Questions and Answers

Ben, our annual winter travels to Florida over the years have been predictable Miami Beach, Boca Raton and throw in an occasional stay in Naples. This years trip has a purpose, where to relocate.
We’ve met a few times and I realize you are a young man, but have you stumbled across a warm winter domestic destination that may not be the most widely known spots in Florida. Maybe somewhere you’d consider your parents might like.
Thanks, Jim

Hi Jim,

As a Florida native (grew up in Naples, lived many years in Miami), I think it depends on what type of trip you’re looking for. If you want great restaurants and lively night life, keep going to Miami. If you want a quiet beach trip, you will have options all over the state. Personally I prefer the beaches on the Gulf Coast, especially in the winter months as the water stays warm. Sanibel/Captiva or Siesta Key would be good options there if you don’t want to go back to Naples.

If you haven’t been to the Keys, they can be a bit more of a trek but the drive is beautiful. Key West is the liveliest and there will be some brand hotels at which to use points, but Islamorada is beautiful and quieter. There are also a number of great quiet spots along the smaller keys too.

Along the East Coast, St. Augustine is a cute town with great history. Also a number of smaller beach towns north of West Palm often have inexpensive hotel deals. I haven’t spent much time in that area to be honest though.

Hope this helps!