The Whirlwind Itinerary from Our Trip to Puerto Rico
It was a very cold and rainy February day in 2022 in Michigan when I spotted the flight deal. I was tired of cold, tired of rain and ready for COVID to be over.
And I remembered that one of my students at the Denver school where I taught English to foreign business executives and university students had raved about the warm, beautiful beaches and friendly faces of his homeland.
So it didn’t require a lot of thought. I was taking a trip to Puerto Rico.
A little background on the Island of Enchantment, in case you’re fuzzy on the details, as I was.
According to Puerto Rico Report, “Puerto Rico is a territory of the United States. It became a U.S. territory in 1898, when it was acquired from Spain after the Spanish-American War. With approximately 3.4 million residents, Puerto Rico is the most highly populated of all United States territories. People who are born in Puerto Rico are U.S. citizens.”
Puerto Rico is 100 miles by 35 miles. More than a million of its residents live in the greater San Juan metropolitan area alone. As the National Park Service explains in Things to Know Before You Come, “It is a vibrant, modern, bilingual, multicultural society, one that has been molded by Spanish, African, Aboriginal and American influences.”
We were going to start our trip to Puerto Rico in Old San Juan, the oldest city in America and home to blue cobblestone streets, pastel-colored colonial architecture, military forts and a busy cruise port.
Heather’s Arrival in Puerto Rico
[H] I’m going to start off by saying, learn how to use Google Flights! By playing with the dates a little, I was able to fly out of my hometown, with a layover in Charlotte, North Carolina, for just slightly more than driving to Chicago and taking a direct flight to Puerto Rico. This is how I ended up arriving a day earlier than Julianne and staying a day later.
I arrived at San Juan airport around 10:30 p.m. and headed straight to the taxi stand. You can Uber from the airport easily; there is a ride-share waiting area in sections 16–19 outside terminal B. However, since I couldn’t find that information online before I went, I took a taxi for $17. When you go to the taxi stand, give them the address; they will tell you how much it will cost, and they tell the driver where you are going. Bring cash! It was an easy process.
If you want details on transportation and accommodations and general helpful tips, read our 12 tips for Visiting Puerto Rico.
El Yunque National Forest, Day 0, Part 1
After picking up my rental car I made a last-minute decision to visit El Yunque, and I’m so glad I did! It’s the only national park that is a tropical rainforest in the United States.
The drive to El Yunque is along a toll road through some soft hilly spaces. I missed the turnoff by a few blocks — it’s not super well marked so keep your eyes peeled.
Julianne is a mountain girl. I live in Indiana. It’s flat here. Anything more than a 2% grade, and I will be gripping the steering wheel. The drive into the park is a narrow winding road that had me tense, but not panicked. I called that a good start!
The visitor’s center is structurally stunning and fits the landscape nicely. Very rarely have I stopped to take pictures of a visitors center when there is a rainforest surrounding me!
After taking in the breathtaking view from the platform, I went to see what I could hike right from there. There is a short loop that takes you briefly into the tropical rainforest, and there are many plants to be in awe of. After I walked around the loop, I went back to the visitors center, refilled my water, used the restroom and stopped to ask some questions about what I should see.
There are several trails you can hike in El Yunque, but most require you to get a pass ahead of time, and several were closed. Visit the official park website for up-to-date information. There are a lot of tours, but you can also go to the La Mina recreation area for the waterfalls without taking a tour; you just have to purchase a pass from the park ahead of time, and you can drive yourself there.
Since I had not reserved anything, there were two options. I could take the road up to the Yokahu Observation Tower or a drive down to Rio Mameyes. Of course, I chose down.
I drove to the Angelito Trailhead to start my journey to the river. Parking can be a challenge. I just found a spot where it looked like my car wouldn’t sink too far into the dirt and went for it!
What I loved about this experience was that despite all the cars, it didn’t feel overly busy. Also, because it’s about a 15-minute hike down to the river, the tour buses and vans were stopping at another point up the road for a quick river dip and not at this trailhead.
The trail is an easy-to-moderate hike, depending on your abilities.
The river is wide and clear and full of rocks, from foot-sized stepping stones to huge boulders. When given the opportunity to play in the water, I’m going to take it. I wandered up and down the river, not venturing too far. I wanted to be in sight of others but far enough to get away from the little gatherings of families and friends enjoying their picnics and time together. I stopped and ate an apple in the sunshine — and put the core back in my bag to pack out — and let the sounds and peace wash over me while the river rushed over my feet. It was pure bliss.
I needed to get back to Old San Juan and check into our apartment, so after I had my fill of playing — and almost biffed it jumping my way back to shore — I hiked back up and out, got in my car and made my way back to Old San Juan.
We had booked an apartment through Booking.com, and they had recommended we park at La Puntilla Parking Lot. The traffic to get into the lot at around 2 p.m. was intense. I waited in line for around 45 minutes. The cost is $3 per day (at least on the day I was there), and I pulled in looking for a spot. I was surprised by how easily I found one after that long wait!
This is where you need to pay attention: I had parked in the government employee section of the parking lot! There were signs that I just didn’t see. It wasn’t until day 2 when we were leaving for Fajardo that we discovered that our rental car was roped in by orange barrels and chains. That’s when I realized my error. After Julianne paid and tried with her not-quite-intermediate Spanish to talk to the parking lot attendant, we were basically told too bad. Fortunately, the chains were not locked, so we untied them from the barrels, moved them, moved our car out and then put them back. WHEW!
Old San Juan is a stunning cacophony of sights and sounds. Cars, people, music! If lively and energetic is your vibe, you’ll love it. It’s densely packed with tourists, even in April, which isn’t exactly high season. I wandered the streets taking it in, snapping pictures nonstop until I finally settled into a seat outside a restaurant serving Mexican food. Honestly, it had an open table, I was hungry, and I wanted an ice-cold Medalla Light, Puerto Rico’s most famous beer.
With that, I was ready to call it a day and waited anxiously for Julianne’s arrival!
Places I Visited
Dinner
El Parasno 251 Calle del Cristo
Accommodations
Old San Juan Apartments, 253 Calle Tanca
(They have 15 apartments that they manage so you need to confirm the address of your actual accommodations.)
Groceries
SuperMax
201 Calle de la Cruz
Julianne’s Arrival in Puerto Rico.
[J] I arrived late in the evening at Luis Muñoz Marín International Airport (SJU) from Denver via Dallas. I took a taxi to our Airbnb in downtown Old San Juan, during which the elderly driver somehow mistook my haphazard Spanish to mean that I lived there and kept asking me for directions, though he had the address. He was hard of hearing, and the Puerto Rican music in his car was loud (perhaps a correlation there?), so I tried to show him on my phone as best I could.
When we got close, he stopped in the middle of the street and hopped out to grab my luggage. I fumbled with cash on the curb, deciding it would be too slow to try to use a credit card. I dropped some bills, which he valiantly chased into the dark while other drivers waited in the street and I counted out U.S. dollars. (The perks of traveling in the States!) He handed me the wayward bills, I gave him some money, and he very solemnly presented me with a cough drop. Whether he thought I dropped that too, or he offered it as a “candy” treat, I’ll never know. He hopped back into his cab and drove off, tailgate still wide open. I set off to find Heather.
Our Airbnb was rustic and romantic. These could also be euphemisms for strange and a little dirty. It had gorgeous wooden doors in the front bedroom leading to a balcony overlooking the street, and timbers running the length of the ceiling. It also had narrow stairs up to the first level and rickety stairs to the loft, where there were two beds and a ceiling so low it had caution tape in parts. There were circular stairs leading from one bathroom to what looked like a fire escape off in the vast distance overhead. There was a fair amount of hair that didn’t belong to us.
But most noticeable was the noise, during the day pumping out from speakers outside the shops below and next door, and emanating from noisy cars and partiers all night long. We quickly learned during our trip to Puerto Rico that this isn’t unusual. My Apple Watch kept giving me noise notifications, as if I could do anything about it. We didn’t sleep much at all. But the interior design was very pretty, and the location was killer.
Old San Juan, Day 1
My first full day of our trip to Puerto Rico, a Sunday, was an immersion into the riot of color and sound in old San Juan. After a stop in a flower-filled plaza of blue cobblestones to hide from a fast but furious rainstorm and seek out coffee while a man sweeping the steps blasted screamo music, we walked to the Castillo San Cristobal, built in 1634 to defend against attacks from land.
It’s part of a fortification system that includes Fort San Felipe del Morro, Fort San Cristobal, Fort San Juan de la Cruz and several miles of old city wall. The oldest European construction in the United States, these forts allowed Spain to guard and control their interests in the Caribbean. Parts were used as recently as World War II. Today the grounds are a World Heritage Site and managed by the National Park Service.
At San Cristobal, be sure to visit the overlook for the Devil’s Sentry Box or the “Garita del Diablo,” from which, according to legends, soldiers mysteriously disappeared. Enjoy the views of the highest points of old San Juan, see how the soldiers use to live, scout out the tunnels, sentry boxes and WWII lookouts, and learn from the exhibitions explaining the history of these forts.
After we left San Cristobal, we stopped for a lively lunch on our walk along the sea, enticed by the music, the colorful walls and the happy flags waving over a side street. The kind server at Palmas El Rincón De Paco allowed me to practice my Spanish. I had a Medalla Light (“Puerto Rican Gatorade,” we were told) and more seafood empanadillas than I could eat. Delicioso!
Then we strolled to Castillo San Felipe del Morro, built in the 1500s to defend against attacks by sea. It was a kite-flying kind of day, with blue skies, blustery gusts and a blazing sun. We needed gallons of water—and some real Gatorade too!
We missed the Santa María Magdalena de Pazzis cemetery, established in the 19th century and tucked under the walls of El Morro, by 20 minutes. (According to the Discover Puerto Rico website, which was a great help in planning our trip to Puerto Rico, it’s always open; but that day the gates closed at 3 p.m.) That may be a good thing, because I can spend hours reading stories of families and lives in a cemetery. It was built on the sea so that the dead could easily begin their journey to “the great beyond.”
After leaving the Castillo San Felipe de Morro, we wandered the stunning streets of Old Town, including the colorful Calle Fortaleza, stopping for refreshments when we spotted a luxurious little bar with two stools available.
We learned that Paloma is not just a cocktail, but also the word “pigeon” in Spanish. We managed to pass through the park without getting tagged by its residents.
And after a few stops so that I could shop for pajamas (I’m the only person who could travel with 48 pounds of stuff, including scuba gear, and still forget a whole clothing category), we went back to our Airbnb for yet another shower (it was so hot and windy) and walked to dinner by the sea. One final moment at a bar with vintage vibes, beautiful beverages and incredible service, and we were done for day one together of our trip to Puerto Rico.
Places We Visited in San Juan
Castillos
San Juan National Historic Site
501 Norzagaray Street
9 a.m.–5 p.m. daily
$10 or National Parks Pass
Lunch
Calle de San Sebastián 281
Cemetary
Santa María Magdalena de Pazzis
FV9J+R4R, Cemetery St.
Drinks
251C Calle del Cristo
Chapel
Capilla del Santo Cristo de la Salud
1 Calle del Cristo
Park
FV7J+HWR, Calle Tetuán
Dinner
Calle Comercio — Plaza Darsenas
Drinks
261 Calle Tetuán
Places We Didn’t Get to in San Juan
151 Calle del Cristo
8:30 a.m.-5:30 p.m.
It’s the second oldest church in the Western Hemisphere and the oldest church on U.S. soil. The church’s presence dates to 1521 and the earliest beginnings of the Spanish colonization of the island. The current structure dates to 1540.
54 Calle Fortaleza
8 a.m.–4:30 p.m.
“The Fortress” was completed in 1540. In 1846, it was remodeled and converted to the governor’s house. Guided walking tours are offered Monday through Friday between 8:15 a.m. and 3:30 p.m. The 30-minute tour includes the gardens and inside the building when the government is not in session. Photo ID is required for everyone 21 years of age or older. As a government building it’s subject to closures without warning.
Fajardo, Day 2
The first half of the day was devoted to travel and work. With Heather as our fearless road master, we drove roughly an hour down to Fajardo, a small town on the eastern side of Puerto Rico.
We were spending the night there to go on a bioluminescent kayak tour that evening and catch the ferry the next morning. Bio bay tours are a huge draw for a trip to Puerto Rico.
We drove around a bit and found a cute restaurant, Pescaito, where we could sample some local mofongo (a hearty dish of mashed plantains with various toppings, such as vegetables or chicken and mushrooms) and snag some laptop time.
Then we found a little beach up the road that wasn’t plagued by the stench of sargassum (more on that later) and put our toes in the sand.
I tried snorkeling, but visibility was zip. I only saw some sort of clear-looking fish at the start. After an hour we made our way to our Airbnb to gather our things for our evening adventure.
We changed into water shorts, water shoes and water-resistant jackets. It was still warm out, but we anticipated some splashing and some mosquitoes.
It was time to face the sargassum. Never heard of it? No?
We hadn’t either until Heather and I took a tour of Laguna Grande Bioluminescent Bay near Fajardo. Hint: We smelled it before we saw it.
This unfortunate-smelling naturally occurring phenomenon is increasingly common thanks to climate change and an unfortunate challenge for the tourist industry. Imagine the smell of a cattle stockyard. And not the happy cows kind. You sort of get used to it after a long while. Sort of. That and your olfactory senses just give up and enter into full retreat.
That being said, the tour of this stunning reserve was fantastic. Perhaps one of the highlights of our trip to Puerto Rico. We went with Puerto Rico Bio Bay Tours, and they went the extra mile to train newbies on kayaking skills and safety, and guide us out through the mangroves to the bay, one of just five in the world where the concentration of dinoflagellates is high enough to be regularly visible.
Those odd little microorganisms weren’t super visible the night we were there, but if you looked closely, you could see the sparkle. It was exciting — like having Disney princess wands for hands when you splashed the water.
Too, the sky, the birds, the mystery of the mangroves, the sunset…it was all simply gorgeous. And Heather and I learned that we are darn fine kayakers together.
We thought we’d celebrate our achievement with a beer at a super fun outdoor restaurant/bar, string lights and all, that we spotted tucked in the woods on our drive to the tour. But it was closed by the time we headed back to our (gloriously spotless, if slightly noisy) Airbnb. As was everything else. We toasted with Whopper Junior meals from Burger King instead.
Places We Visited in Fajardo
Lunch
8 Int Las Cabezas km 6, Fajardo
Tour
Fajardo to Vieques, Day 3
We were on the move again—this time to the stunning island of Vieques!
First we grabbed cafe con leche and los postres de Mami at the sweetest little cafe run by a mother and son. Someone had etched a floral design in pencil across the entire wall, mirroring the riot of flowers and herbs on the patio outside. The garden alone was worth the stop.
Then we navigated the ferry system, including off-site parking for our rental car and the multi-step boarding process. We read up on all of this ahead of time, and we still found additional tips to share with you. We sailed east for an hour from the port at Ceiba.
Upon arriving at Vieques, it was a ten-minute walk (all uphill with my massive suitcase) to the rental shop where we picked up our UTV, our means of transportation for our two days on the island. Fortunately there were oases of brilliant color to stop and photograph along the way. A trip to Puerto Rico is a photographer’s dream.
The roads on the island are narrow and bumpy, traffic signs are sporadic, the locals with cars drive fast, and there are wild horses and chickens roaming about. But it was really kinda marvelous. Wind in our hair, a wild ride to the other side of the island. I probably had dust in my teeth from smiling so much.
We made our way to the La Esperanza side of Vieques in our UTV and checked into our hotel, El Blok, famed for its shadow-casting concrete lattice exterior. We were disappointed to learn that the much-hyped hotel restaurant and bars were closed (low season?), but this gave us a reason to wander down the road to Duffy’s Daq Shack for dinner. It’s everything that you want an island food joint to be, including that sometimes elusive quality—clean.
After delicious refreshments, Heather and I walked further down the road and meandered down paths onto random beaches, where we were captivated by shells, ocean swells and the setting sun, which was somehow softly mellow and gloriously vibrant at the same time. I took too many photos, but now you have some nice choices for a new screensaver. It was really as gorgeous as it looks. More so.
We closed out our very long day early in El Blok’s rooftop hot tub with local beers we’d purchased at a little market in San Juan. You could have pinched me and I still wouldn’t have believed it was all real.
Stops in Ceiba and Vieques
Breakfast
Cafeto 144
144 Av. Lauro Piñero, Ceiba
346 Antonio G. Mellado St., Local #3, Vieques
158 Calle Flamboyan, Vieques
Dinner
140 Calle Flamboyan, Vieques
Vieques, Day 3
I drove the UTV 30 minutes through the middle of Vieques, over skinny loops of hilly roads, past homes, chickens, wild horses, tractors and some very fast cars. It would have been the bee’s knees but for those cars, and I was pretty proud of reaching Mosquito Pier unscathed.
I was there for my first scuba dive since getting certified in cold and murky Grand Traverse Bay in Michigan last summer. This was one of the most nerve-wracking parts of our trip to Puerto Rico for me, and I was super intimidated. But our dive master, Laura, was clear on safety instructions, diligent on setup, and warm and welcoming. I struggled with the typical newbie neutral buoyancy issues, so at one point she even held my hand to keep me well-positioned to view the sea turtles, the zebra fish, the fat starfish stuck to the ocean floor, and the myriad other dazzling sea creatures floating about under the pier. It was one of the coolest things I’ve ever done.
Scuba diving is on the verge of scary for me, which is why I do it. (That and to see amazing marine life!) So after safely making my way back to the other side of the island, it was time for a beer (actually two!) with Heather.
Another delicious round of refreshments at Duffy’s and we hopped back on the UTV to find Playa Negra, the black sand beach. It was a short walk through scrubby muddy jungle, which might explain why there were so few people in this magical little spot. The water was filled with bits of pine and gold-flecked mineral particulate that sparkled in the sun and collected in the creases of our suits, so we rinsed off before our evening’s bio bay tour.
Little did we know that any level of clean was unnecessary.
That night we joined a tour to see one of the world’s most consistently brilliant bioluminescent bays, Mosquito Bay, recognized by the Guinness Book of World Records and a must-see during a trip to Puerto Rico. It was nothing like we expected, and all we could do was laugh.
The sargassum here was again in full effect. Its stench was stomach-turning. And I have a very strong stomach.
The mud that we had to wade through to get into the sargassum and then into our canoe was deep and black under thick dark water, viscous and slimy. The effect was of wading into a soup of manure. I can hardly type these words without feeling a bit nauseated again.
Add to this narrow space a crowd of confused tourists from multiple groups. Tour guides yelling at everyone to hurry. And spotlights that would make prison inmates uncomfortable.
We managed to get into our clear-bottomed boat without retching or tipping. But it’s a contraption too wide and short for successful paddling by two. Heather and I are good kayakers, but we couldn’t help knocking oars.
Others in our group had clearly never paddled any kind of boat before, and our guides offered no instruction. So we endured a bit of kayak bumper car action and, at one point, a father and daughter, heads down, paddling full bore right at our canoe. We had to take desperate evasive action.
Our guide, meanwhile, was far off in the dark distance, yelling aimlessly over and over to our group: Taino! Taino! Are we having fun yet?
Yes, we were having fun. Though not in the way he intended. When you’re at the gates of a smelly, dark hell, you can only laugh.
And yet the bioluminescence was stunning. Rivers upon rivers of micro-stars running under our clear boat, while real stars blazed overhead. Video did nothing, so I fixed this once-in-a-lifetime moment in my memory.
After a rinse in the hotel’s outdoor shower, then a walk straight into the shower of our room fully clothed, we slowly began to peel off layers of muck. The wet and feral-smelling clothes went onto the balcony for sterilization another day.
And we went down to Lazy Jacks for some rum.
Stops in Vieques
61A Calle Orquideas, Bo Esperanza, Vieques
Vieques and San Juan, Day 5
Our trip to Puerto Rico was winding down, and this was our last morning on the island of Vieques, so we toured its greatest hits.
First we visited Sun Bay Beach, a broad and nearly deserted expanse of sand with curly-cue palms and tide pools teeming with life. If we had more time, I’d have loved to have pulled out my snorkeling gear—this beach is said to be a great spot for it. A long rest with a book sounded so inviting, but we had more to see before we left.
We took the UTV over to Vieques National Wildlife Reserve. We skipped the hikes—we’d had our fill of mud and such by then—and went straight to Caracas Beach, a stretch of bright white sand tucked between rock outcroppings where the brilliant blue sea rolled in. It was every bit of what you envision when you think of the Caribbean.
It was time to make our way back to town. Of course, being a nerd I had to throw the UTV into park at a stop sign before we left the reserve and hop out with my Seek app to confirm that yes, those odd plants were giant milkweed. We wondered whether giant monarchs come to visit?
We filled up the tank at the one gas station in town—a whopping $3.44—and bought some local beverages for our wait for the ferry. The proprietor of Scooter Rentals was out to lunch, according to a sign on the door, so I left my massive suitcase in the back end of the mule—who would want to try to steal that 50-pound beast on this sleepy little island?—and we wandered a few shops before walking back to the ferry.
We spent our last hour watching the waves and visiting with the roosters and hens before leaving our island paradise.
Our return to Ceiba by ferry was uneventful. We took a crowded shuttle a mile down the road to the parking lot, fetched the car and began the hour-plus drive back to San Juan, with a stop at Walgreens on the way so that Heather could pick up some cold medications. She began to feel sick midway through our trip to Puerto Rico.
Driving in San Juan is always tricky, but even more so at rush hour. It took Heather’s Super Mario Kart skills, my occasionally helpful observations and my trusty Apple Maps to get us back safely.
Our hotel in the Condado section of San Juan was a nice surprise—not much anticipated, but incredibly clean and cute, offering great service and well situated.
After a hectic drive and a busy day, we decided to eat dinner at the hotel. Best decision ever—the food and service really were impeccable.
We wandered the neighborhood after dinner and stumbled upon a magical sight—the beach alight with a red glow, designed to avoid confusing the sea turtles making their way across the sand at night.
Amid the roar of the surf, the twinkle of lights in the distance and the dark clouds overhead, we paused and soaked in the atmosphere. It was a quiet and thoughtful evening amid a bright, noisy, lively, lovely trip to Puerto Rico.
Vieques National Wildlife Refuge
4JR4+QXF, State Rd 997 km 3.2, Vieques
1853 McLeary Ave, San Juan
Dinner
Dulcesalado
(inside the Tropica Beach Hotel)
Heather, San Juan, Day 6
Sadly, it was time to take Julianne to the airport for her flight and return the rental car there.
I returned our rental car and made my way to the ride-share pickup across the street outside arrivals. The rideshare is clearly marked on pillars along the road outside the airport. I was the only passenger waiting for an Uber at 9 a.m., and he arrived quickly. Soon I was back at the hotel.
This was a Friday and another work day for me, so I stopped at the bakery attached to the hotel and grabbed a cafe latte and a croissant and made my way up to the room to work.
I later moved around, enjoying the different spaces of the hotel, the courtyard and the cozy lobby until the call of the beach was too strong. The hotel has chairs and towels available for guests, so I graciously accepted both and a complimentary bottle of water and made my way to the beach.
The website says the hotel is “steps from the beach,” which paints a mental picture of being on the beach. In reality, it is a city block away — not far by any means, but good to note if you are looking at beach hotels.
The beach is clean, wide and has lots of activity. I like being around other people when I’m on my own, and this Friday afternoon was bustling with activity. By far, my absolute favorite part was watching the dozens of kite surfers! There were so many out on the water, and I was mesmerized. I have never attempted kite surfing; after watching all of these people, it looks like so much fun, and it also looks really hard! They would zip out away from shore, catch the wind, surf toward shore and then do flips and jumps along the way in. I sat there for two hours just watching and taking pictures. It was so enjoyable!
I wrapped up some work and then wandered back down to the hotel restaurant for dinner. Julianne and I had such a great meal the night before that I figured I’d treat myself to one last fancy dinner before heading home.
I had a wonderful meal that included watermelon sushi (vegan), a sopapilla-inspired cheesecake with ice cream and a very dirty gin martini, three olives. Ok, I might have had two martinis. I was in bed by 9 p.m., packed and ready for my 7 a.m. flight home.
Dinner – Dulcesalado
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