There's a lot to be said about the freedom and wide open spaces when one chooses to camp away from the constraints of an organized RV park.  Most snowbirds I know automatically think that they will choose a location in the Western part of the USA, usually Arizona, Nevada and New Mexico, without even considering the possibility that with a bit of forethought and investigation, it is possible to find some really good free boon-docking locations in the Eastern States.
While I do not claim to have a LOT of camping experiences on both sides of the States, I have enough experience to have an opinion of what I prefer.
So, while heading west could be considered the easiest option, sometimes the thought of all of the desert landscape, makes it nice to know that on our next camping foray, we will be surrounded by trees.... many, many trees.  Ahhh.... what a nice thought after camping for months on end in the barren Western landscapes that have become part of the iconic images of western and road trip movies.
The beauty of camping in the BLM lands and Refuges scattered in the west means that you have the opportunity of awaking each day to a magnificent sunrise with a beautiful palette of colors that make up the mountains.  Think Zion in Utah, Valley of Fire in Nevada and don't forget Sedona in beautiful Arizona.  The list of places that provide magnificent vistas and colors, depending on the time of day, is endless.
Put yourself in a very different landscape such as Florida, Tennesse or Louisiana where you cannot expect to have fantastic vistas or great photographic opportunities around every corner. What you will get is the beautiful tropical foliage that fills the eastern landscape, along with the variety of birds and four legged creatures that feed off the lush vegetation.
So, apparently, in the Americas, the world is your oyster when it comes to taking great camping road trips.

Ever since we started camping, we always went by the seat of our pants trying to find the cheapest (free) campsite in the best location and with the best conveniences around us.  Needless to say, there have been many failures in our attempts to find the ultimate place to spend  a few days of peace and serenity.
It is at these times that I sometimes wonder if we would have been best off pre-booking a really nice sounding resort that offers all of the amenities we might enjoy, but with a price tag that goes way out of our budget.
I can say that we have tried these two options - boondocking in the wild and luxuriating in a resort.
So far, I have to say that we really do prefer the 'seat of our pants' scenario, where we arrive at a location and hope that we will find the ultimate (and free) site. However, there are benefits to both options.

Number one. Getting Social -  If you like people; a resort will have them in great supply.  There are constant reminders to attend a pickle ball game, either as a spectator or as a player, or there will usually be some sort of a Happy Hour gathering where we can all gather to share our events of the day and get ideas on what to do the next day.
However, when boondocking, if you like people; they will usually be far away from your home on wheels, purely because that is why they are out in the boondocks, they want their peace and solitude from the masses.  The only way you are going to meet these folk is to be cheeky enough to walk up to their abode, knock on their door, and introduce yourself.  This approach can be fraught with many negative effects.  Either the owner is so anxious for their own privacy, they will refuse to open their door to you, or, at worst, they will stand at their door with a weapon, advising you to leave their property and "don't come back".  However, I think most boondockers, even though they prefer their solitude, also like to meet up with strangers and share a margarita with you so that you can learn about them and what brings them to this out of the way location.
We have been the instigators of a few friendly gatherings with the campers in our surrounding vicinity, and, by most accounts, the events have been appreciated and remembered.  Heck, we even had one group arrive on our doorstep at home, six months later, following a very fun evening around a campfire gathering.

Number two. Getting Active -  If you are an active soul, who likes to be on the go, enjoying various sports and activities, then possibly a resort campground might be just right for you.  There are always organized activities that you can partake in.  Heck, you might even get too tired to attend one of the events because of the number of sporty gatherings you have signed up for.  
On the other hand, when out in the boondocks, if you crave an active lifestyle, there are usually hiking trails and scenic areas to explore, while taking your dog for a walk or just for the fun of it.  Speaking of which, we know that our cats do enjoy being out in the boondocks, enjoying the fresh air and various smells that permeate the air.  In a resort, you pets have to be leashed and controlled.  While this is true in the boondocks too, there is not much concern about encountering another yapping dog around every corner.  My cats love to walk, but they do not appreciate scary encounters with other creatures and will come scurrying back to the safety of their trailer if there is a slight hint of potential trouble with other creatures.

Number three.  Going Solo - Sometimes it is nice to have some 'alone time', either by yourself, or with your other half.  This is often difficult in a campground environment, where you are living a camper door away from your neighbors.  It's almost a certainty that the morning you decide to sleep in for the rest of the day, there will be someone at your door for various reasons. 
This is unlikely in a boon-docking spot where your neighbors are within a few hundred feet away from you.  Usually, it is very easy to find yourself still in your nightgown late in the afternoon, without having seen anyone during the day.  This could be a bad thing too, but, if you are the type of person that wants no disturbances, boon-docking is probably the best option for you.