For the least hassles and maximum boat and person
security look into
Grenada at the bottom of the Windwards. American Airlines has non-stops from
Florida but you would need to get from Colorado to
Miami.
- - Basically under the flight time restrictions you mentioned you are stuck with
Central America. The
west coast below Mexico appears to have some good places for the boat but getting to a major international
airport could be an all-day land adventure.
- - The
east coast of Central American can present a security problem when storing a boat unless it is properly prepared to thwart curious, sticky fingered locals and other cruisers.
- - The
Dominican Republic offers Luperon for in-water hurricane season
storage and 3 international airports for getting to and from the
USA. Security can be a problem but generally it is very secure especially if you have an ex-pat watch the boat.
- - Further down-island in-water
storage during hurricane season is rather risky. Although you can - if you plan ahead - get the boat hauled and stored in an "approved storm season" boatyard in
Puerto Rico. It is not
cheap but quite safe.
- - Everywhere else is a "crapshoot" as to whether any storms will impact the specific area your choose.
Grenada offers the best "odds" on successfully surviving the "in-the-box" storm season. To get out of the "box" you need to go all the way to Trinidad,
Venezuela, A.B.C. Islands or
Cartagena.