1) We've only been once from north sound. I'm sure many will chime in on this.

2) Check with your charter company, they may red line it. We go through on cats.

3) How do you know you won't love going by car better if you've never tried it? There's nothing that great about going in by boat - its how you visit every other site. Try something different - I bet you'll want to do it again. I'm not sure about bringing the dinghy in closer, but if you need to bring it close to shore, that's just another sign that you are better off visiting by car.

4) If you left first thing in the morning, might be ok. Always hard to say though - we've only been to the FMP once in October so a little hard for me to say.

5) Yes, it will work without service as long as the maps are downloaded.

As far as the direction is concerned, there is a 3rd option. Don't make a full circle. We have often never crossed the north side of Tortola.