I treat the boat as a movable
vacation home. There's no reason (and little cost advantage) to stay all winter in one spot or go to the same places every year. For my wife, two months on the boat at a time is her sweet spot.
If you are not a resident of
Florida, it's hard to find reasonable priced insurance for Florida during hurricane season.
If you have
air conditioning, I would keep the boat in Charleston, Savannah, or Brunswick in the water during summer. If you're like me, an occasional week on the boat even in summer heat is necessary for mental
health. There are always fun boat projects to do. When you are retired you have the flexibility to fly very cheaply.
Depending on when you leave Colorado in the fall, spend some time in SC or GA. It's beautiful. Leave in late November and spend three months in Florida - pick different cities each year for variety. Don't stay any one place too long - it gets boring. If
budget allows, spend one of those three months back in Colorado skiing. It will really break things up.
In late Feb or early March
head to The Bahamas when things have warmed up and the winter winds have died down. We use Great Harbor Cay as a base as it's a great community with good air
service. Perhaps a month at GHC and then cruising for a month. Have some friends or
family visit for a week or two (you have no idea how many friends you have until you have a boat in the Bahamas). Stay until early May and then return to your summer
storage point.
By mixing a month at a marina that has good monthly rates with some
anchoring out in between, this really isn't that expensive.