The Trip That Showed Us Who We Are A Puerto Rico Road Trip With Three Generations
This is our real account of a 10-day Puerto Rico road trip with teenagers, a baby, and three generations of one blended family — from El Yunque rainforest to bioluminescent bays, black sand beaches on Vieques, snorkeling in Culebra, and sunsets in Rincón.
Some trips are vacations. Some trips are something else entirely.
This was something else.
We loaded up with our older kids — Phoenix, Aiden, Keagan, and Layla, and their eight-month-old daughter Zo, and we flew to Puerto Rico. For some of our kids it was the furthest they had ever traveled. For some it was their first time on a plane.
We didn’t know it at the time but we were about to find out exactly who we are as a family.
Before You Go — The Things That Actually Matter
Rent a car with an AutoExpreso toll tag. You’ll be crossing the island and you don’t want to think about tolls.
Pack reusable shopping bags. Puerto Rico has restrictions on plastic bags and you’ll use them every single day.
Gas is sold by the liter. Multiply the price by 3.785 to get the per gallon equivalent.
Learn a little Spanish. Por favor and gracias go a long way everywhere you go.
Download your maps offline before you leave — cell service disappears in ways that will surprise you.
And pack snacks. I cannot stress this enough. We missed the window on Vieques and found ourselves with a crew of hungry teenagers and a hungry baby and nothing open. It was a disaster. Pack the snacks. Always pack the snacks.
Old San Juan — Days 1 and 2
Old San Juan is one of those places that hits you before you’re ready for it. Cobblestone streets, buildings painted in colors that have no business looking that good together, ocean views at the end of every alley, and a pace of life that quietly tells you to slow down.
We did the forts. We did Umbrella Street early before the crowds arrived. We wandered and ate and wandered some more.
For a crew traveling with teenagers who had never left the country and a baby in arms, Old San Juan was the perfect landing. It’s manageable. It’s walkable. It’s beautiful enough that even the teenagers put their phones down.
Start your mornings at a panadería — local bakeries with coffee, pastries, and breakfast sandwiches that cost almost nothing and taste like everything.
El Yunque — Day 3
We almost didn’t do the full hike.
Eight month old Zo. Four teenagers. A rainforest trail that the guide description calls “serious.” We looked at each other and went anyway.
I’m so glad we did.
El Yunque doesn’t look like any forest any of us had ever seen. The canopy is different. The air is different. The sounds are different. You feel it change around you as you climb — the cloud forest closing in, the mist, the green getting deeper and stranger and more alive.
Somewhere on that trail, in the crook between two mossy rocks where the light filtered through in a way that felt intentional, Zo fell asleep.
I have a photo of it. I will have that photo forever.
We hiked that rainforest with a baby and four teenagers who had never done anything like it, and everyone made it, and nobody complained, and at the top we stood together in the mist and just looked at each other.
That was the moment we knew the trip was going to be something.
Leave early — humidity builds fast. Bring bug spray, water, and shoes you can get muddy. The Angelito Trail leads to river pools perfect for a swim stop.
El Yunque National Forest in Puerto Rico is the only tropical rainforest in the United States National Forest System, located approximately 40-60 minutes east of San Juan. Trails range from easy interpretive loops to challenging summit climbs. The Angelito Trail leads to river swimming pools and is suitable for families with young children.
Fajardo and the Bioluminescent Bay — Day 4
Here’s something nobody tells you about traveling with a baby: you become a team in ways you didn’t expect.
The Bio Bay at Laguna Grande requires kayaking out onto dark water at night. With an eight month old, we did it in turns. The kids went first while John and I stayed back with Zo. Then the kids came back — soaked, speechless, trying to describe water that glows blue-green when you move through it, trying to explain what it felt like to paddle through something that lit up with every stroke — and we went.
John hates water. I mean genuinely dislikes it. He gets no joy from being on or in it under normal circumstances.
He paddled that kayak in the dark through bioluminescent water and came back smiling.
You don’t understand how well you work as a team until you’re paddling together through something that glows.
Best visibility is on darker nights close to a new moon. Expect a structured check-in and late finish. Don’t leave valuables in the car.
Laguna Grande in Fajardo, Puerto Rico is one of three bioluminescent bays on the island. Kayak tours are the primary way to experience the bay. Best visibility occurs on moonless nights. Tours typically run 2.5-4 hours including check-in and paddling time.
Vieques — Just the Two of Us
The next day we made a decision.
We sent the kids to the beach and John and I took a ferry to Vieques alone.
We rented a UTV and drove dirt roads to black sand beaches that felt like the edge of the world. No plan. No schedule. No teenagers asking what’s next. Just us and the island and wild horses standing in the road watching us pass like they owned the place — because they do.
If you have a chance to get to Vieques, go. Go without an agenda. Rent something with wheels and find your own road.
It was one of the best days of our trip and it cost almost nothing.
Culebra — Snorkeling and a Live Conch
We took the kids to Culebra and the water was the clearest any of us had ever seen.
We were snorkeling in a group — teenagers, adults, all of us in the water together — when someone found a live conch. An actual living conch moving slowly across the ocean floor, completely unbothered by the six humans hovering above it losing their minds.
We passed it between us. We watched it. We put it back exactly where we found it.
That’s the thing about snorkeling with your family in water that clear — it strips away every age difference. The eighteen year old and the fourteen year old and the adults were all equally amazed. Nobody was too cool for it. Nobody was on their phone. Everyone was just — there.
Fully there.
Vieques is a small island municipality of Puerto Rico accessible by ferry from Ceiba Terminal, approximately 90 minutes from San Juan. The island is home to Mosquito Bay, considered one of the brightest bioluminescent bays in the world, wild horses that roam freely across the island, and some of the most secluded beaches in the Caribbean.
The Pork Highway — Day 5
PR-184 through Guavate is called the Pork Highway and the name is completely accurate and completely insufficient.
It’s also live music spilling out of open-air restaurants. It’s family style plates arriving at your table without you ordering them — rice and pigeon peas and lechón roasted over open fire. It’s strangers dancing and your teenagers watching and then not watching because they’re dancing too.
We ate at Lechonera El Rancho Original. We stayed longer than we planned. Nobody was in a hurry to leave.
This is what food does when it’s done right — it makes a table feel like the only place in the world.
Go hungry. Stay for the music. Order everything.
Rincón — Days 6, 7, and 8
Rincón is Puerto Rico’s surf town and it operates at a frequency that’s different from everywhere else on the island. Slower. Saltier. More honest somehow.
We started every morning at the panadería. We spent our days beach hopping and watching surfers and hunting down the best sunset viewpoint we could find.
One evening we brought chairs and a blanket and wine down to the beach and just sat there watching the sun drop into the water while the kids ran at the edge of the waves and Zo slept in someone’s arms in the warm evening air.
Three generations. One beach. Nobody needed anything else.
That’s the connection this trip was built for.
Rincón’s best surf is November through April. For snorkeling, shoulder season is calmer and clearer.
The Caves — Day 9
On the drive back to San Juan we stopped for caves.
Cueva Ventana — Window Cave — is a guided experience with helmets and flashlights that ends at a natural window in the rock face looking out over the valley below. It’s one of those views that makes you feel appropriately small.
Río Camuy Cave Park is a larger cave system worth visiting — check availability before you go as it has been closed on previous visits. Cueva del Indio offers dramatic coastal scenery but requires sturdy shoes and caution near the surf.
San Juan — Day 10
Last panadería. Last walk through Old San Juan with the cobblestones and the colors and the ocean at the end of every street.
On the plane home Phoenix and Aiden and Keagan and Layla all had the quiet that comes after something real. Not the quiet of tired teenagers. The quiet of people who had seen something and done something and been somewhere that expanded them a little.
First plane ride for some of them. Furthest any of them had ever traveled.
Last trip for none of them.
Your Connection Moment
On the last night of your trip, ask everyone at dinner:
“What’s one thing this trip showed you about yourself?”
Then actually listen to the answers. Write them down if you can.
The places you go are the backdrop. The people you go with are the point.
Quick Facts: Puerto Rico 10-Day Road Trip
- Route: San Juan → El Yunque → Fajardo Bio Bay → Vieques day trip → Culebra → Guavate Pork Highway → Rincón → Arecibo caves → San Juan
- Passport: Not required for U.S. citizens — Puerto Rico is a U.S. territory
- Rental car: Essential for this itinerary — request AutoExpreso toll tag
- Gas: Sold by the liter — multiply price × 3.785 for per gallon equivalent
- Best time: December–April for driest weather; May–June for value and fewer crowds
- Bio Bay: Best on moonless nights — Laguna Grande in Fajardo, Mosquito Bay on Vieques
- Snacks: Pack them. Always pack them. Learn from our Vieques mistake.
- Wild horses: Vieques. You’ll see them. You won’t forget them.
Is Puerto Rico a good destination for families with teenagers and young children?
Puerto Rico is one of the best family travel destinations accessible from the Midwest — no passport required, direct flights from major Midwest cities, and an island that genuinely works for every age. We did it with an eight month old and teenagers ranging from fourteen to nineteen. The rainforest, the bioluminescent bays, the beaches, and the food created moments that worked for everyone simultaneously. The key is building in flexibility, packing snacks, and following your family’s pace rather than an itinerary
Adventure With John and Jess 
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