Sadie, two quick follow-ups based on your comments:
"If we do the eastern Caribbean trip, we will probably go east then south to the USVI so that we can experience a longer, off shore trip."
That''s fine, and folks often make that choice when it''s this late in the season (Spring) and they need to transit quickly so they make Trinidad before storm season. The snag in your case will be that the longer you hold off on departing (11/1 is a little early given the hurricane cycle we''re in now) the closer you get to the Christmas Trades when leaving the Bahamas, which makes the offshore ''Hwy 65'' route more difficult to accomplish. So...plan on the offshore run being Plan A but expect that it may be necessary to bail out and end up island hopping, instead (so a few basic charts will come in handy). We cruised with a Swan 50 footer that couldn''t make it to
PR for this reason (it was January, so a little later than what you might be able to arrange).
"We''d like time to visit every island until we''re tired, but that is unrealistic. If we do well budget-wise, we may be able to stay out longer."
Hearing that, I can imagine how the E Caribbean choice would leave open more options. After arriving in Grenada/Trini in June/July, you can stay S to avoid the tropical storm paths and continue westward, then coming back north in Fall to cruise the W Caribbean before returning to the States. If you did the Windward Passage & Central Caribbean initially, you''d have fewer places to enjoy the following fall, altho'' that would give you longer spells for visiting & inland travel while waiting out storm season up the Rio Dulce and then gunkholing in Belize, Mexico and the offshore Atolls.
Both sound like good choices, don''t they?!<g> Good luck on setting up a careful budget with a modest built-in cushion for a surprise or two. You can cruise very cheaply all over the Caribbean so long as you set out with that goal in mind.
Jack