We started out doing double-handed charters back in the 1980's. My wife is game to help sail and pick up moorings though. That said, I knew that I could handle the boat by myself if need be. If you can sail the boat competently by yourself you can probably pull it off. A boat in the 35-foot range is pretty easy to sail by yourself, particularly if it's got an autopilot.

I'd suggest you only do it if your wife is ready to step up a little and help out.