It depends on a few factors for me:

• Would this be their only chance to go? If it is once in a lifetime for them, I carefully pick where I'm taking them, which usually means an area I'm already familiar with.
• Are they up for a little "adventure"? If they are "go-with-the-flow" types, I would be more apt to take them somewhere I also haven't gone.
• If I can find a lot of info on an area I haven't been to, I consider it because I have more of an idea of what to expect.

A couple of examples -

Last year I took my scout troop. They hadn't gone to the BWCA before. For some of them it will be the only time they go. I took them from Moose Lake to Lake One. I hadn't been on most of that loop, but I felt comfortable because there is so much info available on that area. 

This year I am taking a group of guys who may never be able to go again. They will "go-with-the-flow" and don't care where we go as long as we go. I considered a lot of areas but finally settled on one that I had been to a few years ago. It was a good compromise for me since I know it will be a good area for them but I will also get to explore a bit since I didn't do much exploring the last time I was there.

The point is my number one priority is providing them with a good experience. If I think I can do that with a new area, that is a bonus for me. If I have doubts, I take them somewhere I'm familiar with.

As for where specifically to take a group of first-timers, that, of course, entirely depends on the group again. I've provided lots of advice to various first-timers, and each time I recommend different areas. There is no "one-size-fits-all" - other than everybody needs to visit the BWCA/Quetico sometime in their life 

Originally Posted by: Canoer97

Ben, you mentioned Moose Lake to Lake One. How did you do that. I see no clear way or short way to do that as a loop. Just wondering.

We did it over six days with a layover day on Alice - Moose Lake to Lake One

We actually had two groups. The other group went from Lake One to Moose Lake via Ima and Jordan. They also had a layover day on Alice. Their paddling days were shorter - Lake One to Moose Lake

We had a shuttle from Moose Lake to Lake One and vice versa from LaTourell's.

I took my girlfriend for her first trip last year, and it was also my first in a number of years. We'd taken a few test trips in northern Wisconsin beforehand, and in the BWCA we pretty much stuck to Sag and Ottertrack where I have a decent degree of familiarity. It was overcast/rainy most of the time, but we didn't overextend ourselves and we caught tons of fish. She had a blast and has been talking all summer about going back up this September.

After we talked about what made it a success, here are the big takeaways:

• Depending on the level of experience, take one or a few test trips somewhere less remote before buying that BWCA permit.
• Set good expectations. Even easy trips can contain a lot more work than some folks' ideas of camping can include. Don't overreach.
• It's not a bad idea to go somewhere with a little more traffic. You can get more remote as skills and comfort increase.
• Consider base camping. You can always decide to move around if the confidence/competence is there; otherwise it's still a nice, relaxing trip.
• Maintain perspective and a cheery attitude, even when something goes a little sideways (like four days of rain). It goes a long way toward making it a good time.