Mary,
This is an issue I am very interested, for I plan to live this situation, eventually (hopefully?).
Before my reply, please note that I don't know enough about the conditions in the US (lots of participants can give a better input), know only part of the Caribean ( the residents will probably give a better informed opinion) and the place I know better is Brazil.
Also, I never needed to owe a wet suit or heavy weather suit due to the mild weather conditions prevailing in this area of South America. (but the price of tropical sailing is a worn out skin - sun protection lotions are necessary ALL the time - even when fully dressed, according to physicians)
Anyway, for this tropical South America sailor, the perfect parameters seem to be the following:
1) location very close to the tropics (15 to 25 deg. North or South) for ideal temperatures all year round.
2) trade winds.
3) a mix of clean protected waters and offshore sailing access, ideally a lagoon opened to the sea + a reef protected beech + open sea. A bay or river mouth is less desirable due to the tendency to have big cities and heavy economic activities (dirtyness, polution, etc.) in the vicinity
4) white sand beaches, for obvious reasons.
5) Enough infrastructure to assure the beer, spare parts and other amenities - but not too much, otherwise the peace is spoiled.
6) Racing and cruising activities nearby - nice cruising destinations available for day sailing.
7) Weak currency (to make the money last longer)
Based on my limited life experience, the following places fit the description:
a) a Caribean island. Possibly Cayman, one of the Bahamas, the Grenadines, etc. We assumed that money is not a problem, but prices are high, due to the proximity of some US milionaires...
b) The Buzios / Cabo Frio region, north of Rio, Brazil. A great place. Salt water lagoon, protected and offshore waters, easy access, close enough to Rio for infrastructure, currents maintain the water clear and the wind is perfect.
c) Angra dos Reis, South of Rio. The wind is lighter then Buzios, but there are 365 islands to visit, among other cruising destinations. Even better infrastructure. The nuclear plant could spoil all this one day, though.
d) Beaches close to selected cities in the Northeastern coast of Brazil, like Aracaju, Maceió, Natal and Salvador - they lok like the Caribean. Only a bit too close to the Equator and with less sailing activities (but this will be seen as an advantage by some...).
e) Beaches in the island of Florianopolis, Brazil. A bit less paradisiacal, but much more civilized. Only a bit colder due to not being tropical.
I look forward to the input of the Europeans, Australians, New Zealanders, South Africans and maybe someone with asian experience.
Cheers,
