Looking at storage for me locally it isn’t much different than indoor storage in south Florida for the winter. Flights to lauderdale are under 300 bucks a person round trip. Is there something I’m missing? Why haven’t I done this in the past?

Nov-May is the best time of the year to boat in FL, IMHO......

We keep the boat in Cape Coral during the winter and I'll be honest even though the boat is 1000 miles away we use it more down there than we do in the summer.

If your looking for rack storage you better start looking asap.
Not ez to find.

What size is your boat? Where do you fly out of?

If you are looking at Delray Beach or somewhere near west palm beach, Gateway Marina and Palm Beach Yacht Center are very affordable. But as people said, you have to hurry. Gateway is full during the summer unless you are willing to do outside and rack store.

I am looking at doing the same thing. Taking the boat from Miami to Key West in November and then plan on leaving it there for the winter. Thinking Cape Coral / FT Meyers area.

Boating in Florida in the winter is awesome. It is very different than inland lake boating, so make sure you have a good chart plotter and follow the channel markers. What looks like it could be wide open water is likely only a foot deep other than the marked channels.

I have been doing this for 8 years now and it is awesome. I am on the west coast of FL in Sarasota. Indoor storage is $500/month on my trailer ($100 additional for your truck) and I am right next to Innovation Marine for all my service work. When you figure the cost of winterizing, shrinkwrap and/or indoor storage, dewinterizing including full detail and demildew, etc. at Northeast prices, Florida is actually cheaper. The only added cost (both time and money) is the trucking it down and back. I try to piggyback a poker run or event with those times to make a fun trip / vacation. It is great to have the boat available to use all winter long!