A few quick observations from our
experience:
The
Dry Tortugas are a great place to hang out and wait for a good wx window. If needed, you can pick up WX on
VHF or at the
ranger station. The
ferry and the float plane that make daily stops there are also good resources.
We were underwhelmed by NW Cuban coast. If planning on seeing any of
Cuba along this
route, would advise
docking at Marina Hemmingway and traveling by land. There are a few cool cays along the way, but the guarda frontera will turn you away from any attempt to land the dink on the mainland (as of Jan '18). Thus you are unable to see much of NW Cuba by
boat.
NV
Charts were also good for Cuba. +1 on the Rauscher guide.