I haven't been commenting on TTOL much recently so you may not know me... BUT...Stevo...NO ONE on here can advise you on whether a captain for a day is worth it (IMHO) because that is a personal comfort level choice. But, I want to directly answer your question with my take on it....you wrote "Would a check-out captain facilitate that kind of afternoon?" (comfort) The likely answer is "yes" it will help both of you with your comfort and confidence level and if you don't need help with your confidence level, it'll make you feel better because you made her feel better. After meeting my gal in early 2012 I mentioned my love of the BVI and she saw pics and such of my trips since 2003 and she said she wanted to go. I insisted she go through 101, 103 and 104 and I told her I would go through it with her. During the course of the week we hit some VERY NASTY weather in the Texas Gulf and the waves were the kind where you see land one minute and then you are surrounded by water (large waves) (then repeat). She did GREAT at the helm!! She did great at MOB. But days later she confessed that the course scared the hell out of her and I explained the odds of hitting that type of weather in the islands was little to none. I could see the stress in her face and I offered to get a powercat and the stress just released from her face. I am NOT suggesting a powercat but I am suggesting that whatever makes YOU and HER comfort level get to the highest level will ultimately make your trip more enjoyable. If nothing else, when she sees confirmation from another captain that "hey, Steve, you don't need me"...that alone may be where the mental switch is flipped.

As for whether it'll restrict your anchorage...again...not many on here can answer that as that will depend upon who you physically get as a captain and what he is going to allow for e.g. boat from Norman, Peter, drop him off at West End...etc. I personally like the suggestion above of dropping him off at West End...this would allow for one more practice session on the docking, etc...drop him off and then a short sail either to Norman, Cane Garden Bay or JVD.

One final note to those above...when did the "pendant" on the mooring ball become a "painter"?