One possibility would be to sail to Isla Mujeres, then wait for favorable winds and waves, sail to Georgetown
Caymans, wait again for favorable wind
and waves, then go on in to Montego Bay. I would suggest the Montego Bay Yacht Club to clear in. Be patient. Soon come mon.
You will taking the Gulf Stream
head on from Isla to Montego Bay, so beating against wind and big waves might make for a long trip.
Be selective about where you anchor
out in Jamaica. Some places are not safe. Negril would be just fine, IMHO and is fun 24/7. You could anchor
in the NE corner of Bloody Bay and get protection from the prevailing easterlies. For fresh water
, I would see if they would let you fill up with the hose on the Hedonism 2 dock
. The water
is fine to drink.
Jamaica is a beautiful island and I would highly recommend it. There are not too many cruisers there. The folks at MBYC could give you a heads up on places to avoid. British Admiralty Chart 256 is good but if you can find a copy of John Lethbridge's "Yachtsman's Guide to Jamaica", he has many good tips and detailed local charts
. John died a few years back and his book is a little out of date.