I think you're falling into the "average cruiser" trap.
Your vessel has a diesel
and a compliment of sails
and since you're in the relatively short distance Caribbean (compared to the Pacific or Indian Oceans, as an example) that means you can effectively go anywhere you want in any direction you want, the only thing you really need to figure out is the weather.
Some people (most, in truth) prefer to sail downwind or at least with the wind
aft of the beam because it's more comfortable and easier on vessel and crew. Beating to windward is wet, bumpy, and slow compared to its downwind counterpart.
But don't think that just because the average guy with the average boat does things one way that you need to do them that way at all. I, unlike 90% of "average cruisers":
- do not have a roller furler
, in fact I removed mine.
- do not use a genoa
, and again I in fact sold it.
- use paper, pencils, and hand tools for the bulk of my my navigation
- use a manual windlass
or just hand haul chain.
So if you are average in the sense that you like easier downwind runs, that will obviously affect the routes you can take. If you can find periods with relatively flat seas, you can motor
quite effectively in any direction. A typical boat operating at reduced RPMs can get 20 hours out of 10 gallons of diesel
, still making 5-6 knots sow.
If you rig your boat and your mind for windward travel and don't have as much of a "my boat is a floating condo" mindset, then you can travel quite long distances to windward undersail.
Use the pilot charts
, use passageweather.com (or the equivalent) to time departures just right, and remember that most cruisers are basically following along their chart plotter which is basically following along the area's popular cruising guide.
It's a sailboat man. With good seamanship chops you really can go anywhere navigable.