Thanks to all of the readers of my popular piece, Why I Became a Snowbird in my 30’s.
I responded to many of the comments, but I wanted to provide a formal update.
Unfortunately, we have had to give up snowbirding. Over the years we faced many barriers to our trips, but the biggest hurdle is the kids’ schooling.
Inflexible School Systems
During our last trip, we had to finagle a partial trip for our middle schooler, my stepdaughter, because she was only able to take 3 weeks off of school. We thought we were in pretty good shape because it was pre-approved with the school and we were told she’d be given work to do while we were away. We arranged to have her grandparents take care of her because her mother does not live locally.
When it came time to take the trip, the teachers did not have work prepared, and instead told our daughter to enjoy her vacation. Despite the pre-approval and offer to work on vacation, the teachers appeared to penalize her for the remainder of the year, even after she caught up with the rest of the class. We were extremely unhappy with this outcome and registered this worry for future trips.
Now that she is in high school, and if it were just her, we *can* resume our Florida trips because her high school offers online school. She can actually take the first semester in person, which ends around Christmas, and then participate in online school for the rest of the year. All of the high schools in our area offer this option.
Unfortunately, this is our younger daughter’s first year in elementary school. At the orientation we inquired about the possibility of a long trip to Florida in the winter. The administrator looked surprised that we’d even asked something like this; he said the only way we could do it would be to disenroll her from their school, enroll her in Florida, and then reenroll her in Pennsylvania when we returned. And honestly, it sounded too disruptive to go through all those hoops.
Just as I was preparing to write this, I did hear of another family from my area (not the same primary school, though) that actually does this. My immediate concern was how the kids adapted to that much change every year. And to my surprise, they love it. The kids have friends in both locations, and it’s been so regular that no-one even bats an eye at it now. But, I still hesitate because I don’t know if it would be good for my kids. Even during our prior trips at their very young ages, I noticed a considerable transition period both when we’d arrive and when we’d return home.
So, as you can see, the biggest problem for us is schooling. There are also a couple of housing factors that would also complicate things if we decided to do it anyways:
1) The area that we were renting in has gotten more and more expensive every year
2) We do not always rent the same house so the kids could potentially have to go to different schools. And while it would be preferable to buy a property, the higher prices would probably deter us from doing that.
3) Lack of familial support. If you’ve been reading, you know that we don’t have much in the way of family support systems. Instead, we have had to work really hard to build up our child care support networks. To confound matters, when we leave for extended periods of time, we risk our home support network while simultaneously having to build a new temporary one in Florida.
Our New Plan
I’m sorry I cannot report more success in this area because I know a number of you are considering snowbirding with kids. This past winter was really hard for my family, especially my husband. We couldn’t even take a short trip this year because we had a newborn and quite frankly, there are so many of us now. At six people, we now need two hotel rooms to be comfortable. So, around February, my husband wilted despite a couple of his business trips being in sunny locales.
As the cold season approaches again, the topic of how we are going to deal with future winters has become urgent again. One idea is to plan a pick-me-up vacation of at least 10 days in late January/early February. It has to be a sunny location, and we will stretch for even longer even if that means we send the teen home early. Because there are so many of us, we’ll be looking for an Airbnb type place so we can stay centralized in one place and cook for ourselves to offset the cost.
Secondarily, we are going to start trying some active winter trips. Living in the northeast we are within driving distance from many ski resorts so we are going to take some weekend trips to keep up our activity level despite the cold.
And lastly, we’ve all begun to take a supplemental Vitamin D. I learned that we simply do not get enough vitamin D from the sun in our area so a daily supplement can help boost energy levels. I’ve also purchased my husband a sun lamp that he can use in his office to increase his intake of vitamin D.
I’ll let you know how each of these things turn out. I wish there were easier ways to manage schooling for those of us that prefer to snowbird for our health. I can only hope that school systems will become more flexible in the future, and I am looking forward to the later years when our highschoolers will have more flexibility.
One Last Note on Homeschooling
The next obvious question is… if school is the problem, why don’t we homeschool our children?
And the truth of the matter is that we (I mean “I”) could. But, after spending the last six years with my children, I have come to the conclusion that our children would do better in a traditional school setting. I think this is a result of the blend of personalities (including my own) and the ages of each member. Plus, having the children in the home day in and day out makes it difficult for my husband to concentrate on his business. I am open to homeschooling the children as they mature and progress in their education if I am able to test that our learning relationship improves.
I wish I had better news for those of you interested in forging your own path for your family instead the the typical one. I’d love to hear success stories in the comments if you have found a way to make this work for you!

Sorry the Snowbirding didn’t work out for you. You always have the future to plan for 🙂 My plan is to snowbird when my youngest graduates from high school in 5 and a half years – can you tell I’m counting down Lol. We are currently selling our large high maintenance house and buying a smaller non-outside maintenance cluster this month. This will be a good snowbird “up north/summer” home someday and we will save money in property taxes and utilities which will help us in the long run. I wish I could find a career where I could work remotely, what is it that you do?
Thank you! It is definitely something we are planning on. When I was still working full time, I telecommuted in a Finance position in the Pharma industry. Nowadays, I mostly freelance write or trade stocks for income. Lots of big companies are creating flexible jobs, and depending on what you do, you might consider just talking with your boss about the possibility of working from home during the winters.
I came across your blog, as I try to reach decisions about our family. We too are young snowbirds with a 4 yo daughter. We have been doing it for 5 years, my husbands fishing charter business allows us the flexibility, and I have been a SAHM since she was born. We feel all the benefits you have mentioned splitting our time between Florida and Maine, but realize it might come to a close as we approach kindergarten. We have considered 1/2 year up north and 1/2 south, but not sure if the impact that will have. We have also considered a move for just the school year, but I am not sold on leaving our support network and great schools. Sigh…
I’m getting ready to be forced to be a snowbird with a 7 year old and I’m kinda spazzing about it all. We currently live in Florida year round after 4 years in the NE winters. I have lupus and a smorgasbord of other medical problems that are highly affected by the cold. The pain cold causes had me begging the doctor to admit to a hospital for a “break from living” back then. But theres a amazing job offer back up north, that is a literal godsent … so the plan…we will move up north and Jan-April, my daughter and I will come down to our family’s land in Florida. I have a 2 bedroom villa camper that we are going to hookup on my mother’s land for my daughter and I. ( tiny home living? now I know I can homeschool her and that’s the current plan.. kinda …….but I am now thinking about just enrolling her in Florida’s virtual school and let her do that while we are up north. Might work for you if could acquire a permanent address in Florida.