Hi Chuck, I am not an authority on this, as trawlering at sea is new to me. And, I see that several others who have taken their trawlers to the eastern Caribbean have replied, so I'd heed their wisdom. VanSant had (has) a sailboat, and his book was written assuming you would sail. Even so, many who have done it according to his plan have cursed him, as it takes an inordinate amount of time if you wait for WX everywhere; then you are still bashing to windward all the way. When I made passage there, I did so directly from Norfolk to just SE of Bermuda, to 64W, and then southward to the USVI. This took 13 days, but I was sailing, and the Atlantic was benign in the wake of Mitch, which soundly thrashed the Caribbean 1500 rally a few days before. (An aside, IMO, rallies confer a false sense of security, and I would never tie myself to their schedules. Yet, the ads and the seminars bring new victims each year; two boats were lost in that one, and being part of a fleet didn't help them at all). In my six winters in the Windwards, I have met many who have come there in boats similar to yours. Based on that, my sense is that the Mona is probably your biggest challenge, and you will want to arrive, hopefully, somewhere in the "chain" before the Christmas Winds set in and then pick your windows. To do this, you'll not have much time between the end of hurricane season and the end of December. So I'd forget thoughts of a leisurely trip. Further, I will say that passage-making trawlers and motor yachts of under 60 ft are rarities in the Windwards. That should tell you something, but I think it's slowly changing. There's a gal with a GB 46 who charters in the Grenadines, but she's a live-aboard and supports herself that way, keeping mostly to Grenada and Bequia. I also see one N46 almost everywhere I go - a Belgian, and I think he must have fins. But most get to some place like Trinidad, and stay for years, with perhaps a short jaunt a short way up-island after waiting for weather, sometimes for weeks! OTOH, the natives, especially Bajans, think nothing of crossing 90 miles from their home (Barbados) to the "chain" and back (dead to windward) in 40' sportfish and such. So I think good deal of this reluctance is due to lack of familiarity. Can't think of any books, but you might also want to subscribe to the yahoo worldcruising group and ask some questions. I'm sure you'll get plenty of advice there. Might also join rec.boats.cruising and Google for "passages south" in "Groups" as well as "Web." John "Seahorse" Chuck Shipley writes: I guess what I meant by "sneak" is something like what I understand Van Sant has advocated for Bahama/Caribbean cruising.  Short hops carefully chosen in terms of route and weather watching.  We have no reason to be in a hurry -- we shouldn't have a schedule -- I hope we can remember and stick to that... I got a copy of Van Sant from the library and read enough to see that I will want to buy my own copy before we start our serious cruising. Not just "buy", but "study" and "plan". That is part of the fun, yes?  What other books are "mandatory"?