by Jane Rogers
My path to becoming a snowbird wasn’t a typical one — and it certainly wasn’t the easiest. I didn’t have a carefully mapped-out retirement plan or spreadsheets comparing winter destinations. There was never a moment when I boldly declared, “Next year, I’m becoming a snowbird.” If anything, the idea felt too big to say out loud.
As a single, divorced woman who had never lived away from home for an extended period on my own, the thought of spending months in another state felt like a very big deal. Looking back, I’m not sure I would have taken that leap at all if life hadn’t nudged me toward it. What I did know was that I was ready to step outside my everyday routines and try something different.
I lived full-time in the Chicago area, where winters are notoriously difficult. Naples, Florida was already familiar to me as my parents spent more than 25 winters there. I visited often, especially as they got older. From my earliest trips, I remember thinking that someday I’d love to spend my winters there too. I just had no idea how, or if, I could ever make that happen. As it turned out, the path unfolded one piece at a time, and not always in ways I would have chosen.
An Opportunity I Hadn’t Planned
What brought me back to Naples for a longer stay wasn’t a grand decision to become a snowbird. In my late fifties, an opportunity came up to start a seasonal rental business with several partners. Suddenly, I had a reason to be there for more than a vacation. It was exciting, but also well outside my comfort zone. I had never lived away from home on my own for months at a time.
There’s a big difference between visiting somewhere you love and actually living there. On vacation, everything is temporary. When you stay for months, you need groceries, routines, doctors, hairdressers. In other words, you have to build a life. It felt overwhelming.
I wish I could say everything fell neatly into place once I arrived. It didn’t. About six weeks into that first winter, my rental situation fell apart, and I suddenly needed to find somewhere else to live. So there I was, far from the comforts of home, working my regular job remotely while also helping run a new business — and scrambling to find housing during peak season in Southwest Florida.
Going home would have been the easier choice. Rentals were scarce. Just when I started to wonder if I’d have to leave, I found a new listing online and managed to secure it. Once that crisis passed, I began to settle into life in Naples. But between my job and the business, I wasn’t exactly living the leisurely snowbird lifestyle I’d imagined.
Eventually, balancing both jobs became too much. After 18 months, I sold my interest in the business. But I kept returning to Naples each winter. By then, I didn’t need a business reason to be there; I simply wanted to be there.
Beginning to Experience Life as a Snowbird
To make Naples feel like home rather than a winter vacation, I knew I needed to create a community for myself. I started playing pickleball at a local facility and met interesting people from all over the world. I also found a few restaurants recommended by locals, and some became my regular spots. These restaurants were where I got to know the people behind the counters and caught up on local news. Those conversations, along with neighbors with whom I became friendly, started to form part of my everyday life.
I built routines. The farmers market became a weekly event I looked forward to every Saturday. I found a favorite coffee shop that was perfect for people-watching. I spent time taking walks, hanging on the beach, and exploring new parts of town. I loved being outside in the middle of winter, something I rarely had in Chicago.
Some of my favorite moments were the simplest ones like taking a break from work to sit outside on the patio with nowhere I needed to be. I loved to relax in a comfortable chair, enjoying the scenery and appreciating the warmth. Over time, it felt less like I was spending the winter on vacation. I had routines, familiar faces, favorite places. Naples was becoming another home.
The Importance of Staying Connected
Before becoming a snowbird, I worried I might drift away from loved ones. That didn’t happen. Video chats kept me close to my kids, grandkids, and friends — seeing their faces made the distance feel smaller.
Visits from friends and family became one of the things I treasured most. There’s something very special about spending uninterrupted days together, away from everyday responsibilities. At home, time together often has to fit around work, errands, and appointments. In Naples, we could slow down long enough to enjoy long beach days, lingering dinners, and hours of conversation on the lanai. It wasn’t what we were doing that made those visits memorable. It was simply making the time to enjoy being together.
What I Learned Along the Way
With each season, I got better at the logistics of living in two places. Experience teaches you what matters and what doesn’t. But the bigger lesson had nothing to do with logistics. An unexpected opportunity appeared, and I took it. Some things went wrong, but I adjusted. Other things went right. One decision led to another.
Looking back, I’m struck by how little of the path unfolded the way I thought it would. Life presented circumstances that helped me move past my hesitation about spending months away from home on my own. With every obstacle I figured out, my confidence grew.
My background is in operations management, so I’ve always appreciated a good plan. Snowbirding reinforced that, but it also taught me that we can’t plan everything.
The Bottom Line
Our journeys rarely look like the ones we would choose for ourselves. Mine included an unexpected opportunity, a few detours, and more than one uncomfortable moment. Chances are you will have at least one experience that becomes much funnier after some time passes.
Staying open to unexpected opportunities often means moving forward before you can see the full map. Fear can be paralyzing, but try to push past it. When you do, surprises stop feeling like disruptions and start revealing themselves as gentle nudges toward what you wanted all along. Openness doesn’t guarantee an easy path, but it does make room for the experiences that end up mattering.
About the Author: Jane Rogers
Jane Rogers is the author of Snowbird Like a Pro: How to Plan a Winter Getaway from the Midwest & Northeast to Florida, Georgia & the Carolinas. Drawing on years of firsthand snowbird experience, the book walks readers step by step through planning a seasonal stay, from choosing a destination and finding a rental to budgeting, travel, packing, preparing the home they leave behind and settling into everyday snowbird life. Jane splits her time between the Chicago area and Naples, Florida, and is the founder of JRogers Publishing.
Leslie Farin is the Publisher and Founder of 50PlusToday. She is an experienced communications and marketing professional passionate about working with older adults and their families. She works with a team of writers to provide essential and cutting-edge information related to the 50Plus community.
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