As Missouri winter kicks into high gear, this is the time of year when many Midwesterners start to check out the job and housing markets down in sunny Florida. Shorts and flip-flops sound quite nice when compared to the stinging cold face slap that we get when we step outside. I know that it was only a few short years ago when I was considering selling my home and packing the family up for warmer pastures.

But when all the cards are on the table, I know that we aren’t going anywhere. The job market down in Florida isn’t the best, and the concept of the “sunshine tax” is very real when considering moving South. In addition, pretty much all of our family is here in town, and we absolutely adore our home and our neighborhood. Sure, we do have to tolerate some annoyingly brisk days in the winter months, but all places have their pros and cons.

That doesn’t mean of course, that we don’t try and find a way to get down to the Gulf Coast each year. I always have my eye out for a great deal where someone is willing to rent out or even sell a Timeshare for a great price. There is something about that line where the sky meets the sea, it just calls me. I love the beach and the laid back timeline that comes with it. All of these sound like a pretty amazing way to spend a day: renting a boat, fishing from the beach, body surfing, or just building a big sand castle with the kids.

The timeshare thing is interesting because I wouldn’t recommend buying one for everybody. One of my favorite things to do when heading down to the gulf coast is to rent someone else’s timeshare for the week. Your typical timeshare is going to be a bit nicer than a hotel room. There will often be amazing amenities and restaurant options on the premises, and the room itself is likely to be spacious with a full kitchen and multiple bathrooms. The grounds are typically watched by a security guard and are generally kept in pristine condition.

If you already own a timeshare, then you can perhaps look into using these same sites to take advantage of people like me who find themselves Florida dreaming. I would recommend that you don’t just keep your timeshare indefinitely. There are many scenarios where I would consider selling a timeshare, if I no longer wanted to visit the same destination each year. Or just keep your timeshare, and take advantage of their swapping program (if they have one).

In conclusion, yeah, I wish I was in Florida right now. I still don’t totally rule out the idea of moving there some day if I could capture a salary that would make the move worthwhile. For now, the midwest is where we will stay. But like every year about this time, I will have fend off these dreams of Palm Trees and Mickey Mouse.