using an experienced model helps. they generally keep a wrap dress or something like it handy or hidden within reach. much of it also depends on the location.

if there is lots of traffic & activity nearby, it's trickier; so generally getting away from those areas means less problems. that has to do with timing and knowing the location. for instance, joshua tree np on some holiday weekends or trails and rocks that are popular. you both must be aware of the surroundings; allowing for line-of-sight. often I can run interference, going around the trail to ask people to wait a bit. or just grab the reflector and shield the model while they get the wrap dress around them.

always ask the model to bring hiking shoes and clothes for the approach & return as well a ground cover to lay down. for some shoots enough water & some energy food is necessary. depending on the seasons & location, really warm clothes, hand warmers and towels are very important accessories.

Your post said that you were interested in shooting in wilderness, and my experience of that is that you can shoot for hours undisturbed.

That being said, my advice for less lonely places is to shoot on week-days, preferably Monday or Tuesday, and to shoot early in the morning when the light is more favourable and people are least likely to be around.

Should people stumble upon you, the best thing to do is to have the model cover up and for you to approach the people and ask if they are offended and to offer to leave immediately if they are. To date, everyone has said that they were fine with a nude shoot, but we have always moved to a new location, just in case.

Always have at least two people for look outs. Make sure the model can get dressed quickly if she has too and always scout your place.

I hear what you are saying but having additional people along is counter intuitive. Because the larger the group involved in the shoot, the less discreet you can be. Those who are on lookout almost alway draw attention.

it is best to keep it on the down low . Go to the space get your exposure dialed in. Work the pose with the model then have her disrobe and shoot 3 to 4 frames then hand her back her cover up and move to the next spot. One of the other posters mentioned this and it is the best way to go about it.

I shoot between 150 to 200 shoots a year for the last 7 years, many of them out doors. I have never been "busted" by athorities and a person only once in all those years.

You can believe what you want, but I have far more experience in these type of shoots then you and I shoot in many states across the country.

I have shot nudes in a heavily used parks in heavily developed suburban areas many times.  I pick places where there are few to no people.  It is surprising how little a park is used once you get away from the points of interest and the paved (too hard to hold the grass down) trails.  But I am very cautious and clothes are always near by.  I know the places I am going to shoot first, and know where the unpaved trails are because they will carry the interlopers.  Not many people will push through the woods, weeds, poison ivy and briars to experience the interior lands of the park.  Deer ticks, lyme disease and a fear of snakes deter even more people.  The rangers/police often don't want to get out of their cars to come get you.  Unless the person with the cell phone that reports you is actively shadowing your movements, it will be difficult to find you if you are also moving about.

Weekdays, as stated above, are better.

Consider switching out cards in the camera and keeping the card with the nudes someplace more secure, in case someone wants to search your camera and you let them do so.  Don't admit to it.  Don't lie either. 

Be sure to know the law.  Topless women are not illegal in many states, but you had better know that and be able to refer to the law.

I was recently in Rocky Mountain National Park (no models) and some of the other parks around the Denver area.  I found it to be the same.  There is a water fall and access trail with people everywhere.  Step off into the woods and there was no one.   

You can join an on line swinger and/or nudist group(s) and inquirer about nude tolerant places in their forums.  Some of the people own land and are open to allowing photography.

How far is Black's beach for you?

As far as model reimbursement:  It is going to be particular to the model.  I have had models that wanted $100 an hour to sit in the car for two hours each way.  They feel their time is worth $100 an hour and it doesn't matter what they are doing. (Personally, I do not charge my clients for driving time.  If I did, they would hire someone closer.  And so do I.)  With other models, the time starts at the photo site.  But maybe you will pay a higher rate if it takes an investment to get there.  Other models have driven two hours to get to me and charged me less than their usual rate.   I have one location which requires a three mile walk in and out and it is tough terrain, and is a couple of hours drive from me.  If a model got hurt, I could not get her out alone and there is no cell signal.  Nor could she get me out if I got hurt.   If I was to shoot there with a professional model, I would want the time to start at the parking lot, and I would pay her to walk and shoot.  I would prefer to hire a local model to keep the model's investment smaller.  I think the best way to go would be a day rate with a defined limit on the hours and a serious discussion about how many hours shooting I would I get.  So far, I have only shot friends there because of the safety issues and the potential costs.

Most of the nude shoots I've done have been outdoors, most of them ude; you can probably find a reference similar to this one for your region: http://wta.org

One of the locations I've gone to a fair bit is a bit less than three hours each way, so I usually arrange full day shoots for those days. It makes for long days, but I've gotten some great shots there, and I've encountered other hikers very infrequently there even on weekends. Other times I've picked out less popular hiking trails and gotten great results also.

One great and probably underutilized resource for choosing locations for nudes is Google Earth. A lot of landscape and architecture photographers recommend it so that you can go to a location knowing where the sun will be at what time, and what direction the sun will be setting in; very useful if you're planning a sunset shoot over a lake and you're looking for a reflection or similar.

On weekdays a lot of hiking trails are pretty deserted, which can make shooting nudes in nature a lot easier to do without dealing with riffraff.