Sounds like a good plan. Fajardo is good fun. Reminds me of what I believe Havana must look like although I have never been to Havana.

You know Rosey Roads is long since closed. Sad thing.
Viequez is a good stop on the way back as it will give you a ittle better angle on the wind than Culebra. There is a little bay on the east end of Viequez called Bahia Icacos which is very beautiful and makes a good stop for the run back. In late October the weather should be kind. Have a great trip.

Buddy