Two weeks should be plenty of time - especially if you are just doing the SVI and USVI. I would recommend Sail Caribe as well. Nice thing about going with them is that you can do the upwind leg from Culebra to the USVI at your leisure and early in the trip. That way you don't face the potential of being forced to sail/motor from the SVIs to the USVIs into confused 10' swells and 30 knot winds because you have to get the boat back to the charter base in the USVIs. You could still be in a position where you have to get from the USVI to PR in those conditions, but I would much rather be facing a downwind run versus an upwind grind in that case.

With that said, there are several on this board who have chartered from CYOA in the USVI and made the trip to the SVI and back just fine. You're just at the mercy of the weather a bit more. Also, important to note that you are required to check in with boarder patrol when traveling back to Puerto Rico from the USVI. We just gave them a call and they took all of our information over the phone. We chartered from Sail Caribe in early December and it was a nice change of pace from the typical BVI charter - though we did spend a few days in the BVIs as well. I actually wish we would have slowed down and explored the SVIs more and maybe skipped the BVI portion of the trip.

Matt