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Jun 8, 2021 // / Adventures

Adventuring with No Ceiling: Feeling Free in San Juan


Flying kites in San Juan

By KEEN Fan Kara Richardson Whitely

Being an adventurer isn’t always about hiking the highest mountains. For me, it’s about stepping out, inhabiting the spaces where, perhaps, people of my size aren’t often seen. Putting ourselves in places that we haven’t seen ourselves.

But I hadn’t done that in a while. The pandemic has had us all locked up at home and in small circles. Forgetting about or yearning for worlds beyond our four walls.

After a year, as a family, we decided it time to get out (safely). We booked a trip to Puerto Rico. It was close enough (a 3.5-hour flight from my home in New Jersey), but far enough, an island part of the United States that was also super careful about COVID-19. Just the right mix of adventure, chillax, and feeling safe in this new post-pandemic world.


I felt my soul smiling again. I felt my kids smiling again (even behind masks). In this first adventure out and about it was both terrifying and exhilarating to be out again.


And when you haven’t done something in a while – like travel. All things old were new again. Even packing was a joy. I got myself some new, fresh island-y things, shedding my sweatpants and cozy wear for sundresses and shorts. I made sure to include my new KEEN Astoria West sandals, since quality, versatile footwear is key as a 300-pound adventurer.

Exploring San Juan, Puerto Rico

We stayed in San Juan, which is anchored by “El Morro”, and was an anchor for our visit there. The San Juan National Historic Site, built by the Spanish, was once a place to keep people out. This fortress is now a National Park – and now it is for everyone. People come far and wide to explore to feel history beneath their feet and the majestic turquoise blue sea beyond its walls. To catch a glimpse of the colorful homes that extend beyond its walls and now call San Juan home.

There, as I walked, I found myself immersed in it all. Free and yet safe. Each footstep was in such a powerful push forward back into my life of adventure. All the while we carried kites to fly on the lawn, as thousands of people have done before us, a symbol of the being part of normalcy and joy or re-emerging.


It was the start of healing and reconnecting to who I was and how I will be in these days ahead.


But as soon as we left the gates of El Morro, there was a sudden downpour. We rushed down the long entrance and under the bridge of the dry moat. Instead of scrapping our plans, we used the cover of the bridge to assemble our kites and wait for the storm to pass.

The kids danced in the rain as we jumbled through simple yet stressful kite assembly instructions. In a few minutes, it was over. We climbed up the staircase back to the lawn and found our place on the lawn to raise them high and proud. Sometimes they darted dangerously close to us. Sometimes they didn’t want to fly. But when they did, they did so with grace and amazement.

Exploring El Morro in San Juan, Puerto Rico

I felt my soul smiling again. I felt my kids smiling again (even behind masks). In this first adventure out and about it was both terrifying and exhilarating to be out again.

It was the start of healing and reconnecting to who I was and how I will be in these days ahead. We strolled the streets of Old San Juan anew and ready for what’s to come, casting footprints so others can follow.


If you go: A few packing tips

• Bring two swimsuits so one is dry every day.
• Water shoes rule! KEEN Astoria West for city strolling and boat trips. I wore SOLR sandals just about everywhere else, including an El Yunque Rainforest adventure. My kiddos sported the Newport H2.
• Don't forget sunscreen and a great hat.
• We brought kites with us but you can also find them at the gift shop.
• No passport is required as Puerto Rico is a United States territory.
• We found @discoverpuertorico to be an incredible resource for any adventure you want to have on the island

Exploring El Morro in San Juan, Puerto Rico

Tags: Travel Guide Global Travel Adventures

Ready for summer travel

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