Miami to Windward Passage

[Habana Vieja]

Planning on sailing next November from Miami to the Caribbean, we are leaning toward the I-65 offshore route to the BVI's. However, we are giving serious thought to entering via the Windward Passage as well since it would offer the opportunity to visit the Greater Antilles before heading for the Virgins. Any ideas / thoughts on the calmest route(s) from Miami
to and through the Windward Passage would be very welcome.
Thanks,
HV

[skipmac]

Basically two options, through the Bahamas or down the north coast of Cuba via the Old Bahamas Channel. The first lets you island hop, pick your favorite stops, take your time, have fun. The second has few options for stopping but is a bit more direct.

Island hopping a typical route is Bimini, cross the banks to Chub, to Nassau, down the Exumas, east of Long Island, Crooked/Acklins group, Great Inagua to the Passage.

[Jane.Joy]

We started in Key West and island-hopped south of Andros, then Exumas, then Great Inagua. This worked well for us - and if we wouldn't have been pushing up against hurricane season, we would have liked to spend more time "hopping" between Exumas and Great Inagua, as skipmac suggests. In Great Inagua you can wait for good weather and zip through the Windward Passage in a flash, easy-peasy. Then we turned East and slogged our way to Ile a Vache, Haiti. NOT easy-peasy: but worth the trouble, for sure.

[Jane.Joy]

You've probably already heard of this guy? http://www.amazon.com/Thinking-Guide...e+to+caribbean

Frank Virgintino has done guides for Haiti, DR, and PR, among others.