Why I Chose Puerto Rico for a Work Away Month
January has a way of sneaking up on you. After the craziness of the holidays, work ramps up, and the days become shorter, darker, and colder. I, for one, settle into a certain monotony that can only be attributed to wintertime in Boston.
So, as this time of year approached again, I refused to fall back into that familiar cycle and wanted to find a way to bring intentionality back into my days. Ultimately, that is what led me to Dorado, Puerto Rico.
Growing up, my family visited Dorado each year, a place my grandparents loved deeply, filled with familiar faces and the kind of memories that last a lifetime. As I got older, those trips became less frequent, and when I found myself searching for the perfect winter escape, I knew this was the warmth I wanted to return to.
What is Castle’s Work Away Program?
For those unfamiliar, Castle’s Work Away Program is a benefit offered to employees who have been with the company for at least 2 years. It allows you to work anywhere you would like for up to 4 weeks, provided you maintain East Coast hours. To me, this seemed like the perfect opportunity to avoid a post-holiday slump and reframe a time of year often associated with stillness, stress, and snow.
Arriving in San Juan: Starting My Remote Work Routine Offline
I flew out to San Juan, Puerto Rico, on Saturday, January 17th – just one day after returning from a weeklong work trip in Austin, Texas. To say this trip was well-needed was an understatement. Once I found myself comfortably seated on the plane, I deleted all social media apps from my phone and daydreamed about a month offline, and on the shore. The first week went just as I had imagined: minimal plans, a lot of time on the beach, and moments shared with the people I love. I also used this time to settle into my office for the next month, excited to call this place “home.”
Boston vs. Island Time: Finding a Better Pace While Working Remotely
Back in Boston, my days followed a predictable schedule. In Puerto Rico, I focused more on what felt right in the moment. No two days looked the same, and though it remained structured, the passing time felt much more comfortable. I was no longer rushing, and neither was my environment. The people I interacted with lingered in conversation, enjoying meals became a leisurely experience, and it felt as though time was ours to enjoy rather than something I was constantly trying to keep up with.
Keeping East Coast Hours in Puerto Rico
Luckily, the time difference in Puerto Rico is not difficult, since my workdays span 9:30 am-6:30 pm. I filled my mornings and evenings intentionally, and left space for larger excursions on the weekends. Working in events, I had no trouble building a schedule that accounted for everything I wanted to experience, and more.
Weekend Adventures in Puerto Rico: Old San Juan, Rainforests, and Island-Hopping
Weekends took on a rhythm of their own, spending time island-hopping, hiking through rainforests, and wandering the colorful streets of Old San Juan. By Monday, I returned to work feeling recharged from my experiences and more inspired than the week before.
My Favorite Trip: Vieques Island and Sun Bay Beach
My favorite adventure brought me to Vieques, an island I had yet to visit during my previous trips to Puerto Rico. Though the island itself only stretches about 20 miles end to end, it was truly expansive in all the ways that mattered. On a trip where my goal was simply to unplug, I had found the perfect place to do it. We started our mornings with the sound of roosters echoing through Monte Pirata, the island’s highest point, while days unfolded slowly as we wandered past friendly faces and wild horses roaming freely through town. We stopped for lunch at a café that doubled as an art exhibit for local work, and spent a bulk of our time at Sun Bay Beach, soaking in the quiet beauty of its clear, open water.
Coming Home Refreshed: What I Learned About Intentionality
When it was finally time for me to return to Boston, I was greeted by cold air and snowy roads. I returned to my apartment and prepared to go back to the office on Monday just as I had before, but this time I had a new sense of appreciation for the space around me and an excitement to be home.
In deciding to participate in the Work Away program, I was not looking to change my life, but rather to interrupt it. As an event professional, I love structure (maybe a little too much). This experience reminded me that while planning is essential, it is equally important to go off script every now and then. Being intentional does not always require a plane ticket and a packed bag; in fact, it rarely does. Not only did I return home with a fresh sunburn and countless memories that I will carry with me, but also with the clarity that intentionality is not about escaping your routine; it is about learning how to be present within it.
