OK I make it that you arrrive in the Caribbean December 2008 and want to be in Panama (say) Feb 2010. Perfect timing to see a lot.

My instinct would be to sail the island chain until early June 2009. Then start heading south and west. Route: Grenada, Los Testigos, Margarita (duty free).

Then you have a choice of ducking down to the Venezuelan mainland (Puerto La Cruz perhaps) or heading down the out islands: Blanquilla, Cayo Herradura near Tortuga, Los Roques, Los Aves. Bear in mind that in all the out islands there is only one badly stocked store on Gran Roque. You can also go Puerto La Cruz cayo Herradura etc.

Then it's on to Bonaire and Curacao. (Note if a hurricane passes north of Bonaire the wind reverses and Bonaire is untenable. Be prepared to leave for Curacao, a day sail).

We think Aruba is not particularly nice, so a short stay there to jump off to Cartagena, either direct or it is safe to day sail the Columbian coast. It is not safe to sail parts of the Venezuelan coast. Get the latest updates when you are out here.

Timing is important leaving Aruba. Late Sept/early Oct is fine. Much later there are big seas and severe gales around the headland at seventy something west (sorry boat is being painted can't get to the charts).

Plan to stay a fair time in Cartagena (it's beautiful) and then on to the San Blas islands (Kuna Indians) and Panama. You've got plenty of time and should really enjoy the trip.