For decades, my husband and I worked hard in our respective careers. We poured our hearts and souls into our jobs, with the hope that one day we would have a substantial nest egg that would allow us to have a carefree retirement. Little did we know our definition of “paradise” would evolve beyond just financial security. This is the story of how we left behind the familiar comforts of our lives and found our second life across the ocean.
Life before retirement was typical for us; we lived in a comfortable, three-bedroom home in Long Island, went on yearly vacations, and spent weekends visiting our kids and their kids. As the years went on, our son eventually moved to Asia to start a business and our daughter moved to the West Coast for her new job. It suddenly began to feel very lonely, and the thought of enduring another cold winter seemed a little less bearable than before.
California to the Caymans
We talked about moving with either of our children—perhaps life in California would be nice, and it would certainly be interesting living in Bangkok—but neither option really captivated our hearts. And so we thought, how about looking somewhere completely different? We started by researching various places that could be our new home. We made a list of requirements to start: warm weather, affordable cost of living, access to healthcare, and a sense of community.
The decision wasn’t made overnight. It involved numerous pros and cons lists, financial planning sessions, and heart-to-heart conversations—especially with our kids, who were more than a little concerned about our plans. Eventually, we settled on the Cayman Islands, known for its welcoming community and expat-friendly policies. We visited the island twice to get a feel for the lifestyle, and we were hooked! After serious consultations with visa and immigration advisors, we decided to take the leap.
Escape Plan
First, we had to make sure that we would have all the funds we needed to sustain our new life; it was time to sell the family home. As it happened, the day we decided to put the house on the market, the real estate agent in the Cayman Islands sent us a property for sale that was too good to miss out on. We had to move fast, so we contacted Leave The Key Homebuyers Long Island, who gave us a quick cash offer for our home. It was an emotional day when the sale was finalized, but we were ready.
Stepping off the plane felt like stepping into a movie set. The turquoise waters, the swaying palm trees, and the warm smiles of our new neighbors greeted us. Sure, the house we bought needed some repairs, but we were excited about a new project and the chance to create our very own little nook in paradise. It felt a little strange not having a departure date on our “permanent holiday.” We would wake up in the morning and have to pinch ourselves to make sure it wasn’t all just a dream.
Island Time
As life-long New Yorkers, adjusting to island life took some time! The pace of life here is so much slower. Most shops close early, and “island time” is a real concept that we had to learn to embrace. There is just no rushing in the Caribbean; every task is done in its own time and rhythm. We also had to get accustomed to not having convenience and variety at every turn. Instead of massive supermarkets and 24-hour food delivery, we had to adjust to smaller local markets and embrace a simpler and more self-sufficient lifestyle.
Thankfully, the community here is tightly-knit. Neighbors—locals and expats—quickly became friends who shared invaluable advice about the local culture and traditions and how to make the most of our new home. With the financial security from the sale of our home, we spend our days exploring the island and taking in all that nature has to offer. My husband convinced me to try scuba diving for the first time, and being part of the underwater world was a mind-blowing experience. I think we must have been some of their oldest students!
No Regrets
This journey has taught us a lot about ourselves, each other, and how little we need to be happy. We have never felt better and more fulfilled. The abundance of active lifestyle opportunities and the slower pace of life have allowed us to prioritize our mental and physical well-being in our older years. I do miss my children and grandchildren, but they promised to visit next winter. We are eagerly looking forward to showing them our favorite spots on the island.
For those considering a similar change, my advice is to plan thoroughly but also be prepared for the unexpected. Embrace the changes with an open heart and be willing to learn new things along the way. The rewards of a renewed zest for life in a stunning setting are truly worth the challenges! Never in a hundred years would I have guessed that we would find ourselves living on a Caribbean island, but now that we are here, it feels like the best decision we have ever made.