihoods. We took an Uber from the airport to our studio apartment off Ashford Avenue in San Juan. Along the way, we saw signs of hurricane damage and efforts to restore & rebuild. Each palm tree we saw was a tattered pom-pom missing 40% or more of its tassels.
We felt equal amounts of excitement and guilt. It seemed callus of us to be there as pleasure-seeking tourists while so many residents still suffered, but it was a new place for us to explore, so we were excited to be there. Our Uber driver, and many other locals throughout the vacation, assured us that they were happy to see tourists returning to the island. We even had one shopkeeper in the famed Kioskos de Luquillo thank us for coming. This certainly reassured us that it was okay for us to be there.
Let’s get started with some highlights and what we loved about our Puerto Rico vacation.
Highlights: Puerto Rico Nature & Things To Do
Puerto Rico is a nature-lovers paradise that defines natural tropical beauty. A Puerto Rico vacation without planning to spend time in nature is a major misstep. The island has beautiful beaches, mountains, and El Yunque, the only US National Forest (the only US rainforest). The outer beach-lined edges of the island give way to a lush, mountainous terrain at the island’s center. Flowers add pops of bright color, even more vibrant when accentuated against the green backdrop. The color of the ocean varies from deep-blue to turquoise, meeting soft, sky-blue on the horizon. During the daytime, you’ll hear the calls of exotic birds, and you’ll drift off at night to the amusing call of the aptly-named Coqui frogs.
El Yunque National Forest
Due to Maria damage, access to El Yunque was limited to about 20% of the National Park. Though disappointed that we couldn’t see the rainforest in prime condition, and many of the areas we wanted to see were still closed, we loved what we did see. We found a trail in the open section of the park and made way into the recovering rainforest. The trail meandered downhill through humid, lush forest. Breaks in the vegetation granted us occasional peeks out to the coast.
We hiked the last mile out of El Yunque during a sudden deluge of rain that soaked us through (but it only added to the experience and we laughed our way through it). As always, if I’m hiking and a National Geographic map is available, I buy one; they’re a waterproof peace-of-mind that doesn’t require batteries to view.
If you’re staying in San Juan and don’t plan to rent a car, you may want to check out this highly-regarded El Yunque tour with transportation included.
Las Paylas Natural Rock Waterslide (Luquillo)
This was one of the experiences we had that made Puerto Rico feel so authentic and real. There are a couple of ways to access Las Paylas, but the easiest is parking at a private residence that charges a small parking fee, then walking through the residents yard. We pulled up to the “parking lot” nervously chuckling to ourselves, but it was all-good. The property owner, a super-friendly guy, has made a business out of it (I believe we paid $5 to park). As we made way down the private trail to the river, two of the owner’s equally-friendly dogs followed us.
The actual waterslide (formed by water erosion) is very cool, and surprisingly, we left with no tailbone bruising or broken bones, but Las Paylas is more than a novelty waterslide. You can walk downstream for a half-mile in awe of the feature that water has sculpted. There are some precarious spots, but overall, if you watch your step, you’ll be fine. However, I would likely avoid the area after/during heavy rainfall.
Bioluminescent Bay Kayaking (Fajardo)
This was something we nearly left out, but if you’re planning a vacation to Puerto Rico, and it doesn’t include the bio-bay, you’re missing out. Bioluminescent glow is way-cool. Microorganisms called dinoflagellates band together at night and create a magical glow near the surface of the water. Fajardo has one of only five bioluminescent sites worldwide. Sadly, when we visited the glow wasn’t as bright as usual (no thanks to Hurricane Maria). Still, we had a great time. We found the peaceful kayak trip through meandering mangroves to be another vacation highlight. Imagine following a calm water trail through a tunnel of crazy-twisted, intertwined tree trunks and branches.
Our tour was with Bio Bay Kayaks. They were reasonably-priced, prompt, professional, and safety-minded.
Carabalí Rainforest Park ATV Tour (Luquillo)
An ATV tour at Carabalí is a must-do for anyone who loves nature and excitement. The operation is fun, safe, and seemed genuinely concerned about preserving the integrity of the natural area. The tours are guided and pay strict attention to staying on the designated paths. This isn’t an off-road free-for-all.
We took a two-hour ATV tour that only included the guide, my wife, and I. Neither my wife nor I were seasoned ATV operators, so the guide adjusted the pace to match our skill level. This is a very doable activity for someone who has never rode an ATV. It’s a great way to see a lot of nature without having to do all the walking.
Unlike rush hour at home, this tour was the right mix of stop-and-go. We traveled through open fields, rainforest, and into the hills. More than once, we stopped to observe massive iguanas observing us from the trees beside the trail. Though they were neat to see, but they are non-native to Puerto Rico and considered invasive. After a stop, move on, and again, watch the landscape change around us. We took time to stop and swim in a river pool, and relax in the surroundings. Also, this is a great tour suitable for couples and even families with teens.
It ATVs aren’t your thing, check out the Carabali also offers an awesome horseback riding adventure from the rainforest to Luquillo Beach.
Highlights: Puerto Rico Food & Dining
First off, Puerto Rican cuisine is muy, muy bueno. When you plan a vacation to Puerto Rico, don’t overlook the food options. There are tons! There are healthy food options that include fresh seafood and some of the tastiest tropic fruit around, but there is better than healthy food to be had. The real food-joy comes from less-than-healthy local dishes like mofongo and carne frita. There are many other staples in the Puerto Rican fry-it diet. Here are some of our favorite food encounters and restaurants.
Marmalade – Old San Juan
Marmalade is no gimmick. The restaurant is a culinary destination that should not be missed if you are in the area. We’ve never paid more for a dinner out, and we don’t regret it at all. I purposely avoid using the word “expensive,” because what we consider expensive is completely relative. Memories are likely the most valuable things we have in life, and we won’t forget the meal and experience we had at Marmalade (which is surprising considering the number of Jimi Hendricks‘ we consumed).
Luquillo Kioskos (Kiosks) – Luquillo, Puerto Rico
If you’ve never heard of the Kioskos, imagine a long, kinda’ shabby-looking strip mall of 50+ restaurants & shops located along the main highway into Luquillo. It’s not a super-accurate description, but it’s a starting-point. Some of the kiosks looked a little beat up on the outside (and I don’t believe it was due to Hurricane Maria), but don’t let that deter you from stopping. We met some really cool locals and shop (kiosk) keepers and we ate some excellent authentic, local cuisine. So, we frequented the kioskos a few times during our stay in Luquillo and were never disappointed.
Highlights: Puerto Rico Culture & History
The vibrant island culture is a mashup of predominantly Caribbean and Spanish influences. The Puerto Ricans that I encountered had a happy, relaxed (but lively) island vibe. Though it’s a US territory, the music, art, architecture (most notably in the Old San Juan district), and people on the island are distinctively Puerto Rican.
Old San Juan Puerto Rico
No Puerto Rico vacation is complete without a visit to Old San Juan. My first visit to Old San Juan gave me strong mixed feelings. The colorful colonial buildings and narrow streets were no doubt enchanting. Walking down the streets brings you to a completely different time. You can imagine what it was like there a long time ago. There were times when, walking in the shade of those constricted, cobblestone streets I completely forgot about the modern world and the stresses it imposes on us. Before I could bask any deeper into that dreamy, time-travel feeling of times long ago, I would encounter some jarring reminder of modern man.
There were intermittent hordes of tactless cruise ship gringos. There were also random noisy neon-adorned, crap-slinging souvenir shops. The worst, though, was the unending, steady stream of car traffic. It became hard to tell if I was still buzzed from my lunchtime drinks, or if I was slowly dying from carbon monoxide poisoning. The cruise ship tourists are a necessary economic evil; not much can be done about them (maybe redeploy the cannons in El Morro). It’s a given that cruise ship tourists need somewhere to purchase Chinese-made “Puerto Rico” shot glasses, so the souvenir shops must also remain. However, car traffic in the already cramped, central zone has to go. Allowing pedestrian traffic only would vastly improve Old San Juan’s vibe.
All griping aside, I do think it is worthwhile to visit Old San Juan at least once during the daytime and again at night. By nighttime, the area seemed to mellow-out substantially. Most of the cruise ship gypsies have returned to the mothership for dinner or disembarked entirely by early evening. There’s less people and car traffic. The street lighting, glowing against the colorful pastel buildings, transforms the look and feel of the central area entirely. Now, dare I say that Old San Juan at night is a romantic, refined, more mature version of itself daytime self?
Castillo San Felipe del Morro
While visiting Old San Juan, be sure to check out the Castillo San Felipe del Morro, a defensive fortress built by Spain in 1539. The US National Historic Site is massive. It’s hard to believe that they had the capability to built a structure of this scale in the 16th century. The ocean views from the fortress are beyond beautiful. Undoubtedly, worth a visit on your Puerto Rico vacation.
This walking tour is a great way to tour and learn the history of both Old San Juan & El Morro. If you plan to go on a walking tour, it’s recommended that book well in advance as they tend to fill up during peak season.
Art & Music
I like art, but I’m not a enthusiastic art-seeker. However, it was easy to appreciate the art that I did see. Street art, sculptures, and murals are seen across the island in public parks, squares, and markets. There are numerous art galleries and shops (especially in Old San Juan) where you can find the works of local artists.
Be sure to check out La Plaza del Mercado en Santurce / La Placita de Santurce (in San Juan) for some really cool street art and murals. This area is well known for its lively nightlife, dancing, and live music. If you love art and music, you’ll find the best of both there. You Puerto Rico vacation is not complete without checking this area out.
I especially liked the sculptures pictured below (both in San Juan).
Where to Stay: Puerto Rico Vacation Accommodations
Our Stay in Condado, San Juan
When planning a vacation to Puerto Rico, consider what type of accomodation suits you best. Hotels are great if you want full-service and you’re willing to pay more for it. If you want to save some money and have access to your own kitchen, you’re likely better off renting a condo. In addition to some local hotels, all of the standard, international hotel chains are available in San Juan (e.g., Hilton, Marriott). For our Puerto Rico vacation, we opted reserve small studio apartments. At the time, it was a better deal and allowed us the option to cook some meals to save money.
For the first half of our Puerto Rico vacation, we stayed on Ashford Avenue located in the Condado neighborhood of San Juan. The small high-rise studio apartment was exactly what we need. We had an awesome view from inside the apartment and loved sitting outside on the balcony to take in the fresh ocean air. We had a small, well-stocked kitchen if we wanted to prepare something (but we dined-out mostly). I’m sure prices in the area have gone up substantially since our visit, but this stay was very reasonable at the time (again, the aftermath of Hurricane Maria may have influenced the low prices at the time).
When I started planning a vacation to Puerto Rico, I wanted to be sure that we were staying somewhere that was both fun and safe. San Juan certainly has some sketchy neighborhoods and areas that you’ll want to avoid, but we never felt out-of-place while in Condado. Condado is a reasonably safe area that caters to tourists and locals. You’ll find some great local markets, restaurants, casinos, and some of the name-brand hotel chains in this area.
Our Stay in Luquillo, Puerto Rico
For the second half of our Puerto Rico vacation, we stayed in another high-rise studio apartment near the beach in the town of Luquillo. Our apartment was in building 2 of the Playa Azul complex. The newly-renovated apartment had an oversized, expansive balcony with spectacular views out to the ocean. It was nice to have the kitchen and washer and dryer in the unit. We did experience one day where the power went out for about six hours during the day. Puerto Rico’s power grid is held together with duct tape and chewing gum, so we weren’t too surprised when this happened (and it wasn’t really a big deal for us).
Luquillo is about an hour drive southeast of San Juan (we took an Uber back to the airport to rent a car for our time outside of San Juan).
Packing List: What to Pack for Your Puerto Rico Vacation
When planning a Puerto Rico vacation, here are some key items that you will want to consider packing:
- Lightweight, breathable, quick-dry travel clothing
- Comfortable walking shoes (I took my Hoka’s)
- Hiking / All-terrain shoes (if you plan to do any hiking)
- Hat(s)
- Travel Fan! An absolute must on our Puerto Rico vacation!
- Packable travel backpack/daypack (we’ve used these many times)
- Water shoes
- Sunscreen (the sun can be brutal)
- Quick-drying, Travel Beach Towels
- Pop-up Beach Tent (great for the sun and the wind)
- Sunglasses
- Money belt or front-pocket wallet
- Backup battery (we like these with the built-in cords)
Planning a Vacation to Puerto Rico: Our Travel Itinerary
Below is the TripIt travel plan / itinerary that we used when planning a vacation to Puerto Rico. You can use it to plan a Puerto Rico vacation that you’ll never forget!
Apr 6, 2018 | |
5:20 AM Flight: XXX to MCO
Southwest Airlines 2066
8:50 AM Arrive Orlando (MCO) |
Apr 6, 2018 | |
9:25 AM Flight: MCO to SJU
Southwest Airlines 489
12:05 PM Arrive San Juan (SJU) |
Apr 6, 2018 | |
1:00 PM Check in Ashford Imperial Ashford Ave 1302 Condado, San Juan, PR 00907 |
Apr 6, 2018 | |
2:00 PM SuperMax De Diego SuperMax De Diego, Avenida José de Diego, San Juan, Puerto Rico |
Apr 6, 2018 | |
3:00 PM La Ventana al Mar Park la ventana al mar park 1054 Ashford Avenue, San Juan 00907, Puerto Rico Until Apr 6, 2018 3:45 PM |
Apr 6, 2018 | |
4:00 PM Ben & Jerry’s 1049 Ashford Ave, San Juan, PR 00907 |
Apr 6, 2018 | |
5:45 PM Tacozón 1300-1312 Avenida Doctor Ashford, San Juan, 00907, Puerto Rico |
Apr 6, 2018 | |
7:00 PM Bar Gitano 1302 Avenida Doctor Ashford, San Juan, 00907, Puerto Rico |
Apr 7, 2018 | |
8:00 AM Freshmart Condado Av. Magdalena, San Juan, 00907, Puerto Rico |
Apr 7, 2018 | |
10:00 AM Condado Beach Condado Beach Condado Beach, San Juan, Puerto Rico Until Apr 7, 2018 1:00 PM |
Apr 7, 2018 | |
12:00 PM 1950 Condado – Puerto Rican Cuisine 1210 Avenida Doctor Ashford, San Juan, 00907, Puerto Rico |
Apr 7, 2018 | |
6:30 PM Marmalade Restaurant & Wine Bar 317 Fortaleza Street, Old San Juan, PR 00901 |
Apr 8, 2018 | |
8:15 AM Activity null Until Apr 8, 2018 8:30 AM |
Apr 8, 2018 | |
9:00 AM Castillo San Felipe del Morro Castillo San Felipe del Morro Ballajá, San Juan, 00926, Puerto Rico Until Apr 8, 2018 10:00 AM |
Apr 8, 2018 | |
10:30 AM Walk Calle del Cristo Walk calle del cristo Calle del Cristo, San Juan, Puerto Rico Until Apr 8, 2018 10:45 AM |
Apr 8, 2018 | |
11:00 AM San Juan Gate San Juan Gate Cll Caleta De San Juan, San Juan, 00901, Puerto Rico Until Apr 8, 2018 11:30 PM |
Apr 8, 2018 | |
11:30 AM Paseo de la Princesa Paseo de la Princesa 54 Calle Fortaleza, San Juan, 00901, Puerto Rico Until Apr 8, 2018 12:00 PM |
Apr 8, 2018 | |
12:00 PM Verde Mesa 107 Calle Tetuan Esq San Jose, San Juan, 00901, Puerto Rico |
Apr 8, 2018 | |
12:30 PM Santaella 219 Cll Canals, San Juan, PR 00907 |
Apr 8, 2018 | |
1:10 PM The Butterfly People The Butterfly People 257 Calle Dr La Cruz, Viejo San Juan, PR 00901 Until Apr 8, 2018 2:30 PM |
Apr 8, 2018 | |
1:30 PM Puerto Rican Art & Crafts Puerto Rican Art & Crafts 204 Calle Fortaleza, San Juan, 00901, Puerto Rico Until Apr 8, 2018 2:00 PM |
Apr 8, 2018 | |
2:10 PM Casa Cortés ChocoBar 210 Calle San Francisco, San Juan, 00901, Puerto Rico |
Apr 8, 2018 | |
2:40 PM Borinquen Discount Souvenirs Borinquen Discount Souvenirs 303 Calle Fortaleza, San Juan, 00901, Puerto Rico Until Apr 8, 2018 3:00 PM |
Apr 8, 2018 | |
3:00 PM Plaza de la Barandilla Plaza de la Barandilla 151 Calle Tanca, San Juan, Puerto Rico Until Apr 8, 2018 3:30 PM |
Apr 8, 2018 | |
3:45 PM Plaza de Colon Plaza de Colón 208 Calle O’Donnell, San Juan, Puerto Rico Until Apr 8, 2018 4:20 PM |
Apr 8, 2018 | |
4:00 PM Capilla del Santo Cristo Capilla del Santo Cristo de la Salud San Juan, 00901, Puerto Rico Until Apr 8, 2018 4:15 PM |
Apr 8, 2018 | |
4:25 PM Haitian Gallery Haitian Gallery 367 Calle Fortaleza, San Juan, 00901, Puerto Rico Until Apr 8, 2018 4:40 PM |
Apr 8, 2018 | |
5:00 PM Punto de Vista 307 Calle Fortaleza, San Juan, 00901, Puerto Rico |
Apr 8, 2018 | |
5:45 PM Barrachina 104 Fortaleza Street, San Juan, PR 00901 |
Apr 8, 2018 | |
7:00 PM Nuyorican Cafe 312 Calle San Francisco, San Juan, 00901, Puerto Rico |
Apr 8, 2018 | |
9:00 PM Stellaris Casino San Juan Marriott Resort & Stellaris Casino 1309 Ashford Avenue, San Juan, 00907, Puerto Rico Until Apr 8, 2018 11:00 PM |
Apr 9, 2018 | |
8:00 AM Pinky’s 1122, 1110 Avenida Doctor Ashford, San Juan, 00907, Puerto Rico |
Apr 9, 2018 | |
10:00 AM Botanical Gardens Botanical Gardens Visitor Parking Cll Juan Ponce De Leon, San Juan, 00926, Puerto Rico Until Apr 9, 2018 12:00 PM |
Apr 9, 2018 | |
7:30 PM YerbaBuena 1350 Ashford Ave, San Juan, PR 00907 |
Apr 10, 2018 | |
9:00 AM Check out Ashford Imperial Ashford Ave 1302 Condado, San Juan, PR 00907 |
Apr 10, 2018 | |
1:00 PM Pick up Dollar Car Rental 10030 Calle Marginal, Carolina, 00979, Puerto Rico +1 787-791-5500 |
Apr 10, 2018 | |
1:00 PM Walmart Walmart 150 Carr. 940 Ste 180, Fajardo, PR 00738, Puerto Rico Until Apr 10, 2018 2:00 PM |
Apr 10, 2018 | |
3:00 PM Check in Airbnb Ocean Dr Playa Azul Condo, Tower 2-805, Luquillo, Luquillo 00773, Puerto Rico
8 Jewel Luquillo |
Apr 10, 2018 | |
3:00 PM Check in Airbnb Ocean Dr Playa Azul Condo, Tower 2-805, Luquillo, Luquillo 00773, Puerto Rico
8 Jewel Luquillo Beachfront |
Apr 10, 2018 | |
7:00 PM The Brass Cactus PR-193, Luquillo Beach, Luquillo 00773, Puerto Rico |
Apr 11, 2018 | |
7:00 AM El Yunque El Yunque National Forest – El Portal Visitor Center PR-191, Río Grande, 00745, Puerto Rico Until Apr 11, 2018 2:00 PM |
Apr 11, 2018 | |
9:00 AM Angelito Trail Angelito Trail PR-988, Luquillo, 00773, Puerto Rico Until Apr 11, 2018 11:00 AM |
Apr 11, 2018 | |
12:00 PM Lluvia PR-955, Palmer, Río Grande 00745, Puerto Rico |
Apr 11, 2018 | |
1:00 PM Las Paylas Las Paylas PR-983, Luquillo, Puerto Rico Until Apr 11, 2018 2:00 PM |
Apr 11, 2018 | |
7:00 PM La Parrilla Kiosko 2 PR-193, Luquillo, 00773, Puerto Rico |
Apr 12, 2018 | |
8:00 AM The House of Coffee & Bike Rental Luquillo, 00773, Puerto Rico |
Apr 12, 2018 | |
5:45 PM Bioluminescent Bay Bio Bay Kayaks 00738, Fajardo 00738, Puerto Rico Until Apr 12, 2018 8:45 PM |
Apr 13, 2018 | |
9:00 AM Carabali Park 2hr ATV Tour Carabalí Carabalí Rainforest Park, Luquillo 00745, Puerto Rico Until Apr 13, 2018 12:00 PM |
Apr 13, 2018 | |
11:00 AM Playa La Monserrate Balneario La Monserrate (Playa Luquillo) Cll Herminio Diaz Navarro, Luquillo, 00773, Puerto Rico Until Apr 13, 2018 2:00 PM |
Apr 13, 2018 | |
7:00 PM Boardrider’s Surf Bar and Grill 25 Calle Veve Calzada, Calle Herminio Diaz Navarro, Luquillo, PR 00773 |
Apr 14, 2018 | |
12:00 PM Check out Airbnb Ocean Dr Playa Azul Condo, Tower 2-805, Luquillo, Luquillo 00773, Puerto Rico
8 Jewel Luquillo |
Apr 14, 2018 | |
12:00 PM Check out Airbnb Ocean Dr Playa Azul Condo, Tower 2-805, Luquillo, Luquillo 00773, Puerto Rico
8 Jewel Luquillo Beachfront |
Apr 14, 2018 | |
1:00 PM Drop off Dollar Car Rental 10030 Calle Marginal, Carolina, 00979, Puerto Rico +1 787-791-5500 |
Apr 14, 2018 | |
3:25 PM Flight: SJU to XXX
Southwest Airlines 4109
7:30 PM Arrive XXX (XXX) |
Enjoy your Puerto Rico vacation! I’d love to hear about it in the comments! If you have any questions, just ask!